CN111133086B - 包含气味剂的组合物 - Google Patents
包含气味剂的组合物 Download PDFInfo
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- CN111133086B CN111133086B CN201880051501.9A CN201880051501A CN111133086B CN 111133086 B CN111133086 B CN 111133086B CN 201880051501 A CN201880051501 A CN 201880051501A CN 111133086 B CN111133086 B CN 111133086B
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- Prior art keywords
- oil
- methyl
- formula
- fragrance
- carbon atoms
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 239000003205 fragrance Substances 0.000 title claims abstract description 71
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 44
- 230000001877 deodorizing effect Effects 0.000 claims abstract description 36
- 230000000873 masking effect Effects 0.000 claims abstract description 35
- 235000014443 Pyrus communis Nutrition 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 239000000796 flavoring agent Substances 0.000 claims description 45
- 235000019634 flavors Nutrition 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000010981 turquoise Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000004615 ingredient Substances 0.000 abstract description 8
- 125000004805 propylene group Chemical class [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 5
- 235000019568 aromas Nutrition 0.000 abstract 1
- -1 olefin diols Chemical class 0.000 description 97
- 239000003921 oil Substances 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 54
- 150000001299 aldehydes Chemical class 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 25
- 238000003786 synthesis reaction Methods 0.000 description 23
- 125000003342 alkenyl group Chemical group 0.000 description 22
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 241000402754 Erythranthe moschata Species 0.000 description 10
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 10
- 241000220324 Pyrus Species 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 8
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 8
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 8
- 239000004327 boric acid Substances 0.000 description 8
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 8
- 235000019645 odor Nutrition 0.000 description 8
- CZLVPINBLDRZCJ-UHFFFAOYSA-N 2,3,4,4,5,5,6,6-octachlorocyclohex-2-en-1-one Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)(Cl)C(Cl)(Cl)C1=O CZLVPINBLDRZCJ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 229940022663 acetate Drugs 0.000 description 7
- 239000002304 perfume Substances 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 150000003505 terpenes Chemical class 0.000 description 7
- 235000007586 terpenes Nutrition 0.000 description 7
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical compound CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 6
- QOUVUDUTJPGJNG-UHFFFAOYSA-N 3-methyl-2-methylidenebutanal Chemical compound CC(C)C(=C)C=O QOUVUDUTJPGJNG-UHFFFAOYSA-N 0.000 description 6
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 6
- 240000002262 Litsea cubeba Species 0.000 description 6
- 235000012854 Litsea cubeba Nutrition 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- XXROGKLTLUQVRX-UHFFFAOYSA-N hydroxymethylethylene Natural products OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 6
- 150000002825 nitriles Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- OFHHDSQXFXLTKC-UHFFFAOYSA-N 10-undecenal Chemical compound C=CCCCCCCCCC=O OFHHDSQXFXLTKC-UHFFFAOYSA-N 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- RMPSTXQZFXENIH-UHFFFAOYSA-N 6,6-dimethyl-5-methylidenehept-1-en-3-one Chemical compound CC(C)(C)C(=C)CC(=O)C=C RMPSTXQZFXENIH-UHFFFAOYSA-N 0.000 description 4
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
- 241000717739 Boswellia sacra Species 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 4
- 244000131522 Citrus pyriformis Species 0.000 description 4
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000004863 Frankincense Substances 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 229930040373 Paraformaldehyde Natural products 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- YPZUZOLGGMJZJO-UHFFFAOYSA-N ambrofix Natural products C1CC2C(C)(C)CCCC2(C)C2C1(C)OCC2 YPZUZOLGGMJZJO-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 4
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 229960000956 coumarin Drugs 0.000 description 4
- 235000001671 coumarin Nutrition 0.000 description 4
- WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 4
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 4
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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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- 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
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- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
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- 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
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- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
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Abstract
本发明涉及有气味的2‑和/或3‑取代的3‑(烯丙氧基)丙烯,其可用作香味或风味成分,特别是在提供青绿、果香、梨和/或糯质嗅觉气味方面。本发明还涉及包含所述气味剂的新的香料、芳香或除臭/掩蔽组合物。
Description
发明领域
本发明涉及有气味的2-和/或3-取代的3-(烯丙氧基)丙烯(气味剂),其可用作香味或风味材料,特别是提供青绿(green)、果香、梨(pear)和/或糯质(waxy)嗅觉气味给香料、芳香或除臭/掩蔽组合物。本发明也涉及包含所述气味剂2-和/或3-取代的3-(烯丙氧基)丙烯的香味、风味和/或除臭/掩蔽组合物。本发明进一步涉及所述气味剂,其可用于本发明的新的香味、风味和/或除臭/掩蔽组合物。本发明还涉及一种生产所述气味剂/化合物和生产含有所述气味剂/化合物的相应的香味、风味和/或除臭/掩蔽组合物的方法。
发明背景
通常,目前在香料工业和/或调味品工业中使用的许多气味剂都是合成分子。特别地,对新型气味剂/化合物和/或包含所述气味剂/化合物的新型香味、风味和/或除臭/掩蔽组合物有很高的需求和需要。
1-(2-丙烯氧基)-2-叔丁基-2-丙烯在J. Am. Chem. Soc的文章(1991, 113,5817-5824页)中被引用,该文章涉及一项利用单色光,在313-366 nm波长范围内,在甲醇中的10个1,5-己二烯-3-酮的光化学研究。如在该文章的5822页所指明的,在从2,3,3-三甲基-1-丁烯制备5-叔丁基-1,5-己二烯-3-酮(5)期间,1-(2-丙烯氧基)-2-叔丁基-2-丙烯被称为中间体化合物。该文章未公开香味、风味和/或除臭/掩蔽组合物,并且绝对没有证据、也没有任何提示表明存在任何与化合物1-(2-丙烯氧基)-2-叔丁基-2-丙烯有关的嗅觉特性。
烯丙基2-戊基烯丙基醚在Synthsis的文章(Georg Thieme Verlag Stuttgart,DE, 10, 2002年1月1日, 1445-1453页)中被引用,其涉及一种新的取代烯烃二醇的途径,即通过使二氢呋喃和二氢吡喃环氧化物与有机锂反应以立体定向烷基化双开环(stereospecilic alkylative double ring-opening)。如该文章的1449页所指明的,在从三取代的环氧化物制备取代的烯烃二醇期间,烯丙基2-戊基烯丙基醚被称为中间体化合物(方案7)。该文章未公开香味、风味和/或除臭/掩蔽组合物,并且绝对没有证据、也没有任何提示表明存在任何与化合物烯丙基2-戊基烯丙基醚有关的嗅觉特性。
本发明的一个或多个实施方案的优点是,所述气味剂/化合物可以赋予和/或加强特定的嗅觉气味,特别是为香味、风味和/或除臭/掩蔽组合物提供青绿、果香、梨和/或糯质嗅觉气味。
发明概述
本发明公开了包含式(I)的2-和/或3-取代的3-(烯丙氧基)丙烯的新型香味、风味和/或除臭/掩蔽组合物
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基。在根据本发明的一个实施方案中,R1是具有至多5个碳原子的烷基。在根据本发明的一个实施方案中,式(I)的2-和/或3-取代的3-(烯丙氧基)丙烯不包括具有甲基作为R1和氢作为R2的式(I)化合物。在根据本发明的一个实施方案中,式(I)的2-和/或3-取代的3-(烯丙氧基)丙烯包含至少8个碳原子。在根据本发明的一个实施方案中,R1是具有至少2个碳原子的烷基。为了避免产生疑问,基团R1和R2是分开的基团,即它们不会在一起形成环。在另一个实施方案中, 本发明的化合物可以是手性的,例如,它们可以用作立体异构混合物,更具体地说是对映体的混合物;R异构体、S异构体、R和S异构体的外消旋混合物和/或非-外消旋混合物也可被有利地使用。
详细描述
表征根据本发明的化合物的术语"气味剂"意味着,在人类中,它触发了一种气味感觉,这种感觉优选是愉快的;因此,它通常用于加香工业和卫生制品、洗涤剂、清洁剂、个人保健用品、化妆品等。为了本发明和所附权利要求书的目的,术语“气味剂”包括"芳香物质"。芳香物质是通常用来指为食品提供气味和/或风味的物质的术语。
式(I)化合物可单独、作为其混合物,或与基础材料组合使用。
如本文所用的,"基础材料"包括选自广泛范围的天然产品中的所有已知的香味/风味材料,如:精油、提取物、树胶脂(resinoid)或现有可获得的分离物和合成材料,例如:烃、醇、醛和酮、醚和缩醛、酯和内酯、腈、肟或杂环,和/或与一种或多种通常与香味和/或风味组合物中的气味剂联合使用的成分或赋形剂/辅料(例如:溶剂/稀释剂、稳定剂、载体材料和本领域常用的其它辅助剂)的混合物。
根据式(I)的化合物可用于广泛范围的香味应用,例如在任何精细和功能性香料的领域内,例如香料、空气护理产品、家居产品、洗衣产品、身体护理产品和化妆品。所述化合物可以根据具体应用以及其它气味剂成分的性质和量,以大大不同的量使用。
根据本发明的一个优选的实施方案,根据本发明的香味、风味和/或除臭/掩蔽组合物含有至少一种如前所述的根据式(I)的化合物,其量在每种情况下相对于整体组合物为0.0001和95 wt. %之间,例如在0.001和25 wt. %之间,优选在0.01和15 wt. %之间,更有利地在0.1和10 wt. %之间,特别是在1和5 wt. %之间。
根据本发明的一个特别优选的实施方案,除了根据本发明的式(I)化合物外,根据本发明的香味、风味和/或除臭/掩蔽组合物还含有另外的气味剂,其量例如为相对于整体香味和/或风味组合物的0.1-99.9 wt. %,优选5-90 wt. %,特别是15-70 wt. %。
如上文所述的式(I)化合物可简单地通过使至少一种式(I)化合物、或包含所述式(I)化合物的香味组合物与消费品基础直接混合而在消费品基础中使用;或它们可在较早的步骤中用包夹材料例如聚合物、胶囊、微胶囊和/或纳米胶囊、脂质体、成膜剂、吸收剂如活性炭或沸石、环状低聚糖及其两种或更多种的混合物包夹,或它们可以与适合于在施加外部刺激如光、高温、酶、空气、水等时释放香味分子的基质化学结合,然后与消费品基础混合。
因此,本发明可用于现有的制备香味、风味和/或除臭/掩蔽组合物的方法,其包括掺入作为香味、风味和/或除臭/掩蔽成分的式(I)化合物,即通过将该化合物与消费品基础直接混合,或通过混合包含所述式(I)化合物的香味、风味和/或除臭/掩蔽组合物,所述组合物然后可以使用传统的技术和方法与消费品基础混合。如上所述,通过添加嗅觉可接受量的至少一种本发明的式(I)化合物,可以改进、增强和/或改变消费品基础的的气味氛围。
本发明提供包含式(I)化合物的香味、风味和/或除臭/掩蔽组合物。
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基;在一个实施方案中,当R2是氢时,R1不能是叔丁基;在一个实施方案中,当R2是氢时,R1不能是戊基。
在根据本发明的一个实施方案中,香味、风味和/或除臭/掩蔽组合物包含式(I)化合物,其选自2-((烯丙氧基)甲基)己-1-烯、2-((烯丙氧基)甲基)-3-甲基丁-1-烯、2-(烯丙氧基)-4-甲基-3-亚甲基戊烷、4-(烯丙氧基)-2-甲基-3-亚甲基己烷、2-((烯丙氧基)甲基)庚-1-烯、2-((烯丙氧基)甲基)辛-1-烯、2-((烯丙氧基)甲基)十一碳-1-烯、2-((烯丙氧基)甲基)-3,7-二甲基辛-1,6-二烯和/或两种或更多种所述式(I)化合物的混合物。
在一个实施方案中,本发明还要求新的可用于香味、风味和/或除臭/掩蔽组合物的式(I)化合物,
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基,
条件是
- 当R2是氢时,R1不能是叔丁基,和
- 当R2是氢时,R1不能是戊基。
在一个实施方案中,可用于香味、风味和/或除臭/掩蔽组合物的式(I)化合物选自2-((烯丙氧基)甲基)己-1-烯、2-((烯丙氧基)甲基)-3-甲基丁-1-烯、2-(烯丙氧基)-4-甲基-3-亚甲基戊烷、4-(烯丙氧基)-2-甲基-3-亚甲基己烷、2-((烯丙氧基)甲基)辛-1-烯、2-((烯丙氧基)甲基)十一碳-1-烯、2-((烯丙氧基)甲基)-3,7-二甲基辛-1,6-二烯和/或两种或更多种所述化合物的混合物。
申请人还发现,从嗅觉的角度来看,式(I)化合物具有明显青绿、果香、梨和/或糯质特性,这使其本身可直接用于果香组合物,例如梨、榅桲(quince)、猕猴桃(kiwi)和/或菠萝。事实上,式(I)化合物表现出更多的糯质特性,使人想起全天然水果。它还更通用,对相关水果(榅桲/苹果)以及不相关水果(猕猴桃/菠萝)具有易于识别的应用。此外,与其它气味剂例如梨酯(Pear Ester)比较,式(I)化合物具有更大的深度和存在性,以及使得它非常有价值的附加性质,即它们在各种应用媒介、特别是碱性媒介中更大的稳定性。例如,当R1被选择为具有4个碳原子的烷基时,申请人已发现可以获得一个极冗长(diffusive)的、青绿、果香和梨导向的嗅觉气味。
式(I)化合物可以有利地通过使用Williamson醚合成步骤,从相应的式(II)的2-和/或1-取代烯丙醇制备:
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基,
例如在碱例如氢化钠和/或氢氧化钠和/或氢氧化钾的存在下,通过使式(II)的醇与烯丙基溴和/或烯丙基氯反应。然后,所产生的醚优选通过蒸馏提纯。
在所述式(II)的醇化合物中,R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢和/或具有至多5个碳原子的烷基或烯基;R1和R2都可以是直链和/或分支烷基。
在根据本发明的一个实施方案中,式(II)中定义的醇可有利地从式(III)的2-取代丙烯醛合成:
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,
这通过还原,例如用硼氢化钠或氢化铝锂还原,或者通过有机金属试剂的亲核加成,有机金属试剂例如为适宜的烷基卤化镁R2MgX例如MeMgCl。
在根据本发明的一个实施方案中,式(III)的丙烯醛可有利地通过式(IV)的醛与甲醛(或甲醛源)反应来合成
其中R1是具有至多9个碳原子的烷基(直链和/或分支烷基)或具有至多9个碳原子的烯基,例如通过使用甲醛(例如37%的甲醛水溶液)或甲醛源(例如仲甲醛)以及硼酸和仲胺组合,例如硼酸和仲胺如二乙醇胺的组合;在本发明的一个实施方案中,4-甲氧基苯甲酸和二正丁胺的酸碱组合也可用于醛与甲醛的反应。上述醛与甲醛的反应导致如上定义的式(III)的2-取代丙烯醛的形成。
在根据本发明的一个实施方案中,式(I)化合物可有利地通过以下3个连续步骤制备:
- 使式(IV)的醛
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,
经历与甲醛的反应,形成式(III)的2-取代丙烯醛
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,
- 使前一步骤的式(III)的2-取代丙烯醛经历还原或有机金属试剂的亲核加成反应步骤,形成式(II)的1-取代烯丙醇
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基,和
- 使前一步骤的式(II)的1-取代烯丙醇经历Williamson醚合成步骤,形成式(I)化合物
其中R1是具有至多9个碳原子的烷基或者具有至多9个碳原子的烯基,且R2是氢或具有至多5个碳原子的烷基或烯基。
合成根据本发明的式(I)化合物的示意性方案表示如下:
其中在α位置具有两个氢的醛通过与甲醛(以仲甲醛或福尔马林的形式)反应被转化为丙烯醛;用硼氢化钠还原丙烯醛为相应的烯丙醇;使用例如烯丙基氯,使烯丙醇经历Williamson合成,形成双烯丙基醚。
在本发明的一个实施方案中,醇醛缩合,特别是醛与甲醛的反应(第一制备步骤)在基于硼酸和仲胺、优选二乙醇胺的催化剂的存在下进行。通过开发这一具体的制备步骤,申请人大大改进了整个制备方法,这是由于催化剂的低气味影响,例如当与其它使用气味强烈的胺如二乙胺、二丁胺、哌啶或吡咯烷或者气味难闻的酸如脂肪酸的醇醛缩合用催化体系比较,并且由于低催化剂负载量,当与类似的催化体系如二丁胺/己酸或哌啶/硬脂酸比较。所述催化体系组分的可用性、低成本和硼酸与其它具有类似pKa的酸相比相对较低的分子量的组合是特别有利的,因为它对使用所述催化体系的亚甲基化过程的经济方面产生了积极的影响。
在本发明的一个实施方案中,还提供了一种用于使式(IV)-(a)的醛
其中R1是具有至多9个碳原子的烷基、具有至多9个碳原子的烯基、具有至多9个碳原子的炔基、苯基、具有至多9个碳原子的取代的芳基、具有至多9个碳原子的氧代-烷基、具有至多9个碳原子的烷氧基芳基或具有至多9个碳原子的(取代的)苄基,
与甲醛或甲醛源反应,形成式(III)-(a)的2-取代丙烯醛的方法
其中R1是具有至多9个碳原子的烷基、具有至多9个碳原子的烯基、具有至多9个碳原子的炔基、苯基、具有至多9个碳原子的取代的芳基、具有至多9个碳原子的氧代-烷基、具有至多9个碳原子的烷氧基芳基或具有至多9个碳原子的(取代的)苄基。
在本发明的一个实施方案中,式(IV)-(a)的醛的烷基、烯基、炔基和氧代烷基可以是线性、分支或环状的。在根据本发明的一个实施方案中,式(IV)-(a)醛的R1可以是乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、1-戊基、2-戊基、3-戊基、1-己基、2-己基、3-己基、1-庚基、2-庚基、3-庚基、4-庚基、1-辛基、2-辛基、3-辛基、4-辛基、1-壬基、2-壬基、3-壬基、4-壬基、5-壬基、环丙基、环丁基、环戊基、环己基、1-(环己基甲基)、(甲氧基)甲基、(乙氧基)甲基、乙烯基、1-丙烯基、1-异丁烯基、3-丁烯基、5-(2-甲基戊-2-烯)基、4-戊-2-烯基、4-戊-1-烯基、4-(4-甲基戊-1-烯)基、5-(2,5-二甲基己-2-烯)基、2,2,3-三甲基环戊-3-烯-1-基、苄基、苯基或4-甲氧基苯基。
在本发明的一个实施方案中,式(III)-(a)的2-取代丙烯醛的烷基、烯基、炔基和氧代烷基可以是线性、分支或环状的。在根据本发明的一个实施方案中,式(III)-(a)的2-取代丙烯醛的R1是乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、1-戊基、2-戊基、3-戊基、1-己基、2-己基、3-己基、1-庚基、2-庚基、3-庚基、4-庚基、1-辛基、2-辛基、3-辛基、4-辛基、1-壬基、2-壬基、3-壬基、4-壬基、5-壬基、环丙基、环丁基、环戊基、环己基、1-(环己基甲基)、(甲氧基)甲基、(乙氧基)甲基、乙烯基、1-丙烯基、1-异丁烯基、3-丁烯基、5-(2-甲基戊-2-烯)基、4-戊-2-烯基、4-戊-1-烯基、4-(4-甲基戊-1-烯)基、5-(2,5-二甲基己-2-烯)基、2,2,3-三甲基环戊-3-烯-1-基、苄基、苯基或4-甲氧基苯基。
该方法的特征是,该反应(步骤I)是在硼酸和仲胺(例如二丁胺,优选二乙醇胺)的存在下进行的。
在根据本发明的一个实施方案中,式(III)-(a)的丙烯醛(例如式(III)的那些)的合成,即醛与甲醛的反应(步骤I),可有利地通过使式(IV)-(a)的醛(例如式(IV)的那些)与甲醛水溶液(或甲醛的备选来源,例如仲甲醛)在二烷基胺和硼酸的存在下反应来进行,此时二烷基胺与中间体式(IV)-(a)的醛的摩尔比在0.01和99.9之间,例如0.02和0.2之间;和/或硼酸与中间体式(IV)-(a)的醛的摩尔比在0.01和99.9之间,例如在0.02和0.2之间。
在根据本发明的一个实施方案中,式(III)-(a)的丙烯醛的合成(步骤I)优选在不添加附加溶剂的情况下进行,但可以使用任何合适的极性或非极性、质子或非质子溶剂。
在根据本发明的一个实施方案中,式(III)-(a)的丙烯醛的合成在20和95℃之间,更优选在60和80℃之间执行。
在本发明的一个实施方案中,要求的香味、风味和/或除臭/掩蔽组合物被有利地用作香料组合物。根据本发明的香料组合物一般包括香料、古龙水(cologne)、淡香水(eaudu toilette)和/或浓香水(eau de parfum)。在本发明的一个实施方案中,要求的香味、风味和/或除臭/掩蔽组合物被有利地用于化妆品制剂、个人护理产品、清洁产品、织物柔软剂和/或空气清新剂等。此外,在本发明的实施方案范围内的是,本文描述的新型香味、风味和/或除臭/掩蔽组合物和/或新的式(I)化合物可以掺入建筑材料、墙壁和地板覆盖物、车辆部件等中。
一般来说,除了本文描述的新型气味剂和/或香味、风味和/或除臭/掩蔽组合物外,合适的香味、风味或除臭组合物还可以有利地包括常规成分,例如溶剂、载体、稳定剂、乳化剂、保湿剂、分散剂、稀释剂、增稠剂、冲淡剂、其它气味剂和/或辅剂等。
式(I)化合物与许多已知的天然或合成的香味、风味和/或除臭/掩蔽材料相结合,从而天然成分的范围可不仅包括易挥发成分,而且包括半挥发成分和微挥发成分,合成成分的范围可以包括来自多种物质的代表,例如描述于Steffen Arctander, Perfume andFlavor Chemicals, 卷1&2, Montclair, N.J., 1969; Steffen Arctander, Perfumeand Flavor Materials of Natural Origin, Elizabeth, N.J., 1960或Horst Surburg,Johannes Panten, Common Fragrance and Flavor Materials, Wiley-VCH, Weinheim,2016中,以及如从以下非限制性汇编中将明显的。
天然产品如:
香旱芹油(Ajowan oil)、香树油(Amyris oil)、艾蒿油(Armoise oil)、青蒿油(Artemisia oil)、罗勒油(Basil oil)、纯净蜂蜡(Bees wax absolute)、佛手柑油(Bergamot oil)、桦木焦油(Birch tar oil)、黑胡椒油(Black pepper oil)、黑胡椒油树脂(Black pepper oleoresin)、樟脑油(Camphor oil)、依兰油(Cananga oil)、藏茴香油(Caraway oil)、小豆蔻油(Cardamom oil)、胡萝卜籽油、纯净海狸香(Castoreumabsolute)、雪松叶油(Cedar leaf oil)、雪松木油(Cedarwood oil)、芹菜籽油(Celeryseed oil)、春黄菊油(Chamomile oil)、桂皮油(Cinnamon bark oil)、桂叶油、纯净岩蔷薇油(Cistus absolute)、岩蔷薇油(Cistus oil)、香茅油(Citronella oil)、香茅萜(Citronella terpenes)、鼠尾草油(Clary sage oil)、精馏丁香油(Clove oilrectified)、康酿克油(Cognac oil white)、芫荽籽油(Coriander seed oil)、孜然籽油(Cumin seed oil)、柏树油(Cypress oil)、印蒿油(Davana oil)、莳萝籽油(Dill seedoil)、榄香脂油(Elemi oil)、榄香树胶脂(Elemi resinoid)、桉树油(Eucalyptus oil)、冷杉叶油(Fir needle oil)、白松香油(Galbanum oil)、天竺葵油(Geranium oil)、印度姜油(Ginger oil Indian)、葡萄柚油(Grapefruit oil)、愈创木油(Guaiacwood oil)、古芸香胶(Gurjun balsam)、纯净茉莉油(Jasmin absolute)、甘松油(Jatamansi oil)、杜松籽油(Juniper berry oil)、杜松叶油、卡胡尔油(Kachur oil)、纯净劳丹脂(Labdanumabsolute)、劳丹树胶脂(Labdanum resinoid)、熏衣草油(Lavender oil)、柠檬油、柠檬油萜、柠檬香茅草油(Lemongrass oil)、酸橙油(Lime oil)、山苍子油(Litsea cubeba oil)、山苍子萜(Litsea cubeba terpenes)、Lobhan choya树胶脂、橘油(Mandarin oil)、薄荷油(Mentha arvenis oil)、柠檬薄荷油(Mentha citrata oil)、纯净含羞草油(Mimosaabsolute)、没药树胶脂(Myrrh resinoid)、莎草油(Nagarmotha oil)、肉豆蔻油(Nutmegoil)、纯净橡苔(Oakmoss absolute)、橡苔树胶脂(Oakmoss resinoid)、乳香油(Olibanumoil)、乳香树胶脂(Olibanum resinoid)、橙油、牛至油(Origanum oil)、玫瑰草油(Palmarosa oil)、广藿香油(Patchouli oil)、胡椒薄荷油(Peppermint oil)、秘鲁香脂树胶脂(Peru Balsam resinoid)、卑柠油(Petitgrain oil)、松叶油(Pine needle oil)、粉椒油(Pink pepper oil)、纯净玫瑰油(Rose absolut)、玫瑰油(Rose oil)、迷迭香油、檀香木油(Sandalwood oil)、纯净海藻油(Seaweed absolute)、留兰香油(Spearmint oil)、印度苏刚达精油(Sugandh kokila oil)、印度苏刚达香薰油(Sugandh mantri oil)、万寿菊油(Tagete oil)、妥卢香脂树胶脂(Tolu Balsam resinoid)、纯净晚香玉油(Tuberoseabsolute)、姜黄油(Turmeric oil)、松节油(Turpentine oil)、缬草油(Valerian oil)、香根油(Vetiver oil)、香根萜(Vetiver terpenes)。
合成原料,例如:
酯类例如:C16醛、格蓬酯、己酸烯丙基酯、环己基丙酸烯丙基酯、庚酸烯丙基酯、苯氧基乙酸烯丙基酯、乙酸异戊酯、苯甲酸戊酯、丁酸戊酯、己酸戊酯、肉桂酸戊酯、异戊酸戊酯、苯基乙酸戊酯、丙酸戊酯、水杨酸异戊酯、乙酰化香树油(Amyris acetate)、醋酸茴香酯、乙酸苄酯、苯甲酸苄酯、丁酸苄酯、肉桂酸苄酯、甲酸苄酯、异丁酸苄酯、苄基异丁香酚、丙酸苄酯、水杨酸苄酯、惕各酸苄酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸石竹烯酯(Caryophyllene acetate)、乙酸柏木酯(Cedryl acetate)、乙酸肉桂酯、丁酸肉桂酯、顺式-3-己烯基乙酸酯、顺式-3-己烯基苯甲酸酯、顺式-3-己烯基己酸酯、顺式-3-己烯基甲酸酯、顺式-3-己烯基异丁酸酯、顺式-3-己烯基-2-甲基丁酸酯、顺式-3-己烯基丙酸酯、顺式-3-己烯基水杨酸酯、顺式-3-己烯基惕各酸酯、醋酸香茅酯(Citronellyl acetate)、丁酸香茅酯、甲酸香茅酯、异丁酸香茅酯、丙酸香茅酯、惕各酸香茅酯、异丁酸三环癸烯酯(Cyclabute)、环格蓬酯(Cyclogalbanate)、环己基乙酸乙酯、乙酸癸酯、邻苯二甲酸二丁酯、丙二酸二乙酯、邻苯二甲酸二乙酯、醋酸二氢月桂烯酯(Dihydromyrcenyl acetate)、醋酸二甲基辛酯,乙酸二甲基苯基乙基原酯(Dimethyl phenyl ethyl carbinyl acetate)、己二酸二辛酯、邻苯二甲酸二辛酯、乙酸二甲基苄基原酯、丁酸二甲基苄基原酯、乙酸乙基芳樟酯(Ethyl linalyl acetate)、2-甲基丁酸乙酯、3-苯基丙酸乙酯、乙酸乙酯、乙酰乙酸乙酯、苯甲酸乙酯、丁酸乙酯、癸酸乙酯、己酸乙酯、辛酸乙酯、肉桂酸乙酯、庚酸乙酯、乙基己基乙酸酯、异丁酸乙酯、月桂酸乙酯、壬酸乙酯(Ethyl pelargonate)、苯氧基乙酸乙酯、乙基苯基乙酸酯、乙基苯基环氧乙烷甲酸酯(Ethyl phenyl glycidate)、丙酸乙酯、藏红花酸乙酯(Ethyl safranate)、水杨酸乙酯、戊酸乙酯、乙酸丁香酚酯(Eugenyl acetate)、Evernyl、乙酸小茴香酯(Fenchyl acetate)、Floramat、Frescolat ML、乙酸乙基甲基二茂烷酯(Fructone)、三环癸烷羧酸乙酯(Fruitate)、乙酸香叶酯(Geranyl acetate)、丁酸香叶酯、甲酸香叶酯、丙酸香叶酯、惕各酸香叶酯、2-乙基-6,6-二甲基-2-环己烯-1-甲酸乙酯(Givescone)、乙酸愈创木醇酯(Guaiol acetate)、二氢茉莉酮酸酯(Hedionate)、二氢茉莉酮酸甲酯(Hedione)、海菲麝香(Helvetolide)、香菠酯(Herbanate)、乙酸己酯、苯甲酸己酯、丁酸正己酯、己酸己酯、异丁酸己酯、丙酸己酯、水杨酸己酯、乙酸异冰片酯、乙酸异丁酯、异丁基苯基乙酸酯、水杨酸异丁酯、乙酸异丁香酚酯(Isoeugenyl acetate)、乙酸异壬酯、异戊酸酯、2-甲基丁酸异丙酯、肉豆蔻酸异丙酯、茉莉酯(Jasmonyl)、顺式-3-己烯醇碳酸甲酯(Liffarome)、乙酸芳樟酯(Linalyl acetate)、藿檀酯(Mahagonate)、母菊酯(Manzanate)、二氢松香醇醋酸酯(Menthanyl acetate)、醋酸薄荷酯、苯甲酸甲酯、2-甲基丁基乙酸酯、2-甲基戊丁酯(Methyl camomille)、肉桂酸甲酯、环香叶酸甲酯(Methylcyclogeranate)、庚炔羧酸甲酯(Methyl heptine carbonate)、月桂酸甲酯、辛炔羧酸甲酯(Methyl octine carbonate)、苯基乙酸甲酯、水杨酸甲酯、甲基-2-甲基丁酸酯、新福力酯(Neofolione)、乙酸诺吡酯(Nopyl acetate)、乙酸辛烯基酯、乙酸辛酯、异丁酸辛酯、乙酸对甲酚酯(Para cresyl acetate)、异丁酸对甲酚酯、苯基乙酸对甲酚酯、梨酯、2-甲基戊酸2-甲基戊酯(Peranat)、异丁酸苯氧基乙酯、乙酸苯基乙酯、丁酸苯基乙酯、甲酸苯基乙酯、异丁酸苯基乙酯、苯基乙酸苯基乙酯、丙酸苯基乙酯、水杨酸苯基乙酯、惕各酸苯基乙酯、异丁酸苯基丙酯、乙酸异戊烯酯(Prenyl acetate)、罗曼麝香(Romandolide)、Sagecete、乙酸苏合香酯(Styrallyl acetate)、丙酸苏合香酯(Styrallyl propionate)、红桔酯(Tangerinol)、乙酸松油酯(Terpinyl acetate)、Thesaron、反式-2-己烯基乙酸酯、Tropicate、2-叔丁基环己基乙酸酯(Verdox)、乙酸三环癸烯酯(Verdyl acetate)、丙酸三环癸烯酯、乙酸对叔丁基环已酯(Vertenex)、二甲基-3-苯丁醇乙酸酯(Vetikol acetate)、乙酸香根酯(Vetiveryl acetate)、Yasmolys。
内酯类,如:异黄葵内酯(Ambrettolide)、Arova N、3-丙亚基-1-异苯并呋喃酮(Celeriax)、δ-癸内酯、γ-癸内酯、δ-十二内酯、γ-十二内酯、巴西酸亚乙酯(Ethylenebrassylate)、环十五内酯(Exaltolide)、γ-庚内酯、δ-己内酯、γ-己内酯、甲基莱托酮(Methyl laitone)、甲基辛内酯、δ-壬内酯、γ-壬内酯、八氢香豆素、δ-辛内酯、γ-辛内酯、Rootylone、环十六内酯(Silvanone supra)、δ-十一内酯、γ-十一内酯、γ-戊内酯、10-氧杂十六内酯(OHD麝香)、香豆素(Coumarin)、环十五烯内酯(Habanolide)、茉莉内酯(Jasmolactone)。
醛类,如:乙醛、阿道克醛(Adoxal)、C10醛、异C11醛(Aldehyde C11 iso)、C11 moa醛、十一碳烯醛C11 (Aldehyde C11 undecylenic)、十一碳醛C11 (Aldehyde C11undecylic)、月桂醛C12、醛C12 MNA、茴香醛(Anisaldehyde)、戊基肉桂醛、苯甲醛、波洁红醛(Bourgeonal)、樟脑烯醛(Campholenaldehyde)、Cantonal、紫罗兰醛(Cetonal)、肉桂醛、顺式-4-癸烯醛、顺式-6-壬烯醛、柠檬醛、香茅醛、香茅基氧基乙醛(Citronellyloxyacetaldehyde)、可卡醛(Cocal)、枯茗醛(Cuminaldehyde)、Curgix、Cyclal C、兔耳草醛(Cyclamen aldehyde)、铃兰甲醛(Cyclomyral)、女贞醛(Cyclovertal)、癸烯醛9、Dupical、柑青醛(Empetal)、乙基香草醛(Ethyl vanillin)、海风醛(Floralozone)、花青醛(Florhydral)、癸二烯醛(Geraldehyde)、胡椒基丙醛(Helional)、洋茉莉醛(Heliotropin)、庚醛、己醛、己基肉桂醛、新铃兰醛(Hivernal neo)、氢化阿托醛(Hydratropaldehyde)、羟基香茅醛、内十一烯醛(Intreleven aldehyde)、异丁酸香兰酯(Isobutavan)、异环柠檬醛(Isocyclocitral)、异戊醛、铃兰醛(Lilial)、新柠檬醛(Limonenal)、马赛醛(Maceal)、梅弗兰醛(Mefranal)、甜瓜醛(Melonal)、甲基肉桂醛、反式-2顺式-6壬二烯醛、壬醛、辛醛、Oncidal、对甲苯醛(Para tolyl aldehyde)、苯基乙醛、苯基丙醛、甲基柑青醛B (Precyclemone B)、藏红花醛(Safranal)、水杨醛、清风醛(Scentenal)、丁香醛(Syringa aldehyde)、反式-4-癸烯醛, 反式-2-十二烯醛、反式-2-己烯醛、反式-2-壬醛、新女贞醛(Trifernal)、香草醛、藜芦醛(Veratraldehyde)、鲜草醛(Vernaldehyde)。
酮类,如:山楂花酮(Acetanisol)、乙偶姻(Acetoin)、苯乙酮、Aldron、烯丙基紫罗兰酮(Allyl ionone)、苯甲酮、苄基丙酮、西瓜酮(Calone)、莰酮(Camphor)、d-香芹酮、l-香芹酮、喀什米尔木麝香(Cashmeran)、柏木基甲基酮(Cedryl methyl ketone)、二氢茉莉酮酸甲酯(Cepionate)、Claritone、Cosmone、萨利麝香(Crysolide)、Cyclotene、大马烯酮(Damascenone)、大马酮α, 大马酮β、大马酮δ、大马酮γ、二乙酰(Diacetyl)、二氢-β-紫罗兰酮、二氢茉莉酮酸酯(Dihydro isojasmonate)、二甲基辛烯酮、王朝酮(Dynascone)、乙基戊基酮、乙基麦芽酚、葑酮(Fenchone)、榛子酮(Filbertone)、香叶基丙酮(Geranylacetone)、环十六烯酮(Globanone)、庚基环戊酮、α-紫罗兰酮(Ionone α)、β-紫罗兰酮、紫罗兰酮纯(Ionone pure)、鸢尾木(Iriswood)、α-鸢尾酮(Irone α)、龙涎酮(Iso E Super)、异葑酮(Isofenchone)、异茉莉酮T (Isojasmone T)、异洛酮K (Isolone K)、异薄荷酮(Isomenthone)、异佛尔酮、顺式-茉莉酮(Jasmone cis-)、Kambernoir、加菲力士(Kephalis)、6-五甲基庚-3-烯-2-酮(Koavone)、Lavendinal、麦芽酚(Maltol)、薄荷酮、甲基苯乙酮、甲基戊基酮、甲基庚烯酮、甲基己基酮、γ-甲基紫罗兰酮、甲基萘基酮β、甲基壬基酮、麝香烯酮(Muscenone)、麝香酮(Muscone)、桃酮(Nectaryl)、Orinox、OTBC酮、对叔丁基环己酮、Patchwood、粉檀麝香(Phantolid)、Pharaone、胡椒酮(Piperitone)、普利卡酮(Plicatone)、覆盆子酮(Raspberry ketone)、覆盆子酮甲基醚、藏花茚(Safraleine)、螺环格蓬酮纯(Spirogalbanone pure)、吐纳麝香(Tonalid)、三甲基琥珀酮(Trimofix O)、凡路酮(Veloutone)、Vetikon。
醇类,如:羰基合成C13醇(Alcohol oxo C13)、琥珀核(Amber core)、Ambermax、龙涎香八氢萘醇(Ambrinol)、戊基乙烯基原醇(Amyl vinyl carbinol)、茴香醇(Anisicalcohol)、白檀醇(Bacdanol)、苄醇、丁醇、结晶柏木醇(Cedrol crystals)、肉桂醇、香茅醇、花冠醇(Coranol)、癸醇(Decanol)、二甲基苄基原醇、二甲基辛醇、二甲基苯基乙基原醇、二甲基庚醇(Dimetol)、葑醇(Fenchol)、己醇、异冰片(Isoborneol)、异冰片基环己醇、爪哇檀香(Javanol)、Keflorol、四甲基-4-亚甲基-2-庚醇(Kohinool)、月桂醇、Lilyflore、氧化芳樟醇(Linalool oxide)、五月铃兰醇(Mayol)、薄荷醇、赛木香醇(Norlimbanol)、辛醇、沙针醇(Osyrol)、对叔丁基环己醇、苯基异己醇(Phenoxanol)、苯氧基乙醇、苯基乙醇、苯基丙醇、丙二醇、甲基苯戊醇(Rosaphen)、玫瑰二醇、苏合香醇(Styrallyl alcohol)、三环癸烷二甲醇、四氢芳樟醇、四氢月桂烯醇、特木倍醇(Timberol)、甲基癸烯醇(Undecavertol)、顺式-3-己烯醇、左旋香茅醇(Citronellol laevo)、环花醇(Cyclofloranol)、二氢芳樟醇(Dihydrolinalool)、二氢月桂烯醇(Dihydromyrcenol)、二氢月桂烯醇(Dimyrcetol)、黑檀醇(Ebanol)、香叶醇(Geraniol)、异蒲勒醇(Isopulegol)、里哪醇(Linalool)、橙花醇(Nerol)、橙花叔醇(Nerolidol)、反式-2顺式-6壬二烯醇、聚檀香醇(Polysantol)、Rosalva、白雷曼檀香核(Sandalmysore core)、檀香(Sandalore)、萜烯-4-醇(Terpinen-4-ol)、萜品醇(Terpineol)、反式-2-己烯醇。
酚类,如:丁羟茴醚、二氢丁香酚(Dihydroeugenol)、二甲氢醌、二甲间苯二酚、丁香酚纯(Eugenol pure)、愈创木酚、异丁香酚、间甲酚、甲基丹提力士(Methyl diantilis)、对甲酚、丙烯基乙基愈创木酚(Propenyl guaethol)、麝香草酚(Thymol)、香荚兰醇(Ultravanil)。
醚类,如:降龙涎香醚(Ambroxan)、茴香脑(Anethole)、花药(Anther)、苄基异戊基醚、苄基异丙基醚、异戊酸苄酯、鸢尾香木(Boisiris)、柏木甲醚(Cedramber)、降龙涎醚(Cetalox)、癸基甲基醚、二苄基醚、二氢玫瑰氧化物、二苯醚(Diphenyl oxide)、道立米(Doremox)、草蒿脑(Estragole)、乙基芳樟醇、桉油精、佳乐麝香(Galaxolide)、吉兰吡喃(Gyrane)、Herbavert、酸橙氧化物(Lime oxide)、Madrox、甲基异丁香酚、萘基异丁基醚β、橙花醚(Nerol oxide)、萘乙醚(Nerolin bromelia)、对甲苯基丁醚、对甲苯基甲基醚、Petiole、苯基乙基甲基醚、2,4-二甲基-4-苯基呋喃(Rhubafuran)、玫瑰氧化物(Roseoxide)、芳香玫瑰醚(Rosyrane)、龙涎香醚(Trisamber)、Vetylbois K、萘基甲基醚(Yarayara)。
缩醛如:乙缩醛CD、乙缩醛R、龙涎缩醛(Amberketal)、乙氧基环十二烷基甲烷(Boisambrene forte)、柠檬醛二乙缩醛(Citrathal)、1,1-二乙氧基乙烷、翠绿亚胺(Emeraldine)、Freshopal、薰衣草噁烷(Herboxane)、Indoflor、Jacinthaflor、Magnolan、香辣醚(Spirambrene)、苯乙醛二甲缩醛(Viridine)、爱林塔尔(Elintaal)、克力二噁茂烷(Glycolierral)、卡拉花醛(Karanal)、圆柚甲烷(Methyl pamplemousse)。
烃类,如:红没药烯(Bisabolene)、莰烯、蒈烯δ3 (Carene delta 3)、石竹烯(Caryophyllene)、柏木烯(Cedrene)、对伞花烃(Cymene para)、二戊烯(Dipentene)、二苯基甲烷、异长叶烯(Isolongifolene)、d-柠檬烯、长叶烯(Longifolene)、月桂烯(Myrcene)、萘、罗勒烯(Ocimene)、蒎烯α、蒎烯β、苯乙烯、萜品烯γ、萜品油烯(Terpinolene)、1,3,5-十一碳三烯、异丙基格篷(Verdoracine)。
硫化合物,如:Corps cassis、二丁基硫醚、二甲基硫醚、2-己基-3-氧代环戊羧酸甲酯(Exovert)、西柚硫醇(Grapefruit thiol)、噁烷(Oxane)、巯基马来酮(Ribesmercaptan)、硫噻唑(Sulfurol)、桉叶硫醚(Thiocineol)。
腈类,如:肉桂腈(Cinnamyl nitrile)、香茅腈(Citronellyl nitrile)、3.7-二甲基-6-辛烯腈(Citronitrile)、Clonal、枯茗腈(Cumin nitrile)、己基环戊酮、鸢尾腈、3,7-二甲基-2,6-辛二烯腈(Lemonile)、牡丹腈(Peonile)、十三烷基腈、Agrumen nitrile、正癸腈。
肟类,如:二甲基二环辛酮肟(Buccoxime)、雷冰诺星(Labienoxime)、榄青酮(Stemone)。
氮杂环,如:2-乙酰吡嗪、2-乙酰吡啶、仲丁基喹啉、Corps racine、2-乙基-3,5(或6)-二甲基吡嗪、糠基吡咯、吲哚、异丁基喹啉、2-异丁基-3(或6)-甲氧基吡嗪、异丙基喹啉、Maritima、对甲基喹啉、3-甲基吲哚(Skatol)、2,3,5-三甲基吡嗪。
硝基化合物如:麝香酮(Musk Ketone)。
希夫碱类,如:橙花素(Aurantiol)、半日花素(Helianthral)、女贞缩醛(Ligantraal)、玲兰素(Verdantiol)。
其它材料如:乙酰苯胺、环胺(Gardamide)、对苯二甲酰胺、邻氨基苯甲酸二甲基酯、邻氨基苯甲酸甲酯、正丁酸、癸酸、己酸、辛酸、苯基乙酸、石竹烯氧化物、环氧柏木醚(Cedroxyde)、Tobacarol。
因此,式(I)化合物可用于生产组合物,和如从上述汇编中可以明显看出的,广泛的已知气味剂/香味、风味和/或除臭/掩蔽材料。在这样的组合物的生产中,早先提及的已知的香味、风味和/或除臭/掩蔽材料可以根据香料商已知的方法使用,例如,根据W. A.Poucher, Perfumes, Cosmetics and Soaps 2, 第7版, Chapman and Hall, 伦敦1974。
在本发明的一个实施方案中,要求的香味、风味和/或除臭/掩蔽组合物除了包含烯丙醚外,还至少包含一种酯和/或一种醇,优选至少是酯和醇的混合物;所述酯和/或醇优选是从本文上面定义的列表中选择的。在本发明的一个实施方案中,要求的气味剂组合物的特征是式(I)化合物与酯和/或醇一起的总含量超过25 wt%,优选超过50wt%,例如超过75wt%,或甚至超过90wt%。
在本发明的另一个实施方案中,要求的香味、风味和/或除臭/掩蔽组合物除了包含烯丙醚外,还包含它们各自的通式(II)的母体醇。在本发明的一个实施方案中,要求的气味剂组合物的特征是通式(I)的烯丙基醚与它们各自的式(II)母体醇一起的总含量超过5wt%,例如超过25 wt%,优选超过50 wt%,例如超过75 wt%,或甚至超过90 wt%。
通过以下实施例进一步说明本公开内容,这些实施例绝不应被解释为进一步的限制。本领域技术人员会很容易地理解,所描述的具体方法和结果仅仅是说明性的。
本公开内容的化合物的所有立体异构体,无论是混合物或纯的或基本纯的形式都被考虑。本公开内容的化合物可以在任何碳原子处有不对称中心,因此,要求的化合物可能以对映体形式或非对映体形式存在,或以其混合物存在。制备方法可以利用外消旋体、(纯)对映体、对映体的非外消旋混合物、非对映体或非对映体的混合物作为起始材料。当非对映体或对映体产物作为混合物获得时,它们可以通过常规方法分离,例如色谱分离、分级结晶或通过非对映体盐的形成来分离。在想要的情况下,也可以通过遵循适当的对映选择性或非对映选择性反应来获得所需的对映体或非对映体。
实施例
实施例1:
2-((烯丙氧基)甲基)己-1-烯的合成:
步骤-1:合成2-亚甲基己醛:
在10-15℃,将己醛(3.88 kg, 38.7 mol, 1 eq.)经2小时时间加入到37%甲醛(3.78 kg, 46.5 mol, 1.2 eq.)、二正丁胺(252 g, 1.95 mol, 0.05 eq.)和对-茴香酸(295 g, 1.94 mol, 0.05 eq.)的含水混合物中,同时搅拌。加入完成后,将反应混合物于50℃搅拌2 h。随后,使反应混合物冷却至25℃,分离有机相,用水洗涤(3 x 2 L)并经硫酸钠(250 g)干燥。真空(45-49˚C/53毫巴)蒸馏粗产物,得到2-亚甲基己醛(3.98 kg, 91%),为无色液体。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.30-1.47 (m,4H), 2.03-2.07 (m, 2H), 4.85-4.86 (m, 1H), 5.00 (m, 1H), 10.05 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 13.6, 22.0, 27.3, 29.9, 133.7, 150.5,194.5。
步骤-2:合成2-亚甲基己-1-醇:
于10-15℃,将硼氢化钠(383 g, 10.1 mol, 272 meq.)经4小时时间加入到2-亚甲基己醛(4.18 kg, 37.3 mol, 1 eq.)和水(5.60 L)的混合物中,同时搅拌。然后于25℃将反应混合物搅拌3 h。随后,用10%氯化氢水溶液(3 L)猝灭反应混合物。分离有机相,用水(1 x 3 L)、10%碳酸钠水溶液(1 x 3 L)和盐水(1 x 3 L)顺序洗涤。真空(52-54℃/4毫巴)蒸馏有机相(4.13 kg),得到2-亚甲基己-1-醇(3.94 kg, 92%),为无色液体。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.30-1.47 (m,4H), 2.03-2.07 (m, 3H), 4.05 (s, 2H), 4.85-4.86 (m, 1H), 5.00 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 13.8, 22.6, 32.8, 35.6, 65.4, 108.6,149.0。
步骤-3:合成2-(烯丙氧基)甲基)己-1-烯:
于25℃,将粉末状氢氧化钾(1.76 kg, 31.4 mol, 1.99 eq.)经2小时时间加入2-亚甲基己-1-醇(1.80 kg, 15.8 mol, 1 eq.)和四-正丁基溴化铵(255 g, 791 mmol,0.05 eq.)的混合物中。然后于10-15℃,经6小时时间加入烯丙基氯(3.01 kg, 39.3 mol),同时搅拌。于25℃搅拌反应混合物16 h。随后,通过Büchner漏斗过滤反应混合物,并用甲基叔丁基醚(1 L)洗涤固体。用水(2 L)、5%氯化氢水溶液(300 mL)、5%碳酸钠水溶液(1 L)和盐水(2 L)顺序洗涤滤液。减压下去除挥发物(45℃/ 133毫巴)。真空(34-36℃/ 3毫巴)蒸馏残留物(2.46 kg),得到2-((烯丙氧基)甲基)己-1-烯(1.91 kg, 78%),为无色液体。GC纯度97.5 %。
1H NMR (400 MHz, CDCl3): δ 0.91 (t, J = 7.2 Hz, 3H), 1.31-1.47 (m,4H), 2.03-2.07 (m, 2H), 3.91-3.94 (s, 2H), 3.94-3.96 (m, 2H), 4.89 (s, 1H),5.00 (s, 1H), 5.15-5.19 (m, 1H), 5.25-5.30 (m, 1H), 5.87-5.97 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 12.6, 21.2, 28.5, 31.5, 69.5, 71.7, 109.8,115.5, 133.5, 145.0。
实施例2
合成2-((烯丙氧基)甲基)-3-甲基丁-1-烯:
步骤-1:合成3-甲基-2-亚甲基丁醛:
将3-甲基丁醛(391 g, 4.54 mol)在搅拌的同时加入到37%甲醛水溶液(368 g,4.54 mol)、二正丁胺(30.0 g, 232 mmol)和对-茴香酸(35.0 g, 230 mmol)的混合物中。然后将该混合物在70℃搅拌1 h。随后,使反应混合物冷却至20℃,加入饱和碳酸氢钠水溶液。分离有机相,通过蒸馏提纯粗产物(105-106℃,1巴),得到3-甲基-2-亚甲基丁醛(53 g,13 %),为无色液体。
步骤-2:合成3-甲基-2-亚甲基丁-1-醇:
在0℃,将硼氢化钠(800 mg, 21.1 mmol)在搅拌的同时分批加入到3-甲基-2-亚甲基丁醛(5.00 g, 50.9 mmol)在二氯甲烷(3 mL)和甲醇(6 mL)中的混合物中。然后,将该反应混合物在0℃搅拌15 min.,接着在20℃搅拌2 h。随后,加入2 M氯化氢水溶液,直到气体形成消失。然后,加入氯化钠(2.40 g, 40.8 mmol)。用水稀释混合物,用甲基叔丁基醚提取。分离有机相,用盐水洗涤,经硫酸钠干燥并在减压下去除挥发物(50℃, 400毫巴)。采用灯泡蒸馏法(bulb-to-bulb distillation)蒸馏残留物,得到3-甲基-2-亚甲基丁-1-醇(2.4 g, 48%),为无色液体。
步骤-3:合成2-((烯丙氧基)甲基)-3-甲基丁-1-烯:
在4℃、氮气气氛下,将60%氢化钠在矿物油中的悬浮液(3.00 g, 75.0 mmol)分批加入到3-甲基-2-亚甲基丁-1-醇(5.00 g, 49.9 mmol)的四氢呋喃(50 mL)溶液中。然后在4℃加入烯丙基溴(12.1 g, 100 mmol)。将该反应混合物在20℃搅拌3天。然后加入异丙醇(10 mL),接着加入水(10 mL)。分离有机相,而水相用甲基叔丁基醚提取(3 x)。合并有机相并在减压下去除挥发物(50℃, 6毫巴)。通过灯泡蒸馏法(110℃, 6毫巴)纯化残留物(6.00g),得到2-((烯丙氧基)甲基)-3-甲基丁-1-烯(1.40 g, 20 %),为无色液体。
实施例3:
合成4-(烯丙氧基)-2-甲基-3-亚甲基己烷:
步骤-1:合成3-甲基-2-亚甲基丁醛:
于25℃经2 h时间将3-甲基丁醛(200 g, 2.32 mol, 1 eq.)加入到37%甲醛水溶液(207 g, 2.55 mol, 1.1 eq.)、二正丁胺(15.0 g, 116 mmol, 0.05 eq.)和对-茴香酸(17.6 g, 116 mmol, 0.05 eq.)的混合物中,然后将该反应混合物在70℃加热4 h。使反应混合物冷却至25℃,分离有机相,用水洗涤(3 x 100 mL),并经硫酸钠(100 g)干燥。真空(42-45℃/ 100毫巴)蒸馏粗混合物,得到3-甲基-2-亚甲基丁醛(167 g, 73%),为无色液体。
1H NMR (400 MHz, CDCl3): δ 1.01 (d, J = 7.2 Hz, 6H), 2.69-2.76 (m,1H), 5.89 (s, 1H), 6.18 (d, J = 0.8 Hz, 1H), 9.46 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 20.2, 24.2, 131.1, 155.6, 193.5。
步骤-2:合成5-甲基-4-亚甲基己-3-醇:
在5℃,将3-甲基-2-亚甲基丁醛(100 g, 1.01 mol, 1 eq.)的四氢呋喃(500 mL)溶液经2小时时间加入到乙基氯化镁2M的四氢呋喃(611 g, 1.22 mol, 1.21 eq.)的预冷却的(-5℃)溶液中,同时搅拌。使反应混合物经3小时时间温热至25℃,然后在25℃搅拌4h。随后,加入40%氯化铵水溶液(250 mL),接着加入甲基叔丁基醚(300 mL),同时搅拌。然后,分离有机相并用甲基叔丁基醚(1 x 300 mL)提取水相。用盐水(100 mL)洗涤合并的有机相并经硫酸钠(100 g)干燥。减压下去除挥发物,真空(45-50℃/7-10毫巴)蒸馏残留物,得到5-甲基-4-亚甲基己-3-醇(70.5 g, 54%),为无色液体。
1H NMR (400 MHz, CDCl3): δ 0.85 (t, J = 7.6 Hz, 3H), 0.96 (d, J = 5.6Hz, 3H), 1.01 (d, J = 7.2 Hz, 3H), 1.43-1.63 (m, 2H), 2.16-2.23 (m, 2H),3.94-3.97 (m, 1H), 4.84 (s, 1H), 4.95 (s, 1H).
13C NMR (100 MHz, CDCl3): δ 8.3, 20.8, 20.9, 26.4, 28.3, 73.5, 105.3,156.5。
步骤-3:合成4-(烯丙氧基)-2-甲基-3-亚甲基己烷:
在25℃,将粉末状氢氧化钾(131 g, 2.33 mol, 2 eq.)经1小时时间加入到5-甲基-4-亚甲基己-3-醇(150 g, 1.17 mol, 1 eq.)和四正丁基溴化铵(18.7 g, 58.0 mmol,50 meq.)的混合物中。然后在25-35℃,经2小时时间加入烯丙基氯(224 g, 2.93 mol, 2.5eq.)。将该反应混合物在25℃搅拌16 h。随后,加入水(300 mL),接着加入甲基叔丁基醚(300 mL)。分离有机相,用水洗涤(3 x 300 mL),经硫酸钠(100 g)干燥。减压下去除挥发物。真空(52-59℃/7-13毫巴)蒸馏残留物,得到4-(烯丙氧基)-2-甲基-3-亚甲基己烷(78.7g, 40.0%),为无色液体。GC纯度= 96%。
1H NMR (400 MHz, CDCl3): δ 0.82 (t, J = 7.4 Hz, 3H), 0.96 (d, J = 6.8Hz, 3H), 1.00 (d, J = 6.8 Hz, 3H), 1.47-1.54 (m, 2H), 2.13-2.20 (m, 1H), 3.53(t, J = 6.8 Hz, 1H), 3.65-3.71 (m, 1H), 3.89-3.94 (m, 1H), 4.90 (s, 2H),5.05-5.08 (m, 1H), 5.15-5.21 (m, 1H), 5.78-5.84 (m, 1H).
13C NMR (100 MHz, CDCl3): δ 9.2, 21.6, 22.7, 26.0, 28.2, 68.0, 83.2,108.6, 115.2, 134.3, 154.5。
实施例4
合成2-(烯丙氧基)-4-甲基-3-亚甲基戊烷
2-(烯丙氧基)-4-甲基-3-亚甲基戊烷通过以下如在实施例3中类似的方法步骤制备。对于步骤-2,使用MeMgCl代替EtMgCl。收率28%。
实施例5
合成2-((烯丙氧基)甲基)庚-1-烯
2-((烯丙氧基)甲基)庚-1-烯根据在实施例1中描述的程序制备。收率51%。
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 7.0 Hz, 3H), 1.26-1.35 (m,4H), 1.45 (五重峰, J = 7.4 Hz, 2H), 2.05 (t, J = 7.7 Hz, 2H), 3.92 (s, 2H),3.96 (d, J = 5.5 Hz, 2H), 4.90 (s, 1H), 5.01 (s, 1H), 5.18 (d, J = 10.4 Hz,1H), 5.28 (br. d, J = 17.2 Hz, 1H), 5.92 (ddt, J = 17.1, 10.8, 5.6 Hz, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.6, 27.3, 31.6, 33.1, 70.9, 73.0,111.1, 116.8, 134.9, 146.3。
实施例6
合成2-((烯丙氧基)甲基)辛-1-烯
2-((烯丙氧基)甲基)辛-1-烯根据在实施例1中描述的程序制备。收率54%。
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 6.9 Hz, 3H), 1.29-1.47 (m,6H), 1.44 (五重峰, J = 7.7 Hz, 2H), 2.05 (t, J = 7.7 Hz, 2H), 3.92 (s, 2H),3.96 (br. d, J = 5.6 Hz, 2H), 4.90 (s, 1H), 5.00 (s, 1H), 5.18 (dd, J = 10.4,1.5 Hz, 1H), 5.28 (br. dd, J = 17.2, 1.7 Hz, 1H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.6, 27.6, 31.8, 33.2, 70.9, 73.0,111.1, 116.8, 134.9, 146.3。
实施例7
合成2-((烯丙氧基)甲基)十一碳-1-烯
步骤-1:合成2-亚甲基-1-十一醛:
将十一醛(1.70 kg, 10.0 mol)加入到37%甲醛水溶液(892 g, 11 mol)、二乙醇胺(137 g, 1.30 mol)和硼酸(8.11 g, 130 mmol)的混合物中。将该混合物在80℃搅拌6h。然后使混合物冷却至20℃并用2M盐酸水溶液(80 mL)、碳酸氢钠水溶液(80 mL),和盐水(80mL)洗涤。通过真空蒸馏(56-70℃/ 1毫巴)纯化粗产物,得到2-亚甲基-1-十一醛(1.50 kg,82 %),为无色液体。
步骤-3:2-((烯丙氧基)甲基)十一碳-1-烯根据在实施例1中描述的程序制备。收率61%。
1H NMR (600 MHz, CDCl3): δ 0.89 (br. t, J = 7.0 Hz, 3H), 1.20-1.35(m, 12H), 1.40-150 (m, 2H), 2.05 (t, J = 7.8 Hz, 2H), 3.91 (s, 2H), 3.96 (d,J = 5.6 Hz, 2H), 4.89 (s, 1H), 5.00 (s, 1H), 5.23 (br. ddd, J = 13.8, 11.8,1.5 Hz, 2H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 14.1, 22.7, 27.6, 29.3, 29.4, 29.5, 29.6,31.9, 33.2, 70.9, 73.1, 111.1, 116.8, 134.9, 146.4。
实施例8
合成2-((烯丙氧基)甲基)-3,7-二甲基辛-1,6-二烯
步骤-1:合成3,7-二甲基-2-亚甲基辛-6-烯醛:
将香茅醛(344 g, 2.23 mol)在搅拌的同时加入到仲甲醛(87.0 g, 2.90 mol)、二乙醇胺(16.4 g, 16.0 mmol)和苯甲酸(19.1 g, 16.0 mmol)的混合物中。然后在90℃搅拌该混合物6 h。随后,加入盐水并分离有机相,得到粗3,7-二甲基-2-亚甲基辛-6-烯醛(398 g, 92%)。
步骤-2和3:如实施例5中执行。
1H NMR (600 MHz, CDCl3): δ 1.05 (d, J = 6.9 Hz, 3H), 1.30-1.53 (m,2H), 1.59 (s, 3H), 1.68 (s, 3H), 1.95 (br. q, J = 7.5 Hz, 2H), 2.19 (六重峰,J = 6.9 Hz, 1H), 3.94 (s, 2H), 3.97 (d, J = 5.5 Hz, 2H), 4.91 (s, 1H), 5.05(d, J = 1.4 Hz, 1H), 5.09 (br. t, J = 5.8 Hz, 1H), 5.18 (br. dd, J = 10.4,1.4 Hz, 1H), 5.28 (br. dd, J = 17.2, 1.6 Hz, 1H), 5.89-5.96 (m, 1H).
13C NMR (600 MHz, CDCl3): δ 17.7, 19.9, 25.7, 25.9, 35.7, 36.5, 71.0,72.0, 110.0, 116.8, 124.6, 131.4, 134.9, 150.9。
以上化合物的嗅觉特性在下表中给出。
式(I)化合物 | 嗅觉气味 |
实施例1: R1 = n-Bu, R2 = H | 极冗长,青绿,果香,梨 |
实施例2: R1 = i-Pr, R2 = H | 冗长,草本的,百里香,微甜,樟脑状,酚型 |
实施例3: R1 = i-Pr, R2 = Et | 冗长,轻微凉爽,薄荷/青绿/草本的 |
实施例4: R1 = i-Pr, R2 = Me | 冗长,针叶树,果香,微甜 |
实施例5: R1 = 正戊基、R2 = H | 果香,花香,青绿/草本的 |
实施例6: R1 = n-Hex, R2 = H | 果香,梨,糯质, 青绿,非常天然, 微甜,熟西洋梨 |
实施例7: R1 = n-C9H19, R2 = H | 果香,什锦水果味,柑橘,甜味,略干脂肪 |
实施例8: 2-((烯丙氧基)甲基)-3,7-二甲基辛-1,6-二烯 | 醚性的,青绿,略带花香,果香,梨,定向梨酯 |
通过以下实施例进一步说明本公开内容,这些实施例绝不应被解释为进一步的限制。本领域的技术人员会很容易地理解,所描述的具体方法和结果仅仅是说明性的。
实施例9-11
在以下实施例9-11中,实施例1的化合物被包含在3个不同的组合物中。从以0.3wt%的香料组合物投配的沐浴露(shower gel)进行嗅觉评估。
实施例9和比较例9 -辛香组合物:
比较例9 | 实施例9 | |
份数 | 份数 | |
精馏丁香油 | 315 | 315 |
肉桂醛 | 280 | 280 |
肉桂腈 | 200 | 200 |
山苍子萜 | 70 | 70 |
肉豆蔻油 | 15 | 15 |
苯甲醛 | 12 | 12 |
乙基麦芽酚 | 5 | 5 |
甲基辛内酯PFW | 3 | 3 |
实施例1 化合物 | 0 | 30 |
DPG | 100 | 70 |
总份数 | 1000 | 1000 |
加入3.0wt%的实施例1化合物,使辛香组合物明显更高性能和冗长,突出了天然肉桂的特性,并绕过刺鼻的腈方面。此外,还引入了一种新鲜的、果香的特性,其将混合物中的各种香料特性整合。
实施例10和比较例10 - 馥香组合物:
比较例10 | 实施例10 | |
份数 | 份数 | |
苯乙醇 | 270 | 270 |
香叶醇80/20 | 190 | 190 |
Kflorol 90 PFW | 150 | 150 |
吐纳麝香PFW | 80 | 80 |
香豆素 | 75 | 75 |
葛罗索醒目薰衣草油 | 70 | 70 |
乙酸苄酯 | 55 | 55 |
Verotyl PFW | 10 | 10 |
实施例1 化合物 | 0 | 5 |
DPG | 100 | 95 |
总计 | 1000 | 1000 |
在馥香组合物中仅添加0.5wt%的实施例1化合物,提高了组合物的性能和弥漫性,无缝地掺混以软化葛罗索醒目薰衣草油(Lavendin Grosso Oil)的樟脑状特性。组合物的复杂性显著增强。虽然目标的果香/青绿特征并不十分明显,但组合物的新鲜度和“干净”的印象大大增强了。
实施例11和比较例11 - 柑橘组合物:
比较例11 | 实施例11 | |
份数 | 份数 | |
冷榨橙油 | 560 | 560 |
山苍子萜 | 180 | 180 |
香茅腈 | 64 | 64 |
乙酸对叔丁基环己酯 | 50 | 50 |
醛C10 | 40 | 40 |
乙基麦芽酚 | 2.5 | 2.5 |
反式-2-十二烯醛 | 2 | 2 |
δ大马酮 | 1.5 | 1.5 |
实施例1 化合物 | 0 | 30 |
DPG | 100 | 70 |
总计 | 1000 | 1000 |
“过量”的3.0wt%的实施例1化合物显著地改变了该组合物的嗅觉特性,将其从柑橙/柠檬特性转变为苦涩的青酸橙,导向泰国柠檬叶(kaffir lime leaf)与葡萄柚方面。此外,本已很强的组合物的性能显著且以意想不到的方式增加,目标的青绿特性与反式-2-十二烯醛和山苍子萜协同地相互作用。
Claims (9)
1.香味、风味和/或除臭/掩蔽组合物,其包含至少一种式(I)的2-和/或3-取代的3-(烯丙氧基)丙烯
其中R1是具有4个碳原子的烷基,且R2是氢,
条件是当R2是氢时,R1不能是叔-丁基。
2.根据权利要求1所述的香味、风味和/或除臭/掩蔽组合物,其中式(I)化合物是2-((烯丙氧基)甲基)己-1-烯。
3.根据权利要求1所述的香味、风味和/或除臭/掩蔽组合物,其中式(I)化合物的含量是在0.0001和95 wt%之间。
4.根据权利要求1所述的香味、风味和/或除臭/掩蔽组合物,其至少包含一种酯和/或一种醇。
5.根据权利要求4所述的香味、风味和/或除臭/掩蔽组合物,其中式(I)化合物与酯和/或醇一起的总含量超过25 wt%。
6.可用于香味、风味和/或除臭/掩蔽组合物的式(I)化合物,
其中R1是具有4个碳原子的烷基,且R2是氢,
条件是
- 当R2是氢时,R1不能是叔丁基。
7.根据权利要求6所述的式(I)化合物,其中所述式(I)化合物是2-((烯丙氧基)甲基)己-1-烯。
8.香味、风味和/或除臭/掩蔽组合物在提供青绿、果香、梨和/或糯质嗅觉气味的加香或调味产品中的用途,所述组合物包含至少一种式(I)的2-和/或3-取代的3-(烯丙氧基)丙烯
其中R1是具有4个碳原子的烷基,且R2是氢。
9.式(I)化合物在提供青绿、果香、梨和/或糯质嗅觉气味的加香或调味产品中的用途,
其中R1是具有4个碳原子的烷基,且R2是氢。
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