JP7489983B2 - ドデカ-4,8,11-トリエン-1-オール及びその香料としての使用 - Google Patents
ドデカ-4,8,11-トリエン-1-オール及びその香料としての使用 Download PDFInfo
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- JP7489983B2 JP7489983B2 JP2021532832A JP2021532832A JP7489983B2 JP 7489983 B2 JP7489983 B2 JP 7489983B2 JP 2021532832 A JP2021532832 A JP 2021532832A JP 2021532832 A JP2021532832 A JP 2021532832A JP 7489983 B2 JP7489983 B2 JP 7489983B2
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- dodeca
- trien
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- oil
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- SIYBPTIIYPOCTE-UHFFFAOYSA-N dodeca-4,8,11-trienal Chemical compound C=CCC=CCCC=CCCC=O SIYBPTIIYPOCTE-UHFFFAOYSA-N 0.000 claims description 18
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- SGIIQKAMTIJXBU-UHFFFAOYSA-N pentan-2-ol Chemical compound CC[CH]C(C)O SGIIQKAMTIJXBU-UHFFFAOYSA-N 0.000 description 1
- 239000001024 permanent hair color Substances 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
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- 239000010665 pine oil Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
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- 239000001367 polianthes tuberosa l. flower oil Substances 0.000 description 1
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- 150000003138 primary alcohols Chemical class 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JSASXSHMJYRPCM-UHFFFAOYSA-N r-3-(methylthio)-1-hexanol Chemical compound CCCC(SC)CCO JSASXSHMJYRPCM-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
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- 239000010673 savory oil Substances 0.000 description 1
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- 235000021286 stilbenes Nutrition 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 239000000516 sunscreening agent Substances 0.000 description 1
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- 230000035900 sweating Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- HBPNTDBLHQHPLH-UHFFFAOYSA-N tetradecyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C HBPNTDBLHQHPLH-UHFFFAOYSA-N 0.000 description 1
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- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
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- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000001789 thuja occidentalis l. leaf oil Substances 0.000 description 1
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- 229960000790 thymol Drugs 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 229940088660 tolu balsam Drugs 0.000 description 1
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- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- IMRYETFJNLKUHK-UHFFFAOYSA-N traseolide Chemical compound CC1=C(C(C)=O)C=C2C(C(C)C)C(C)C(C)(C)C2=C1 IMRYETFJNLKUHK-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- WKSPQBFDRTUGEF-UHFFFAOYSA-N tridec-2-enenitrile Chemical compound CCCCCCCCCCC=CC#N WKSPQBFDRTUGEF-UHFFFAOYSA-N 0.000 description 1
- DBWSGRFEGVADLQ-UHFFFAOYSA-N trideca-3,12-dienenitrile Chemical compound C=CCCCCCCCC=CCC#N DBWSGRFEGVADLQ-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
- FAGMGMRSURYROS-UHFFFAOYSA-M trihexadecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC FAGMGMRSURYROS-UHFFFAOYSA-M 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- HETFMJQWNWIBPN-UHFFFAOYSA-N undec-2-enenitrile Chemical compound CCCCCCCCC=CC#N HETFMJQWNWIBPN-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- WCTNXGFHEZQHDR-UHFFFAOYSA-N valencene Natural products C1CC(C)(C)C2(C)CC(C(=C)C)CCC2=C1 WCTNXGFHEZQHDR-UHFFFAOYSA-N 0.000 description 1
- 239000001238 valeriana officinalis l. root oil Substances 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 239000001846 viola odorata l. leaf absolute Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000001529 viverra civetta schreber and viverra zibeth a schreber absolute Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 0.000 description 1
- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- HZRFVTRTTXBHSE-AYJHFOLZSA-N α-cedrene epoxide Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C1(C)OC1C2 HZRFVTRTTXBHSE-AYJHFOLZSA-N 0.000 description 1
- PFSTYGCNVAVZBK-KVDYQJCMSA-N α-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/C\C=C(\C)C=C PFSTYGCNVAVZBK-KVDYQJCMSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
- NOPLRNXKHZRXHT-PVMFERMNSA-N β-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/CCC(=C)C=C NOPLRNXKHZRXHT-PVMFERMNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(i)少なくとも1種の追加の香料、又は
(ii)少なくとも1種の非香料キャリア、又は
(iii)少なくとも1種の抗酸化剤、又は
(iv)少なくとも1種のデオドラント活性剤、又は
(v)成分(i)から(iv)のうちの少なくとも2種の混合物)
を含む香料組成物に関する。
ゲラニルアセテート(3,7-ジメチル-2,6オクタジエン-1イルアセテート)、アルファ-ヘキシルシンナムアルデヒド、2-フェノキシエチルイソブチレート(Phenirat1)、ジヒドロミルセノール(2,6-ジメチル-7-オクテン-2-オール)、メチルジヒドロジャスモネート(好ましくは、シス型異性体の含量が60wt%超である)(Hedione9、Hedione HC9)、4,6,6,7,8,8-ヘキサメチル-1,3,4,6,7,8-ヘキサヒドロシクロペンタ[g]ベンゾピラン(Galaxolid3)、テトラヒドロリナロオール(3,7-ジメチルオクタン-3-オール)、エチルリナロオール、ベンジルサリチレート、2-メチル-3-(4-tert-ブチルフェニル)プロパナール(Lysmeral2)、シンナミルアルコール、4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-インデニルアセテート及び/又は4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-6-インデニルアセテート(Herbaflorat1)、シトロネロール、シトロネリルアセテート、テトラヒドロゲラニオール、バニリン、リナリルアセテート、スチロリルアセテート(1-フェニルエチルアセテート)、オクタヒドロ-2,3,8,8-テトラメチル-2-アセトナフトン及び/又は2-アセチル-1,2,3,4,6,7,8-オクタヒドロ-2,3,8,8-テトラメチルナフタレン(Iso E Super3)、ヘキシルサリチレート、4-tert-ブチルシクロヘキシルアセテート(Oryclone1)、2-tert-ブチルシクロヘキシルアセテート(Agrumex HC1)、アルファ-イオノン(4-(2,2,6-トリメチル-2-シクロヘキセン-1-イル)-3-ブテン-2-オン)、n-アルファ-メチルイオノン、アルファ-イソメチルイオノン、クマリン、テルピニルアセテート、2-フェニルエチルアルコール、4-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセンカルボキサルデヒド(Lyral3)、アルファ-アミルシンナムアルデヒド、エチレンブラシレート、(E)-及び/又は(Z)-3-メチルシクロペンタデカ-5-エノン(Muscenon9)、15-ペンタデカ-11-エノリド及び/又は15-ペンタデカ-12-エノリド(Globalide1)、15-シクロペンタデカノリド(Macrolide1)、1-(5,6,7,8-テトラヒドロ-3,5,5,6,8,8-ヘキサメチル-2-ナフタレニル)エタノン(Tonalid10)、2-イソブチル-4-メチルテトラヒドロ-2H-ピラン-4-オール(Florol9)、2-エチル-4-(2,2,3-トリメチル-3-シクロペンテン-1-イル)-2-ブテン-1-オール(Sandolen1)、cis-3-ヘキセニルアセテート、trans-3-ヘキセニルアセテート、trans-2/cis-6-ノナジエノール、2,4-ジメチル-3-シクロヘキセンカルボキサルデヒド(Vertocitral1)、2,4,4,7-テトラメチルオクタ-6-エン-3-オン(Claritone1)、2,6-ジメチル-5-ヘプテン-1-アール(Melonal2)、ボルネオール、3-(3-イソプロピルフェニル)ブタナール(Florhydral2)、2-メチル-3-(3,4-メチレンジオキシフェニル)プロパナール(Helional3)、3-(4-エチルフェニル)-2,2-ジメチルプロパナール(Florazon1)、7-メチル-2H-1,5-ベンゾジオキセピン-3(4H)-オン(Calone)、3,3,5-トリメチルシクロヘキシルアセテート(好ましくは、シス型異性体の含量が、70wt%以上である)及び2,5,5-トリメチル-1,2,3,4,4a,5,6,7-オクタヒドロナフタレン-2-オール(Ambrinol S1)からなる群から選択される1種、好ましくは2種、3種、4種、5種、6種、7種、8種又はそれ以上の香料であってよい。したがって、本発明の文脈において、上記香料(複数可)は、好ましくは本明細書で定義されたような本発明の化合物と組み合わせられる。
1ドイツ、Symrise GmbHの商標、
2BASF SEの商標、
3アメリカ、International Flavors & Fragrances Inc.の商標、
9スイス、Firmenich S.A.の商標、
10オランダ、PFW Aroma Chemicals B.V.の商標。
を挙げることができる。
- アミノ酸(例えばグリシン、アラニン、アルギニン、セリン、トレオニン、ヒスチジン、チロシン、トリプトファン)及びその誘導体、
- イミダゾール(例えばウロカニン酸)及びその誘導体、
- ペプチド、例えばD,L-カルノシン、D-カルノシン、L-カルノシン(=β-アラニル-L-ヒスチジン)及びその誘導体、
- カロテノイド、カロテン(例えばアルファ-カロテン、ベータカロテン、リコペン、ルテイン)又はその誘導体、
- クロロゲン酸及びその誘導体、
- リポ酸及びその誘導体(例えばジヒドロリポ酸)、
- アウロチオグルコース、プロピルチオウラシル及び他のチオール(例えばチオレドキシン、グルタチオン、システイン、シスチン、シスタミン及びグリコシル、N-アセチル、メチル、エチル、プロピル、アミル、ブチル及びラウリル、パルミトイル、オレイル、ガンマ-リノレイル、コレステリル及びそのグリセリルエステル)並びにその塩、
- ジラウリルチオジプロピオネート、ジステアリルチオジプロピオネート、チオジプロピオン酸及びその誘導体(エステル、エーテル、ペプチド、脂質、ヌクレオチド、ヌクレオシド及び塩)、
- スルホキシミン化合物(例えばブチオニンスルホキシミン、ホモシステインスルホキシミン、ブチオニンスルホン、ペンタ-、ヘキサ-、ヘプタチオニンスルホキシミン)、
- (金属)キレート剤(例えばアルファ-ヒドロキシ脂肪酸、パルミチン酸、フィチン酸、ラクトフェリン)、
- アルファ-ヒドロキシ酸(例えばクエン酸、乳酸、リンゴ酸)、
- フミン酸、胆汁酸、胆汁抽出物、ビリルビン、ビリベルジン、ボルジン(=植物ペウムス・ボルドゥス(Peumus boldus)からのアルカロイド、ボルドー抽出物、
- EDTA、EGTA及びその誘導体、
- 不飽和脂肪酸及びその誘導体(例えばガンマ-リノレン酸、リノール酸、オレイン酸)、
- 葉酸及びその誘導体、
- ユビキノン及びユビキノール並びにその誘導体、
- ビタミンC及び誘導体(例えばアスコルビルパルミテート、Mgアスコルビルホスフェート、アスコルビルアセテート)、
- トコフェロール及び誘導体(例えばビタミンEアセテート)、
- ビタミンA及び誘導体(例えばビタミンAパルミテート)、
- ガムベンゾインのコニフェリルベンゾエート、ルチン酸(rutic acid)及びその誘導体、アルファ-グリコシルルチン、フェルラ酸、フルフリリデングルシトール、
- ブチルヒドロキシトルエン(BHT)、ブチルヒドロキシアニソール(BHA)、
- ノルジヒドログアイアシン酸(nordihydroguaiacic acid)、ノルジヒドログアイアレチン酸、トリヒドロキシブチロフェノン、尿酸及びその誘導体、マンノース及びその誘導体、
- スーパーオキシドディスムターゼ、
- 亜鉛及びその誘導体(例えばZnO、ZnSO4)、
- セレン及びその誘導体(例えばセレノメチオニン)並びに
- スチルベン及びその誘導体(例えばスチルベンオキシド、trans-スチルベンオキシド)からなる群から選択され得る。
(i)ドデカ-4,8,11-トリエン-1-オールとは異なる少なくとも1種の追加の香料、又は
(ii)少なくとも1種の非香料キャリア、又は
(iii)少なくとも1種の抗酸化剤、又は
(iv)少なくとも1種のデオドラント活性剤、又は
(v)成分(i)から(iv)のうちの少なくとも2種の混合物)を混合することにより実行できる。
1. 調製例
ドデカ-4,8,11-トリエナールをWO2010/086313に記載されているように、調製し、精製した。100gのドデカ-4,8,11-トリエナールを、400mlのエタノールに溶解した。次いで、12.2gのNaBH4を、室温にて溶液に段階的様式で添加した。混合物を室温にて2.5時間撹拌した後で、反応を、300mlの水の添加により停止した。エタノールを蒸発により除去し、反応生成物を、300mlの酢酸エチルを使用して水相から抽出した。このように得られた有機相をブライン溶液で洗浄し、次いで硫酸ナトリウムで乾燥させた。有機溶媒の蒸発後、約76%のドデカ-4,8,11-トリエン-1-オールを含有する94.6gの粗生成物を得た。生成物を、蒸留により精製し、ドデカ-4,8,11-トリエン-1-オールを88%の純度で得た。精製した生成物を、NMRにより分析し、結果から、(4Z,8E)-ドデカ-4,8,11-トリエン-1-オール及び(4E,8Z)-ドデカ-4,8,11-トリエン-1-オールの存在が3:2の比で指し示された。
(4Z,8E)-ドデカ-4,8,11-トリエン-1-オール
13C NMR (125 MHz, CDCl3): d = 23.61 (C10), 27.17 (C6), 32.49 (C7), 32.51 (C11), 36.72 (C3), 62.22 (C12), 114.85 (C1), 128.04 (C4), 129.30 (C5), 129.76 (C9), 130.95(C8), 137.26 (C2).
(4E,8Z)-ドデカ-4,8,11-トリエン-1-オール
13C NMR (125 MHz, CDCl3): d = 28.86 (C10), 27.18 (C6), 31.55 (C7), 32.32 (C11), 36.72 (C3), 62.14 (C12), 114.57 (C1), 126.92 (C4), 129.97 (C5), 130.21 (C9), 130.32(C8), 137.94 (C2).
ドデカ-4,8,11-トリエン-1-オールの匂いの質及び強さを試験するために、香りストリップ試験を行った。
実施例1の化合物を、表2及び3による芳香組成物に配合した。
Claims (16)
- ドデカ-4,8,11-トリエン-1-オールである化合物。
- (4Z,8E)-ドデカ-4,8,11-トリエン-1-オール、(4E,8Z)-ドデカ-4,8,11-トリエン-1-オール、(4E,8E)-ドデカ-4,8,11-トリエン-1-オール、(4Z,8Z)-ドデカ-4,8,11-トリエン-1-オール及びそれらの2種以上の混合物から選択される、請求項1に記載の化合物。
- (4Z,8E)-ドデカ-4,8,11-トリエン-1-オールである、請求項2に記載の化合物。
- (4E,8Z)-ドデカ-4,8,11-トリエン-1-オールである、請求項2に記載の化合物。
- (4Z,8E)-ドデカ-4,8,11-トリエン-1-オール及び(4E,8Z)-ドデカ-4,8,11-トリエン-1-オールを含む立体異性体の混合物である、請求項2に記載の化合物。
- (4Z,8E)-ドデカ-4,8,11-トリエン-1-オール及び(4E,8Z)-ドデカ-4,8,11-トリエン-1-オールが、10:1~1:10のモル比で存在する、請求項5に記載の化合物。
- 混合物が、(4E,8E)-ドデカ-4,8,11-トリエン-1-オール若しくは(4Z,8Z)-ドデカ-4,8,11-トリエン-1-オール、又は(4E,8E)-ドデカ-4,8,11-トリエン-1-オール及び(4Z,8Z)-ドデカ-4,8,11-トリエン-1-オールの両方をさらに含む、請求項5又は6に記載の化合物。
- 請求項1から7のいずれか一項に記載の化合物、及び
(i)ドデカ-4,8,11-トリエン-1-オールとは異なる少なくとも1種の追加の香料、又は
(ii)少なくとも1種の非香料キャリア、又は
(iii)少なくとも1種の抗酸化剤、又は
(iv)少なくとも1種のデオドラント活性剤、又は
(v)成分(i)から(iv)のうちの少なくとも2種の混合物
を含む、香料組成物。 - すぐに使用できるアロマ付き組成物である、請求項8に記載の香料組成物。
- すぐに使用できるアロマ付き組成物が、芳香組成物、ボディケア組成物、口腔又は歯科衛生用品、衛生用品、洗浄組成物、繊維用洗剤組成物、香りディスペンサー用組成物、食品、栄養補助食品、医薬組成物及び作物保護組成物から選択される、請求項9に記載の香料組成物。
- 香料としての、請求項1から7のいずれか一項に記載の化合物の使用。
- 香料組成物を調製するための、請求項1から7のいずれか一項に記載の化合物の使用。
- 香料組成物のアロマ特性を変更するための、請求項1から7のいずれか一項に記載の化合物の使用。
- 香料組成物が、すぐに使用できるアロマ付き組成物である、請求項12又は13に記載の使用。
- すぐに使用できるアロマ付き組成物が、芳香組成物、ボディケア組成物、口腔又は歯科衛生用品、衛生用品、洗浄組成物、繊維用洗剤組成物、香りディスペンサー用組成物、食品、栄養補助食品、医薬組成物及び作物保護組成物から選択される、請求項14に記載の使用。
- 請求項1から7のいずれか一項に記載の化合物を調製する方法であって、
(i)ドデカ-4,8,11-トリエナールを、カルボニル基のヒドロキシル基への還元反応に供して、ドデカ-4,8,11-トリエン-1-オールを得る工程、
及び任意選択で、
(ii)ドデカ-4,8,11-トリエン-1-オールを単離するさらなる工程
を含む、方法。
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EP18211704.4 | 2018-12-11 | ||
PCT/EP2019/084411 WO2020120469A1 (en) | 2018-12-11 | 2019-12-10 | Dodeca-4,8,11-trien-1-ol and its use as aroma chemical |
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JP2008527023A (ja) | 2005-01-19 | 2008-07-24 | ヴェ. マヌ フィル | 新規芳香化合物、合成法及び該化合物の使用 |
JP2012516300A (ja) | 2009-01-28 | 2012-07-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ドデカトリエナールの単離法、及びその香料としての使用 |
JP2017533981A (ja) | 2014-10-14 | 2017-11-16 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 香料としてのヘキサデカ−8,15−ジエナールの使用 |
JP2018522896A (ja) | 2015-07-27 | 2018-08-16 | ジボダン エス エー | フレグランス成分としての2,4,7−トリメチルオクタ−6−エン−1−オール |
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JPS61172839A (ja) * | 1985-01-28 | 1986-08-04 | T Hasegawa Co Ltd | 持続性香気香味賦与乃至改良補強剤 |
DE10322635A1 (de) * | 2003-05-20 | 2004-12-23 | Symrise Gmbh & Co. Kg | Verwendung von alpha-Terpenen als Riechstoffe |
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2018
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2019
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- 2019-12-10 CN CN201980081865.6A patent/CN113166006B/zh active Active
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Publication number | Priority date | Publication date | Assignee | Title |
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JP2008527023A (ja) | 2005-01-19 | 2008-07-24 | ヴェ. マヌ フィル | 新規芳香化合物、合成法及び該化合物の使用 |
JP2012516300A (ja) | 2009-01-28 | 2012-07-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ドデカトリエナールの単離法、及びその香料としての使用 |
JP2017533981A (ja) | 2014-10-14 | 2017-11-16 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 香料としてのヘキサデカ−8,15−ジエナールの使用 |
JP2018522896A (ja) | 2015-07-27 | 2018-08-16 | ジボダン エス エー | フレグランス成分としての2,4,7−トリメチルオクタ−6−エン−1−オール |
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CN113166006B (zh) | 2023-09-26 |
US11542217B2 (en) | 2023-01-03 |
EP3894381B1 (en) | 2022-10-19 |
CN113166006A (zh) | 2021-07-23 |
ES2930235T3 (es) | 2022-12-09 |
JP2022512160A (ja) | 2022-02-02 |
MX2021006978A (es) | 2021-07-15 |
EP3666749A1 (en) | 2020-06-17 |
PL3894381T3 (pl) | 2023-02-13 |
EP3894381A1 (en) | 2021-10-20 |
WO2020120469A1 (en) | 2020-06-18 |
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