CN115003662A - 气味剂和包含气味剂的组合物 - Google Patents
气味剂和包含气味剂的组合物 Download PDFInfo
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- CN115003662A CN115003662A CN202180010005.0A CN202180010005A CN115003662A CN 115003662 A CN115003662 A CN 115003662A CN 202180010005 A CN202180010005 A CN 202180010005A CN 115003662 A CN115003662 A CN 115003662A
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- Prior art keywords
- hex
- pyran
- formula
- pent
- ethyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 126
- 239000003205 fragrance Substances 0.000 title claims abstract description 50
- 239000000796 flavoring agent Substances 0.000 claims abstract description 47
- 235000019634 flavors Nutrition 0.000 claims abstract description 47
- 230000000873 masking effect Effects 0.000 claims abstract description 32
- 239000002781 deodorant agent Substances 0.000 claims abstract description 9
- -1 2-pentyl Chemical group 0.000 claims description 310
- 150000001875 compounds Chemical class 0.000 claims description 96
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 238000000034 method Methods 0.000 claims description 39
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- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 14
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000006017 1-propenyl group Chemical group 0.000 claims description 12
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000006024 2-pentenyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 claims description 8
- 125000006039 1-hexenyl group Chemical group 0.000 claims description 8
- 125000006023 1-pentenyl group Chemical group 0.000 claims description 8
- 125000006040 2-hexenyl group Chemical group 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
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- 125000006041 3-hexenyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 8
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- DJJMUTBSKOJOKE-UHFFFAOYSA-N 3,3,4-trimethyl-2,6-diphenyloxan-4-ol Chemical compound CC1(C)C(C)(O)CC(C=2C=CC=CC=2)OC1C1=CC=CC=C1 DJJMUTBSKOJOKE-UHFFFAOYSA-N 0.000 claims description 3
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- FUJMVKMOEMGMGE-UHFFFAOYSA-N C(C)C1OC(CC(C1(C)C)=C)C1=CC=C(C=C1)OC Chemical compound C(C)C1OC(CC(C1(C)C)=C)C1=CC=C(C=C1)OC FUJMVKMOEMGMGE-UHFFFAOYSA-N 0.000 claims description 3
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- JTAUXMYGKRLOKF-UHFFFAOYSA-N C(CCC)C1C=C(C(C(O1)CC)(C)C)C Chemical compound C(CCC)C1C=C(C(C(O1)CC)(C)C)C JTAUXMYGKRLOKF-UHFFFAOYSA-N 0.000 claims description 2
- NPRBMTDRWSPSBI-UHFFFAOYSA-N CC1OC(C=C(C1(C)C)C)C Chemical compound CC1OC(C=C(C1(C)C)C)C NPRBMTDRWSPSBI-UHFFFAOYSA-N 0.000 claims description 2
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- 230000001877 deodorizing effect Effects 0.000 abstract description 21
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/18—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member containing only hydrogen and carbon atoms in addition to the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D309/22—Radicals substituted by oxygen atoms
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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
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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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0068—Deodorant 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
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- Oil, Petroleum & Natural Gas (AREA)
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Abstract
本发明涉及新类别的有气味的式X的四氢吡喃‑4‑醇衍生物和/或式Y1和Y2的其烯烃衍生物,其可用作香味或风味材料,特别是在向香水、香气或除臭/掩蔽组合物提供樟脑、木质、泥土和/或广藿香样香调方面。本发明还涉及包含所述新类别的有气味的四氢吡喃‑4‑醇衍生物和/或其烯烃衍生物的香味、风味和/或除臭/掩蔽组合物。
Description
技术领域
本发明涉及新类别的有气味的四氢吡喃-4-醇衍生物和/或其烯烃衍生物,其可用作香味或风味材料,特别是在向香水、香气或除臭/掩蔽组合物提供樟脑、木质、泥土和/或广藿香样香调(note)方面。本发明还涉及包含所述新类别的有气味的四氢吡喃-4-醇衍生物和/或其烯烃衍生物的香味、风味和/或除臭/掩蔽组合物。本发明此外涉及可用于本发明的新型香味、风味和/或除臭/掩蔽组合物的所述气味剂。本发明还涉及用于产生所述气味剂/化合物和含有所述气味剂/化合物的相应香味、风味和/或除臭/掩蔽组合物的方法。
更特别地,本发明涉及2,6-二取代-3,3,4-三甲基四氢-2H-吡喃-4-醇衍生物(X)和/或2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物(Y1)和/或2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物(Y2) (气味剂),其可用作香味或风味材料,特别是在向香水、香气或除臭/掩蔽组合物提供樟脑、木质、泥土和/或广藿香样香调方面。
背景技术
对天然香味成分供应的日益限制已经彻底改变合成香味成分的领域。如今,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/掩蔽组合物的需求不断增加。
广藿香油为一种非常重要的天然油,广泛用于香味创造。广藿香油通过对广藿香灌木干燥和发酵的叶子进行蒸汽蒸馏而产生。广藿香油呈现出一种木质香脂香味,并且这种气味概况完美融合了樟脑、木质和泥土香调。尽管以约35-40%存在于广藿香油中的(-)-广藿香醇已描述为其主要气味组成部分,但其合成极具挑战性。对于可易于合成的融合有木质、樟脑和泥土香调,并且赋予组合物广藿香样气味概况的新型化合物的需求不断增加。
US2009263336 (A1)要求保护一种制备式(A)化合物的方法,
所述方法包括使式(B)的化合物与异戊二烯醇反应,
在存在酸的情况下,反应在选自甲苯、二甲苯、三甲苯、环己烷和甲基环己烷的有机溶剂中,在约70℃的温度下回流,优选地在80℃-90℃,并且甚至更优选地在约80℃。酸优选地选自对甲苯磺酸(PTSA)、硫酸和其他负载酸。
M.Markert、I.Buchem、H.Krüger和R.Mahrwald在Tetrahedron [Volume 60,Issue 4, 19 January 2004, Pages 993-999]中发表了一篇关于LiClO4-活化的醛的立体和区域选择性烷基化的文章。
例如,他们公开了一种方案,其中在存在LiClO4/对甲苯磺酸乙酯的情况下醛(苯甲醛或脂肪族醛)与醇或相应的钛(IV)-醇盐反应以得到叔吡喃醇。通过该方法,人们仅能合成在2和6位具有相同取代的那些吡喃醇。进一步地,如该文章提及的,使用苯甲醛的产率(产率46-77%)一般地高于其中使用脂肪族醛的那些产率(产率26-36%)。
已知2-烷基-4-甲基四氢-2H-吡喃-4-醇衍生物具有花香、铃兰情况。铃兰吡喃或2-异丁基-4-甲基四氢-2H-吡喃-4-醇具有玫瑰和铃兰气味。Rossiter, K.在Chimia第55卷(2001)第388-396页中报道,在铃兰吡喃结构的5位引入两个甲基(或二甲基化)会破坏铃兰特性。事实上,所得化合物4,5,5-三甲基-2-(2-甲基丙基)四氢吡喃-4-醇的顺式异构体具有硫磺、橡胶和油性气味,而其反式异构体则无气味。
令人意外的是,我们发现伴随着在四氢吡喃-4-醇部分的5位引入两个甲基(或二甲基化),如果在紧邻氧原子的位置但在与初始烷基不同的位置引入烷基,则所得2,6-二烷基-3,3,4-三甲基四氢-2H-吡喃-4-醇衍生物具有樟脑、木质、泥土、广藿香样特征。
仅报道了一种这样的2,6-二取代-3,3,4-三甲基-取代的四氢吡喃醇。例如,Markert, M.等人在Tetrahedron第60卷,2004年,第993-999页中报道了3,3,4-三甲基-2,6-二苯基四氢-2H-吡喃-4-醇,其中该化合物通过苯甲醛和四(2,3-二甲基丁-2-基)氧基)钛之间在存在高氯酸锂的情况下的反应制备为非对映体的混合物(83:17)。然而,该文章中未公开香味、风味和/或除臭/掩蔽组合物,并且绝对没有证据也没有任何迹象表明存在与3,3,4-三甲基-2,6-二苯基四氢-2H-吡喃-4-醇相关的任何嗅觉性质。
没有报道类似于2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物(Y1)的物质。没有报道提供任何证据或任何迹象表明存在与2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物(Y1)相关的任何嗅觉性质。
类似地,没有报道类似于2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物(Y2)的物质。没有报道提供任何证据或任何迹象表明存在与2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物(Y2)相关的任何嗅觉性质。
发明内容
本发明公开新型香味、风味和/或除臭/掩蔽组合物,组合物包含选自式(X)化合物的2,6-二取代-3,3,4-三甲基四氢-2H-吡喃-4-醇衍生物和/或选自式(Y1)化合物的2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物和/或选自式(Y2)化合物的2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物,其中式(X)、(Y1)和(Y2)为
其中R1为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基或苯基或取代的苯基;R2为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基;R3为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基或苯基或取代的苯基和R4为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基,条件是(X)不能为3,3,4-三甲基-2,6-二苯基四氢-2H-吡喃-4-醇。
因此,根据本发明,(X)不能为3,3,4-三甲基-2,6-二苯基四氢-2H-吡喃-4-醇。
在本发明的一个实施方案中,R1为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基;R2为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基;R3为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基和R4为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基。
根据本发明,基团R1和R2为分开的基团,即它们不会一起形成环。根据本发明,基团R3和R4为分开的基团,即它们不会一起形成环。
在本发明的一个实施方案中,R1为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基、苯基或取代的苯基。
在本发明的一个实施方案中,R2为H、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在本发明的一个实施方案中,R3为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基、苯基或取代的苯基。
在本发明的一个实施方案中,R4为H、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
在另一个实施方案中,本发明的式(X)化合物可为手性的,例如其可用作立体异构体(对映体或非对映体)的混合物,更具体地讲用作对映体的混合物;也可有利地使用RRR异构体、SSS异构体、RSR异构体、SRS异构体、SSR异构体、RRS异构体、SRR异构体、RSS异构体、RRR、SSS、RSR、SRS、SSR、RRS、RSS、SRR异构体的外消旋混合物和/或非外消旋混合物。在另一个实施方案中,本发明的式(Y1)或(Y2)化合物可为手性的,例如其可用作立体异构体(对映体或非对映体)的混合物,更具体地讲用作对映体的混合物;也可有利地使用RR异构体、SS异构体、RS异构体、SR异构体、RR、SS、RS、SR异构体的外消旋混合物和/或非外消旋混合物。在另一个实施方案中,式(X)的醇化合物和/或式(Y1)和/或(Y2)的烯烃也可有利地以纯的形式使用。
简明结构(Y)可有利地用于描绘2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物(Y1)和2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物(Y2)两种类型的化合物;基团R1、R2、R3和R4如上文定义。
具体实施方式
表征本发明化合物的术语“气味剂”意指其在人类中引发优选令人愉悦的气味感觉;因此,其常规用于给工业和卫生用品、洗涤剂、清洁剂、个人卫生产品、化妆品等加香。为了本发明和所附权利要求的目的,术语“气味剂”包括“香气物质”。香气物质为通常用于指定为食品提供气味和/或风味的物质的术语。
式(X)的醇化合物和/或式(Y1)和/或(Y2)的烯烃可单独、作为其混合物或以与基础材料的组合使用。
如本文使用的“基础材料”包括选自广泛范围的天然产物的所有已知香味/风味材料,如:精油、提取物、树脂或分离物和目前可获得的合成材料,比如:烃类、醇类、醛类和酮类、醚类和缩醛类、酯类和内酯类、腈类、肟类或杂环类,和/或与一种或多种常规与香味和/或风味组合物中的气味剂结合使用的成分或赋形剂/佐剂(例如:本领域常用的溶剂/稀释剂、稳定剂、载体材料和其他助剂)的混合物。
式(X)的醇化合物和/或式(Y1)和/或(Y2)的烯烃可例如在任何精细和功能性香水业比如香水、空气护理产品、家居产品、洗衣产品、身体护理产品和化妆品领域,用于广泛范围的香味应用。取决于具体应用和其他气味剂成分的性质和数量,化合物可以广泛变化的量采用。
根据本发明的一个优选实施方案,本发明的香味、风味和/或除臭/掩蔽组合物以在每种情况下相对于整个组合物0.00001-99.9 wt.%之间,例如在0.0001-95 wt.%之间,例如在0.001-25 wt.%之间,优选地在0.01-15 wt.% 之间,更有利地在0.1-10 wt.%之间,特别是在1-5 wt.%之间的量含有至少一种如先前所述的式(X)的醇化合物和/或式(Y1)和/或(Y2)的烯烃。
根据本发明一个特别优选的实施方案,除本发明式(X)的醇化合物和/或式(Y1)和/或(Y2)的烯烃之外,本发明的香味、风味和/或除臭/掩蔽组合物例如以相对于整个香味和/或风味组合物0.1-99.9 wt.%,优选地以5-90 wt.%,特别是15-70 wt.%的量含有另外的气味剂。
如上文描述的式(X)的醇类和/或式(Y1)和/或(Y2)的烯烃可简单地通过直接混合至少一种式(X)化合物和/或至少一种式(Y1)化合物和/或至少一种式(Y2)化合物或包含所述式(X)和/或(Y1)和/或(Y2)化合物的香味组合物与消费品基料而用于消费品基料中;或者其可在较早步骤用捕获材料例如聚合物、胶囊、微胶囊和/或纳米胶囊、脂质体、成膜剂、吸收剂(比如活性炭或沸石)、环状寡糖、环状甘脲以及其两种或更多种的混合物捕获,或者其可化学键合于适于在施加外部刺激(比如光、酶、空气、水等)后释放香味分子的基质上,并然后与消费品基料混合。
因此,本发明可用于制造香味、风味和/或除臭/掩蔽组合物的现有方法,方法包括通过将化合物直接混合到消费品基料中,或者通过混合包含所述一种或多种式(X)和/或(Y1)和/或(Y2)化合物的香味、风味和/或除臭/掩蔽组合物,然后可使用常规技术和方法将其与消费品基料混合而引入作为香味、风味和/或除臭/掩蔽成分的一种或多种式(X)和/或(Y1)和/或(Y2)化合物。通过加入嗅觉可接受的量的至少一种如上文所述的本发明的式(X)和/或(Y1)和/或(Y2)化合物,可改善、增强和/或修改消费品基料的气味香调。
本发明公开新型香味、风味和/或除臭/掩蔽组合物,组合物包含如上文定义的2,6-二取代-3,3,4-三甲基四氢-2H-吡喃-4-醇衍生物和/或如上文定义的2,6-二取代-3,3-二甲基-4-亚甲基四氢-2H-吡喃衍生物和/或如上文定义的2,6-二取代-3,3,4-三甲基-3,6-二氢-2H-吡喃衍生物。
在本发明的一个特定实施方案中,要求保护如上文定义的式(X)和/或(Y1)和/或(Y2)化合物;所述化合物可用于本发明的香水、香气和/或除臭/掩蔽组合物。
在一个实施方案中,用于香味、风味和/或除臭/掩蔽组合物的式(X)化合物选自以下化合物:
1) 2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
2) 2,3,3,4,6-五甲基四氢-2H-吡喃-4-醇
3) 2-异丙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇
4) 6-乙基-2-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
5) 6-乙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇
6) 2,3,3,4-四甲基-6-丙基四氢-2H-吡喃-4-醇
7) 6-异丙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇
8) 2-乙基-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇
9) 2-乙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇
10) 2-乙基-3,3,4-三甲基-6-丙基四氢-2H-吡喃-4-醇
11) 2-乙基-6-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
12) 2-乙基-6-异丁基-3,3,4-三甲基四氢-2H-吡喃-4-醇
13) 6-乙基-2,2,4,5,5-五甲基四氢-2H-吡喃-4-醇
14) 2,6-二乙基-2,4,5,5-四甲基四氢-2H-吡喃-4-醇
15) 6-乙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇
16) 6-异丙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇
17) 6-乙基-2-异丁基-3,3,4-三甲基四氢-2H-吡喃-4-醇
18) 2-(2,3-二甲基丁-3-烯-2-基)-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇
19) 2-(2,3-二甲基丁-3-烯-2-基)-2-乙基-4,5,5,6-四甲基四氢-2H-吡喃-4-醇
在一个实施方案中,用于香味、风味和/或除臭/掩蔽组合物的式(Y)化合物选自以下化合物:
20) 2,3,3-三甲基-4-亚甲基-6-丙基四氢-2H-吡喃或2,3,3,4-四甲基-6-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
21) 6-乙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-乙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
22) 2,3,3,6-四甲基-4-亚甲基四氢-2H-吡喃和2,3,3,4,6-五甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
23) 6-异丙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-异丙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
24) 6-异丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-异丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
25) 6-丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
26) 2-乙基-3,3,6-三甲基-4-亚甲基四氢-2H-吡喃或2-乙基-3,3,4,6-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
27) 2,6-二乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃或2,6-二乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
28) 2-乙基-3,3-二甲基-4-亚甲基-6-丙基四氢-2H-吡喃或2-乙基-3,3,4-三甲基-6-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
29) 6-丁基-2-乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃或6-丁基-2-乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
30) 6-乙基-3,3-二甲基-4-亚甲基-2-丙基四氢-2H-吡喃或6-乙基-3,3,4-三甲基-2-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
31) 2-乙基-6-(4-甲氧基苯基)-3,3-二甲基-4-亚甲基四氢-2H-吡喃或2-乙基-6-(4-甲氧基苯基)-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
在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(X)或式(Y)的化合物,其选自上述任何化合物和/或选自两种或更多种所述化合物的混合物。
申请人令人意外地发现,从嗅觉的角度来看,式(X)和(Y)的化合物具有广藿香样气味。事实上,化合物(X)和(Y)呈现出清新的樟脑以及泥土和木质香调的平衡融合。化合物(X)和(Y)在吸墨纸上保留性非常强和扩散性非常高。事实上,化合物(X)和(Y)在木质、馥奇和花香方面表现得极好。这些化合物与其他木质和麝香香调融合得非常好。
在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物有利地用作香水业组合物。本发明的香水业组合物通常包括香水、古龙水、淡香水和/或浓香水。在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物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,处于本发明实施方案范围内的是可将本文所述的新型香味、风味和/或除臭/掩蔽组合物和/或新型式(X)或式(Y)化合物整合到建筑材料、墙壁和地板覆盖物、汽车部件等中。
通常,除本文所述的新型气味剂和/或香味、风味和/或除臭/掩蔽组合物之外,合适的香味、风味或除臭组合物可有利地包括常规成分,比如溶剂、载体、稳定剂、乳化剂、保湿剂、分散剂、稀释剂、增稠剂、冲淡剂、其他气味剂和/或佐剂等。
式(X)或式(Y)化合物与许多已知的天然或合成香味、风味和/或除臭/掩蔽材料组合,其中天然成分的范围不仅可包括易于挥发的而且可包括半挥发和微挥发性组分,并且合成成分的范围可包括来自许多类别物质的代表,比如在Steffen Arctander, Perfumeand Flavor Chemicals, vol.1&2, Montclair, N.J., 1969; Steffen Arctander,Perfume and Flavor Materials of Natural Origin, Elizabeth, N.J., 1960或HorstSurburg, Johannes Panten, Common Fragrance and Flavor Materials, Wiley-VCH,Weinheim, 2016中描述的,并且从以下非限制性汇编中显而易见:
天然产物比如:
香旱芹油(Ajowan oil)、香树油(Amyris oil)、艾蒿油(Armoise oil)、青蒿油(Artemisia oil)、丁香罗勒油(Basil oil)、蜂蜡净油(Bees wax absolute)、香柠檬油(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)、白樟油(Camphor oil)、卡南迦油(Cananga oil)、页蒿子油(Caraway oil)、小豆蔻油(Cardamom oil)、胡萝卜籽油(Carrot seed oil)、海狸香净油(Castoreum absolute)、雪松叶油(Cedar leaf oil)、柏木油(Cedarwood oil)、芹菜籽油(Celery seed oil)、春黄菊油(Chamomile oil)、桂皮油(Cinnamon bark oil)、桂叶油(Cinnamon leaf oil)、岩玫瑰净油(Cistus absolute)、岩玫瑰油(Cistus oil)、香茅油(Citronella oil)、香茅萜(Citronella terpenes)、香紫苏油(Clary sage oil)、精馏丁香油(Clove oil rectified)、康酿克油(白) (Cognac oil white)、芫荽籽油(Corianderseed oil)、枯茗籽油(Cumin seed oil)、柏油(Cypress oil)、印蒿油(Davana oil)、莳萝籽油(Dill seed oil)、榄香脂油(Elemi oil)、榄香树脂(Elemi resinoid)、桉树油(Eucalyptus oil)、松针油(Fir needle oil)、白松香油(Galbanum oil)、香叶油(Geranium oil)、印度姜油(Ginger oil Indian)、西柚油(Grapefruit oil)、黄兰花油(Guaiacwood oil)、古云香脂(Gurjun balsam)、茉莉净油(Jasmin absolute)、甘松油(Jatamansi oil)、杜松子油(Juniper berry oil)、杜松叶油(Juniper leaf oil)、卡胡尔油(Kachur oil)、赖百当净油(Labdanum absolute)、赖百当树脂(Labdanum resinoid)、薰衣草油(Lavender oil)、柠檬油(Lemon oil)、柠檬油萜(Lemon oil terpenes)、柠檬草油(Lemongrass oil)、酸橙油(Lime oil)、山苍子油(Litsea cubeba oil)、山苍子萜(Litseacubeba terpenes)、Lobhan choya树脂、桔子油(Mandarin oil)、薄荷油(Mentha arvenisoil)、柠檬薄荷油(Mentha citrata oil)、银白金合欢净油(Mimosa absolute)、没药树脂(Myrrh resinoid)、莎草油(Nagarmotha oil)、肉豆蔻油(Nutmeg oil)、橡苔净油(Oakmossabsolute)、橡苔树脂(Oakmoss resinoid)、乳香油(Olibanum oil)、乳香树脂(Olibanumresinoid)、橙油(Orange oil)、牛至油(Origanum oil)、玫瑰草油(Palma rosa oil)、广藿香油(Patchouli oil)、薄荷素油(Peppermint oil)、秘鲁香膏树脂(Peru Balsamresinoid)、橙叶油(Petitgrain oil)、松针油(Pine needle oil)、粉红胡椒油(Pinkpepper oil)、玫瑰净油(Rose absolut)、玫瑰油(Rose oil)、迷迭香油(Rosemary oil)、檀香油(Sandalwood oil)、海草净油(Seaweed absolute)、留兰香油(Spearmint oil)、印度苏刚达油(Sugandh kokila oil)、Sugandh mantri oil、万寿菊油(Tagete oil)、妥鲁香脂树脂(Tolu Balsam resinoid)、晚香玉净油(Tuberose absolute)、姜黄油(Turmericoil)、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:
酯类比如:C16醛、格蓬酯、己酸烯丙酯、环己基丙酸烯丙酯、庚酸烯丙酯、苯氧乙酸烯丙酯、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、苯乙酸戊酯、丙酸戊酯、水杨酸异戊酯、乙酰化香树油(Amyris acetate)、乙酸茴香酯、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(Benzylisoeugenol)、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、乙酸柏木酯、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、乙酸香茅酯、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、Cyclabute、环格蓬酯(Cyclogalbanate)、环己基乙基乙酸酯、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、乙酸二氢月桂烯酯、二甲基辛基乙酸酯、乙酸二甲基苯乙基原酯(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(Dimethyl benzyl carbinyl acetate)、丁酸二甲基苄基原酯(Dimethyl benzyl carbinyl butyrate)、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)、苯氧乙酸乙酯、乙基苯基乙酸酯、苯环氧丙酸乙酯(Ethyl phenyl glycidate)、丙酸乙酯、藏红花酸乙酯、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、FrescolatML、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(Geranyl butyrate)、甲酸香叶酯(Geranyl formate)、丙酸香叶酯(Geranyl propionate)、惕各酸香叶酯(Geranyl tiglate)、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、乙酸异龙脑酯、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、乙酸异壬酯、异戊酸酯(Isopentyrate)、2-甲基丁酸异丙酯、肉豆蔻酸异丙酯(Isopropyl myristate)、茉莉酯(Jasmonyl)、绿花酚(Liffarome)、乙酸芳樟酯、藿檀酯(Mahagonate)、母菊酯(Manzanate)、二氢松香醇乙酸酯(Menthanylacetate)、乙酸薄荷酯、苯甲酸甲酯、2-甲基丁基乙酸酯、春黄菊甲酯(Methyl camomille)、肉桂酸甲酯、环香叶酸甲酯(Methyl cyclogeranate)、庚炔羧酸甲酯(Methyl heptinecarbonate)、月桂酸甲酯、辛炔羧酸甲酯(Methyl octine carbonate)、甲基苯基乙酸酯、水杨酸甲酯、甲基-2-甲基丁酸酯、新福力酯(Neofolione)、乙酸诺卜酯(Nopyl acetate)、乙酸辛烯酯、乙酸辛酯、异丁酸辛酯、乙酸对甲苯酯(Para cresyl acetate)、异丁酸对甲苯酯(Para cresyl isobutyrate)、苯基乙酸对甲苯酯(Para cresyl phenyl acetate)、梨酯(Pear ester)、戊酸甲酯(Peranat)、苯氧基乙基异丁酸酯、乙酸苯乙酯、丁酸苯乙酯、甲酸苯乙酯、异丁酸苯乙酯、苯乙酸苯乙酯、丙酸苯乙酯、水杨酸苯乙酯、惕各酸苯乙酯、异丁酸苯丙酯、乙酸异戊二烯酯(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、乙酸邻叔丁基环己酯(Verdox)、乙酸三环癸烯酯(Verdyl acetate)、丙酸三环癸烯酯(Verdyl propionate)、乙酸对叔丁基环已酯(Vertenex)、乙酸维木酯(Vetikolacetate)、乙酸香根酯(Vetiveryl acetate)、Yasmolys。
内酯类比如:黄葵内酯(Ambrettolide)、Arova N、3-亚丙基苯并呋喃酮(Celeriax)、癸内酯δ、癸内酯γ、十二内酯δ、十二内酯γ、巴西酸乙二醇酯、环十五内酯(Exaltolide)、庚内酯γ、己内酯δ、己内酯γ、甲基内酯(Methyl laitone)、甲基辛内酯、壬内酯δ、壬内酯γ、八氢香豆素、辛内酯δ、辛内酯γ、Rootylone、环十六内酯(Silvanonesupra)、十一内酯δ、十一内酯γ、戊内酯γ、10-氧杂十六内酯(10-OxaHexaDecanolide)(OHD麝香)、香豆素、环十五烯内酯(Habanolide)、茉莉内酯(Jasmolactone)。
醛类比如:乙醛、阿道克醛(Adoxal)、C10醛、异C11醛、C11 moa醛(Aldehyde C11moa)、C11十一碳烯醛、C11十一烷基醛、C12月桂醛、C12 MNA醛、茴香醛(Anisaldehyde)、戊基肉桂醛、苯甲醛、波吉洪醛(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(Citral)、香茅醛(Citronellal)、香茅基氧基乙醛、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、道比卡尔(Dupical)、柑青醛(Empetal)、乙基香草醛、海风醛(Floralozone)、花青醛(Florhydral)、香叶醛(Geraldehyde)、新洋茉莉醛、洋茉莉醛、庚醛、己醛、己基肉桂醛、新清冬醛(Hivernal neo)、氢化阿托醛(Hydratropaldehyde)、羟基香茅醛(Hydroxycitronellal)、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、苯乙醛、苯丙醛、甲基柑青醛B(Precyclemone B)、藏红花醛(Safranal)、水杨醛、清风醛(Scentenal)、丁香醛(Syringaaldehyde)、反式-4-癸烯醛、反式-2-十二烯醛、反式-2-己烯醛、反式-2-壬烯醛、新女贞醛(Trifernal)、香草醛、藜芦醛(Veratraldehyde)、鲜草醛(Vernaldehyde)。
酮类比如: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(Carvone d-)、l-香芹酮、喀什米尔木(Cashmeran)、柏木基甲基酮(Cedryl methylketone)、二氢茉莉酮酸甲酯(Cepionate)、卡瑞酮(Claritone)、天籁麝香(Cosmone)、萨利麝香(Crysolide)、甲基环戊烯醇酮(Cyclotene)、大马烯酮(Damascenone)、大马酮α(Damascone alpha)、大马酮β、大马酮δ、大马酮γ、双乙酰(Diacetyl)、二氢-β-紫罗兰酮(Dihydro beta ionone)、二氢异茉莉酮酸酯(Dihydro isojasmonate)、二甲基辛烯酮(Dimethyl octenone)、王朝酮(Dynascone)、乙基戊基酮、乙基麦芽酚(Ethyl maltol)、葑酮(Fenchone)、榛子酮(Filbertone)、香叶基丙酮(Geranyl acetone)、8-环十六烯-1-酮(Globanone)、庚基环戊酮(Heptyl cyclopentanone)、紫罗兰酮α、紫罗兰酮β、纯紫罗兰酮、鸢尾木(Iriswood)、鸢尾酮α (Irone α)、龙涎酮、异葑酮(Isofenchone)、异茉莉酮T、异洛酮K (Isolone K)、异薄荷酮(Isomenthone)、异佛尔酮(Isophorone)、顺式-茉莉酮(Jasmone cis-)、Kambernoir、加菲力士(Kephalis)、高芳烯(Koavone)、 Lavendinal、麦芽酚(Maltol)、薄荷酮(Menthone)、甲基苯乙酮、甲基戊基酮、甲基庚烯酮、甲基己基酮、甲基紫罗兰酮γ、甲基萘基酮β (Methyl naphthyl ketone beta)、甲基壬基酮(Methyl nonylketone)、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)、法老酮(Pharaone)、胡椒酮(Piperitone)、普利卡酮(Plicatone)、覆盆子酮(Raspberry ketone)、覆盆子酮甲基醚(Raspberryketone methyl ether)、藏花茚(Safraleine)、纯螺环格蓬酮(Spirogalbanone pure)、吐纳麝香(Tonalid)、舒牟馥O (Trimofix O)、凡路酮(Veloutone)、Vetikon。
醇类比如:氧代C13醇(Alcohol oxo C13)、琥珀芯(Amber core)、Ambermax、龙涎醇(Ambrinol)、戊基乙烯基原醇(Amyl vinyl carbinol)、茴香醇(Anisic alcohol)、白檀醇(Bacdanol)、苄醇、丁醇、结晶柏木醇(Cedrol crystals)、肉桂醇、香茅醇(Citronellol)、花冠醇(Coranol)、癸醇、二甲基苄基原醇(Dimethyl benzyl carbinol)、二甲基辛醇、二甲基苯乙基原醇、二甲基庚醇(Dimetol)、葑醇(Fenchol)、己醇、异龙脑(Isoborneol)、环己异龙脑酯(Isobornyl cyclohexanol)、爪哇檀香(Javanol)、Keflorol、Kohinool、月桂醇、风铃醇(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、苯乙醇、苯丙醇、丙二醇、甲基苯戊醇(Rosaphen)、玫瑰二醇(Rose glycol)、苏合香醇(Styrallyl alcohol)、三环癸烷二甲醇(Tricyclodecanedimethanol)、四氢芳樟醇、四氢月桂烯醇(Tetrahydro myrcenol)、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、二氢月桂烯醇(Dihydromyrcenol)、二聚月桂烯醇(Dimyrcetol)、黑檀醇(Ebanol)、香叶醇(Geraniol)、异蒲勒醇(Isopulegol)、芳樟醇、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(Sandalmysore core)、檀香(Sandalore)、萜烯-4-醇(Terpinen-4-ol)、萜品醇(Terpineol)、反式-2-己烯醇。
酚类比如:丁基羟基茴香醚(Butylated hydroxyanisole)、二氢丁香酚、二甲基氢醌、间苯二甲醚(Dimethyl resorcinol)、纯丁香酚(Eugenol pure)、愈创木酚、异丁香酚(Isoeugenol)、间甲酚(Meta cresol)、甲基单提利士(Methyl diantilis)、对甲酚(Paracresol)、浓馥香兰素(Propenyl guaethol)、百里香酚(Thymol)、香荚兰醇(Ultravanil)。
醚类比如: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、二苄醚、二氢玫瑰氧化物(Dihydro rose oxide)、二苯醚、道立米(Doremox)、草蒿脑(Estragole)、乙基芳樟醇、桉油精(Eucalyptol)、佳乐麝香(Galaxolide)、吉兰吡喃(Gyrane)、Herbavert、酸橙氧化物(Lime oxide)、甲基环十二烷醚(Madrox)、甲基异丁香酚、β萘基异丁基醚、橙花醚(Nerol oxide)、橙花素(Nerolinbromelia)、对甲酚丁醚(Para cresyl butyl ether)、对甲酚甲醚(Para cresyl methylether)、Petiole、苯乙基甲基醚、2,4-二甲基-4-苯基四氢呋喃(Rhubafuran)、玫瑰氧化物(Rose oxide)、芳香玫瑰醚(Rosyrane)、Trisamber、Vetylbois K、β-萘基甲基醚(Yarayara)。
缩醛类比如:缩醛CD、缩醛R、龙涎缩醛(Amberketal)、乙氧基环十二烷氧基甲烷(Boisambrene forte)、柠檬醛(Citrathal)、1,1-二乙氧基乙烷、翠绿亚胺(Emeraldine)、Freshopal、薰衣草噁烷(Herboxane)、吲哚素(Indoflor)、Jacinthaflor、曼可罗(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、圆柚甲烷(Methyl pamplemousse)。
烃类比如:红没药烯、莰烯(Camphene)、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(Limonene d-)、长叶烯(Longifolene)、月桂烯(Myrcene)、萘、罗勒烯、蒎烯α (Pinene alpha)、蒎烯β 、苯乙烯、萜品烯γ(Terpinene gamma)、萜品油烯(Terpinolene)、1,3,5-十一碳三烯(Undecatriene)、异丙基格篷(Verdoracine)。
含硫化合物比如:Corps cassis、二丁基硫醚、二甲基硫醚、Exovert、西柚硫醇(Grapefruit thiol)、噁烷(Oxane)、巯基马来酮(Ribes mercaptan)、硫噻唑(Sulfurol)、桉叶硫醚(Thiocineol)。
腈类比如:肉桂腈、香茅腈(Citronellyl nitrile)、柠檬腈(Citronitrile)、Clonal、枯茗腈(Cumin nitrile)、己基环戊酮、鸢尾腈(Irisnitrile)、柠檬腈(Lemonile)、牡丹腈(Peonile)、十三烷基腈(Tridecyl nitrile)、Agrumen腈(Agrumen nitrile)、正十二烷基腈。
肟类比如:布枯肟(Buccoxime)、雷冰诺星(Labienoxime)、榄青酮(Stemone)。
含氮杂环类比如:2-乙酰基吡嗪、2-乙酰基吡啶、仲丁基喹啉、2-(3-苯基丙基)吡啶(Corps racine)、2-乙基-3,5(或6)-二甲基吡嗪、1-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、粪臭素(Skatol)、2,3,5-三甲基吡嗪。
硝基化合物比如:麝香酮(Musk Ketone)。
希夫碱类比如:橙花素(Aurantiol)、半日花素(helianthral)、ligantraal、玲兰素。
其他材料比如:乙酰苯胺、环胺(Gardamide)、水果酰胺(Paradisamide)、邻甲氨基苯甲酸二甲酯(Dimethyl anthranilate)、邻氨基苯甲酸甲酯(Methyl anthranilate)、正丁酸、癸酸、己酸、辛酸、苯乙酸、丁香烯氧化物、环氧柏木醚(Cedroxyde)、Tobacarol。
因此,式(X)或式(Y)化合物和广泛范围的已知气味剂/香味、风味和/或除臭/掩蔽材料(如从前述汇编中显而易见的)可用于生产组合物。在这种组合物的生产中,先前提及的已知香味、风味和/或除臭/掩蔽材料可根据调香师已知的方法,比如根据W. A.Poucher, Perfumes, Cosmetics and Soaps 2,第7版, Chapman和Hall, London 1974使用。
在本发明的一个实施方案中,要求保护的香味、风味和/或除臭/掩蔽组合物,除式(X)或式(Y)化合物之外,还包含至少一种酯和/或一种醇(除化合物(X)以外,如果存在的话),优选地为酯和醇的至少一种混合物;所述酯和/或醇优选地选自上文定义的列表。在本发明的一个实施方案中,要求保护的气味剂组合物其特征为式(X)或式(Y)化合物以及酯和/或醇一起的总含量,高于25 wt%,优选地高于50 wt%,例如高于75 wt%,或者甚至高于90wt%。
制备
通过使4,4,5-三甲基己-5-烯-3-醇和丙醛反应筛选用于选择性形成2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇(X)的各种酸。所有反应均于室温(25℃)下在含有0.5当量相应酸的甲苯中进行。
显然,磷酸、三氟乙酸和三氯化铁在选择性形成期望的叔醇(X)方面效果好得多,而异构烯烃(Y1+Y2)的形成程度要小得多。另一方面,所有其他的酸以不佳的产率得到期望的醇(X)和/或在大多数情况下主要形成异构烯烃。
三氟乙酸为一种昂贵且具有腐蚀性的酸,而三氯化铁为有害且具有腐蚀性的,并且可能非常危险。磷酸(H3PO4)为一种比三氟乙酸和三氯化铁相对更弱的酸。而且,磷酸的腐蚀性比三氟乙酸和三氯化铁弱得多。
为避免使用甲苯,水中各种浓度的磷酸用于4,4,5-三甲基己-5-烯-3-醇和丙醛之间的反应。令人意外的是,发现反应效果非常好,并且以良好的产率形成期望的产物2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇。发现含水磷酸效果好,并以良好的产率形成由式(X)表示的化合物。
在本发明的一个优选实施方案中,由通式(X)表示的化合物可有利地在存在磷酸,优选地为含水(优选地按重量计10%~85%)磷酸,更具体地讲在30%-60%含水磷酸之间,更具体地讲在55%-60%含水磷酸(0.1-1.0当量)之间的情况下,于0℃-45℃之间的温度下,由相应的式(I)醇和式(II)羰基化合物(醛或酮)以一步合成。在这种情况下,也可有利地形成少量相应的化合物(Y)。在本文中,每种化合物Y优选地为外型异构体Y1和内型异构体Y2的混合物。
其中R1、R2、R3和R4如上文定义。
例如,R1为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基或苯基或取代的苯基;R2为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基;R3为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基和R4为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基。
在文献中,已知高烯丙醇(比如异戊二烯醇)与羰基化合物(比如醛或酮)的Prince环合得到2,4-二取代四氢吡喃-4-醇。然而,没有由式(I)表示的高烯丙基醇与羰基化合物的Prince反应的实例。事实上,可以预期在酸性条件下,由式(I)表示的相应仲醇或叔醇可能经历脱水或者重排然后脱水。
在本发明的一个实施方案中,令人意外地发现,在适当浓度(例如55-60%)的含水磷酸(0.1-1.0当量)下,式(I)的醇在0℃-45℃下经历与羰基化合物的Prince环合,得到2,6-二取代-3,3,4-三甲基四氢-2H-吡喃-4-醇衍生物(X);
其中R1、R2、R3和R4如上文定义。
例如,R1为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基或苯基或取代的苯基;R2为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基;R3为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基和R4为H或具有至多6个碳原子的烷基或具有至多6个碳原子的烯基。
式(I)化合物和式(II)化合物的基团R1、R2、R3和R4与式(X)和/或式(Y1)和/或式(Y2)的相应合成化合物和/或其混合物的基团R1、R2、R3和R4相同。
根据本发明,基团R1和R2为分开的基团,即它们不会一起形成环。根据本发明,基团R3和R4为分开的基团,即它们不会一起形成环。
由通式(Y)表示的化合物可有利地在存在质子酸比如对甲苯磺酸(0.1-1.0当量)的情况下,于2℃-45℃下在有机溶剂(比如二氯乙烷(EDC))中由相应的醇(I)和羰基化合物(II,醛或酮)以一步合成。事实上,典型的化合物Y优选地为外型异构体Y1和内型异构体Y2的混合物。在这种情况下,也可形成少量的相应化合物(X),其中R1、R2、R3和R4如上文定义。
通式(I)的化合物可如在WO2019228903中那样合成。
或者
通式(I)的化合物可通过硼氢化钠介导的相应的式(III)羰基化合物的还原或通过向(III)中加入适当的格氏试剂R2MgX来制备;
其中R1为具有至多6个碳原子的烷基或具有至多6个碳原子的烯基或苯基或取代的苯基;R2为具有至多6个碳原子的烷基或烯基。
通式(III)的化合物可由2,3-二甲基丁-1-烯或2,3-二甲基丁-2-烯和相应的酸酐或羧酸R1COOH的酰氯在存在任何路易斯酸(比如AlCl3或ZnCl2)或质子酸(比如甲磺酸)的情况下制备。
实施例1
2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇的合成
方法A:在25℃下向4,4,5-三甲基己-5-烯-3-醇(250 g, 1.75 mmol)和磷酸(84.1g的85%溶液, 71.5 g, 0.73 mmol)于水(50 g)中的溶液中经4小时缓慢加入丙醛(125 g,2.15 mmol)。在25℃下搅拌反应混合物2 h之后,将其用水(500 mL)稀释并分离水层。用10%碳酸氢钠溶液(300 mL)然后水(500 mL)洗涤有机层。真空浓缩有机层,并将所得粗品进行分馏(66℃,3 mbar),得到作为两种非对映体的混合物(92:8, 无色液体)的2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇(220.0 g, 62%)。
1H NMR (400 MHz, CDCl3), 主要非对映体: δ 3.22-3.28 (m, 1H), 3.01 (dd,J = 2.4 Hz, 10.0 Hz, 1H), 1.52-1.61 (m, 1H), 1.41-1.61 (m, 2H), 1.30-1.39 (m,2H), 1.26 (s, 3H), 0.92-1.01 (m, 10 H), 0.81 (s, 3 H); 13C NMR (100 MHz,CDCl3): δ 83.6, 73.3, 43.8, 41.2, 29.2, 23.2, 22.7, 19.2, 15.9, 11.8, 10.2。
气味概况:广藿香样、清新、樟脑、泥土、木质。
实施例2
2,3,3,4,6-五甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和乙醛得到。
1H NMR (400 MHz, CDCl3), 两种非对映体以77:23比率的混合物;主要非对映体δ3.57-3.49 (m, 1H), 3.37 (q, J = 6.4 Hz, 1H), 1.61-1.55 (m, 1H), 1.37 (dd, J =12.8, 2.4 Hz, 1H), 1.21 (s, 3H), 1.13 (d, J = 4.4 Hz, 3H), 1.03 (d, J = 6.4Hz, 3H), 0.90 (s, 3H), 0.75 (s, 3H)。
气味概况:干燥木质、芳香。
实施例3
2-异丙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自2,4,4,5-四甲基己-5-烯-3-醇和乙醛得到。
气味概况:樟脑、广藿香样。
实施例4
6-乙基-2-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇的合成
使用方法A自2,4,4,5-四甲基己-5-烯-3-醇和丙醛得到。
气味概况:樟脑、广藿香样。
实施例5
6-乙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和丙醛得到。
气味概况:强烈的木质。
实施例6
2,3,3,4-四甲基-6-丙基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和丁醛得到。
1H NMR (400 MHz, CDCl3), 两种非对映体以55:45比率的混合物; δ 3.50-3.43(m, 1H), 3.38-3.31 (m, 2H), 3.09-3.06 (m, 1H), 1.59-1.52 (m, 5H), 1.39-1.33(m, 3H), 1.32-1.26 (m, 4H), 1.21 (s, 3H), 1.20 (s, 3H), 1.12 (d, J = 6.4 Hz,3H), 1.02 (d, J = 6.4 Hz, 3H), 0.89 (s, 3H), 0.88 (s, 3H), 0.84 (t, J = 7.2Hz, 3H), 0.83 (t, J = 7.2 Hz, 3H), 0.75 (s, 3H), 0.74 (s, 3H)。
气味概况:木质。
实施例7
6-异丙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和异丁醛得到。
1H NMR (400 MHz, CDCl3), 两种非对映体以60:40比率的混合物;主要非对映体δ3.48-3.38 (m, 1H), 2.89-2.88 (m, 1H), 1.2 (s, 3H), 1.82-1.74 (m, 1H), 1.62-1.52 (m, 2H), 1.09 (d, J = 6.4 Hz, 3H), 0.88-0.86 (重叠峰, 6H), 0.8 (s, 6H)。
气味概况:木质。
实施例8
2-乙基-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和2-丁酮得到。
气味概况:木质樟脑、芳香松树。
实施例9
2-乙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和乙醛得到。
1H NMR (400 MHz, CDCl3) δ 3.52-3.40 (m, 1H), 3.0-2.91 (dd, 1H), 1.62-1.54 (m, 1H), 1.40-1.35 (m, 2H), 1.32-1.25 (m, 1H), 1.21 (s, 3H), 1.13 (d, J= 6.0 Hz, 3H), 0.91 (t, J = 7.2 Hz, 3H), 0.88 (s, 3H), 0.75 (s, 3H)。
气味概况:木质。
实施例10
2-乙基-3,3,4-三甲基-6-丙基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和丁醛得到。
气味概况:雪松木质香调、果香。
实施例11
2-乙基-6-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和异丁醛得到。
气味概况:木质、樟脑。
实施例12
2-乙基-6-异丁基-3,3,4-三甲基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和异戊醛得到。
感官概况:草香(green)、木质、干草、桉树样。
实施例13
6-乙基-2,2,4,5,5-五甲基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和丙酮得到。
气味概况:木质、少许甲酚。
实施例14
2,6-二乙基-2,4,5,5-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自4,4,5-三甲基己-5-烯-3-醇和2-丁酮得到。
1H NMR (400 MHz, CDCl3) δ 3.21-3.18 (m, 1H), 3.04-2.95 (m, 1H), 1.59-1.46 (m, 3H), 1.42-1.30 (m, 3H), 1.21 (s, 3H), 0.94-0.87 (重叠的4个Me信号, 12H), 0.75 (s, 3H)。
气味概况:干燥木质。
实施例15
6-乙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇的合成
通过方法A自2,3,3-三甲基庚-1-烯-4-醇和丙醛作为立体异构体的混合物得到。
气味概况:木质。
实施例16
6-异丙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇的合成
通过方法A自2,3,3-三甲基庚-1-烯-4-醇和异丁醛作为立体异构体的混合物得到。
气味概况:木质。
实施例17
6-乙基-2-异丁基-3,3,4-三丁基四氢-2H-吡喃-4-醇的合成
自方法A使用2,3,3,6-四甲基庚-1-烯-4-醇和丙醛得到。
1H NMR (400 MHz, CDCl3),两种非对映体以90:10比率的混合物;主要非对映体δ3.23-3.16 (m, 1H), 3.13 (dd, J = 10.4, 1.6 Hz, 1H), 2.95 (dd, J = 10.4, 2.4Hz, 1H)。
气味概况:木质。
实施例18
2-(2,3-二甲基丁-3-烯-2-基)-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和3,3,4-三甲基戊-4-烯-2-酮得到。
感官概况:樟脑、芳香。
实施例19
2-(2,3-二甲基丁-3-烯-2-基)-2-乙基-4,5,5,6-四甲基四氢-2H-吡喃-4-醇的合成
使用方法A自3,3,4-三甲基戊-4-烯-2-醇和4,4,5-三甲基己-5-烯-3-酮得到。
感官概况:木质、芳香。
实施例20
2,3,3-三甲基-4-亚甲基-6-丙基四氢-2H-吡喃或2,3,3,4-四甲基-6-丙基-3,6-二氢-2H-吡喃的合成
方法B:向3,3,4-三甲基戊-4-烯-2-醇(10 g, 38 mmol)和对甲苯磺酸一水合物(2.97 g, 15.60 mmol)在1,2-二氯乙烷(100 mL)中的溶液中经1 h滴加丁醛(6.75 g, 94mmol)。将所得反应混合物在室温下搅拌2 h,并然后将其用水稀释,通过加入饱和NaHCO3中和并用二氯甲烷(3 x 50 mL)萃取。有机层用水、盐水洗涤,经无水Na2SO4干燥并过滤。减压去除有机溶剂,得到粗品化合物,将其通过柱色谱法(230-400目硅胶)使用0-20%乙酸乙酯/己烷纯化,得到4.2 g烯烃(实施例29)和4.8 g醇(实施例4)。使用Kugelrohr装置对两种产物进行蒸馏,以得到用于嗅觉评估的相应样品(综合产率为63%)。
气味概况:木质。
实施例21
6-乙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-乙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃的合成
使用方法B自3,3,4-三甲基戊-4-烯-2-醇和丙醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质、樟脑。
实施例22
2,3,3,6-四甲基-4-亚甲基四氢-2H-吡喃和2,3,3,4,6-五甲基-3,6-二氢-2H-吡喃的合成
使用方法B自3,3,4-三甲基戊-4-烯-2-醇和乙醛作为非对映体和外型/内型异构体的混合物得到。
1H NMR (400 MHz, CDCl3)
气味概况:苔藓、木质、甜豌豆香调。
实施例23
6-异丙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-异丙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃的合成
使用方法B自3,3,4-三甲基戊-4-烯-2-醇和异丁醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质樟脑。
实施例24
6-异丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-异丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃的合成
使用方法B自3,3,4-三甲基戊-4-烯-2-醇和异戊醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质。
实施例25
6-丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃的合成
使用方法B自3,3,4-三甲基戊-4-烯-2-醇和丁醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质。
实施例26
2-乙基-3,3,6-三甲基-4-亚甲基四氢-2H-吡喃和2-乙基-3,3,4,6-四甲基-3,6-二氢-2H-吡喃的合成
使用方法B自4,4,5-三甲基己-5-烯-3-醇和乙醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:樟脑、木质。
实施例27
2,6-二乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃和2,6-二乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃的合成
使用方法 B自4,4,5-三甲基己-5-烯-3-醇和丙醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质、樟脑。
实施例28
2-乙基-3,3-二甲基-4-亚甲基-6-丙基四氢-2H-吡喃和2-乙基-3,3,4-三甲基-6-丙基-3,6-二氢-2H-吡喃的合成
使用方法 B自4,4,5-三甲基己-5-烯-3-醇和丁醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质粉状、美食、焦糖、甘草、龙蒿、茉莉,
实施例29
6-丁基-2-乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃和6-丁基-2-乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃的合成
使用方法B自4,4,5-三甲基己-5-烯-3-醇和戊醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质、醛、草香、生甘蔗样、花香、茶、烟草、胡芦巴。
实施例30
6-乙基-3,3-二甲基-4-亚甲基-2-丙基四氢-2H-吡喃和6-乙基-3,3,4-三甲基-2-丙基-3,6-二氢-2H-吡喃的合成
使用方法 B自2,3,3-三甲基庚-1-烯-4-醇和丙醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质。
实施例31
2-乙基-6-(4-甲氧基苯基)-3,3-二甲基-4-亚甲基四氢-2H-吡喃和2-乙基-6-(4-甲氧基苯基)-3,3,4-三甲基-3,6-二氢-2H-吡喃的合成
使用方法 B自4,4,5-三甲基己-5-烯-3-醇和4-甲氧基苯甲醛作为非对映体和外型/内型异构体的混合物得到。
气味概况:木质、粉状、花香、茴香。
组合物评估实施例
在以下发明中,对含有不同基准化合物的各种木质组合物调和(accord)进行了评估,并且与含有来自实施例1的化合物的组合物调和进行了比较。组合物A含有来自实施例1的化合物,即2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇作为在IPM (肉豆蔻酸异丙酯)中的10% w/w溶液。组合物B含有商购化合物Clearwood,组合物C含有商购化合物PTBC酮,组合物D含有商品化合物OTBC酮;和最后,组合物E仅含有IPM并用作空白。
所有以上组合物均用于洗发水以及织物柔软剂中。
实施例 | A | B | C | D | E |
原料(按重量计的份数) | |||||
Kambernoir SHK | 10 | 10 | 10 | 10 | 10 |
白檀醇 | 8 | 8 | 8 | 8 | 8 |
柏木基甲基酮 | 8 | 8 | 8 | 8 | 8 |
乙酸丁香酚酯 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
龙涎酮 | 40 | 40 | 40 | 40 | 40 |
乙酸异龙脑酯 | 10 | 10 | 10 | 10 | 10 |
环己异龙脑酯(IBCH) | 8 | 8 | 8 | 8 | 8 |
对叔丁基环己基乙酸酯(PTBCA) | 10 | 10 | 10 | 10 | 10 |
作为在IPM中的10% w/w溶液的2,6-二乙基-3,3,4-三甲基四氢-2<i>H</i>-吡喃-4-醇 | 5.5 | 0 | 0 | 0 | 0 |
在IPM中的1% Clearwood | 0 | 5.5 | 0 | 0 | 0 |
PTBC酮 | 0 | 0 | 5.5 | 0 | 0 |
OTBC酮 | 0 | 0 | 0 | 5.5 | 0 |
IPM | 0 | 0 | 0 | 0 | 5.5 |
总计 | 100 | 100 | 100 | 100 | 100 |
显然,作为IPM中的10% w/w溶液引入按重量计5.5%的2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇会产生强烈的木质广藿香样效果。当用于洗发水时,其给人更全面的感觉,并给掺混物带来沉重感。另一方面,当在以上调和中使用IPM中按重量计1%的Clearwood时,仅观察到柔软的木质效果。PTBC酮的使用呈现出樟脑和木质效果,而OTBC酮组合物赋予掺混物以薄荷和木质特性。
Claims (17)
2.权利要求1的化合物,其中
R1为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基、苯基或取代的苯基;
R2为H、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基;
R3为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基、苯基或取代的苯基;
R4为H、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、异丁基、正戊基、2-戊基、3-戊基、正己基、2-己基、3-己基、乙烯基、1-丙烯基、丙-1-烯-2-基、烯丙基、1-丁烯基、2-丁烯基、丁-3-烯-2-基、1-戊烯基、戊-2-烯-1-基、戊-3-烯-1-基、戊-4-烯-1-基、戊-1-烯-2-基、2-戊烯基、戊-3-烯-2-基、戊-4-烯-2-基、戊-2-烯-3-基、戊-1-烯-3-基、1-己烯基、己-2-烯-1-基、己-3-烯-1-基、己-4-烯-1-基、己-5-烯-1-基、己-1-烯-2-基、2-己烯基、己-3-烯-2-基、己-4-烯-2-基、己-5-烯-2-基、3-己烯基、己-1-烯-3-基、己-2-烯-3-基、己-3-烯-3-基、己-4-烯-3-基或己-5-烯-3-基。
3.前述权利要求中任何一项的并且选自以下的式(X)化合物:
2,6-二乙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
2,3,3,4,6-五甲基四氢-2H-吡喃-4-醇
2-异丙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇
6-乙基-2-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
6-乙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇
2,3,3,4-四甲基-6-丙基四氢-2H-吡喃-4-醇
6-异丙基-2,3,3,4-四甲基四氢-2H-吡喃-4-醇
2-乙基-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇
2-乙基-3,3,4,6-四甲基四氢-2H-吡喃-4-醇
2-乙基-3,3,4-三甲基-6-丙基四氢-2H-吡喃-4-醇
2-乙基-6-异丙基-3,3,4-三甲基四氢-2H-吡喃-4-醇
2-乙基-6-异丁基-3,3,4-三甲基四氢-2H-吡喃-4-醇
6-乙基-2,2,4,5,5-五甲基四氢-2H-吡喃-4-醇
2,6-二乙基-2,4,5,5-四甲基四氢-2H-吡喃-4-醇
6-乙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇
6-异丙基-3,3,4-三甲基-2-丙基四氢-2H-吡喃-4-醇
6-乙基-2-异丁基-3,3,4-三甲基四氢-2H-吡喃-4-醇
2-(2,3-二甲基丁-3-烯-2-基)-2,4,5,5,6-五甲基四氢-2H-吡喃-4-醇
2-(2,3-二甲基丁-3-烯-2-基)-2-乙基-4,5,5,6-四甲基四氢-2H-吡喃-4-醇。
4.权利要求1或2中任何一项的并且选自以下的式(Y1)和/或(Y2)的化合物:
2,3,3-三甲基-4-亚甲基-6-丙基四氢-2H-吡喃或2,3,3,4-四甲基-6-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-乙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃和6-乙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
2,3,3,6-四甲基-4-亚甲基四氢-2H-吡喃和2,3,3,4,6-五甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-异丙基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-异丙基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-异丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-异丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-丁基-2,3,3-三甲基-4-亚甲基四氢-2H-吡喃或6-丁基-2,3,3,4-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
2-乙基-3,3,6-三甲基-4-亚甲基四氢-2H-吡喃或2-乙基-3,3,4,6-四甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
2,6-二乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃和2,6-二乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
2-乙基-3,3-二甲基-4-亚甲基-6-丙基四氢-2H-吡喃和2-乙基-3,3,4-三甲基-6-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-丁基-2-乙基-3,3-二甲基-4-亚甲基四氢-2H-吡喃或6-丁基-2-乙基-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物,
6-乙基-3,3-二甲基-4-亚甲基-2-丙基四氢-2H-吡喃或6-乙基-3,3,4-三甲基-2-丙基-3,6-二氢-2H-吡喃,或优选地其混合物,
2-乙基-6-(4-甲氧基苯基)-3,3-二甲基-4-亚甲基四氢-2H-吡喃或2-乙基-6-(4-甲氧基苯基)-3,3,4-三甲基-3,6-二氢-2H-吡喃,或优选地其混合物。
5.前述权利要求中任何一项的化合物,其中R1为具有多达6个碳原子的烷基或具有多达6个碳原子的烯基;R2为H或具有多达6个碳原子的烷基或具有多达6个碳原子的烯基;R3为具有多达6个碳原子的烷基或具有多达6个碳原子的烯基和R4为H或具有多达6个碳原子的烷基或具有多达6个碳原子的烯基。
6.权利要求5的化合物,其中R1为具有多达6个碳原子的烷基;R2为H或具有多达6个碳原子的烷基;R3为具有多达6个碳原子的烷基或具有多达6个碳原子的烯基和R4为H或具有多达6个碳原子的烷基或具有多达6个碳原子的烯基。
7.权利要求1-3中任何一项的式(X)和权利要求1、2或4中任何一项的式(Y1)化合物的混合物。
8.权利要求1-3中任何一项的式(X)和权利要求1、2或4中任何一项的式(Y2)化合物的混合物。
9.权利要求1、2或4中任何一项的式(Y1)和式(Y2)化合物的混合物。
10.权利要求1-3中任何一项的式(X)和权利要求1、2或4中任何一项的式(Y1)和式(Y2)化合物的混合物。
11.包含前述权利要求中任何一项的化合物或混合物的香味、风味和/或除臭/掩蔽组合物。
12.权利要求11 的香味、风味和/或除臭/掩蔽组合物,其中式(X)和/或式(Y1)和/或式(Y2)化合物的含量包含在0.00001-99.9 wt.%之间,例如在0.0001-95 wt%之间。
13.权利要求11和12中任何一项的香味、风味和/或除臭/掩蔽组合物,其另外包含至少一种酯和/或一种除化合物(X)以外的其他醇,如果化合物(X)存在的话,优选地为酯和除化合物(X)以外的其他醇的至少一种混合物,如果化合物(X)存在的话。
14.权利要求13的香味、风味和/或除臭/掩蔽组合物,其中式(X)和/或式(Y1)和/或式(Y2)化合物以及酯和/或醇一起的含量高于25 wt%,优选地高于50 wt%,例如高于75 wt%,或者甚至高于90 wt%。
15.用于制备权利要求1-10中任何一项的式(X)和/或式(Y1)和/或式(Y2)化合物和/或其混合物的方法,其中
在存在以下任一的情况下:
- 磷酸,优选地为含水磷酸,更优选地为磷酸含量为按重量计10%-85%的含水磷酸,或
- 质子酸,
式(I)化合物与式(II)化合物反应,其中基团R1、R2、R3和R4如权利要求1-10中定义的,
以形成权利要求1-10中任何一项的所述式(X)和/或式(Y1)和/或式(Y2)化合物和/或其混合物,其中式(I)化合物和式(II)化合物的基团R1、R2、R3和R4与所述式(X)和/或式(Y1)和/或式(Y2)化合物和/或其混合物的基团R1、R2、R3和R4相同。
16.用于制备权利要求15的式(X)化合物的方法,其中所述反应在存在磷酸含量为按重量计30%-60%的含水磷酸的情况下进行。
17.用于制备权利要求15的式(Y1)和/或式(Y2)化合物的方法,其中所述反应在存在作为质子酸的对甲苯磺酸的情况下和在有机溶剂,优选地为二氯乙烷中进行。
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