CN115697279A - 香料前体共轭物 - Google Patents
香料前体共轭物 Download PDFInfo
- Publication number
- CN115697279A CN115697279A CN202180039566.3A CN202180039566A CN115697279A CN 115697279 A CN115697279 A CN 115697279A CN 202180039566 A CN202180039566 A CN 202180039566A CN 115697279 A CN115697279 A CN 115697279A
- Authority
- CN
- China
- Prior art keywords
- fragrance
- pro
- compound
- delivery system
- perfume
- 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.)
- Pending
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- 239000003205 fragrance Substances 0.000 title claims abstract description 77
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 239000002304 perfume Substances 0.000 claims description 48
- 239000003094 microcapsule Substances 0.000 claims description 14
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-UHFFFAOYSA-N 0.000 claims description 13
- 238000006845 Michael addition reaction Methods 0.000 claims description 7
- 239000002979 fabric softener Substances 0.000 claims description 7
- OEVIJAZJVZDBQL-UHFFFAOYSA-N 1-(5,5-dimethylcyclohexen-1-yl)pent-4-en-1-one Chemical compound CC1(C)CCC=C(C(=O)CCC=C)C1 OEVIJAZJVZDBQL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- VHBOIZSCWFNPBM-UHFFFAOYSA-N 2-[(4-methylphenyl)methylidene]heptanal Chemical compound CCCCCC(C=O)=CC1=CC=C(C)C=C1 VHBOIZSCWFNPBM-UHFFFAOYSA-N 0.000 claims description 3
- BGTBFNDXYDYBEY-FNORWQNLSA-N 4-(2,6,6-Trimethylcyclohex-1-enyl)but-2-en-4-one Chemical compound C\C=C\C(=O)C1=C(C)CCCC1(C)C BGTBFNDXYDYBEY-FNORWQNLSA-N 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 2
- VPGZKDXGOZRHSB-UHFFFAOYSA-N 4-methyldec-3-en-5-one Chemical compound CCCCCC(=O)C(C)=CCC VPGZKDXGOZRHSB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
- 239000000047 product Substances 0.000 description 44
- 239000000203 mixture Substances 0.000 description 35
- 238000009472 formulation Methods 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 17
- -1 thiol compounds Chemical class 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 8
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
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- 235000019645 odor Nutrition 0.000 description 7
- 239000000344 soap Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 6
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- 238000003818 flash chromatography Methods 0.000 description 6
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- 239000007921 spray Substances 0.000 description 6
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- 230000000638 stimulation Effects 0.000 description 5
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- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 4
- YCIXWYOBMVNGTB-UHFFFAOYSA-N 3-methyl-2-pentylcyclopent-2-en-1-one Chemical compound CCCCCC1=C(C)CCC1=O YCIXWYOBMVNGTB-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000002386 air freshener Substances 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 3
- OAPHLAAOJMTMLY-GQCTYLIASA-N Ethyl 2-methylbut-2-enoate Chemical compound CCOC(=O)C(\C)=C\C OAPHLAAOJMTMLY-GQCTYLIASA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000006065 biodegradation reaction Methods 0.000 description 3
- 239000000645 desinfectant Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 2
- VHBOIZSCWFNPBM-RVDMUPIBSA-N (2e)-2-[(4-methylphenyl)methylidene]heptanal Chemical compound CCCCC\C(C=O)=C/C1=CC=C(C)C=C1 VHBOIZSCWFNPBM-RVDMUPIBSA-N 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- PGTWZHXOSWQKCY-UHFFFAOYSA-N 1,8-Octanedithiol Chemical compound SCCCCCCCCS PGTWZHXOSWQKCY-UHFFFAOYSA-N 0.000 description 2
- YBUIAJZFOGJGLJ-SWRJLBSHSA-N 1-cedr-8-en-9-ylethanone Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1C(C)=C(C(C)=O)C2 YBUIAJZFOGJGLJ-SWRJLBSHSA-N 0.000 description 2
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 2
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 2
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 2
- KCMITHMNVLRGJU-CMDGGOBGSA-N Allyl cinnamate Chemical compound C=CCOC(=O)\C=C\C1=CC=CC=C1 KCMITHMNVLRGJU-CMDGGOBGSA-N 0.000 description 2
- 241000402754 Erythranthe moschata Species 0.000 description 2
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 2
- VSBHYRPUJHEOBE-UHFFFAOYSA-N Maltyl isobutyrate Chemical compound CC(C)C(=O)OC1=C(C)OC=CC1=O VSBHYRPUJHEOBE-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
- 230000001166 anti-perspirative effect Effects 0.000 description 2
- 239000003213 antiperspirant Substances 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
- MIZGSAALSYARKU-UHFFFAOYSA-N cashmeran Chemical compound CC1(C)C(C)C(C)(C)C2=C1C(=O)CCC2 MIZGSAALSYARKU-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- IVLCENBZDYVJPA-ARJAWSKDSA-N cis-Jasmone Natural products C\C=C/CC1=C(C)CCC1=O IVLCENBZDYVJPA-ARJAWSKDSA-N 0.000 description 2
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- 239000012459 cleaning agent Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
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- BLBJUGKATXCWET-UHFFFAOYSA-N cyclaprop Chemical compound C12CC=CC2C2CC(OC(=O)CC)C1C2 BLBJUGKATXCWET-UHFFFAOYSA-N 0.000 description 2
- 238000004851 dishwashing Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000001696 ethyl (E)-2-methylbut-2-enoate Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
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- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
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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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
-
- 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
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- A61K2800/10—General cosmetic use
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- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Stabilization Of Oscillater, Synchronisation, Frequency Synthesizers (AREA)
Abstract
本发明涉及香料前体化合物及其制备。还披露了含有这些香料前体化合物的递送系统和消费产品。
Description
技术领域
本发明涉及用于在消费产品中受控释放香料分子的香料前体(profragrance)化合物。
背景技术
香料前体已经在香料行业用于为不稳定香料分子提供保护并以受控的方式增强递送。
共轭化合物已经用作香料前体。WO 2003/049666 A2描述了用于受控释放香料成分的含硫共轭化合物。US 2016/0222327 A1披露了硫醚共轭物作为香料前体。在暴露于诸如光、水、热量或pH变化等触发条件时，这些共轭物分解并释放香料分子和硫醇化合物。还参见WO 2002/038120A1。然而，由于释放不完全，香料前体经常具有微弱的感知香味强度。许多副产物硫醇化合物具有强烈的令人不快的气味，这需要通过添加剂来抑制。
需要开发具有高释放率但没有令人不快的气味的香料前体。
发明内容
本发明提供了新颖的香料前体化合物及其在用于诸如织物护理产品、个人护理产品、家庭护理产品等消费产品时出乎意料的有利的以高感知香味强度的香料分子递送。
本发明的一个方面涉及香料前体化合物，其是一种或两种香料分子和3,6-二氧杂-1,8-辛烷-二硫醇的迈克尔加成产物，其中该一种或两种香料分子中的每一种具有α,β-不饱和羰基。当香料前体化合物是两种香料分子和3,6-二氧杂-1,8-辛烷-二硫醇的迈克尔加成产物时，这两种香料分子可以不同或相同。
优选地，该一种或两种香料分子选自由以下组成的组：香豆素、异茉莉酮、1-(5,5-二甲基-1-环己烯基)戊-4-烯-1-酮、2-(4-甲基亚苄基)庚醛、突厥酮(damascone)、丁-2-烯酸2-甲基戊-3-基酯、以及4-甲基癸-3-烯-5-酮。
本发明的另一个方面涉及一种含有上述的香料前体化合物的递送系统。也在本发明范围内的是含有这些香料前体化合物中的一种或多种的消费产品。还包括在本发明范围内的是含有这些香料前体化合物中的一种或多种的香料组合物，以及通过添加嗅觉可接受量的这些香料前体化合物中的一种或多种来改善、增强或改性香料配制品的方法。
具体实施方式
已经出人意料地且出乎意料地发现，本发明的香料前体化合物可以有效递送具有高香味性能的香料分子。
这些香料前体化合物具有以下通用结构：
其中R1和R2中的每一个可以是H或香料部分，前提是R1和R2中的至少一个是香料部分。当R1和R2都是香料部分时，它们可以相同或不同。每个香料部分衍生自具有α,β-不饱和羰基(
其中波状边界表示共价键合)的α,β-不饱和香料分子。此α,β-不饱和香料分子能够与3,6-二氧杂-1,8-辛烷-二硫醇反应以形成具有式A的化合物的迈克尔加成产物。
示例性的具有式A的化合物包括以下方案1中示出的那些：
方案1.
合适的α,β-不饱和香料分子包括：
方案2.
其他合适的α,β-不饱和香料分子包括(E)-2-(4-甲基亚苄基)庚醛(AcaleaTM)、肉桂酸烯丙酯、肉桂酸乙酯、(Z)-3-苯基丙烯腈(CinnamalvaTM)、3-苯基丙烯醛(肉桂醛)、(E)-2-甲基丁-2-烯酸乙酯(惕各酸乙酯)、2-亚苄基辛醛(己基肉桂醛)、3-甲基-2-戊基环戊-2-烯-1-酮(二氢茉莉酮)、(Z)-3-甲基-2-(戊-2-烯-1-基)环戊-2-烯-1-酮(顺式茉莉酮)、异丁酸2-甲基-4-氧代-4H-吡喃-3-基酯(异丁酸麦芽酚酯)、(E)-2-甲基-3-苯基丙烯醛(甲基肉桂醛)、以及1-(3,6,8,8-四甲基-2,3,4,7,8,8a-六氢-1H-3a,7-桥亚甲基薁-5-基)乙-1-酮
优选的α,β-不饱和香料分子是(E)-2-(4-甲基亚苄基)庚醛(AcaleaTM)、肉桂酸烯丙酯、肉桂酸乙酯、3-苯基-丙烯醛(肉桂醛)、惕各酸乙酯、3-甲基-2-戊基环戊-2-烯-1-酮(二氢茉莉酮)、以及(Z)-3-甲基-2-(戊-2-烯-1-基)环戊-2-烯-1-酮(顺式茉莉酮)。
本发明的香料前体化合物可以作为独立的游离成分用于任何香料组合物和消费产品中。它们还可以掺入递送系统，该递送系统包括微胶囊递送系统(WO 2015/023961A1)、聚合物辅助递送系统(聚合物颗粒，参见US 8,187,580)、纤维辅助递送系统(US 2010/0305021)、环糊精复合物(US 6,287,603和US 2002/0019369)、凝聚物复合物(coacervatecomplex)(WO 2019/179939 A1和US 10,092,023B2)、及其任何组合。优选地，递送系统是可持续的或可生物降解的。
如本文所用，关于材料(诸如作为整体的微胶囊和/或微胶囊壳的生物聚合物)的“可生物降解的”没有实际或感知的健康和/或环境问题，并且能够经历和/或确实经历了物理、化学、热、微生物和/或生物降解。理想地，当微胶囊和/或生物聚合物通过经济合作与发展组织(OECD)测试中的一项或多项测试时，该微胶囊和/或生物聚合物被认为是“可生物降解的”，这些测试包括但不限于OECD 301/310(快速生物降解)、OECD 302(固有生物降解)、ISO 17556(固体刺激研究)、ISO 14851(淡水刺激研究)、ISO 18830(海洋沉积物刺激研究)、OECD 307(土壤刺激研究)、OECD 308(沉积物刺激研究)和OECD 309(水刺激研究)。在特定实施例中，如使用OECD 310测试所确定，微胶囊是易于生物降解的。根据OECD 310的快速生物降解性的通过水平为在28天测试期内，在10天窗口期中达到60％的ThC02产量，其中10天窗口期在生物降解程度达到10％时开始。
合适的微胶囊递送系统各自含有分散在水相中的多个微胶囊，其中这些微胶囊中的每一个都具有核-壳结构，该结构具有单个微胶囊核和包封微胶囊核的微胶囊壳。微胶囊核具有活性材料诸如香料前体、香料、香精、恶臭冲消活性物质、化妆品活性物质、营养物等。微胶囊壁由包封聚合物形成，该包封聚合物可以选自由以下组成的组：溶胶-凝胶聚合物(例如，二氧化硅)、聚丙烯酸酯、聚丙烯酰胺、聚(丙烯酸酯-共-丙烯酰胺)、聚脲、聚氨酯、淀粉、明胶和阿拉伯胶、凝聚物复合物、聚(三聚氰胺-甲醛)、聚(脲-甲醛)、蛋白质、多醣、多元酚、及其组合。
本发明的化合物的用途广泛适用于加香产品，包括香水与古龙水的制备、个人护理产品(诸如香皂、沐浴露、和头发护理产品)、织物护理产品、空气清新剂、以及化妆品制剂的加香。本发明还可用于加香清洁剂，诸如洗涤剂、洗碗材料、擦洗组合物(scrubbingcomposition)、窗户清洁物等。
在这些制剂中，本发明的香料前体化合物可以单独使用或与其他加香组合物、溶剂、辅助剂等组合使用。也可使用的其他成分的性质与种类是本领域技术人员已知的。许多类型的香料成分可以在本发明中使用，唯一的限制是与所使用的其他组分的相容性。合适的香料成分包括但不限于水果诸如杏仁、苹果、樱桃、葡萄、梨、菠萝、橙子、草莓、树莓；麝香；花香诸如类薰衣草、类玫瑰、类鸢尾、类康乃馨。其他令人愉悦的气味包括衍生自松树、云杉和其他林木气味的草本和林地气味。香料成分还可以衍生自各种油(诸如精油)或衍生自植物材料(诸如薄荷、留兰香等)。
US专利号4,534,891中提供了一系列合适的香料成分，该专利的内容通过援引如所陈述地以其整体并入。合适的香料成分的另一个来源见于W.A.Poucher于1959年编辑的Perfumes,Cosmetics and Soaps[香水，化妆品和香皂]，第二版中。在该专著中提供的香料成分之中有刺槐、金合欢、素心兰、仙客来、蕨、栀子、山楂、天芥菜、金银花、风信子、茉莉、丁香、百合、木兰、含羞草、水仙、鲜切的干草、橙花、兰花、木犀草、香豌豆、三叶草、晚香玉、香草、紫罗兰、桂竹等。
本发明的香料前体化合物可以与互补的香料化合物组合使用。如本文所使用的术语“互补的香料化合物”定义为选自由以下组成的组的香料化合物：2-[(4-甲基苯基)亚甲基]-庚醛(Acalea)、异戊基氧基乙酸烯丙酯(烯丙基戊基乙醇酸酯)、(3,3-二甲基环己基)乙基乙基丙烷-1,3-二酸酯(Applelide)、(E/Z)-1-乙氧基-1-癸烯(Arctical)、2-乙基-4-(2,2,3-三甲基-3-环-戊烯-1-基)-2-丁烯-1-醇(Bacdanol)、2-甲基-3-[(1,7,7-三甲基双环[2.2.1]庚-2-基)氧基]外-1-丙醇(Bornafix)、1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4H-茚-4-酮(Cashmeran)、三甲基环戊烯基甲基氧杂二环辛烷(Cassiffix)、1,1-二甲氧基-3,7-二甲基-2,6-辛二烯(柠檬醛DMA)、3,7-二甲基-6-辛烯-1-醇(香茅醇(Citronellol))、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基乙酸酯(Cyclacet)、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1H-茚-5/6-基丙酸酯(Cyclaprop)、3A,4,5,6,7,7A-六氢-4,7-桥亚甲基-1G-茚-5/6-基丁酸酯(Cyclobutanate)、1-(2,6,6-三甲基-3-环己烯-1-基)-2-丁烯-1-酮(Delta Damascone)、3-(4-乙基苯基)-2,2-二甲基丙腈(Fleuranil)、3-(O/P-乙基苯基)2,2-二甲基丙醛(海风醛(Floralozone))、四氢-4-甲基-2-(2-甲基丙基)-2H-吡喃-4-醇(Floriffol)、1,3,4,6,7,8-六氢-4,6,6,7,8,8-六甲基环戊-γ-2-苯并吡喃(加乐麝香(Galaxolide))、1-(5,5-二甲基-1-环己烯-1-基)戊-4-烯-1-酮(Galbascone)、E/Z-3,7-二甲基-2,6-辛二烯-1-基乙酸酯(乙酸香叶酯(Geranyl Acetate))、α-甲基-1,3-苯并二氧杂环戊二烯-5-丙醛(Helional)、1-(2,6,6-三甲基-2-环己烯-1-基)-1,6-庚二烯-3-酮(Hexalon)、(Z)-3-己烯基-2-羟基苯甲酸酯(水杨酸顺式-3-己烯酯(Hexenyl Salicylate,CIS-3))、4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(α-紫罗兰酮(Iononeα))、1-(1,2,3,4,5,6,7,8-八氢-2,3,8,8-四甲基-2-萘基)-乙-1-酮(Iso E Super)、3-氧代-2-戊基环戊烷乙酸甲酯(Kharismal)、2,2,4-三甲基-4-苯基-丁腈(Khusinil)、3,4,5,6,6-五甲基庚-3-烯-2-酮(Koavone)、3/4-(4-羟基-4-甲基-戊基)环己烯-1-甲醛(Lyral)、3-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)-3-丁烯-2-酮(γ-甲基紫罗兰酮(Methyl Iononeγ))、1-(2,6,6-三甲基-2-环己烯-1-基)戊-1-烯-3-酮(α-甲基紫罗兰酮额外(Methyl IononeαExtra)、甲基紫罗兰酮N(Methyl Ionone N))、3-甲基-4-苯基丁-2-醇(Muguesia)、环十五碳-4-烯-1-酮(Musk Z4)、3,3,4,5,5-五甲基-11,13-二氧杂三环[7.4.0.0<2,6>]十三碳-2(6)-烯(Nebulone)、3,7-二甲基-2,6-辛二烯-1-基乙酸酯(橙花醇乙酸酯(NerylAcetate))、3,7-二甲基-1,3,6-辛三烯(罗勒烯(Ocimene))、邻甲苯基乙醇(Peomosa)、3-甲基-5-苯基戊醇(Phenoxanol)、1-甲基-4-(4-甲基-3-戊烯基)环己-3-烯-1-甲醛(Precyclemone B)、4-甲基-8-亚甲基-2-金刚烷醇(Prismantol)、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Sanjinol)、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇(Santaliff)、萜品醇、2,4-二甲基-3-环己烯-1-甲醛(Triplal)、十氢-2,6,6,7,8,8-六甲基-2H-茚并[4,5-B]呋喃(Trisamber)、乙酸2-叔丁基环己基酯(Verdox)、乙酸4-叔丁基环己基酯(Vertenex)、乙酰基柏木烯(Vertofix)、3,6/4,6-二甲基环己-3-烯-1-甲醛(Vertoliff)和(3Z)-1-[(2-甲基-2-丙烯基)氧基]-3-己烯(Vivaldie)。
术语“香料配制品”、“香料组合物”、和“加香组合物”含义相同并且是指包括例如醇、醛、酮、酯、醚、内酯、腈、天然油、合成油、和硫醇的香料成分的混合物的消费组合物，将这些化合物混合使得单个组分的组合气味产生令人愉悦或希望的香味。本发明的香料配制品是包含本发明的化合物的消费组合物。本发明的香料配制品包含本发明的化合物并且进一步包含如上定义的互补的香料化合物。
术语“香料分子”是指从香料前体化合物中释放的最终香料成分。
术语“香料产品”意指含有增加香味或掩蔽恶臭的香料成分的消费产品。香料产品可包括例如香水；古龙水；条皂；液体皂；沐浴露；泡泡浴液(foam bath)；化妆品；皮肤护理产品诸如霜剂、洗剂和剃须产品；用于洗发、漂洗、调理、漂白、着色、染色和造型的头发护理产品；除臭剂和止汗剂；女性护理产品诸如卫生棉条和女性卫生巾；婴儿护理产品诸如尿布、围嘴和擦拭物；家庭护理产品诸如卫生纸(bath tissue)、化妆纸(facial tissue)、手帕纸(paper handkerchief)或擦手纸(paper towel)；织物产品诸如织物柔软剂和织物清新剂；空气护理产品诸如空气清新剂和香味递送系统；化妆品制剂；清洁剂和消毒剂诸如洗涤剂、洗碗材料、擦洗组合物、玻璃和金属清洁物(诸如窗户清洁物)、台面清洁物、地面和地毯清洁物、厕所清洁物和漂白添加剂；清洗剂诸如通用、重垢、和手洗或精细织物清洗剂(包括衣物洗涤剂和漂洗添加剂)；牙齿和口腔卫生产品诸如牙膏、牙凝胶、牙线、义齿清洁物、义齿胶粘剂、洁牙剂、牙齿增白剂和漱口剂；健康护理和营养产品以及食物产品诸如小吃和饮料产品。本发明的香料产品是含有本发明的化合物的消费产品。本发明的香料产品含有本发明的化合物并且进一步含有如上定义的互补的香料化合物。
短语“改善、增强或改性香料配制品”中的术语“改善”应理解为意指将香料配制品提升至更希望的特征。术语“增强”应理解为意指使香料配制品的效果更好或为该香料配制品提供改善的特征。术语“改性”应理解为意指为香料配制品提供特征的变化。
术语“嗅觉可接受量”应理解为意指香料配制品中化合物的量，其中化合物将贡献其独特的嗅觉特征。然而，香料配制品的嗅觉效果将是香料成分各自效果的总和。因此，本发明的化合物可用于改善或增强香料配制品的芳香特征，或用于改性该配制品中其他成分所贡献的嗅觉反应。该嗅觉可接受量可以取决于许多因素(包括其他成分、它们的相对量和希望的嗅觉效果)而改变。
香料配制品中使用的本发明的化合物的量从0.0001至70重量百分比、优选从0.005至50重量百分比、更优选从0.5至25重量百分比、并且甚至更优选从1至10重量百分比变化。本领域技术人员将能够使用希望量以提供希望的香味效果和强度。除了本发明的化合物之外，其他材料也可以与香料配制品结合使用以包封和/或递送香味。一些众所周知的材料是，例如，但不限于，聚合物，低聚物，和其他辅助剂如表面活性剂、乳化剂，脂质包括脂肪、蜡和磷脂质，有机油，矿物油，矿脂，天然油，固香剂(perfume fixative)，纤维，淀粉，糖和固体表面材料如沸石和二氧化硅。
当在香料配制品中使用时，这些成分对易受攻击的香料分子提供保护并在触发情况下时以额外的香调释放它们，以使得香料配制品更合意和引人注意，并增加了感知价值。在这些香料分子中发现的气味品质有助于美化和增强成品一致性，以及改善香料组合物中其他材料的性能。
另外，本发明的化合物还可用于在诸如人体排汗、环境气味诸如霉菌和霉、浴室等恶臭冲消应用中保护香料分子。这些香料分子基本上消除了对恶臭的感知和/或防止形成此类恶臭，因此可以与大量消费产品一起使用。
本文提供消费产品的实例以说明本发明的各个方面。但是，它们不旨在限制本发明的范围。消费产品可以包括例如常规的房间清新剂(或除臭剂)组合物，诸如房间清新剂喷雾剂、气雾剂或其他喷雾剂；香味扩散剂、芯或其他液体系统、或固体，例如香盒和塑料中的蜡烛或蜡碱、香囊或干喷雾剂中的粉末或如在固体凝胶棒中的凝胶；如通过洗衣机应用所应用的衣物除臭剂，诸如应用于洗涤剂、粉末、液体、增白剂或织物柔软剂、织物清新剂、亚麻喷雾剂、壁橱区(closet block)、壁橱气雾喷雾剂(closet aerosol spray)、或衣物存储区域中或干洗中以克服衣物上残留的溶剂香调；浴室配件诸如擦手纸、卫生纸、卫生巾、湿巾、一次性洗布、一次性尿布和尿布桶除臭剂；清洁物诸如消毒剂和抽水马桶清洁物；化妆品产品诸如止汗剂和除臭剂；呈粉末、气雾、液体或固体形式的一般身体除臭剂；或头发护理产品诸如发胶、调理剂、漂洗剂、头发着色剂和染色剂、烫发剂、脱毛剂、直发剂；理发应用(hair groom application)诸如润发油、霜剂和洗剂；含有成分诸如二硫化硒、煤焦油或水杨酸盐的含药头发护理产品、或洗发剂；或足部护理产品诸如爽足粉、液体或古龙水；须后水和身体乳液；或香皂和合成洗涤剂诸如皂条、液体、泡沫或粉末；气味控制诸如在制造过程期间(诸如纺织整理业和印刷业(油墨和纸))；流出物控制诸如在涉及制浆、畜牧场和肉类处理的工艺中；污水处理；垃圾袋或垃圾处置；或者在产品气味控制中，如在纺织制成品、橡胶制成品或汽车空气清新剂中；农业和宠物护理产品，诸如狗和鸡舍流出物以及家畜和宠物护理产品诸如除臭剂、洗发剂或清洁剂，或动物卫生砂材料；以及在大规模封闭式空气系统诸如礼堂、和地铁以及运输系统中。
因此，可以看到本发明的组合物通常是其中恶臭冲消剂与载体一起存在的组合物，凭借该载体或从该载体可以将该恶臭冲消剂引入到其中存在恶臭的空气空间内，或引入到其上沉积有恶臭的基底。例如，载体可以是气雾推进剂诸如氯氟甲烷，或固体诸如蜡、塑料材料、橡胶、惰性粉末或凝胶。在芯型空气清新剂中，载体是低挥发性的基本上无味的液体。在若干应用中，本发明的组合物含有表面活性剂或消毒剂，而在其他应用中，恶臭冲消剂存在于纤维基底上。在本发明的许多组合物中也存在香料组分，其赋予组合物香味。上述香料全部可以使用。
恶臭冲消有效量应理解为意指功能性产品中使用的本发明的恶臭冲消剂减弱给定的恶臭的同时降低气味水平的组合强度的感官有效的量，其中给定的恶臭是存在于空气空间中或已沉积于基底上。所使用的恶臭冲消剂的确切量可以取决于恶臭冲消剂的类型、所使用的载体类型、和所希望的恶臭冲消的水平而变化。一般来说，存在的恶臭冲消剂的量是获得希望结果所需要的普通剂量。这样的剂量是本领域技术人员已知的。在优选的实施例中，当与恶臭固体或液体功能性产品例如香皂和洗涤剂结合使用时，本发明的化合物可以以范围从0.005至50重量百分比、优选从0.01至20重量百分比、并且更优选从0.05至5重量百分比的量存在，并且当与恶臭的气态功能性产品结合使用时，本发明的化合物可以以范围从0.1至10mg/立方米空气的量存在。
作为本发明的具体实施例提供以下内容。本发明的其他修改对本领域技术人员将是显而易见的。此类修改应理解为在本发明的范围内。除非另行说明，否则如本文所使用的所有百分比是重量百分比，ppm应理解为代表每百万份的份数，L应理解为升，mL应解为毫升，g应理解为克，Kg应理解为千克，mol应理解为摩尔，psi应理解为每平方英寸的磅力，并且mmHg应理解为汞(Hg)的毫米数(mm)。如实例中使用的IFF应理解为意指美国纽约州纽约市的国际香精香料公司(International Flavors&Fragrances Inc.)。
本发明通过下文中的非限制性实例进行了更为详细地描述。无需进一步详尽说明，据信本领域技术人员可以基于本文中的说明，将本发明利用至其最大程度。将本文引用的所有出版物都通过援引以其整体并入。
实例1
向2H-色满-2-酮(II，6g，41.1mmol)和1,8-二氮杂二环[5.4.0]十一碳-7-烯(“DBU”，0.625g，4.11mmol)在四氢呋喃(“THF”，10g)中的溶液中添加2,2'-(乙烷-1,2-二基双(氧基))双(乙烷-1-硫醇)(I，3.74g，20.5mmol)。将反应混合物在室温下搅拌5小时。在减压下去除溶剂以提供清澈的微黄色油状物，将其通过快速色谱法纯化以给出0.83g的4-((2-(2-(2-巯基-乙氧基)乙氧基)乙基)硫代)色满-2-酮(IV，12％)和0.4g的4,4'-(((乙烷-1,2-二基双(氧基))双(乙烷-2,1-二基))双(硫烷二基))双(色满-2-酮)(III，4％)。
化合物III的1H NMR(400MHz,氯仿-d)δ:7.31(m,4H),7.11(m,4H),4.40(t,J＝4.14Hz,2H),3.64(m,8H),3.07(m,4H),2.71(m,4H)。
化合物IV的1H NMR(400MHz,氯仿-d)δ:7.33(m,2H),7.13(m,2H),4.45(t,J＝4.15Hz,1H),3.65(m,8H),3.10(m,2H),2.71(m,4H),1.58(t,J＝8.19Hz,1H)。
实例2
向(E)-丁-2-烯酸2-甲基戊-3-基酯(V，6g，35.2mmol)和DBU(0.537g，3.52mmol)在THF(10g)中的溶液中添加2,2'-(乙烷-1,2-二基双(氧基))双-(乙烷-1-硫醇)(I，3.21g，17.6mmol)。将反应混合物在室温下搅拌6小时。在减压下去除溶剂。将粗产物通过快速色谱法纯化以给出3.5g的3,14-二甲基-7,10-二氧杂-4,13-二硫杂十六碳二酸双(2-甲基-戊-3-基)酯(VI，38％)和1.1g的3-((2-(2-(2-巯基乙氧基)乙氧基)乙基)硫代)丁酸2-甲基戊-3-基酯(VII，18％)。
化合物VI的1H NMR(500MHz,氯仿-d)δ:4.67(m,2H),3.60(m,8H),3.23(m,2H),2.73(m,4H),2.63(m,2H),2.43(m,2H),1.81(m,2H),1.53(m,4H),1.31(d,J＝6.60Hz,6H),0.86(m,18H)。
化合物VII的1H NMR(500MHz,氯仿-d)δ:4.69(m,1H),3.63(m,8H),3.26(m,1H),2.61-2.80(m,5H),2.44(m,1H),1.82(m,1H),1.57(t,J＝8.23Hz,1H),1.53(m,2H),1.33(d,J＝6.88Hz,3H),0.88(m,9H)。
实例3
向2-己基环戊-2-烯-1-酮(VIII，6g，36.1mmol)和DBU(0.549g，3.61mmol)在THF(10g)中的溶液中添加2,2'-(乙烷-1,2-二基双(氧基))双(乙烷-1-硫醇)(I，3.29g，18.04mmol)。将反应混合物在室温下搅拌6小时。在减压下去除溶剂以提供微浑浊油状物，将其通过快速色谱法纯化以给出1.4g的3,3'-(((乙烷-1,2-二基双(氧基))双(乙烷-2,1-二基))双(硫烷-二基))双(2-己基环戊-1-酮)(IX，15％)和0.7g的2-己基-3-((2-(2-(2-巯基乙氧基)-乙氧基)乙基)硫代)环-戊-1-酮(X，11％)。
化合物IX的1H NMR(500MHz,氯仿-d)δ:3.65(m,8H),3.09(m,2H),2.75(m,4H),2.41(m,4H),2.11(m,2H),1.98(m,2H),1.83(m,2H),1.58(m,4H),1.19-1.46(m,16H),0.86(m,6H)。
化合物X的1H NMR(500MHz,氯仿-d)δ:3.62(m,8H),3.12(m,1H),2.78(m,2H),2.67(m,2H),2.41(m,2H),2.14(m,1H),1.98(m,1H),1.85(m,1H),1.57(m,3H),1.19-1.45(m,8H),0.86(m,3H)。
实例4
向1-(2,6,6-三甲基环己-3-烯-1-基)丁-2-烯-1-酮(XI，6g，31.2mmol)和DBU(0.475g，3.12mmol)在THF(10g)中的溶液中添加化合物I(2.84g，15.6mmol)。将反应混合物在室温下搅拌6小时。在减压下去除溶剂以提供清澈的亮黄色油状物，将其通过快速色谱法纯化以给出2.6g的3,14-二甲基-1,16-双(2,6,6-三甲基环己-3-烯-1-基)-7,10-二氧杂-4,13-二硫杂十六烷-1,16-二酮(XII，29％)和0.9g的3-((2-(2-(2-巯基乙氧基)乙氧基)乙基)硫代)-1-(2,6,6-三甲基环己-3-烯-1-基)丁-1-酮(XIII，15％)。
化合物XII的1H NMR(500MHz,氯仿-d)δ:5.52(m,2H),5.45(m,2H),3.62(m,8H),3.33(,2H),2.69(m,8H),2.51(m,2),2.19(m,2H),1.96(m,2H),1.68(m,2H),1.29(d,J＝6.92Hz,6H),0.92(m,18H)。
化合物XIII的1H NMR(500MHz,氯仿-d)δ:5.52(m,1H),5.43(m,1H),3.62(m,8H),3.33(m,1H),2.47-2.92(m,2H),2.72(m,4H),2.51(m,1H),2.20(m,1H),1.95(m,1H),1.68(m,1H),1.57(t,J＝8.23Hz,1H),1.29(m,3H),0.95(m,6H),0.87(m,3H)。
实例5
向1-(5,5-二甲基环己-1-烯-1-基)戊-4-烯-1-酮(XIV，6g，31.2mmol)和DBU(0.475g，3.12mmol)在THF(10g)中的溶液中添加2,2'-(乙烷-1,2-二基双(氧基))双(乙烷-1-硫醇)(I，2.84g，15.6mmol)。将反应混合物在室温下搅拌6小时。在减压下去除溶剂以给出微黄色油状物，将其通过快速色谱法纯化以产生3.9g的1,1'-((((乙烷-1,2-二基双(氧基))双(乙烷-2,1-二基))双(硫烷二基))双-(5,5-二甲基-环己烷-2,1-二基))双(戊-4-烯-1-酮)(XV，44％)和0.6g的1-(2-((2-(2-(2-巯基乙氧基)乙氧基)乙基)硫代)-5,5-二甲基环己基)-戊-4-烯-1-酮(XVI，11％)。
化合物XV的1H NMR(500MHz,氯仿-d)δ:5.80(m,2H),5.00(m,4H),3.54(m,8H),2.63(m,12H),2.31(m,4H),1.95(m,2H),1.54(m,2H),1.40(m,4H),1.21(m,4H),0.9(m,12H)。
化合物XVI的1H NMR(400MHz,氯仿-d)δ:5.76-5.91(m,1H),4.94-5.12(m,2H),3.53-3.69(m,8H),2.46-2.82(m,8H),2.28-2.42(m,2H),1.93-2.07(m,1H),1.53-1.66(m,2H),1.38-1.51(m,2H),1.16-1.34(m,2H),0.95(s,3H),0.94(s,3H)。
实例6
向(E)-4-甲基癸-3-烯-5-酮(XVII，5g，29.7mmol)和DBU(0.18g，1.19mmol)在四氢呋喃(“THF”，5g)中的溶液中添加2,2'-(乙烷-1,2-二基双(氧基))双(乙烷-1-硫醇)(I，2.17g，11.9mmol)。将反应混合物在室温下搅拌24小时。在减压下去除溶剂以提供黄色油状物，将其通过快速色谱法纯化以给出6.17g的8,19-二乙基-7,20-二甲基-12,15-二氧杂-9,18-二硫杂二十六烷-6,21-二酮(XVIII，73％)和0.5g的3-((2-(2-(2-巯基乙氧基)乙氧基)乙基)硫代)-4-甲基癸-5-酮(XIX，11％)。
化合物XVIII的1H NMR(400MHz,氯仿-d)δ:3.51-3.71(m,8H),2.79-2.90(m,2H),2.60-2.78(m,6H),2.38-2.58(m,4H),1.39-1.74(m,8H),1.22-1.38(m,8H),1.19(d,J＝7.0Hz,80％的6H),1.07(d,J＝6.9Hz,20％的6H),0.98-1.04(m,6H),0.89(t,J＝7.1Hz,6H)。
对比化合物IV’、IV”、IX’、和X’
遵循与实例1所述相同的程序，制备对比化合物IV’，除了使用1,8-辛烷二硫醇代替2,2'-(乙烷-1,2-二基双(氧基))双(乙烷-1-硫醇)。使用1-十二烷硫醇(C12SH)制备对比化合物IV”。类似地，遵循实例3中的程序使用1,8-辛烷二硫醇制备对比化合物IX’。还使用1-十二烷硫醇制备对比化合物X’。
这些对比化合物的化学结构在下面示出。
织物柔顺剂顶部空间释放研究
在织物柔顺剂顶部空间研究中对化合物IV和对比化合物IV’和IV”进行评价。化合物II用作对照物。
样品制备：将每种化合物以1wt％添加到织物柔顺剂基质中，并使其浸软24小时。
清洗工艺：将三个4×5英寸棉布样本用经1000倍水稀释的织物柔顺剂处理。处理后，将过量水旋出。将样本在高热量下烘干30分钟。
顶部空间收集：将经干燥的样本置于加仑尺寸罐的底部，加盖并在40℃下平衡3小时。平衡后，在40℃水浴中时从每个罐中收集1升的顶部空间物。在清洗工艺后的初始时间点(T＝0)、T＝7天和T＝14天时，重复收集三次。
顶部空间分析：在带有四极质谱仪的Agilent 7890气相色谱仪上运行顶部空间样品。基于标准响应系数和收集的体积，将峰面积转换为蒸气浓度。
出乎意料地，化合物IV在GC顶部空间中以最高水平释放，多达215.2ng/L。相比之下，化合物II以29.2ng/L释放，对比化合物IV’以65.8ng/L释放，并且对比化合物IV”以53.1ng/L释放。对于这些结果，参见下表1。
化合物IX和X也与对比化合物IX’和X’一起进行了评价。化合物VIII用作对照物。
出乎意料地，化合物IX在GC顶部空间中以354.4ng/L的水平释放，并且化合物X以478ng/L的水平释放，比对比化合物和对照物高得多。参见下表1。
表1.
| 化合物 | GC顶部空间释放，ng/L |
| IV | 215.2 |
| 对比IV’ | 65.8 |
| 对比IV” | 53.1 |
| 对照物II | 29.2 |
| IX | 354.4 |
| 对比IX’ | 86.9 |
| X | 478 |
| 对比X’ | 167.5 |
| 对照物VIII | 19.2 |
Claims (11)
1.一种香料前体化合物，其是一种或两种香料分子和3,6-二氧杂-1,8-辛烷-二硫醇的迈克尔加成产物，其中所述一种或两种香料分子中的每一种具有α,β-不饱和羰基。
2.如权利要求1所述的香料前体化合物，其中，所述香料前体化合物是一种香料分子和3,6-二氧杂-1,8-辛烷-二硫醇的迈克尔加成产物。
3.如权利要求1所述的香料前体化合物，其中，所述香料前体化合物是两种香料分子和3,6-二氧杂-1,8-辛烷-二硫醇的迈克尔加成产物，并且所述两种香料分子是不同的或相同的。
4.如权利要求1-3中任一项所述的香料前体化合物，其中，所述一种或两种香料分子中的每一种选自由以下组成的组：香豆素、异茉莉酮、1-(5,5-二甲基-1-环己烯基)戊-4-烯-1-酮、2-(4-甲基亚苄基)-庚醛、突厥酮、丁-2-烯酸2-甲基戊-3-基酯、以及4-甲基癸-3-烯-5-酮。
5.如权利要求1所述的香料前体化合物，其中，所述香料前体化合物选自由以下组成的组：
6.一种递送系统，其含有如权利要求1-5中任一项所述的香料前体化合物。
7.如权利要求6所述的递送系统，其中，所述递送系统是微胶囊递送系统、聚合物颗粒递送系统、纤维辅助递送系统、环糊精复合物、凝聚物复合物、或其任何组合。
8.如权利要求6或7所述的递送系统，其中，所述递送系统是可生物降解的。
9.一种消费产品，其含有如权利要求1-5中任一项所述的香料前体化合物。
10.如权利要求9所述的消费产品，其中，所述消费产品是织物柔顺剂。
11.一种制备如权利要求1-5中任一项所述的香料前体化合物的方法，所述方法包括使3,6-二氧杂-1,8-辛烷-二硫醇与一种或两种香料分子反应以形成迈克尔加成产物的步骤，其中所述一种或两种香料分子中的每一种具有α,β-不饱和羰基。
Applications Claiming Priority (3)
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|---|---|---|---|
| US202063034148P | 2020-06-03 | 2020-06-03 | |
| US63/034148 | 2020-06-03 | ||
| PCT/US2021/035646 WO2021247824A1 (en) | 2020-06-03 | 2021-06-03 | Profragrance conjugates |
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| Publication Number | Publication Date |
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| CN115697279A true CN115697279A (zh) | 2023-02-03 |
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| CN202180039566.3A Pending CN115697279A (zh) | 2020-06-03 | 2021-06-03 | 香料前体共轭物 |
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| US (1) | US20230227750A1 (zh) |
| EP (1) | EP4161472A4 (zh) |
| CN (1) | CN115697279A (zh) |
| BR (1) | BR112022024694A2 (zh) |
| WO (1) | WO2021247824A1 (zh) |
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| CN104837478A (zh) * | 2012-12-14 | 2015-08-12 | 宝洁公司 | 个人护理组合物 |
| US20170204223A1 (en) * | 2016-01-15 | 2017-07-20 | International Flavors & Fragrances Inc. | Polyalkoxy-polyimine adducts for use in delayed release of fragrance ingredients |
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| US3194830A (en) * | 1959-10-14 | 1965-07-13 | Eastman Kodak Co | Diesters of saturated aliphatic dicar-boxylic acids containing both oxygen and sulphur in the chain |
| ATE409512T1 (de) * | 2001-12-13 | 2008-10-15 | Firmenich & Cie | Verbindungen zur kontrollierten freigabe aktiver molekülen |
| RU2529512C2 (ru) * | 2012-12-19 | 2014-09-27 | Федеральное государственное бюджетное учреждение науки Институт нефтехимии и катализа Российской академии наук | Способ получения 1,8-{ бис[(пент-2,4-дион-3-ил)метилсульфанил]} -3,6-диоксаоктана и 4,4`-{ бис[(пент-2,4-дион-3-ил)метилсульфанил]} -дифенилоксида |
| IL277590B2 (en) * | 2018-03-29 | 2024-04-01 | Basf Se | A preparation for electroplating with a tin-silver alloy containing a complexing agent |
| EP3656824A1 (en) * | 2018-11-26 | 2020-05-27 | Agfa-Gevaert Nv | Radiation curable inkjet for manufacturing printed circuit boards |
-
2021
- 2021-06-03 WO PCT/US2021/035646 patent/WO2021247824A1/en unknown
- 2021-06-03 US US17/928,815 patent/US20230227750A1/en active Pending
- 2021-06-03 BR BR112022024694A patent/BR112022024694A2/pt not_active Application Discontinuation
- 2021-06-03 EP EP21818475.2A patent/EP4161472A4/en active Pending
- 2021-06-03 CN CN202180039566.3A patent/CN115697279A/zh active Pending
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| US20100330009A1 (en) * | 2007-03-09 | 2010-12-30 | Ciba Corporation | Coumestan-like antioxidants and uv absorbants |
| CN104837478A (zh) * | 2012-12-14 | 2015-08-12 | 宝洁公司 | 个人护理组合物 |
| US20170204223A1 (en) * | 2016-01-15 | 2017-07-20 | International Flavors & Fragrances Inc. | Polyalkoxy-polyimine adducts for use in delayed release of fragrance ingredients |
| CN108601958A (zh) * | 2016-02-15 | 2018-09-28 | 爱客多有限公司 | 香料前体组合物 |
| CN108203622A (zh) * | 2016-12-20 | 2018-06-26 | 国际香料和香精公司 | 新型感官化合物 |
| US20190315821A1 (en) * | 2018-02-23 | 2019-10-17 | La Jolla Pharmaceutical Company | Compositions comprising hepcidin and methods of use thereof |
| CN114341323A (zh) * | 2019-12-19 | 2022-04-12 | 弗门尼舍有限公司 | 提供持久花香和果香气味的化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2021247824A1 (en) | 2021-12-09 |
| BR112022024694A2 (pt) | 2023-02-28 |
| EP4161472A1 (en) | 2023-04-12 |
| EP4161472A4 (en) | 2024-06-26 |
| US20230227750A1 (en) | 2023-07-20 |
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