US20170367388A1 - Substituted butanol derivatives and their use as fragrance and flavor materials - Google Patents
Substituted butanol derivatives and their use as fragrance and flavor materials Download PDFInfo
- Publication number
- US20170367388A1 US20170367388A1 US15/701,171 US201715701171A US2017367388A1 US 20170367388 A1 US20170367388 A1 US 20170367388A1 US 201715701171 A US201715701171 A US 201715701171A US 2017367388 A1 US2017367388 A1 US 2017367388A1
- Authority
- US
- United States
- Prior art keywords
- substituted
- unsubstituted
- straight chain
- chain alkyl
- branched chain
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003205 fragrance Substances 0.000 title claims description 70
- 239000000463 material Substances 0.000 title claims description 11
- 239000000796 flavoring agent Substances 0.000 title abstract description 36
- 235000019634 flavors Nutrition 0.000 title abstract description 35
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 239000000203 mixture Substances 0.000 claims abstract description 75
- -1 acetoxy, carboxy Chemical group 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
- 150000002825 nitriles Chemical class 0.000 claims abstract description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 7
- 125000005596 alkyl carboxamido group Chemical group 0.000 claims abstract description 7
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 6
- 239000002304 perfume Substances 0.000 claims description 6
- 125000005228 aryl sulfonate group Chemical group 0.000 claims description 4
- 229920001277 pectin Polymers 0.000 claims description 4
- 235000010987 pectin Nutrition 0.000 claims description 4
- 239000001814 pectin Substances 0.000 claims description 4
- 229920000881 Modified starch Polymers 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 235000019426 modified starch Nutrition 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 230000001413 cellular effect Effects 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims 2
- 239000003995 emulsifying agent Substances 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 116
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- 239000007788 liquid Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 36
- 229910001868 water Inorganic materials 0.000 description 33
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 27
- 239000004615 ingredient Substances 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 238000002156 mixing Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 235000009508 confectionery Nutrition 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 239000013058 crude material Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 12
- 0 *OCCC(C)(C)OC Chemical compound *OCCC(C)(C)OC 0.000 description 11
- 241000402754 Erythranthe moschata Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 10
- STSHVQBNUBDXBK-UHFFFAOYSA-N 2-(3-methoxy-3-methylbutoxy)acetic acid Chemical compound COC(C)(C)CCOCC(O)=O STSHVQBNUBDXBK-UHFFFAOYSA-N 0.000 description 9
- 244000299461 Theobroma cacao Species 0.000 description 9
- 235000019219 chocolate Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- NECUSNMNQDWANI-UHFFFAOYSA-N 2-(3-methoxy-3-methylbutoxy)acetaldehyde Chemical compound COC(C)(C)CCOCC=O NECUSNMNQDWANI-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 8
- 241000207199 Citrus Species 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 235000020971 citrus fruits Nutrition 0.000 description 7
- 239000008367 deionised water Substances 0.000 description 7
- 229910021641 deionized water Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 5
- 235000013361 beverage Nutrition 0.000 description 5
- 229940125833 compound 23 Drugs 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 4
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- CTEQCXPKFCBRQG-UHFFFAOYSA-N 1-but-3-en-2-yloxy-3-methoxy-3-methylbutane Chemical compound COC(C)(C)CCOC(C)C=C CTEQCXPKFCBRQG-UHFFFAOYSA-N 0.000 description 4
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- YKOFCKQKPOQJLH-UHFFFAOYSA-N 3-methoxy-3-methyl-1-(3-methylbut-2-enoxy)butane Chemical compound COC(C)(C)CCOCC=C(C)C YKOFCKQKPOQJLH-UHFFFAOYSA-N 0.000 description 4
- UXBKPHASQDLUKP-UHFFFAOYSA-N 3-methoxy-3-methyl-1-prop-2-enoxybutane Chemical compound COC(C)(C)CCOCC=C UXBKPHASQDLUKP-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
- 244000241257 Cucumis melo Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical class OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 235000006679 Mentha X verticillata Nutrition 0.000 description 4
- 235000002899 Mentha suaveolens Nutrition 0.000 description 4
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 4
- 240000008790 Musa x paradisiaca Species 0.000 description 4
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 4
- 235000014443 Pyrus communis Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 229930007744 linalool Natural products 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QAEWNPPEUKTDNB-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) 2-ethoxyacetate Chemical compound CCOCC(=O)OCCC(C)(C)OC QAEWNPPEUKTDNB-UHFFFAOYSA-N 0.000 description 3
- LIDDRRXORKZDBY-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) 4-methylbenzenesulfonate Chemical compound COC(C)(C)CCOS(=O)(=O)C1=CC=C(C)C=C1 LIDDRRXORKZDBY-UHFFFAOYSA-N 0.000 description 3
- IUFWRPFAOUOHTF-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) prop-2-enyl carbonate Chemical compound COC(C)(C)CCOC(=O)OCC=C IUFWRPFAOUOHTF-UHFFFAOYSA-N 0.000 description 3
- MLHIRRYQYUUWDF-UHFFFAOYSA-N 1-(2,2-dimethoxyethoxy)-3-methoxy-3-methylbutane Chemical compound COC(OC)COCCC(C)(C)OC MLHIRRYQYUUWDF-UHFFFAOYSA-N 0.000 description 3
- ALJBAFRRZFFLCO-UHFFFAOYSA-N 3-methoxy-3-methyl-1-(2-methylprop-2-enoxy)butane Chemical compound COC(C)(C)CCOCC(C)=C ALJBAFRRZFFLCO-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
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- 229910000104 sodium hydride Inorganic materials 0.000 description 3
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- OWSKJORLRSWYGK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propanoate Chemical compound CCC(=O)OCCC(C)(C)OC OWSKJORLRSWYGK-UHFFFAOYSA-N 0.000 description 2
- CDBHEYRASRNAPX-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) propyl carbonate Chemical compound CCCOC(=O)OCCC(C)(C)OC CDBHEYRASRNAPX-UHFFFAOYSA-N 0.000 description 2
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- GRCDYXNQTHGYDJ-UHFFFAOYSA-N 2-(3-methoxy-3-methylbutoxy)propanal Chemical compound COC(C)(C)CCOC(C)C=O GRCDYXNQTHGYDJ-UHFFFAOYSA-N 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
- ZPTPIMZILKBBHN-UHFFFAOYSA-N 3-(3-methoxy-3-methylbutoxy)butanal Chemical compound COC(C)(C)CCOC(C)CC=O ZPTPIMZILKBBHN-UHFFFAOYSA-N 0.000 description 2
- HMLZLKJHCJDBRU-UHFFFAOYSA-N 3-(3-methoxy-3-methylbutoxy)propanal Chemical compound COC(C)(C)CCOCCC=O HMLZLKJHCJDBRU-UHFFFAOYSA-N 0.000 description 2
- NUTYUAFSQDAKDE-UHFFFAOYSA-N 3-methoxy-3-methyl-1-(2-methylpropoxy)butane Chemical compound COC(C)(C)CCOCC(C)C NUTYUAFSQDAKDE-UHFFFAOYSA-N 0.000 description 2
- NDUMXKDTDIFBRT-UHFFFAOYSA-N 3-methoxy-3-methyl-1-propoxybutane Chemical compound CCCOCCC(C)(C)OC NDUMXKDTDIFBRT-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 2
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- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
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- 238000006703 hydration reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- RERASOSSWQIKNJ-UHFFFAOYSA-N imidazolidin-4-ylurea Chemical compound NC(=O)NC1CNCN1 RERASOSSWQIKNJ-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 150000002499 ionone derivatives Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 239000013541 low molecular weight contaminant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
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- NJTGANWAUPEOAX-UHFFFAOYSA-N molport-023-220-454 Chemical compound OCC(O)CO.OCC(O)CO NJTGANWAUPEOAX-UHFFFAOYSA-N 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
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- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
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- 230000009965 odorless effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- OJTDGPLHRSZIAV-UHFFFAOYSA-N propane-1,2-diol Chemical compound CC(O)CO.CC(O)CO OJTDGPLHRSZIAV-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- SESSOVUNEZQNBV-UHFFFAOYSA-M sodium;2-bromoacetate Chemical compound [Na+].[O-]C(=O)CBr SESSOVUNEZQNBV-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 235000020679 tap water Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
-
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
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- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
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- A—HUMAN NECESSITIES
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- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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- A23L2/56—Flavouring or bittering agents
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- A—HUMAN NECESSITIES
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- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/198—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/003—Esters of saturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
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-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Definitions
- the present invention relates to compounds useful as fragrance or flavor components in fragrance or flavor compositions.
- fragrance industry is constantly reliant on the development of new chemicals with favorable organoleptic properties to provide perfumers and other persons the capability of creating new, unique fragrances for applications such as personal care products, air care products, perfumes, colognes and the like.
- 3-methoxy-3-methyl-1-butanol also known as SolfitTM
- SolfitTM is known in the perfume industry and has been applied in many consumer products (WO 9512379; JP 2001226246; JP 2005290236; JP 001104462).
- the structure of 3-methoxy-3-methyl-1-butanol is shown below:
- esters derived from this alcohol have been employed as solvents for consumer products (EP 462605A2).
- Ether analogues of this alcohol have been used as intermediates to useful homoallylic alcohol entities (U.S. Pat. No. 4,990,697).
- the present invention is directed to the synthesis and application of 3-methoxy-3-methyl- 1-butanol derivatives having unique and desired odor or organoleptic characteristics.
- the compounds of the present invention can be employed alone or incorporated as perfumery ingredients to enhance already existing fragrance compositions, solvents, media and the like.
- the present invention provides fragrance compounds of the formula (I),
- R′ is an unsubstituted or substituted C 1-6 straight chain alkyl, an unsubstituted or substituted C 3-6 branched chain alkyl, an unsubstituted or substituted C 3-6 straight chain alkenyl, an unsubstituted or substituted C 3-6 branched chain alkenyl, an unsubstituted or substituted C 3-6 cycloalkyl, an unsubstituted or substituted C 1-6 alkoxy, nitrile, halo, an unsubstituted or substituted phenyl, an unsubstituted or substituted benzyl, an unsubstituted or substituted naphthyl, an unsubstituted or substituted aryl, an unsubstituted or substituted piperazino, an unsubstituted or substituted morpholinyl, amino, an unsubstituted or substituted C 1-6 alkylamino, an unsubstituted or substituted
- R 1 as shown in formula I above is an unsubstituted or substituted C 1-6 straight chain alkyl, an unsubstituted or substituted C 3-6 branched chain alkyl, an unsubstituted or substituted C 3-6 straight chain alkenyl, an unsubstituted or substituted C 3-6 branched chain alkenyl, an unsubstituted or substituted C 3-6 cycloalkyl, an unsubstituted or substituted C 1-6 alkoxy, nitrile, halo, amino, an unsubstituted or substituted C 1-6 alkylamino, an unsubstituted or substituted C 1-6 dialkylamino, carboxy-C 1-5 alkylamino, carboxy-C 1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C 1-6 straight chain alkyl
- R 1 is a C 1-6 straight chain alkyl, C 3-6 branched chain alkyl, an unsubstituted or substituted C 1-6 alkenyl, an unsubstituted or substituted C 1-6 acyl, or aryl.
- the invention provides fragrance compounds of the formula (II),
- R 2 is the same as described for R′ above in paragraph 6.
- R 2 is as R 1 is described above in paragraphs 7 or 8.
- R 2 may be hydrogen.
- the alkyl 3-methoxy-3-methyl-1-butanol esters represented by formula II have a strong fruity note associated with them.
- the invention provides fragrance compounds of the formula
- R 3 is the same as described for R 2 above.
- the carbonate compounds represented by formula III have weak, varying odor characteristics but maintain a light and soft quality.
- the invention provides fragrance compounds of the formula (IV),
- R 4 is the same as described for R 2 above.
- a compound of formula (IV) will result from the condensation reaction.
- Glycolates represented by formula IV generally have a consistent light, powdery musk property.
- the invention provides fragrance compounds of the formula (V),
- the invention provides fragrance compounds of the formula (VI),
- R 6 and/or R 7 are hydrogen or a methyl group.
- Preferred fragrance compounds are set forth in the table below, in which R n refers to the R group of the respective formula.
- the fragrance compound is selected from 3-methoxy-3-methylbutyl 2-ethoxyacetate, 2-(3-methoxy-3-methylbutoxy)ethanal, 1-methoxy-1,1-dimethyl-3-(3-methylbut-2-enyloxy)propane, 1-methoxy-1,1-dimethyl-3-prop-2-enyloxypropane, and 1-methoxy-1,1-dimethyl-3-(1-methylprop-2-enyloxy)propane.
- the present invention provides a method to modify, enhance or improve olfactory and/or organoleptic property (e.g odor or flavor property) of a fragrance or flavor composition by adding to said composition an olfactory or organoleptic effective quantity of the compound of formulas (I-VI).
- a fragrance compound is added to a fragrance carrier, fragrance base or both to provide a fragrance composition.
- a flavor compound is added to a flavor carrier to provide a flavor composition. It is understood here also that the invention may be described as the use of any composition containing formulas (I-VI) in fragrance and/or flavor compositions.
- the present invention is directed to the use of the above compounds as fragrances in a fragrance composition.
- the compounds can be incorporated alone, as a mixture of two or more of said compounds, or as an enhancer to an existing fragrance composition (discussed below). These compounds add a favorable olfactory effect to the desired product.
- the compounds are typically present in an amount of from about 0.001 to about 30.0 by weight of the total fragrance composition. Typically a more preferred embodiment would contain between 0.01% and 20% by weight and a most preferred embodiment would contain between 0.01% and 10% by weight. None of these examples shown are meant to be limiting or restrictive on the use of the material as stated.
- One embodiment of the present inventions provides a method to modify, enhance or improve the odor properties of a fragrance composition by adding to said composition an olfactory effective quantity of the compound of formulas (I-VI).
- the invention may also be described as the use of any composition containing compound (I-VI) which can be advantageously employed in the fragrance industry as active ingredients.
- compositions may contain or consist of at least one ingredient selected from a group consisting of a fragrance carrier and a fragrance base. Such compositions may also consist of at least one fragrance adjuvant.
- Said fragrance carriers may be a liquid or a solid and typically do not significantly alter the olfactory properties of the fragrance ingredients.
- Some non-limiting examples of fragrance carriers include an emulsifying system, encapsulating materials, natural or modified starches, polymers, gums, pectins, gelatinous or porous cellular materials, waxes, and solvents which are typically employed in fragrance applications.
- Said fragrance base refers to any composition comprising at least one fragrance co-ingredient.
- these co-ingredients belong to chemical classes such as, but not limited to: alcohols, aldehydes, ketones, esters, ethers, acetals, oximes, acetates, nitriles, terpenes, saturated and unsaturated hydrocarbons and essential oils of natural or synthetic origins.
- Table 2 provides an example of a formulated fragrance in which compounds of the present invention can be added.
- olfactory effective quantity will be defined as the amount of said compound in a fragrance composition in which the individual component will contribute its characteristic olfactory properties, for example an olfactory property found to be more hedonistically appealing.
- a person of ordinary skill in the art may optimize the olfactory effect of the fragrance composition based on the incorporation of a fragrance compound of the present invention.
- the fragrance compounds may be used individually, or a part of mixture such that the sum of the effects of all fragrance ingredients present in the mixture yields a higher hedonistic rating. Therefore, the compounds embodied in the present invention can be employed to modify the characteristics of existing fragrance composition via their own olfactory properties or through additively effecting the contributions of other ingredient(s) present within the said composition.
- the quantity will vary widely depending on the other ingredients present, their relative amounts, the desired effect and the nature of the product.
- Compounds of formulas (I-VI) can be employed alone or incorporated into mixtures to enhance already existing flavor compositions. These compounds add a favorable organoleptic property and effect to the desired product.
- the compounds are typically present in an amount of from about 0.01% to about 20.0% by weight of the total flavor composition. Typically a more preferred embodiment would contain between 0.01% and 10% by weight and a most preferred embodiment would contain between 0.01% and 5% by weight. None of these examples shown are meant to be limiting or restrictive on the use of the material as stated.
- organoleptic effective quantity will be defined as the amount of said compound in a flavor composition in which the individual component will contribute its characteristic flavor properties.
- the organoleptic effect of the flavor composition will be the sum of the effects of all flavor ingredients present. Therefore, the compounds embodied in the present invention can be employed to modify the characteristics of the flavor composition via their own organoleptic properties or through additively effecting the contributions of other ingredient(s) present within the said composition.
- the quantity will vary widely depending on the presence of other ingredients present, their relative amounts, the desired effect and the nature of the product.
- the flavor carrier may be a liquid or a solid and typically do not significantly alter the olfactory or organoleptic properties of the flavor ingredients, respectively.
- Some non-limiting examples of flavor carriers include an emulsifying system, encapsulating materials, natural or modified starches, polymers, pectins, proteins, polysaccharides, gums and solvents which are typically employed in flavor applications.
- flavor carrier may also encompass the food or beverage to which the fragrance compound (i.e. compounds encompassed by formulas I-VI) are added.
- foods or beverages include, but are not limited to carbonated fruit beverages, carbonated cola drinks, wine coolers, cordials, flavored water, powders for drinks (e.g., powdered sports or “hydrating” drinks), hard candy, soft candy, taffy, chocolates, sugarless candies, chewing gum, bubble gum, condiments, spices and seasonings, dry cereal, oatmeal, granola bars, soups, alcoholic beverages, energy beverages, juices, teas, coffees, salsa, gel beads, film strips for halitosis, gelatin candies, pectin candies, starch candies, lozenges, cough drops, throat lozenges, throat sprays, toothpastes and mouth rinses.
- Compounds of formulas (I-VI) can be employed alone or incorporated into mixtures to enhance already existing fragrance compositions, solvents, media and the like.
- the use of such compounds is applicable to a wide variety of products in the perfume industry for consumer use such as, but not limited to: sprays, candles, air fresheners, perfumes, colognes, gels, soft solids, solids, devices for introducing said compounds into a space (e.g., a plug-in electrical device or a battery operated device), a liquid wicking system, personal care products such as soaps, talcum powder, antiperspirants, personal wash bar, personal wash liquid, personal wipe, deodorants, shampoos, conditioners, styling sprays, mousses, hair wipes, hair sprays, hair pomades, shower gels and shaving lotions; cosmetics such as oils, lotions and ointments; as well as detergents (e.g., synthetic detergent), fabric care products (e.g., fabric washing liquids and powders, fabric softeners, fabric conditioner
- the sprays can be aqueous or non-aqueous.
- the candles and gels can be opaque, translucent, or transparent, and may contain optional ingredients to enhance their appearance.
- the plug-in and battery-operated devices can include devices that vaporize the fragrance by heat, evaporation, or nebulization.
- Such compounds is also applicable to a wide variety of products in the flavor industry such as, but not limited to: foodstuffs such as baked goods, dairy products, desserts, etc.; beverages such as juices, sodas, flavored waters, etc.; confectionaries such as sweets, hard candy, gums, gelatinous materials, etc.
- the flavor compositions can also be added to pharmaceutical applications, such as lozenges, strips to deliver medicines or personal care products (e.g. fresh breath strips), cough syrup or other liquid or bucally administered medicines.
- Compounds of formula III may be isolated from the reaction of 3-methoxy-3-methyl-1-butanol (SolfitTM) with an alkyl chloroformate. The synthesis proceeds in a straight forward, facile manner. Table 1 lists the olfactory properties of various novel compounds synthesized in accordance to formula (III). The fragrance compounds encompassed by formula III generally maintain a light and soft quality.
- glycolates encompassed by formula (V) can be isolated in high yields when the reaction specifically employs 2-(3-methoxy-3-methylbutoxy)acetic acid with a respective alcohol to undergo esterification in similar fashion to the syntheses of compounds of formula (IV).
- reactions involving an alkyl halo-acetate with 3-methoxy-3-methyl-1-butoxide result in a low yield of the desired glycolate due to a mixture of undesired side products.
- This example illustrates the synthesis of 3-(2,2-dimethoxyethoxy)-1-methoxy-1,1-dimethylpropane.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-prop-2-enyloxypropane.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(2-methylprop-2-enyloxy)propane.
- This compound was synthesized employing a procedure analogous to Example 1 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and methallyl chloride (20.7 mL, 0.21 mol).
- the isolated crude material was fractionally distilled (103° C., 36.0 torr) resulting in a colorless, pure liquid (28.8 g, 79.3%). Odor: citrus, green, lemon, slight orange.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(3-methylbut-2-enyloxy)propane.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-propoxypropane.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(2-methylpropoxy)propane.
- This example illustrates the synthesis of 1-methoxy-1-dimethyl-3-(3-methylbutoxy)propane.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl propanoate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-methylpropanoate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl (2E)-2-methylbut-2-enoate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl methoxyformate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl prop-2-enyloxyformate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl propoxyformate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-methoxyacetate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-ethoxyacetate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-(methylethoxy)acetate.
- This example illustrates the synthesis of 2-(3-methoxy-3-methylbutoxy)acetic acid.
- a suspension of sodium hydride (4.70 g, 0.19 mol) in anhydrous THF (100 mL) was warmed to approximately 40° C. under an inert atmosphere.
- a portion of 3-methoxy-3-methyl-1-butanol (20.0 g, 0.17 mol) was then added dropwise via syringe over a period of 20 minutes during which time the temperature of the mixture was slowly raised to 70° C. at 5 degree intervals.
- sodium bromoacetate 28.2 g, 0.18 mol was added in small portions over a period of 20 minutes and the mixture was stirred vigorously at 70° C. for 4 hours.
- This example illustrates the synthesis of methyl 2-(3-methoxy-3-methylbutoxy)acetate.
- This example illustrates the synthesis of ethyl 2-(3-methoxy-3-methylbutoxy)acetate.
- This example illustrates the synthesis of methylethyl 2-(3-methoxy-3-methylbutoxy)acetate.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate.
- This example illustrates the synthesis of 1-methoxy-3-(3-methoxy-3-methylbutoxy)-1,1-dimethylpropane.
- a suspension of sodium hydride (2.35 g, 93.1 mmol) in anhydrous THF (60 mL) was warmed to approximately 40° C. under an inert atmosphere.
- a portion of 3-methoxy-3-methyl-1-butanol (10.0 g, 84.6 mmol) was then added dropwise via syringe over a period of 20 minutes during which time the temperature of the mixture was slowly raised to 70° C. at 5 degree intervals.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(1-methylprop-2-enyloxy)propane.
- This example illustrates the synthesis of 2-(3-methoxy-3-methylbutox y)propanal.
- Example 1 A portion of the dimethyl acetal, 3-(2,2-dimethoxyethoxy)-1-methoxy-1,1-dimethylpropane (Example 1), (27.6 g, 0.13 mol) was dissolved in a large excess of neat formic acid (74.0 g, 1.61 mol) and stirred vigorously for 4 hours. Upon completion (monitored via GC), the solution was treated with H 2 O (150 mL) and extracted with ethyl acetate (3 ⁇ 100 mL). The organic phases were collected and dried with MgSO 4 and the solvent was removed under reduced pressure.
- This example illustrates the synthesis of 3-(3-methoxy-3-methylbutoxy)propanal.
- This example illustrates the synthesis of 3-(3-methoxy-3-methylbutoxy)butanal.
- This example illustrates the synthesis of bis(3-methoxy-3-methylbutyl ethane)-1,2-dioate.
- This formulation is for dilution in a bucket at approximately one part concentrate to ten parts tap water.
- Neodol® 91-8, Dowanol® DPnB, and fragrance were mixed in a suitable vessel until completely uniform and clear.
- Neodol® 91-8, Dowanol® DPnB, and fragrance were mixed in a suitable vessel until completely uniform and clear.
- the formulation was then filled into suitable plastic containers (PET preferred), with the proper trigger or pump closure.
- Glucopon® was added to water heated to 65° C. and mix at medium speed until clear.
- pH was adjusted with sulfuric acid solution to pH of 8.0 to 8.5.
- Seq. #1 was heated to 75° C. and mixed together at medium speed using an overhead mixer until clear.
- Seq. #2 was added slowly to Seq. #1 with mixing. Mixing was continued until Seq. #2 is completely was hydrated. Hydration was checked by dipping a metal spatula into and out of the solution to observe if there are any gum particles that have not hydrated.
- Seq. #4 was premixed and heated until completely melted at approximately 65° C.
- Part 1 was placed on a Homomixer at low to medium speed, and Part 2 added to Part 1 and mixed for 1 minute.
- Part 4 was premixed at 35° C. and added to the batch, while cooling down at low speed to 30° C.
- Part 5 was added at 30° C. with mixing at low speed.
- Liquid fragrance was added slowly while mixing.
- Seq. #3 was added to batch without heating, in order of addition, and cooled down to 35° C. with low agitation.
- Seq. #5 was added to the batch with low agitation and cooled down to 25° C.
- Seq.#5 was added slowly to batch and mixing continued at low speed until room temperature was reached. Citric acid was added to a pH of 5.5-6.0 and sodium chloride was added to achieve the desired viscosity. Fragrance Seq.#6 was weighed and added to the formulation while mixing.
- Toothpaste with flavor and the claimed compound(s) was prepared according to the formulation below.
- Green tea flavor was prepared according to the formulation below utilizing the claimed compound(s)
- Black tea flavor was prepared according to the formula below utilizing the claimed compounds.
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Abstract
The present invention is related to substituted butanol derivatives of the formula:
wherein R is an unsubstituted or substituted C1-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, an unsubstituted or substituted C3-6 cycloalkyl, an unsubstituted or substituted C1-6 alkoxy, nitrile, halo, amino, an unsubstituted or substituted C1-6 alkylamino, an unsubstituted or substituted C1-6 dialkylamino, carboxy-C1-6 alkylamino, carboxy-C1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, an unsubstituted or substituted C1-6 alkylcarboxy, an unsubstituted or substituted C1-6 alkylthio, an unsubstituted or substituted C1-6 alkyloxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido or an unsubstituted or substituted C1-6 dialkylcarboxamido. Such compounds are useful in flavor or flavor compositions.
Description
- This application is a continuation of and claims priority to U.S. patent application Ser. No. 14/714,010, filed May 15, 2015 (now U.S. Pat. No. 9,756,872), which is a divisional of U.S. patent application Ser. No. 12/981,758, filed Dec. 30, 2010 (now U.S. Pat. No. 9,060,535), which is a continuation of International Application No. PCT/U.S.2008/068781, filed Jun. 30, 2008, which is incorporated by reference in its entirety herein, and from which priority is claimed.
- The present invention relates to compounds useful as fragrance or flavor components in fragrance or flavor compositions.
- The fragrance industry is constantly reliant on the development of new chemicals with favorable organoleptic properties to provide perfumers and other persons the capability of creating new, unique fragrances for applications such as personal care products, air care products, perfumes, colognes and the like.
- 3-methoxy-3-methyl-1-butanol, also known as Solfit™, is known in the perfume industry and has been applied in many consumer products (WO 9512379; JP 2001226246; JP 2005290236; JP 001104462). The structure of 3-methoxy-3-methyl-1-butanol is shown below:
- Some esters derived from this alcohol have been employed as solvents for consumer products (EP 462605A2). Ether analogues of this alcohol have been used as intermediates to useful homoallylic alcohol entities (U.S. Pat. No. 4,990,697).
- The present invention is directed to the synthesis and application of 3-methoxy-3-methyl- 1-butanol derivatives having unique and desired odor or organoleptic characteristics. The compounds of the present invention can be employed alone or incorporated as perfumery ingredients to enhance already existing fragrance compositions, solvents, media and the like.
- In one embodiment, the present invention provides fragrance compounds of the formula (I),
- wherein R′ is an unsubstituted or substituted C1-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, an unsubstituted or substituted C3-6 cycloalkyl, an unsubstituted or substituted C1-6 alkoxy, nitrile, halo, an unsubstituted or substituted phenyl, an unsubstituted or substituted benzyl, an unsubstituted or substituted naphthyl, an unsubstituted or substituted aryl, an unsubstituted or substituted piperazino, an unsubstituted or substituted morpholinyl, amino, an unsubstituted or substituted C1-6 alkylamino, an unsubstituted or substituted C6-12 arylamino, an unsubstituted or substituted C1-6 dialkylamino, an unsubstituted or substituted C6-12 diarylamino, carboxy-C1-6 alkylamino, carboxy-C1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, thio, an unsubstituted or substituted C1-6 alkylthio, an unsubstituted or substituted C1-6 alkyloxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido, an unsubstituted or substituted C1-6 dialkylcarboxamido, an unsubstituted or substituted phenoxy, an unsubstituted or substituted benzyloxy, phenylcarbonyl, benzylcarbonyl, an unsubstituted or substituted nitrophenyl, C1-6 trialkylsilyl or nitro, an unsubstituted or substituted C1-12 straight chain alkyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkyl sulfonate, an unsubstituted or substituted C1-12 straight chain alkenyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkenyl sulfonate, an unsubstituted or substituted C1-12 straight chain aryl sulfonate or an unsubstituted or substituted C1-12 branched chain aryl sulfonate.
- In a preferred embodiment, R1 as shown in formula I above, is an unsubstituted or substituted C1-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, an unsubstituted or substituted C3-6 cycloalkyl, an unsubstituted or substituted C1-6 alkoxy, nitrile, halo, amino, an unsubstituted or substituted C1-6 alkylamino, an unsubstituted or substituted C1-6 dialkylamino, carboxy-C1-5 alkylamino, carboxy-C1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, an unsubstituted or substituted C1-6 alkylcarboxy, an unsubstituted or substituted C1-6 alkylthio, an unsubstituted or substituted C1-6 alkyloxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido or an unsubstituted or substituted C1-6 dialkylcarboxamido.
- In a more preferred embodiment, R1 is a C1-6 straight chain alkyl, C3-6 branched chain alkyl, an unsubstituted or substituted C1-6 alkenyl, an unsubstituted or substituted C1-6 acyl, or aryl.
- In another embodiment, the invention provides fragrance compounds of the formula (II),
- wherein R2 is the same as described for R′ above in paragraph 6. In an alternative embodiment, R2 is as R1 is described above in paragraphs 7 or 8. Additionally, R2 may be hydrogen. Usually, the alkyl 3-methoxy-3-methyl-1-butanol esters represented by formula II have a strong fruity note associated with them.
- In another embodiment, the invention provides fragrance compounds of the formula
- wherein R3 is the same as described for R2 above. Generally, the carbonate compounds represented by formula III have weak, varying odor characteristics but maintain a light and soft quality.
- In another embodiment, the invention provides fragrance compounds of the formula (IV),
- wherein R4 is the same as described for R2 above. For example, when the alcohol, 3-methoxy-3-methyl-1-butanol, is reacted with an alkoxy acetic acid, a compound of formula (IV) will result from the condensation reaction. Glycolates represented by formula IV generally have a consistent light, powdery musk property.
- In another embodiment, the invention provides fragrance compounds of the formula (V),
- wherein R5 is the same as described for R2 above. Compounds encompassed by formula (V) often possess variations of plastic and green olfactory notes.
- In another embodiment, the invention provides fragrance compounds of the formula (VI),
- wherein R6 and/or R7 is a hydrogen or an unsubstituted or substituted C1-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl group and n=0-1. Preferably, R6 and/or R7 are hydrogen or a methyl group.
- Preferred fragrance compounds are set forth in the table below, in which Rn refers to the R group of the respective formula.
-
TABLE 1 Com- pound For- No. mula Rn Olfactory Description 1 I —CH2CH(OCH3)2 weak, marine-like, clean 2 I —CH2CH═CH2 citrus, herbal, pine, sweet orange, candy 3 I —CH2C(CH3)═CH2 citrus, green, lemon, slight orange 4 I —CH2CH═C(CH3)2 green, chocolate, sweet, bitter 5 I —CH(CH3)CH═CH2 strong, mint, citrus, rose 6 I —CH2CH2CH3 woody, floral, slightly bitter banana 7 I —CH2CH(CH3)2 woody, green pear, slight chocolate 8 I —CH2CH2CH(CH3)2 chocolate, liqueur, sour, slightly pungent 9 I —CH2CH2C(OCH3)(CH3)2 mold, mildew 10 II —H woody, camphoraceous, dry, chemical 11 II —CH2CH3 fruity, banana, floral, bubble gum 12 II —CH(CH3)2 fruity, green, pear, apple, sour 13 II —C(CH3)═CHCH3 sugary, sweet sap, green 14 III —CH3 weak, light, green, floral 15 III —CH2CH═CH2 weak, soft chocolate, airy 16 III —CH2CH2CH3 weak, soft musk, light vanilla 17 IV —CH3 weak, fruity, slight coconut, powder musk 18 IV —CH2CH3 powder musk, fresh, soft, light, clean 19 IV —CH(CH3)2 very weak, powder musk 20 V —CH3 metallic green, plastic 21 V —CH2CH3 vegetable green, spicy, plastic 22 V —CH(CH3)2 green, licorice, slightly mint, fresh 23 VI —H (R6) (n = 0) fresh, melon, clean, floral, muguet, green 24 VI —CH3 (R6) (n = 0) fresh, watery melon, clean, floral, muguet 25 VI —H (R6), —H (R7) (n = 1) waxy, oily, muguet, light floral 26 VI —CH3 (R6) —H (R7) waxy, oily, fatty (n = 1) - In one embodiment the fragrance compound is selected from 3-methoxy-3-methylbutyl 2-ethoxyacetate, 2-(3-methoxy-3-methylbutoxy)ethanal, 1-methoxy-1,1-dimethyl-3-(3-methylbut-2-enyloxy)propane, 1-methoxy-1,1-dimethyl-3-prop-2-enyloxypropane, and 1-methoxy-1,1-dimethyl-3-(1-methylprop-2-enyloxy)propane.
- In one aspect, the present invention provides a method to modify, enhance or improve olfactory and/or organoleptic property (e.g odor or flavor property) of a fragrance or flavor composition by adding to said composition an olfactory or organoleptic effective quantity of the compound of formulas (I-VI). In one embodiment, a fragrance compound is added to a fragrance carrier, fragrance base or both to provide a fragrance composition. In an alternative embodiment, a flavor compound is added to a flavor carrier to provide a flavor composition. It is understood here also that the invention may be described as the use of any composition containing formulas (I-VI) in fragrance and/or flavor compositions.
- The present invention is directed to the use of the above compounds as fragrances in a fragrance composition. The compounds can be incorporated alone, as a mixture of two or more of said compounds, or as an enhancer to an existing fragrance composition (discussed below). These compounds add a favorable olfactory effect to the desired product. The compounds are typically present in an amount of from about 0.001 to about 30.0 by weight of the total fragrance composition. Typically a more preferred embodiment would contain between 0.01% and 20% by weight and a most preferred embodiment would contain between 0.01% and 10% by weight. None of these examples shown are meant to be limiting or restrictive on the use of the material as stated.
- One embodiment of the present inventions provides a method to modify, enhance or improve the odor properties of a fragrance composition by adding to said composition an olfactory effective quantity of the compound of formulas (I-VI). The invention may also be described as the use of any composition containing compound (I-VI) which can be advantageously employed in the fragrance industry as active ingredients.
- Such compositions may contain or consist of at least one ingredient selected from a group consisting of a fragrance carrier and a fragrance base. Such compositions may also consist of at least one fragrance adjuvant.
- Said fragrance carriers may be a liquid or a solid and typically do not significantly alter the olfactory properties of the fragrance ingredients. Some non-limiting examples of fragrance carriers include an emulsifying system, encapsulating materials, natural or modified starches, polymers, gums, pectins, gelatinous or porous cellular materials, waxes, and solvents which are typically employed in fragrance applications.
- Said fragrance base refers to any composition comprising at least one fragrance co-ingredient. In general, these co-ingredients belong to chemical classes such as, but not limited to: alcohols, aldehydes, ketones, esters, ethers, acetals, oximes, acetates, nitriles, terpenes, saturated and unsaturated hydrocarbons and essential oils of natural or synthetic origins.
- Table 2 provides an example of a formulated fragrance in which compounds of the present invention can be added.
-
TABLE 2 Fragrance Formulation (ingredients are listed in parts per formulation based on a total of 1000 parts by weight, and also shown as WT % by formula amount) % MATERIAL Parts/1000 Wt % Acetyl Tetralin 20 2.0 Ambretone 5 0.5 Benzy Acetate 100 10.0 Bergamot Synth 25 2.5 Citral Synth @ 10% 10 1.0 Citronellol, Laevo 40 4.0 Citronellyl Acetate, Laevo 5 0.5 Citronellyl Nitrile, Laevo 7 0.7 Cyclacet 45 4.5 Trepanol 15 1.5 DH Myrcenol 125 12.5 Dynascone @10% 5 0.5 Eugenol 5 0.5 Geranium Oil 10 1.0 Hedione 27 2.7 Heliotropine 8 0.8 Hindinol 5 0.5 Ionone, Beta 25 2.5 Iso Bornyl Methyl Ether 25 2.5 Iso E Super 25 2.5 Iso Propxy Ethyl Salicylate 10 1.0 Linalool Syn 85 8.5 Linalyl Acetate 15 1.5 Melonal @10% 5 0.5 Methyl Ionone, Gamma 55 5.5 Norlimbanol Dextro @10% 6 0.6 Orange Oil Brazilian 25 2.5 Phenyl Ethyl Alcohol 30 3.0 Rose Oxide 3 0.3 Styrallyl Acetate 8 0.8 Tamarine Base 41.310G 3 0.3 Terpineol 20 2.0 Thesaron 7 0.7 Triplal Extra 3 0.3 Undecalactone, Gamma 20 2.0 Vanillin 5 0.5 Vertenex 85 8.5 Ylang Oil Extra 3 0.3 2-(3-methoxy-3-methylbutoxy)ethanal 80 8.0 [Compound 23; TABLE 1] - As used herein, olfactory effective quantity will be defined as the amount of said compound in a fragrance composition in which the individual component will contribute its characteristic olfactory properties, for example an olfactory property found to be more hedonistically appealing. A person of ordinary skill in the art may optimize the olfactory effect of the fragrance composition based on the incorporation of a fragrance compound of the present invention. The fragrance compounds may be used individually, or a part of mixture such that the sum of the effects of all fragrance ingredients present in the mixture yields a higher hedonistic rating. Therefore, the compounds embodied in the present invention can be employed to modify the characteristics of existing fragrance composition via their own olfactory properties or through additively effecting the contributions of other ingredient(s) present within the said composition. The quantity will vary widely depending on the other ingredients present, their relative amounts, the desired effect and the nature of the product.
- Compounds of formulas (I-VI) can be employed alone or incorporated into mixtures to enhance already existing flavor compositions. These compounds add a favorable organoleptic property and effect to the desired product. The compounds are typically present in an amount of from about 0.01% to about 20.0% by weight of the total flavor composition. Typically a more preferred embodiment would contain between 0.01% and 10% by weight and a most preferred embodiment would contain between 0.01% and 5% by weight. None of these examples shown are meant to be limiting or restrictive on the use of the material as stated.
- As used herein, organoleptic effective quantity will be defined as the amount of said compound in a flavor composition in which the individual component will contribute its characteristic flavor properties. However, the organoleptic effect of the flavor composition will be the sum of the effects of all flavor ingredients present. Therefore, the compounds embodied in the present invention can be employed to modify the characteristics of the flavor composition via their own organoleptic properties or through additively effecting the contributions of other ingredient(s) present within the said composition. The quantity will vary widely depending on the presence of other ingredients present, their relative amounts, the desired effect and the nature of the product.
- The flavor carrier may be a liquid or a solid and typically do not significantly alter the olfactory or organoleptic properties of the flavor ingredients, respectively. Some non-limiting examples of flavor carriers include an emulsifying system, encapsulating materials, natural or modified starches, polymers, pectins, proteins, polysaccharides, gums and solvents which are typically employed in flavor applications.
- As used herein, the term “flavor carrier” may also encompass the food or beverage to which the fragrance compound (i.e. compounds encompassed by formulas I-VI) are added. Examples of such foods or beverages include, but are not limited to carbonated fruit beverages, carbonated cola drinks, wine coolers, cordials, flavored water, powders for drinks (e.g., powdered sports or “hydrating” drinks), hard candy, soft candy, taffy, chocolates, sugarless candies, chewing gum, bubble gum, condiments, spices and seasonings, dry cereal, oatmeal, granola bars, soups, alcoholic beverages, energy beverages, juices, teas, coffees, salsa, gel beads, film strips for halitosis, gelatin candies, pectin candies, starch candies, lozenges, cough drops, throat lozenges, throat sprays, toothpastes and mouth rinses.
- Compounds of formulas (I-VI) can be employed alone or incorporated into mixtures to enhance already existing fragrance compositions, solvents, media and the like. The use of such compounds is applicable to a wide variety of products in the perfume industry for consumer use such as, but not limited to: sprays, candles, air fresheners, perfumes, colognes, gels, soft solids, solids, devices for introducing said compounds into a space (e.g., a plug-in electrical device or a battery operated device), a liquid wicking system, personal care products such as soaps, talcum powder, antiperspirants, personal wash bar, personal wash liquid, personal wipe, deodorants, shampoos, conditioners, styling sprays, mousses, hair wipes, hair sprays, hair pomades, shower gels and shaving lotions; cosmetics such as oils, lotions and ointments; as well as detergents (e.g., synthetic detergent), fabric care products (e.g., fabric washing liquids and powders, fabric softeners, fabric conditioners), wipes, dishwashing liquids and powders, and household cleaning agents (e.g., hard surface cleaning liquids and powders and aqueous and non-aqueous sprays). The sprays can be aqueous or non-aqueous. The candles and gels can be opaque, translucent, or transparent, and may contain optional ingredients to enhance their appearance. The plug-in and battery-operated devices can include devices that vaporize the fragrance by heat, evaporation, or nebulization.
- The use of such compounds is also applicable to a wide variety of products in the flavor industry such as, but not limited to: foodstuffs such as baked goods, dairy products, desserts, etc.; beverages such as juices, sodas, flavored waters, etc.; confectionaries such as sweets, hard candy, gums, gelatinous materials, etc. The flavor compositions can also be added to pharmaceutical applications, such as lozenges, strips to deliver medicines or personal care products (e.g. fresh breath strips), cough syrup or other liquid or bucally administered medicines.
- Compounds of formula I may be isolated from the reaction of 3-methoxy-3-methyl-1-butoxide with an alkyl halide. Similarly, reaction of this alkoxide with an allyl halide results in a compound of formula (I) as well. Table 1 lists the olfactory properties of various novel compounds synthesized in accordance to formula (1). In particular, the unsaturated 3-methoxy-3-methyl-1-butanol ether derivatives described in the present invention all contain citrus and/or green notes incorporated into their odor compositions. Saturation of these olefinic substituents via hydrogenation results in a woody, fruitier olfactory character.
- Compounds encompassed by formula II can be synthesized via simple condensation reactions between the alcohol, 3-methoxy-3-methyl-1-butanol, and the respective carboxylic acid. Alternatively, compounds of formula (II) can be synthesized by direct reaction of the alcohol with the respective acid chloride. Table 1 lists the odor characteristics of various novel compounds synthesized in accordance to formula (H).
- The syntheses of all compounds related to formula (H) proceed with high yields. As represented in Table 1, the majority of the alkyl 3-methoxy-3-methyl-1-butanol esters have a strong fruity note associated with them.
- Compounds of formula III may be isolated from the reaction of 3-methoxy-3-methyl-1-butanol (Solfit™) with an alkyl chloroformate. The synthesis proceeds in a straight forward, facile manner. Table 1 lists the olfactory properties of various novel compounds synthesized in accordance to formula (III). The fragrance compounds encompassed by formula III generally maintain a light and soft quality.
- The syntheses of compounds (glycolates) encompassed by formula (IV) proceeded smoothly and in high yield. Simple esterification of various alkoxy carboxylic acids with 3-methoxy-3-methyl-1-butanol in the presence of a catalytic amount of acid resulted in the desired products. Glycolates of this nature have a consistent light, powdery musk property. The musk qualities associated with these chemical entities have been reported in other glycolate-type compounds (See, e.g., U.S. Published Application No. 2006/0052277, which is hereby incorporated by reference).
- The present inventors have found that glycolates encompassed by formula (V) can be isolated in high yields when the reaction specifically employs 2-(3-methoxy-3-methylbutoxy)acetic acid with a respective alcohol to undergo esterification in similar fashion to the syntheses of compounds of formula (IV). Alternatively, reactions involving an alkyl halo-acetate with 3-methoxy-3-methyl-1-butoxide result in a low yield of the desired glycolate due to a mixture of undesired side products.
- The synthesis of the compound of formula (VI) in which n=0 and R6=hydrogen proceeded smoothly via its dimethyl acetal precursor. Cleavage of the acetal group under acidic conditions afforded the respective acetaldehyde. This compound can also be synthesized via ozonolysis of allyl 3-methoxy-3-methyl-1-butanol ether. Such an approach was taken for the compound of formula (VI) in which n=0 and R6=methyl. Both compounds possess odor characteristics which can be described as clean, melon-like and fresh with very strong diffusive properties.
- The synthesis of compounds of formula (VI) in which n=1 and R6=hydrogen or a methyl group was based on a revised adaptation of previously reported syntheses between alcohols and α-β-unsaturated aldehydes (U.S. Pat. No. 2,694,733; Feldman, D. P.; Stonkus, V. V.; Shimanskaya, M N.; Avots, A. A. Russ. J. Gen. Chem. 1995, 65, 250-253). In the present case, acrolein and crotonaldehyde have been chosen as the α-β-unsaturated aldehydes. In each of the previously reported syntheses for reactions of this type, specific conditions involving the buffer capacity of the system were stressed. The syntheses reported here proceeded with extremely low yields (<5%) when employing such conditions. The present inventors found that the presence of a catalytic amount of acid greatly promotes the formation of the desired aldehydes. As listed in Table 1, such aldehydes of this nature have a much more waxy, fatty-type aroma than the acetaldehyde analogues (n=0).
- This example illustrates the synthesis of 3-(2,2-dimethoxyethoxy)-1-methoxy-1,1-dimethylpropane.
- A suspension of sodium hydride (11.8 g, 0.47 mol) in anhydrous THF (400 mL) was warmed to approximately 40° C. under an inert atmosphere. A portion of 3-methoxy-3-methyl-1-butanol (50.0 g, 0.42 mol) was then added dropwise via syringe over a period of 20 minutes during which time the temperature of the mixture was slowly raised to 70° C. at 5 degree intervals. After one hour, bromoacetaldehyde dimethyl acetal (54.0 mL, 0.46 mol) was added dropwise via syringe over a period of 30 minutes and the mixture was stirred vigorously at 70° C. for 16 hours. After this time, the mixture was cooled to room temperature, treated with H2O (200 mL) and extracted with diethyl ether (3×200 mL). The organic phases were collected and washed with saturated NaHCO3 (aq.) (2×200 mL) followed by H2O (2×100 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting light yellow liquid was fractionally distilled (87° C., 3.00 torr) to yield the desired colorless, pure ether (57.0 g, 65.5%). Odor: weak, marine-like, clean. GC/MS(EI): m/z(%)—206(1), 191(1), 159(1), 143(3), 127(4), 111(5), 97(3), 89(2), 85(13), 75(100), 73(37), 69(8), 58(4), 55(3), 47(8), 45(15), 43(7). 1H NMR (CDCl3); δ 1.16 (s, 6H), 1.81 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.38 (s, 6H), 3.47 (d, J=5.04 Hz, 2H), 3.55 (t, J=7.33 Hz, 2H), 4.48 (t, J=5.04 Hz, 1H). 13C NMR (CDCl3): δ 25.4, 39.3, 49.2, 53.9, 68.0, 70.8, 73.7, 102.9.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-prop-2-enyloxypropane.
- This compound was synthesized employing a procedure analogous to Example 1 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and allyl chloride (16.4 mL, 0.20 mol). The isolated crude material was fractionally distilled (22° C., 0.80 torr) resulting in a colorless, pure liquid (22.5 g, 70.8%). Odor: citrus, herbal, pine, sweet orange, candy. GC/MS(EI): m/z(%)—158(1), 143(2), 126(1), 111(3), 97(1), 87(9), 85(7), 73(100), 71(14), 57(9), 55(9), 45(7), 43(13), 41(25). 1H NMR (CDCl3): δ 1.16 (s, 6H), 1.80 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.50 (t, J=7.79 Hz, 2H), 3.96 (d, J=5.96 Hz, 2H), 5.15 (dd, J=11.9 Hz, 1H), 5.25 (dd, J=18.8 Hz, 1H), 5.90 (m, 1H). 13C NMR (CDCl3): δ 25.4, 39.3, 49.2, 66.7, 71.9, 73.8, 116.8, 135.1.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(2-methylprop-2-enyloxy)propane.
- This compound was synthesized employing a procedure analogous to Example 1 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and methallyl chloride (20.7 mL, 0.21 mol). The isolated crude material was fractionally distilled (103° C., 36.0 torr) resulting in a colorless, pure liquid (28.8 g, 79.3%). Odor: citrus, green, lemon, slight orange. GC/MS(EI): m/z(%)—172(1), 157(1), 140(1), 125(9), 111(2), 101(2), 95(7), 87(9), 85(10), 73(100), 71(11), 69(14), 55(36), 45(9), 43(12), 41(10). 1H NMR (CDCl3): δ 1.17 (s, 6H), 1.72 (s, 3H), 1.81 (t, J=6.87 Hz, 2H), 3.18 (s, 31-1), 3.47 (t, J=7.33 Hz, 2H), 3.85 (s, 2H), 4.87 (s, 1H), 4.94 (s, 1H). 13C NMR (CDCl3): δ 19.5, 25.5, 39.4, 49.2, 66.5, 73.8, 75.0, 111.8, 142.6.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(3-methylbut-2-enyloxy)propane.
- This compound was synthesized employing a procedure analogous to Example 1 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and prenyl chloride (23.9 mL, 0.21 mol). The isolated crude material was fractionally distilled (66° C., 3.00 torr) resulting in a colorless, pure liquid (30.4 g, 77.0%). Odor: green, chocolate, sweet, bitter. GC/MS(E1): m/z(%)—186(1), 171(1), 154(1), 139(58), 103(4), 85(44), 78(4), 73(100), 69(86), 55(11), 45(12), 43(12), 41(26). 1H NMR (CDCl3): δ 1.15 (s, 6H), 1.66 (s, 3H), 1.73 (s, 3H), 1.79 (t, J=7.33 Hz, 2H), 3,17 (s, 3H), 3.48 (t, J=7.33 Hz, 2H), 3.93 (d, J=6.87 Hz, 2H), 5.34 (t, J=7.33 Hz, 1H). 13C NMR (CDCl3): δ 18.1, 25.5, 25.9, 39.2, 49.2, 66.5, 67.5, 73.8, 121.2, 136.8.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-propoxypropane.
- A portion of the unsaturated ether, 1-methoxy-1,1-dimethyl-3-prop-2-enyloxypropane, (20.0 g, 0.13 mol) was dissolved in absolute EtOH (120 mL) and to this was added 5% (w/w) catalyst (5% Pd-C). The suspension was stirred at ambient temperature and treated with H2 (250 psi) for 16 hours. Upon completion, the suspension was filtered through a glass frit (M) filter packed with filter paper and celite and rinsed with ethyl acetate. The solvent was removed under reduced pressure via rotary evaporation affording a light yellow liquid which was fractionally distilled (58° C., 9.70 torr) to yield the desired colorless, pure ether (11.9 g, 59.1%). Odor: woody, floral, slightly bitter banana. GC/MS(EI): m/z(%)—160(1), 145(2), 128(8), 113(12), 87(8), 73(100), 71(20), 55(7), 43(24), 41(11). 1H NMR (CDCl3): 5 0.90 (t, J=7.33 Hz, 3H), 1.16 (s, 61-1), 1.58 (m, 2H), 1.78 (t, J=7.33 Hz, 21-1), 3.17 (s, 31-1), 3.35 (t, J=6.42 Hz, 2H), 3.47 (t, J=7.79 Hz, 2H). 13C NMR (CDCl3): δ 10.7, 23.0, 25.5, 39.2, 49.2, 67.0, 72.8, 73.9.
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(2-methylpropoxy)propane.
- This compound was synthesized employing a procedure analogous to Example 5 using 1-methoxy-1,1-dimethyl-3-(2-methylprop-2-enyloxy)propane (20.0 g, 0.12 mol). The isolated crude material was fractionally distilled (53° C., 5.00 torr) resulting in a colorless, pure liquid (16.0 g, 80.0%). Odor: woody, green pear, slight chocolate. GC/MS(EI): m/z(%)—174(1), 159(1), 142(5), 127(3), 99(2), 87(9), 85(5), 73(100), 71(17), 57(26), 43(11), 41(14). 1H NMR (CDCl3): δ 0.88 (d, J=6.87 Hz, 6H), 1.16 (s, 6H), 1.78 (t, J=7.33 Hz, 2H), 1.83 (m, 1H), 3.15 (d, J=6.42 Hz, 2H), 3.18 (s, 3H), 3.47 (J=733 Hz, 2H). 13C NMR (CDCl3): δ 19.5, 25.5, 28.5, 39.2, 49.2, 67.2, 73.9, 78.1.
- This example illustrates the synthesis of 1-methoxy-1-dimethyl-3-(3-methylbutoxy)propane.
- This compound was synthesized employing a procedure analogous to Example 5 using 1-methoxy-1,1-dimethyl-3-(3-methylbut-2-enyloxy)propane (20.0 g, 0.11 mol). The isolated crude material was distilled via Kugelrohr apparatus (25° C., 0.15 torr) resulting in a colorless, pure liquid (9.93 g, 49.2%). Odor: chocolate, liqueur, sour, slightly pungent. GC/MS(EI): m/z(%)—188(1), 173(1), 156(4), 141(11), 99(7), 87(11), 73(100), 71(38), 55(11), 43(30), 41(14). 1H NMR (CDCl3):δ 0.89 (d, J=6.87 Hz, 6H), 1.16 (s, 6H), 1.45 (q, J=6.87 Hz, 2H), 1.67 (m, 1H), 1.78 (t, J=7.33 Hz, 2H), 3.18 (s, 3H), 3.41 (t, J=6.87 Hz, 2H), 3.47 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 22.7, 25.2, 25.5, 38.7, 39.2, 49.2, 67.1, 69.5, 73.9.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl formate,
- A portion of 3-methoxy-3-methyl-1-butanol (30.0 g, 0.25 mol) was dissolved in neat formic acid (60.9 g, 1.27 mol) and was stirred at ambient temperature for approximately 6 hours. Upon completion (monitored via GC), H2O (100 mL) was added and the solution was extracted with diethyl ether (3×75 mL). The organic phases were collected and washed with saturated NaHCO3 (aq.) (3×100 mL) followed by H2O (2×50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting light yellow liquid was fractionally distilled (57° C., 9.00 torr) to yield the desired colorless, pure product (20.9 g, 56.3%). Odor: woody, camphoraceous, dry, chemical. GC/MS(EI): m/z(%)—146(1), 131(1), 85(43), 73(100), 69(14), 55(15), 43(12), 41(13). 1H NMR (CDCl3): δ 1.18 (s, 6H), 1.85 (t, J=7.33 Hz, 2H), 3.18 (s, 3H), 4.27 (t, J=7.33 Hz, 2H), 8.03 (s, 1H). 13C NMR (CDCl3): δ 25.2, 38.3, 49.3, 60.7, 73.5, 161.3.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl propanoate.
- A portion of 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) was dissolved in anhydrous THF (200 mL) and purged with nitrogen. To this solution was added the propionyl chloride (20.2 mL, 0.23 mol) dropwise over a 15-minute period. The solution was stirred at ambient temperatures for 2 hours. Upon completion (monitored via GC), H2O (100 mL) was added and the solution was extracted with diethyl ether (3×75 mL). The organic phases were collected and washed with saturated NaHCO3 (aq.) (3×100 mL) followed by H2O (2×50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting yellow liquid was fractionally distilled (110° C., 36.0 torr) to yield the desired colorless, pure product (29.4 g, 80.1%). Odor: fruity, banana, floral, bubble gum. GC/MS(EI): m/z(%)—173(1), 159(1), 143(1), 101(1), 85(57), 73(100), 69(27), 57(24), 55(16), 43(10), 41(10). 1H NMR (CDCl3): δ 1.12 (t, J=7.33 Hz, 3H), 1.17 (s, 61-1), 1.81 (t, J=7.33 Hz, 21-1), 2.30 (t, J=7.33 Hz, 2H), 3.18 (s, 3H), 4.15 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 9.2, 25.3, 27.7, 38.3, 49.3, 61.0, 73.6, 174.6.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-methylpropanoate.
- This compound was synthesized employing a procedure analogous to Example 9 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and isobutyryl chloride (24.4 mL, 0.23 mol). The isolated crude material was fractionally distilled (58° C., 3.00 torr) resulting in a colorless, pure liquid (29.6 g, 74.2%). Odor: fruity, green, pear, apple, sour. GC/MS(EI): m/z(%)—188(1), 173(1), 157(1), 115(1), 101(1), 85(55), 73(100), 71(12), 69(25), 55(13), 43(26), 41(15). 1H NMR (CDCl3): δ 1.14 (d, J=7.33 Hz, 611), 1.18 (s, 6H), 1.81 (t, J=7.33 Hz, 2H), 2.51 (m, 1H), 3.18 (s, 3H), 4.15 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 19.0, 25.3, 34.1, 38.3, 49.3, 61.0, 73.6, 177.3.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl (2E)-2-methylbut-2-enoate.
- Portions of tiglic acid (12.6 g, 0.13 mol) and p-toluene sulfonic acid (1.21 g, 6.35 mmol) were dissolved in 3-methoxy-3-methyl-1-butanol (45.0 g, 0.38 mol) and stirred vigorously while heated at 40° C. for 27 hours. After this time, the solution was cooled to room temperature and diethyl ether was added (100 mL). The solution was washed with saturated NaHCO3 (3×75 mL) followed by H2O (100 mL). The aqueous fractions were back-extracted with diethyl ether (50 mL) and the organic layers were dried with MgSO4. The solvent removed via rotary evaporation and the resulting clear liquid was fractionally distilled (76° C., 1.23 torr) to afford the desired colorless, pure ester (5.25 g, 20.8%). Odor: sugary, sweet sap, green. GC/MS(EI): m/z(%)—200(1), 185(1), 169(1), 127(1), 101(6), 85(50), 73(100), 69(16), 55(26), 43(7), 41(8). 1H NMR (CDCl3): δ 1.18 (s, 6H), 1.76 (d, J=7.79 Hz, 3H), 1.81 (s, 3H), 1.85 (t, J=7.33 Hz, 2H), 3.19 (s, 3H), 4.21 (t, J=7.33 Hz, 2H), 6.83 (dq, J=8.71 Hz, 1H). 13C NMR (CDCl3): δ 12.1, 14.4, 25.4, 38.3, 49.3, 61.1, 73.6, 128.8, 137.0, 168.3.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl methoxyformate.
- A portion of 3-methoxy-3-methyl-1-butanol (30.0 g, 0.25 mol) was dissolved in anhydrous THF (100 mL) and purged with nitrogen. To this solution was added methyl chloroformate (21.5 mL, 0.28 mol) dropwise. The solution was cooled to 0° C. and stirred vigorously. To this solution was added pyridine (22.6 mL, 0.28 mol) slowly, which resulted in a very exothermic reaction and the immediate formation of a white precipitate. Upon completion (monitored via GC) (<1 hour), H2O (100 mL) was added and the solution was extracted with diethyl ether (3×75 mL). The organic phases were collected and washed with 10% HCl (aq.) (3×75 mL) followed by brine solution (2×50 mL) and H2O (2×50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting yellow liquid was fractionally distilled (84° C., 9.00 torr) to yield the desired colorless, pure product (35.7 g, 80.0%). Odor: weak, light, green, floral. GUNNED: m/z(%)—176(1), 161(1), 101(2), 85(43), 73(100), 69(22), 59(5), 55(12), 45(6), 43(8), 41(8). 1H NMR (CDCl3); δ 1.17 (s, 6H), 1.86 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.75 (s, 3H), 4.22 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 25.3, 38.3, 49.3, 54.8, 64.8, 73.4, 155.9.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl prop-2-enyloxyformate.
- This compound was synthesized employing a procedure analogous to Example 12 using 3-methoxy-3-methyl-1-butanol (25.0 g, 0.21 mol) and allyl chloroformate (25.5 mL, 0.23 mol). The isolated crude material was fractionally distilled (86° C., 3.00 torr) resulting in a colorless, pure liquid (37.3 g, 87.0%). Odor: weak, soft chocolate, airy. GC/MS(EI): m/z(%)—202(1), 187(1), 146(1), 108(1), 101(4), 85(45), 73(100), 69(39), 55(11), 43(8), 41(17). 1H NMR (CDCl3); δ 1.18 (s, 6H), 1.87 (t, J=7.79 Hz, 2H), 3.18 (s, 3H), 4.23 (t, J=7.33 Hz, 2H), 4.60 (d, J=5.50 Hz, 2H), 5.25 (dd, J=10.54 Hz, 1H), 5.34 (dd, J=18.33 Hz, 1H), 5.91 (m, 1H). 13C NMR (CDCl3): δ 25.3, 38.3, 49.3, 64.8, 68.4, 73.4, 118.9, 131.8, 155.1.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl propoxyformate.
- A portion of the unsaturated carbonate, 3-methoxy-3-methylbutyl prop-2-enyloxyformate, (20.0 g, 99.0 mmol) was dissolved in absolute EtOH (120 mL) and to this was added 1% (w/w) catalyst (5% Pd-C). The suspension was stirred at ambient temperature and treated with H2 (250 psi) for 2 hours. Upon completion (monitored via GC), the suspension was filtered through a glass frit (M) filter packed with filter paper and celite and rinsed with ethyl acetate. The solvent was removed under reduced pressure via rotary evaporation affording a light yellow liquid which was fractionally distilled (86° C., 3.20 torr) to yield the desired colorless, pure product (18.5 g, 91.5%). Odor: weak, soft musk, light vanilla. GC/MS(EI): m/z(%)—204(1), 189(1), 101(2), 85(34), 73(100), 69(18), 55(9), 43(12), 41(12). 1H NMR (CDCl3): δ 0.95 (t, J=7.79 Hz, 3H), 1.18 (s, 6H), 1.67 (m, 2H), 1.87 (t, J=7.79 Hz, 2H), 3.18 (s, 3H), 4.08 (t, J=6.87 Hz, 2H), 4.22 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 10.3, 22.1, 25.3, 38.3, 49.3, 64.6, 69.6, 73.6, 155.6.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-methoxyacetate.
- A portion of methoxyacetic acid (20 g, 0.22 mol) was dissolved in CH2Cl2 (160 mL) and dimethylformamide (40 mL). The solution was treated with oxalyl chloride (27.1 mL, 0.31 mol) in CH2Cl2 (100 mL) dropwise and stirred at room temperature for 2 hours. The temperature was then increased to 40° C. and the solution was stirred for an additional 40 minutes. The solution was then cooled to room temperature, purged with nitrogen gas for 5 minutes and then cooled to 0° C. The cooled solution was treated with a mixture of 3-methoxy-3-methyl-1-butanol (26.2 g, 0.22 mol) and pyridine (19.8 mL, 0.22 mol) in CH2Cl2 (50 mL) dropwise and was stirred at that temperature for 2 hours. Upon completion, 10% HCl (aq.) was added and the organic layer was washed (3×100 mL) followed by H2O (100 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting yellow liquid was fractionally distilled (71° C., 1.26 torr) to yield the desired colorless, pure product (25.8 g, 61.1%). Odor: weak, fruity, slight coconut, powder musk. GC/MS(EI): m/z(%)—190(1), 175(1), 128(1), 85(37), 73(100), 55(9), 45(24), 41(11). 1H NMR (CDCl3); δ 1.17 (s, 6H), 1.84 (t, J=7.79 Hz, 2H), 3.17 (s, 3H), 3.43 (s, 3H), 4.00 (s, 2H), 4.25 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 25.3, 38.3, 49.3, 59.4, 61.6, 70.0, 73.5, 170.4.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-ethoxyacetate.
- Portions of ethoxyacetic acid (50 g, 0.47 mol) and p-toluenesulfonic acid (4.50 g, 23.5 mmol) were dissolved in 3-methoxy-3-methyl-1-butanol (167 g, 1.41 mol) and stirred vigorously while heated at 40° C. for 5 hours. After this time, the solution was cooled to room temperature and diethyl ether was added (100 mL). The solution was washed with saturated NaHCO3 (3×75 mL) followed by H2O (100 mL). The aqueous fractions were back-extracted with diethyl ether (50 mL) and the organic layers were dried with MgSO4. The solvent removed via rotary evaporation and the resulting clear liquid was fractionally distilled (70° C., 1.04 torr) to afford the desired colorless, pure product (68.4 g, 71.2%). Odor: powder musk, fresh, soft, light, clean. GC/MS(EI): m/z(%)—204(1), 189(1), 128(4), 85(32), 73(100), 59(9), 55(7), 45(7). 1H NMR (CDCl3); δ 1.17 (s, 6H), 1.24 (t, J=6.87 Hz, 3H), 1.84 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.57 (q, J=7.33 Hz, 2H), 4.04 (s, 2H), 4.25 (t, J=7.79 Hz, 2H). 13C NMR (CDCl3): δ 15.1, 25.3, 38.3, 49.3, 61.6, 67.3, 68.2, 73.5, 170.7.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 2-(methylethoxy)acetate.
- This compound was synthesized employing a procedure analogous to Example 16 using 3-methoxy-3-methyl-1-butanol (56.0 g, 0.48 mol) and methylethoxyacetic acid (14.0 g, 0.12 mol). The isolated crude material was fractionally distilled (72° C., 0.96 torr) resulting in a colorless, pure liquid (10.3 g, 39.9%). Odor: very weak powder musk. GC/MS(EI): m/z(%)—218(1), 203(1), 187(1), 160(1), 145(1), 128(8), 101(4), 85(40), 73(100), 69(52), 55(8), 45(10), 43(24), 41(12). 1H NMR (CDCl3): δ 1.16 (s, 6H), 1.19 (d, J=5.96 Hz, 6H), 1.83 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.65 (m, 1H), 4.04 (s, 2H), 4.23 (t, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 21.8, 25.2, 38.5, 49.2, 61.5, 65.9, 72.6, 73.5, 170.9.
- This example illustrates the synthesis of 2-(3-methoxy-3-methylbutoxy)acetic acid.
- A suspension of sodium hydride (4.70 g, 0.19 mol) in anhydrous THF (100 mL) was warmed to approximately 40° C. under an inert atmosphere. A portion of 3-methoxy-3-methyl-1-butanol (20.0 g, 0.17 mol) was then added dropwise via syringe over a period of 20 minutes during which time the temperature of the mixture was slowly raised to 70° C. at 5 degree intervals. After one hour, sodium bromoacetate (28.2 g, 0.18 mol) was added in small portions over a period of 20 minutes and the mixture was stirred vigorously at 70° C. for 4 hours. Upon completion (monitored via GC), the mixture was cooled to room temperature, treated with diethyl ether (100 mL) and washed with 10% HCl (aq.) (3×75 mL) followed by brine solution (100 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The crude light yellow liquid was not purified further for use in subsequent reactions. Yield: (29.2 g, 98.0%). Odor. harsh, chemical. GC/MS(EI): m/z(%)—176(1), 161(1), 129(2), 85(30), 73(100), 69(14), 55(9), 45(7). 1H NMR (CDCl3): δ 1.21 (s, 6H), 1.83 (t, J=5.96 Hz, 2H), 3.21 (s, 3H), 3.66 (t, J=5.96 Hz, 2H), 3.75 (s, 1H), 4.06 (s, 2H). 13C NMR (CDCl3): δ 25.2, 39.3, 49.4, 68.3, 68.6, 75.0, 173.1.
- This example illustrates the synthesis of methyl 2-(3-methoxy-3-methylbutoxy)acetate.
- A portion of 2-(3-methoxy-3-methylbutoxy)acetic acid (Example 18) (28.0 g, 0.16 mol) was diluted with methanol (50 mL) and treated with p-toluenesulfonic acid (1.51 g, 7.95 mmol) and stirred vigorously at 40° C. for 3 hours. After this time, the solution was cooled to room temperature and diethyl ether was added (100 mL). The solution was washed with saturated NaHCO3 (3×75 mL) followed by H2O (100 mL).
- The aqueous fractions were back-extracted with diethyl ether (50 mL) and the organic layers were dried with MgSO4. The solvent removed via rotary evaporation and the resulting light yellow liquid was fractionally distilled (60° C., 1.00 torr) to afford the desired colorless, pure product (18.9 g, 62.6%). Odor: metallic green, plastic. GC/MS(EI): m/z(%)—190(1), 175(1), 143(3), 99(8), 85(67), 73(100), 69(27), 55(11), 45(25). 1H NMR (CDCl3): δ 1.16 (s, 6H), 1.84 (t, J=7.33 Hz, 2H), 3.16 (s, 3H), 3.58 (t, J=7.33 Hz, 2H), 3.73 (s, 3H), 4.06 (s, 2H). 13C NMR (CDCl3): δ 25.4, 39.1, 49.2, 51.9, 68,2, 68.4, 73.7, 171.0.
- This example illustrates the synthesis of ethyl 2-(3-methoxy-3-methylbutoxy)acetate.
- This compound was synthesized employing a procedure analogous to Example 19 using 2-(3-methoxy-3-methylbutoxy)acetic acid (14.0 g, 79.5 mmol) and ethanol (28 mL). The isolated crude material was fractionally distilled (65° C., 0.97 torr) resulting in a colorless, pure liquid (7.50 g, 46.9%). Odor: vegetable green, spicy, plastic. GC/MS(EI): m/z(%)—204(1), 189(1), 157(3), 99(10), 85(64), 73(100), 69(24), 55(9), 45(11). 1H NMR (CDCl3): δ 1.16 (s, 6H), 1.27 (t, J=7.33 Hz, 3H), 1.84 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.59 (t, J=7.33 Hz, 2H), 4.04 (s, 2H), 4.20 (q, J=7.33 Hz, 2H). 13C NMR (CDCl3): δ 14.3, 25.4, 39.1, 49.3, 60.9, 68.2, 68.6, 73.7, 170.6.
- This example illustrates the synthesis of methylethyl 2-(3-methoxy-3-methylbutoxy)acetate.
- This compound was synthesized employing a procedure analogous to Example 19 using 2-(3-methoxy-3-methylbutoxy)acetic acid (28.0 g, 0.16 mol) and 2-propanol (75 mL). The isolated crude material was fractionally distilled (70° C., 0.93 torr) resulting in a colorless, pure liquid (21.4 g, 61.8%). Odor: green, licorice, slightly mint, fresh. GC/MS(EI): m/z(%)—218(1), 203(1), 188(1), 171(1), 146(1), 129(5), 119(3), 99(12), 85(68), 73(100), 69(34), 55(9), 45(15), 43(21), 41(13). 1H NMR (CDCl3): δ 1.17 (s, 6H), 1.25 (d, J=6.42 Hz, 6H), 1.85 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.60 (t, J=7.33 Hz, 2H), 4.01 (s, 2H), 5.08 (m, 1H). 13C NMR (CDCl3): δ 21.9, 25.4, 39.1, 49.3, 68.2, 68.5, 68.7, 73.7, 170.2.
- This example illustrates the synthesis of 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate.
- A portion of p-toluenesulfonyl chloride (32.9 g, 0.17 mol) was dissolved in pyridine (50 mL) and cooled to 0° C. To this solution was added 3-methoxy-3-methyl-1-butanol (20.0 g, 0.17 mol) dropwise slowly via syringe. A white precipitate formed immediately and the mixture was stirred at 0° C. for one hour followed by an additional 3 hours at room temperature. After this time, the mixture was treated with diethyl ether (100 mL) and washed with 10% HCl (aq.) (3×75 mL), saturated NaHCO3 (aq.) (2×75 mL) and H2O (2×50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting crude light yellow liquid was not purified further for use in subsequent reactions. Yield: (42.0 g, 91.1%). Odor: odorless. GC/MS(EI): m/z(%)—272(1), 257(1), 207(1), 173(1), 155(4), 91(21), 85(55), 73(100), 69(17), 65(10), 55(8), 45(5), 43(6). 1H NMR (CDCl3): δ 1.11 (s, 6H), 1.85 (t, J=7.33 Hz, 2H), 2.43 (s, 3H), 3.08 (s, 3H), 4.11 (t, J=7.33 Hz, 2H), 7.33 (d, J=8.25 Hz, 2H), 7.77 (d, J=8.25 Hz, 2H). 13C NMR (CDCl3): δ 21.7, 25.2, 38.8, 49.3, 67.4, 73.3, 128.0, 129.9, 133.2, 144.8.
- EXAMPLE 23
- This example illustrates the synthesis of 1-methoxy-3-(3-methoxy-3-methylbutoxy)-1,1-dimethylpropane.
- A suspension of sodium hydride (2.35 g, 93.1 mmol) in anhydrous THF (60 mL) was warmed to approximately 40° C. under an inert atmosphere. A portion of 3-methoxy-3-methyl-1-butanol (10.0 g, 84.6 mmol) was then added dropwise via syringe over a period of 20 minutes during which time the temperature of the mixture was slowly raised to 70° C. at 5 degree intervals. After one hour, the sulfonate product from Example 22 (23.0 g, 84.6 mmol) was added in small portions After this time, the mixture was cooled to room temperature, treated with diethyl ether (100 mL) and washed with saturated NaHCO3 (aq.) (2×100 mL) followed by brine solution (2×50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting light yellow liquid was fractionally distilled (73° C., 0.95 torr) to yield the desired colorless, pure ether (13.2 g, 71.7%). Odor: mold, mildew. GC/MS(EI): m/z(%)—218(1), 171(1), 154(2), 139(21), 115(3), 99(10), 85(39), 73(100), 69(36), 55(9), 45(18), 43(14), 41(12). 1H NMR (CDCl3); δ 1.15 (s, 12H), 1.77 (t, J=7.33 Hz, 4H), 3.17 (s, 6H), 3.47 (t, J=7.33 Hz, 4H). 13C NMR (CDCl3): δ 25.5, 39.3, 49.2, 67.2, 73.8.
- EXAMPLE 24
- This example illustrates the synthesis of 1-methoxy-1,1-dimethyl-3-(1-methylprop-2-enyloxy)propane.
- This compound was synthesized employing a procedure analogous to Example 23 using 3-methoxy-3-methylbutyl 4-methylbenzenesulfonate (37.9 g, 0.14 mol) and 3-butene-2-ol (12.4 mL, 0.14 mol). The isolated crude material was fractionally distilled (40° C., 2.45 torr) resulting in a colorless, pure liquid (14.0 g, 58.6%). Odor: strong, mint, citrus, rose. GC/MS(EI): m/z(%)—172(1), 157(1), 117(1), 95(3), 85(14), 73(100), 69(12), 55(33), 45(6), 41(8). 1H NMR (CDCl3): δ 1.15 (s, 6H), 1.22 (d, J=5.96 Hz, 3H), 1.77 (m, 2H), 3.16 (s, 3H), 3.37 (dq, J=9.16 Hz, 1H), 3.52 (dq, J=8.71 Hz, 1H), 3.79 (t, J=6.87 Hz, 1H), 5.10 (d, J=12.37 Hz, 1H), 5.16 (d, J=16.95 Hz, 1H), 5.72 (dt, J=7.33 Hz, 1H). 13C NMR (CDCl3): δ 21.4, 25.5, 39.4, 49.2, 64.5, 73.9, 115.6, 140.6.
- This example illustrates the synthesis of 2-(3-methoxy-3-methylbutox y)propanal.
- A portion of 1-methoxy-1,1-dimethyl-3-(1-methylprop-2-enyloxy)propane (5.75 g, 33.3 mmol) was dissolved in CH2Cl2 (50 mL) and cooled to −78° C. The solution was purged with ozone for approximately one hour. Once the solution became blue, O2 was bubbled through it for 30 minutes until the color disappeared and the reaction was quenched via addition of triphenylphosphine (10.5 g, 40.0 mmol). The solvent was removed via rotary evaporation and the resulting residue was suspend in a hexane:diethyl ether (1:1) mixture overnight in the refrigerator. The mixture was filtered and the precipitate was rinsed with hexane. The filtrate was placed on a rotary evaporator and the solvent was removed under reduced pressure. The isolated crude material was distilled via Kugelrohr apparatus (64° C., 0.40 torr) resulting in a colorless liquid (4.57 g, 78.8%). Odor: fresh, watery melon, clean, floral, muguet. GC/MS(EI): m/z(%)—174(1), 159(1), 145(1), 127(3), 113(36), 101(5), 85(24), 73(100), 69(75), 59(41), 57(14), 55(11), 45(26), 43(19), 41(22). 1H NMR (CDCl3): δ 1.17 (s, 6H), 1.27 (d, J=6.87 Hz, 3H), 1.84 (dt, J=6.42 Hz, 2H), 3.18 (s, 3H), 3.61 (m, 2H), 3.76 (dq, J=8.71 Hz, 1H), 9.64 (d, J=1.83 Hz, 1H). 13C NMR (CDCl3): δ 15.3, 25.4, 39.6, 49.3, 66.5, 73.7, 80.5, 204.0.
- This example illustrates the synthesis of 2-(3-methoxy-3-methylbutoxy)ethanal.
- A portion of the dimethyl acetal, 3-(2,2-dimethoxyethoxy)-1-methoxy-1,1-dimethylpropane (Example 1), (27.6 g, 0.13 mol) was dissolved in a large excess of neat formic acid (74.0 g, 1.61 mol) and stirred vigorously for 4 hours. Upon completion (monitored via GC), the solution was treated with H2O (150 mL) and extracted with ethyl acetate (3×100 mL). The organic phases were collected and dried with MgSO4 and the solvent was removed under reduced pressure. The resulting light yellow liquid was carefully distilled via Kugelrohr apparatus first to remove any leftover formic acid (25° C., 1.00 torr) followed by isolation of the desired aldehyde (40° C., 0.10 torr) resulting in a colorless, pure liquid (13.0 g, 60.2%). Odor: fresh, melon, clean, floral, muguet, green. GC/MS(EI): m/z(%)—161(1), 145(2), 113(1), 99(6), 85(29), 73(100), 69(27), 55(9), 45(23), 43(14), 41(11). 1H NMR (CDCl3); δ 1.17 (s, 6H), 1.85 (t, J=7.33 Hz, 2H), 3.17 (s, 3H), 3.61 (t, J=7.33 Hz, 2H), 4.06 (s, 2H), 9.71 (s, 1H). 13C NMR (CDCl3): δ 25.4, 39.3, 49.3, 68.4, 73.7, 76.5, 201.0.
- This example illustrates the synthesis of 3-(3-methoxy-3-methylbutoxy)propanal.
- A portion of 3-methoxy-3-methyl-1-butanol (10.0 g, 84.6 mmol) was treated with acrolein (25.1 mL, 0.34 mol) and a small aliquot of concentrated HCl (7 drops). The solution was stirred vigorously at 40° C. in subdued light for 3 days. After this time, the solution was cooled to room temperature and ethyl acetate (75 mL) was added. The solution was washed with saturated NaHCO3 (aq.) (100 mL) followed by H2O (50 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting light yellow liquid was distilled (58° C., 0.92 torr) to yield the desired colorless aldehyde (8.21 g, 55.9%). Odor: waxy, oily, muguet, light floral. GC/MS(EI): m/z(%)—174(1), 159(1), 127(5), 85(19), 73(100), 69(7), 57(9), 55(8), 45(12), 43(11). 1H NMR (CDCl3): δ 1.14 (s, 611), 1.76 (t, J=7.33 Hz, 2H), 2.64 (dt, J=4.12 Hz, 2H), 3.16 (s, 3H), 3.51 (t, J=7.33 Hz, 2H), 3.74 (t, J=5.96 Hz, 2H), 9.77 (t, J=2.29 Hz, 1H). 13C NMR (CDCl3): δ 25.4, 39.2, 44.0, 49.2, 64.6, 67.6, 73.8, 201.4.
- This example illustrates the synthesis of 3-(3-methoxy-3-methylbutoxy)butanal.
- This compound was synthesized employing a procedure analogous to Example 27 using 3-methoxy-3-methyl-1-butanol (10.0 g, 84.6 mmol) and crotonaldehyde (42.9 mL, 0.51 mol). The isolated crude material was fractionally distilled (48° C., 0.35 torr) resulting in a colorless liquid (3.24 g, 20.4%). Odor: waxy, oily, fatty. GC/MS(EI): m/z(%)—188(1), 173(1), 141(3), 101(5), 85(18), 73(100), 69(11), 55(7), 43(20), 41(15). 1H NMR (CDCl3): δ 1.14 (s, 6H), 1.23 (d, J=6.42 Hz, 3H), 1.74 (t, J=6.87 Hz, 2H), 2.45 (qd, J=22.91 Hz, 1H), 2.60 (qd, J=26.12 Hz, 1H), 3.17 (s, 3H), 3.43 (m, 1H), 3.60 (m, 1H), 3.93 (m, 1H), 9.77 (t, J=2.29 Hz, 1H). 13C NMR (CDCl3): 5 19.9, 25.4, 39.6, 49.2, 50.6, 64.9, 71.0, 73.8, 201.7.
- This example illustrates the synthesis of bis(3-methoxy-3-methylbutyl ethane)-1,2-dioate.
- A portion of 3-methoxy-3-methyl-1-butanol (5.00 g, 42.3 mmol) was dissolved in CH2Cl2 (25 mL) and cooled to 0° C. An aliquot of oxalyl chloride (2.21 mL, 25.4 mmol) was slowly added dropwise via syringe to the vigorously stirring solution. After one hour, the solution was warmed to room temperature and washed with saturated NaHCO3 (aq.) (2×50 mL) followed by brine solution (30 mL) and H2O (30 mL). The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure. The resulting clear liquid was distilled via kugelrohr apparatus (160° C., 0.15 torr) to yield the desired colorless, viscous oxalate (4.50 g, 73.3%). Odor: weak, chemical. GC/MS(EI): m/z(%)—290(1), 275(1), 257(1), 227(1), 191(1), 159(1), 101(2), 85(37), 73(100), 69(21), 55(6), 43(7), 41(9). 1H NMR (CDCl3): δ 1.19 (s, 12H), 1.91 (t, J=7.33 Hz, 4H), 3.18 (s, 6H), 4.37 (t, J=7.79 Hz, 4H). 13C NMR (CDCl3): δ 25.3, 37.9, 49.4, 63.8, 73.5, 158.0.
- The below examples demonstrate the use of the fragrance formulation of Table 2 in various consumer products. These examples are illustrative only and are not intended to limit the scope of the invention in any way. Unless otherwise noted, all percentages set forth in the examples are by weight (wt). Q.S. means a sufficient quantity.
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Ingredient Supplier Percentage Purpose Neodol ® 91-8 Shell 6.00 Surfactant Dowanol ® DPnB Dow 6.00 Solvent Kathon ® CG Rohm & Haas 0.10 Preservative Fragrance of Table 2 Takasago Int'I 1.25 Fragrance D.I. Water — 86.65 Solvent Dye Pylam Q.S. Color - This formulation is for dilution in a bucket at approximately one part concentrate to ten parts tap water.
- Procedure:
- 1. The Neodol® 91-8, Dowanol® DPnB, and fragrance were mixed in a suitable vessel until completely uniform and clear.
- 2. Water was added slowly with constant agitation to the solution in # 1. Kathon® was added with mixing and stirring continued for 1 minute. The final formulation was clear.
- 3. Dye was added match standard.
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Ingredient Supplier Percentage Purpose Neodol ® 91-8 Shell 1.50 Surfactant Dowanol ® DPnB Dow 4.00 Solvent Fragrance of Table 2 Takasago Int'l 0.40 Fragrance Kathon ® CG Rohm & Haas 0.07 Preservative D.I. Water — 94.03 Solvent - Procedure:
- 1. Neodol® 91-8, Dowanol® DPnB, and fragrance were mixed in a suitable vessel until completely uniform and clear.
- 2. Water was added slowly to the solution in # 1 with constant agitation. The final formulation was clear. Kathon® CG was added with stirring.
- The formulation was then filled into suitable plastic containers (PET preferred), with the proper trigger or pump closure.
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Ingredient INCI or Nomenclature Percentage Water Water Q.S. Glucopon ® 625UP (1) Alkyl Polyglucosides 12.50 Standapol ® ES-40 (1) Alkyl Ether Sulfates 25.60 Versene ® 100 (38%) (2) Tetrasodium EDTA 00.40 MEA (2) Monoethanolamine 01.00 Sulfuric Acid (25% Aq.) Acid 03.00 Sodium Chloride (25%) Salt 01.20 Takasago Fragrance(3) Fragrance of Table 2 00.75 100.00 - Suppliers
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- (1) Cognis Corporation
- (2) The DOW Chemical Co.
- (3) Takasago International Corporation
- Procedure:
- 1. Glucopon® was added to water heated to 65° C. and mix at medium speed until clear.
- 2. Standapol® was added and mixing continued until the mixture was clear and homogenous.
- 3. The mixture was removed from the heat and remaining ingredients were added in order, with mixing at slow to medium speed each addition.
- 4. pH was adjusted with sulfuric acid solution to pH of 8.0 to 8.5.
- 5. Viscosity was adjusted with sodium chloride.
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Ingredient Supplier Percentage Purpose Deionized Water — 83.50 Solvent Rewoquat ® WE-16E Degussa 15.00 Softener Sodium Chloride — 0.50 Thickening Fragrance of Table 2 Takasago 1.00 Fragrance - Procedure:
- 1. Rewoquae, fragrance and water were mixed in a suitable vessel until the mixture was translucent to opaque.
- 2. Sodium chloride was added with mixing and mixed for 5 minutes.
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INCI or PER- SEQ. INGREDIENTS Nomenclature CENT Part 1 1 Deionized water Water QS 1 Versene ® 220 (1) Tetrasodium EDTA 00.05 2 Carbopol ® 934 (2) Carbomer 934 00.30 3 Glycerin Glycerin 01.00 3 Propylene Glycol Propylene Glycol 01.00 Part 2 4 Myrj ® 52S (sprayed) (4) PEG-40 Stearate 01.80 4 Liponate ® GC (5) Caprylic/Capric 13.00 Triglyceride 4 Liponate ® IPM (5) Isopropyl Myristate 08.50 4 Span ® 65S (sprayed) (4) Sorbitan Tristearate 02.00 4 Pharmalan ®, USP (6) Lanolin 00.50 4 White Protopet ® IS (7) Petrolatum 00.30 4 Propylparaben (8) Propylparaben 00.10 Part 3 1 Deionized Water Water 10.00 1 TEA Triethanolamine 00.30 Part 4 1 Deionized Water Water 01.00 1 Unicide ® U-13 (5) Imidazolidinyl Urea 00.25 Part 5 1 Germaben ® II (3) Propylene Glycol 00.70 (and) Diazo-lidinyl Urea (and) Methylparaben (and) Propylparaben Part 6 1 Takasago Fragrance Fragrance of Table 2 QS Oil - Suppliers:
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- (1) Dow Chemical
- (2) Noveon
- (3) Sutton/ISP
- (4) Uniqema
- (5) Lipo Chemicals, Inc.
- (6) Croda
- (7) Crompton/Witco
- (8) Tri-K
- Procedure:
- Part 1
- 1. Seq. #1 was heated to 75° C. and mixed together at medium speed using an overhead mixer until clear.
- 2. Seq. #2 was added slowly to Seq. #1 with mixing. Mixing was continued until Seq. #2 is completely was hydrated. Hydration was checked by dipping a metal spatula into and out of the solution to observe if there are any gum particles that have not hydrated.
- 3. Seq. #3 was added in order to the batch without heating.
- Part 2
- 4. Seq. #4 was premixed and heated until completely melted at approximately 65° C.
- 5. Part 1 was placed on a Homomixer at low to medium speed, and Part 2 added to Part 1 and mixed for 1 minute.
- 6. The batch was placed back onto the overhead mixer at medium speed and premixed Part 3 was added without heating to the batch for approximately 2 minutes.
- 7. Mix was continued at low speed and the mixture was cooled to 35° C.
- 8. Part 4 was premixed at 35° C. and added to the batch, while cooling down at low speed to 30° C.
- 9. Part 5 was added at 30° C. with mixing at low speed.
- Liquid fragrance was added slowly while mixing.
- 10. Lotion was placed in jars and allowed to at room temperature for 24 hours.
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PER- SEQ. INGREDIENTS INCI CENT 1 Deionized water Water 66.50 1 Methyl Paraben (1) Methyl Paraben 00.25 2 Liponic ® EG-1 (2) Glycereth-26 01.00 2 Glycerin (3) Glycerin 01.00 2 Lipopeg ® 6000DS (2) PEG-150 Distearate 00.50 3 Monamid ® 716 (4) Lauramide DEA 03.50 3 Standapol ® ES-2 (3) Sodium Laureth 25.00 Sulfate 3 Velvetex ® BK-35 (3) Cocamidopropyl 15.00 Betaine 4 Deionized Water Water 01.00 4 Unicide ® U-13 (2) Imidazolidinyl Urea 00.25 5 Fragrance as defined 00.50 in Table 2 above 6 Citric acid (25% QS Solution) - Suppliers:
-
- (1) TRI-K
- (2) Lipo Chemicals, Inc.
- (3) Cognis/Henkel
- (4) Uniqema
- Procedure:
- 1. The methyl paraben was added slowly to the DI water heated to 65° C. with mixing at medium/high speed using an overhead mixer until completely into solution and clear. (Seq.#1)
- 2. Seq. #2 was added to Sequence #1 at low speed until completely clear.
- 3. Seq. #3 was added to batch without heating, in order of addition, and cooled down to 35° C. with low agitation.
- 4. Seq. #4 was premixed until clear, and added to batch.
- 5. Seq. #5 was added to the batch with low agitation and cooled down to 25° C.
- 6. Seq. #6 was added to adjust batch to desired pH. The product was placed in jars, pouring very slowly onto the sides of the jars to eliminate any additional aeration. pH=adjust to: 6.64+/−0.2; viscosity=18,640 cps (+/−10%) with Brookfield LV Sp. #4 @ 30 rpm
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PER- SEQ. INGREDIENTS INCI CENT 1 Deionized water Water Q.S. 2 Versene ® 220 (1) Teterasodium EDTA 00.05 3 Methocel ® E4M (2) Hydroxypropyl 00.30 (*prep) Methylcellulose 4 Standapol ® T (3) TEA Lauryl Sulfate 18.00 4 Standapol ®A (3) Ammonium Lauryl 08.00 Sulfate 4 Monamid ® 150-LMWC (4) Lauramide DEA 04.00 4 Palmitic Acid (5) Palmitic Acid 00.30 5 Glydant ®2000 (6) DMDM Hydantoin 00.15 5 Sodium Chloride, Granular (7) Sodium hloride 00.34 5 Citric Acid (8) Citric Acid 00.43 6 Takasago perfume oil (9) Fragrance of Table 2 Q.S. - Suppliers:
-
- (1) AND
- (2) DOW CHEMICAL CO.
- (3) COGNIS/HENKEL
- (4) UNIQEMA
- (5) Takasago International Corp (TIC), USA
- (6) LONZA
- (7) FISHER SCIENTIFIC
- (8) TIC, USA
- (9) TIC, USA
- Procedure:1. ⅓ of Seq.#1 and Seq.#2 was heated to 85° C. Methocel powder was by mixing thoroughly using ⅕ to ⅓ of the required total amount of water as hot water (80-90° C.). Mixing was continued with overhead mixer at medium speed until all of the particles were wetted down, and a consistent dispersion was obtained. The remainder of the water containing Seq. #2 was added as cold water while mixing. The solution was cooled down to less than 30° C. Mixing was continued after the proper temperature was achieved for approximately 20 minutes. After preparation was completed, the Methocel® solution was reheated to 60° C.
- 2. Seq.#4 at 60 to 65° C. was added slowly to the batch in order of addition with mixing continued at low speed.
- 3. Seq.#5 was added slowly to batch and mixing continued at low speed until room temperature was reached. Citric acid was added to a pH of 5.5-6.0 and sodium chloride was added to achieve the desired viscosity. Fragrance Seq.#6 was weighed and added to the formulation while mixing.
- 4. Viscosity:=2020cps. (±10%) taken at 20° C., (Brookfield LV Sp.#3 @ 12rpm), pH=5.5 (+1-0.5)
- The below examples demonstrate the use of the materials claimed in flavor formulations in various consumer products. These examples are illustrative only and are not intended to limit the scope of the invention in any way. In these examples, all % are % (wt), unless otherwise noted and Q.S. means a sufficient quantity.
- Toothpaste with flavor and the claimed compound(s) was prepared according to the formulation below.
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Components WT % 2-(3-methoxy-3-methylbutoxy)ethanal [Compound 23; 0.50 TABLE 1] Calcium hydrogen phosphate (dihydrate) 50.00 Glycerin 25.00 Sodium lauryl sulfate 1.40 Carboxyrnethyl cellulose sodium salt 1.50 Saccharin sodium salt 0.20 Sodium benzoate 0.10 Strawberry type flavor 0.70 Purified water balance qs Total 100.00 - Peach flavor utilizing the claimed compound(s) was prepared according to the formulation below utilizing the claimed compounds.
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Components WT % 2-(3-methoxy-3-methylbutoxy)ethanal[Compound 23; 0.20 TABLE 1] Benzaldehyde 0.20 methyl cyclohexyl)ethanone 0.30 Ethyl acetate 2.0 Ethyl butyrate 0.8 Ethyl maltol 0.3 γ-Undecalactone 0.5 Linalool 0.5 Peach flavor base 5.0 Ethyl alcohol balance q.s. Total 100.00 - Green tea flavor was prepared according to the formulation below utilizing the claimed compound(s)
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Components WT % Benzyl alcohol 1.0 2-(3-methoxy-3-methylbutoxy)ethanal [Compound 23; 0.3 TABLE 1] Cis-3-hexenol 0.3 Dimethyl sulfide 0.1 Geraniol 0.6 l-menthol 2.5 Linalool 0.9 Nerolidol 0.2 Terpineol 0.2 Green tea base 5.0 Ethyl alcohol balance qs Total 100.00 - Black tea flavor was prepared according to the formula below utilizing the claimed compounds.
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Components WT % α-Ionone 0.2 α-Ionone 0.2 Benzaldehyde 1.0 2-(3-methoxy-3-methylbutoxy)ethanal [Compound 23; 1.0 TABLE 1] Cis-3-hexenol 6.0 δ-Decalactone 2.5 δ-Dodecalactone 2.0 Damascenone 0.1 Linalool 3.5 Geraniol 6.0 Citral 1.0 Linalool oxide 1.6 Methyl salicylate 2.0 Phenylethyl alcohol 6.0 Hexyl aldehyde 1.0 Propylene glycol balance qs Total 100.00
Claims (9)
1. A fragrance composition comprising:
a compound represented by the formula (I):
wherein R1 is an unsubstituted or substituted C2-6 straight chain alkyl, an unsubstituted or substituted C3-4 or C6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, nitrile, an unsubstituted or substituted phenyl, an unsubstituted or substituted benzyl, an unsubstituted or substituted naphthyl, an unsubstituted or substituted aryl, an unsubstituted or substituted piperazino, an unsubstituted or substituted morpholinyl, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido, an unsubstituted or substituted C1-6 dialkylcarboxamido, an unsubstituted or substituted nitrophenyl, C1-6 trialkylsilyl, an unsubstituted or substituted C1-12 straight chain alkyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkyl sulfonate, an unsubstituted or substituted C1-12 straight chain alkenyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkenyl sulfonate, an unsubstituted or substituted C1-12 straight chain aryl sulfonate, or an unsaturated sulfonate; or
R2 is an unsubstituted or substituted C4-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, an unsubstituted or substituted C1-6 alkoxy, nitrile, halo, an unsubstituted or substituted phenyl, an unsubstituted or substituted benzyl, an unsubstituted or substituted naphthyl, an unsubstituted or substituted aryl, an unsubstituted or substituted piperazino, an unsubstituted or substituted morpholinyl, amino, an unsubstituted or substituted C1-6 alkylamino, an unsubstituted or substituted C6-12 arylamino, an unsubstituted or substituted C1-6 dialkylamino, an unsubstituted or substituted C6-12 diarylamino, carboxy-C1-6 alkylamino, carboxy-C1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, thio, an unsubstituted or substituted C1-6 alkylthio, an unsubstituted or substituted C1-6 alkyloxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido, an unsubstituted or substituted C1-6 dialkylcarboxamido, an unsubstituted or substituted phenoxy, an unsubstituted or substituted benzyloxy, phenyl carbonyl, benzyl carbonyl, an unsubstituted or substituted nitrophenyl, C1-6 trialkylsilyl or nitro, an unsubstituted or substituted C1-12 straight chain alkyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkyl sulfonate, an unsubstituted or substituted C1-12 straight chain alkenyl sulfonate, an unsubstituted or substituted C1-12 branched chain alkenyl sulfonate, an unsubstituted or substituted C1-12 straight chain aryl sulfonate, or an unsaturated sulfonate; or
R1 or R2 is an unsubstituted or substituted C3-6 cycloalkyl; and
a fragrance carrier or fragrance base.
2. The composition of claim 1 ,
wherein R1 is an unsubstituted or substituted C2-6 straight chain alkyl, an unsubstituted or substituted C3-4 or C6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, nitrile, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, an unsubstituted or substituted C1-6 alkylcarboxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido, or an unsubstituted or substituted C1-6 dialkylcarboxamido; or
R2 is an unsubstituted or substituted C4-6 straight chain alkyl, an unsubstituted or substituted C3-6 branched chain alkyl, an unsubstituted or substituted C3-6 straight chain alkenyl, an unsubstituted or substituted C3-6 branched chain alkenyl, an unsubstituted or substituted C1-6 alkoxy, nitrile, halo, amino, an unsubstituted or substituted C1-6 alkylamino, an unsubstituted or substituted C1-6 dialkylamino, carboxy-C1-6 alkylamino, carboxy-C1-6 dialkylamino, an unsubstituted or substituted acetoxy, carboxy, an unsubstituted or substituted carboxyethyl, an unsubstituted or substituted C1-6 alkylcarbonyl, an unsubstituted or substituted C1-6 alkylcarboxy, an unsubstituted or substituted C1-6 alkylthio, an unsubstituted or substituted C1-6 alkyloxy, carboxamido, an unsubstituted or substituted C1-6 alkylcarboxamido, or an unsubstituted or substituted C1-6 dialkylcarboxamido; or
R1 or R2 is an unsubstituted or substituted C3-6 cycloalkyl.
3. The composition of claim 1 ,
wherein R1 is a C2-6 straight chain alkyl, C3-6 branched chain alkyl, an unsubstituted or substituted C1-6 alkenyl, an unsubstituted or substituted C1-6 acyl, or aryl; or
R2 is a C4-6 straight chain alkyl, C3-6 branched chain alkyl, an unsubstituted or substituted C1-6 alkenyl, an unsubstituted or substituted C1-6 acyl, or aryl.
4. The composition of claim 1 , wherein the compound is present in an amount from about 0.001% to about 30% by weight.
5. The composition of claim 1 , wherein the fragrance carrier is an emulsifying agent, an encapsulating material, natural or modified starches, polymers, gums, pectins, gelatinous or porous cellular materials, or waxes.
6. A method of improving, enhancing, or modifying the olfactory properties of a product comprising adding an olfactory effective amount of a composition of claim 1 to the product.
7. The method of claim 6 , wherein the olfactory effective amount is from about 0.001% to about 30% by weight.
8. A consumer product comprising the composition of claim 1 .
9. The consumer product of claim 8 , where the consumer product is an air care product, candle, perfume, cologne, personal care product, cosmetic, detergent, fabric care product, or household cleaning agent.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/701,171 US20170367388A1 (en) | 2008-06-30 | 2017-09-11 | Substituted butanol derivatives and their use as fragrance and flavor materials |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/US2008/068781 WO2010002386A1 (en) | 2008-06-30 | 2008-06-30 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US12/981,758 US9060535B2 (en) | 2008-06-30 | 2010-12-30 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US14/714,010 US9756872B2 (en) | 2008-06-30 | 2015-05-15 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US15/701,171 US20170367388A1 (en) | 2008-06-30 | 2017-09-11 | Substituted butanol derivatives and their use as fragrance and flavor materials |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US14/714,010 Continuation US9756872B2 (en) | 2008-06-30 | 2015-05-15 | Substituted butanol derivatives and their use as fragrance and flavor materials |
Publications (1)
Publication Number | Publication Date |
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US20170367388A1 true US20170367388A1 (en) | 2017-12-28 |
Family
ID=44531512
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US12/981,758 Expired - Fee Related US9060535B2 (en) | 2008-06-30 | 2010-12-30 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US14/714,010 Expired - Fee Related US9756872B2 (en) | 2008-06-30 | 2015-05-15 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US15/701,171 Abandoned US20170367388A1 (en) | 2008-06-30 | 2017-09-11 | Substituted butanol derivatives and their use as fragrance and flavor materials |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
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US12/981,758 Expired - Fee Related US9060535B2 (en) | 2008-06-30 | 2010-12-30 | Substituted butanol derivatives and their use as fragrance and flavor materials |
US14/714,010 Expired - Fee Related US9756872B2 (en) | 2008-06-30 | 2015-05-15 | Substituted butanol derivatives and their use as fragrance and flavor materials |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9060535B2 (en) | 2008-06-30 | 2015-06-23 | Takasago International Corporation | Substituted butanol derivatives and their use as fragrance and flavor materials |
DE102015217890A1 (en) * | 2015-09-17 | 2017-03-23 | Henkel Ag & Co. Kgaa | Transparent liquids, in particular textile treatment compositions containing fragrance and microcapsules with odor modulation compound |
TW201936061A (en) * | 2017-09-11 | 2019-09-16 | 日商三得利控股股份有限公司 | Colorless transparent beverage containing linalool |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6041648B2 (en) | 1977-06-27 | 1985-09-18 | 株式会社クラレ | Method for purifying 3-methyl-3-methoxybutanol |
US4124644A (en) * | 1977-06-30 | 1978-11-07 | International Flavors & Fragrances Inc. | Process for preparing substituted oxyacetaldehydes and acetals thereof |
JPS59166600A (en) | 1983-03-10 | 1984-09-19 | 株式会社クラレ | Detergent |
US4990697A (en) | 1988-10-26 | 1991-02-05 | Kuraray Co., Ltd. | Process for producing homoallyl alcohols |
US5081104A (en) * | 1990-06-20 | 1992-01-14 | Kurary Co., Ltd. | Fragrance dispensing composition with controlled evaporation rate and air fragrance dispenser for dispensing same |
EP0887335A1 (en) | 1997-06-23 | 1998-12-30 | Givaudan-Roure (International) S.A. | Precursor compounds |
CA2428787A1 (en) | 2000-11-15 | 2002-05-23 | Banyu Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
JP4518957B2 (en) | 2002-11-29 | 2010-08-04 | ジボダン エス エー | Aliphatic compounds as perfumes with pepper properties |
EP1711231A1 (en) * | 2003-10-31 | 2006-10-18 | Firmenich Sa | Fragrance delivery system for surface cleaners and conditioners |
JP3780420B2 (en) | 2004-03-31 | 2006-05-31 | 小林製薬株式会社 | Aroma liquid composition for humidifier |
US7932293B2 (en) * | 2007-06-20 | 2011-04-26 | International Flavors & Fragrances Inc. | Aldehyde compositions and methods for providing fragrance containing the same |
US9060535B2 (en) | 2008-06-30 | 2015-06-23 | Takasago International Corporation | Substituted butanol derivatives and their use as fragrance and flavor materials |
-
2010
- 2010-12-30 US US12/981,758 patent/US9060535B2/en not_active Expired - Fee Related
-
2015
- 2015-05-15 US US14/714,010 patent/US9756872B2/en not_active Expired - Fee Related
-
2017
- 2017-09-11 US US15/701,171 patent/US20170367388A1/en not_active Abandoned
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US9756872B2 (en) | 2017-09-12 |
US20110217245A1 (en) | 2011-09-08 |
US20150245641A1 (en) | 2015-09-03 |
US9060535B2 (en) | 2015-06-23 |
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