CN116457328A - 醛组合物 - Google Patents
醛组合物 Download PDFInfo
- Publication number
- CN116457328A CN116457328A CN202180074887.7A CN202180074887A CN116457328A CN 116457328 A CN116457328 A CN 116457328A CN 202180074887 A CN202180074887 A CN 202180074887A CN 116457328 A CN116457328 A CN 116457328A
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- China
- Prior art keywords
- aldehyde
- formula
- composition
- represented
- mass
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 117
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title abstract 6
- 150000001299 aldehydes Chemical class 0.000 claims description 157
- 239000002304 perfume Substances 0.000 claims description 44
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 238000005882 aldol condensation reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- UIFVCPMLQXKEEU-UHFFFAOYSA-N 2,3-dimethylbenzaldehyde Chemical compound CC1=CC=CC(C=O)=C1C UIFVCPMLQXKEEU-UHFFFAOYSA-N 0.000 claims description 11
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003205 fragrance Substances 0.000 description 45
- -1 sundry goods Substances 0.000 description 37
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 239000000796 flavoring agent Substances 0.000 description 23
- 235000019634 flavors Nutrition 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002994 raw material Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 14
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- 239000003054 catalyst Substances 0.000 description 12
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- 238000005481 NMR spectroscopy Methods 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 9
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- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 8
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 7
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 7
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 7
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- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 7
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- 239000002904 solvent Substances 0.000 description 7
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- XXIKYCPRDXIMQM-UHFFFAOYSA-N Isopentenyl acetate Chemical compound CC(C)=CCOC(C)=O XXIKYCPRDXIMQM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- JOZKFWLRHCDGJA-UHFFFAOYSA-N citronellol acetate Chemical compound CC(=O)OCCC(C)CCC=C(C)C JOZKFWLRHCDGJA-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 6
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WSTQLNQRVZNEDV-CSKARUKUSA-N (e)-4-methyldec-3-en-5-ol Chemical compound CCCCCC(O)C(\C)=C\CC WSTQLNQRVZNEDV-CSKARUKUSA-N 0.000 description 5
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 5
- 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 4
- UWKAYLJWKGQEPM-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl acetate Chemical compound CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 4
- JRJBVWJSTHECJK-PKNBQFBNSA-N 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one Chemical compound CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C JRJBVWJSTHECJK-PKNBQFBNSA-N 0.000 description 4
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- 235000019502 Orange oil Nutrition 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229940022663 acetate Drugs 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- BLBJUGKATXCWET-UHFFFAOYSA-N cyclaprop Chemical compound C12CC=CC2C2CC(OC(=O)CC)C1C2 BLBJUGKATXCWET-UHFFFAOYSA-N 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 4
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
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- 230000035807 sensation Effects 0.000 description 4
- 235000019615 sensations Nutrition 0.000 description 4
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical compound CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 description 3
- YYMCVDNIIFNDJK-XFQWXJFMSA-N (z)-1-(3-fluorophenyl)-n-[(z)-(3-fluorophenyl)methylideneamino]methanimine Chemical compound FC1=CC=CC(\C=N/N=C\C=2C=C(F)C=CC=2)=C1 YYMCVDNIIFNDJK-XFQWXJFMSA-N 0.000 description 3
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 3
- MZZRKEIUNOYYDF-UHFFFAOYSA-N 2,4-dimethylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1C=C(C)CCC1C=O MZZRKEIUNOYYDF-UHFFFAOYSA-N 0.000 description 3
- SJWKGDGUQTWDRV-UHFFFAOYSA-N 2-Propenyl heptanoate Chemical compound CCCCCCC(=O)OCC=C SJWKGDGUQTWDRV-UHFFFAOYSA-N 0.000 description 3
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- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 description 3
- OALYTRUKMRCXNH-UHFFFAOYSA-N 5-pentyloxolan-2-one Chemical compound CCCCCC1CCC(=O)O1 OALYTRUKMRCXNH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
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- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
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- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/73—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with hydrogenation
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/35—Ketones, e.g. benzophenone
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Abstract
一种醛组合物，其含有下述式(1)所示的醛和下述式(2)所示的醛，式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03。
Description
技术领域
涉及醛组合物、其制造方法、以及含有该醛组合物的香料组合物。
背景技术
已知作为醛的3-(烷基苯基)-2-烷基丙醛类中，存在作为调和香料原料有用的物质。
例如非专利文献1中记载了具有铃兰样的香气的3-(对叔丁基苯基)-2-甲基丙醛(对叔丁基-α-甲基氢化肉桂醛、铃兰醛)、具有甜瓜、黄瓜那样的感觉的兔耳草、铃兰样的香气的3-(对异丙基苯基)-2-甲基丙醛(兔耳草醛)、具有甜的香水草、茴香样花香的3-(3,4-亚甲基二氧基苯基)-2-甲基丙醛(新洋茉莉醛)等作为调和香料原料是有用的。
另外，专利文献1中，作为从抗拒氧化的稳定性和香味韧性(fragrance tenacity)的观点考虑具有有利的气味特性的化合物，公开了3-(5-叔丁基-2-甲基-1-苯基)丙醛等新型芳香族化合物。
现有技术文献
非专利文献
非专利文献1：印藤元一著、“增订修订版合成香料化学和商品知识(増補改訂版合成香料化学と商品知識)”、1996年、213～215页、228页、化学工业日报社
专利文献
专利文献1：日本特开平7-330653号公报
发明内容
发明要解决的问题
特别是花系的香料和调和香料被用于香味产品、化妆品、洗涤剂、卫生用产品、杂货、药物、食品等各种领域。为了提高这些产品的价值，开发了新的香味，寻求具有新的香味的香料。
因此，本发明的目的在于，提供具有有新鲜的海风感(日文：マリン感)的花、植物样的香味，作为香料有用、进而作为调和香料原料也有用的醛组合物。
用于解决问题的方案
本发明人等将各种醛和含有它们多种的组合物合成、配混，评价其香气，结果发现，特定的醛和含有它们的组合物具有优异的香味、以及作为调和香料的原料是优异的，从而完成了本发明。
即，本发明如以下所述。
[1]一种醛组合物，其含有下述式(1)所示的醛和下述式(2)所示的醛，式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03。
[2]一种香料组合物，其含有上述[1]所述的醛组合物。
[3]下述式(1)所示的醛。
[4]一种香料组合物，其含有上述[3]所述的醛。
[5]一种醛的制造方法，其依次具有使下述通式(3)所示的二甲基苯甲醛与丙醛进行醇醛缩合的醇醛缩合工序、和氢化工序，得到下述通式(4)所示的醛。
发明的效果
根据本发明，可以提供具有有新鲜的海风感的花、植物样的香味，作为香料有用、进而作为调和香料原料也有用的醛组合物。
具体实施方式
以下，在本说明书中，“XX～YY”的记载指的是“XX以上且YY以下”。
[醛组合物]
本发明的醛组合物，其含有下述式(1)所示的醛和下述式(2)所示的醛，式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03。
＜式(1)所示的醛＞
本发明的醛组合物中含有的式(1)所示的醛为3-(3,4-二甲基苯基)-2-甲基丙醛。式(1)所示的醛具有有海风感的花的香味。式(1)所示的醛作为香料也是有用的、作为调和香料原料也是有用的。
＜式(2)所示的醛＞
本发明的醛组合物中含有的式(2)所示的醛为3-(2,3-二甲基苯基)-2-甲基丙醛。通过在本发明的醛组合物中含有式(2)所示的醛，新鲜的海风感显著改善。
＜醛组合物的组成等＞
本发明的醛组合物中的前述式(1)所示的醛和前述式(2)所示的醛的总含量优选为95质量％以上、更优选96质量％以上、进一步优选97质量％以上。上限值没有限制，若为100质量％以下即可。
本发明的醛组合物中的前述式(1)所示的醛和前述式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03、更优选97/3～99.9/0.1、进一步优选98/2～99.5/0.5。
通过前述式(1)所示的醛和前述式(2)所示的醛的质量比处于前述范围内，本发明的醛组合物形成特别是具有新鲜的海风感的花、植物样的香味。
本发明的醛组合物中的前述式(1)所示的醛的含量优选为96质量％以上、更优选97质量％以上、进一步优选98质量％以上，另外优选为99.97质量％以下、更优选99.9质量％以下、进一步优选99.5质量％以下。
本发明的醛组合物中的前述式(2)所示的醛的含量优选为0.03质量％以上、更优选0.1质量％以上、进一步优选0.5质量％以上，另外优选为4质量％以下、更优选3质量％以下、进一步优选2质量％以下。
本发明的醛组合物可以含有下述式(5)所示的不饱和醛，但是优选为尽可能少量、更优选2质量％以下、进一步优选1质量％以下、更进一步优选0.5质量％以下、更进一步优选0.1质量％以下、更进一步优选不含有。
式(5)所示的不饱和醛为3-(3,4-二甲基苯基)-2-甲基丙烯醛。
本发明的醛组合物通过实质上不含有式(5)所示的醛，香味进一步具有新鲜感。
本发明的醛组合物可以含有下述式(6)所示的醇。
式(6)所示的醇为3-(3,4-二甲基苯基)-2-甲基丙醇。
本发明的醛组合物中含有前述式(6)所示的醇的情况下，组合物中的前述式(6)所示的醇的含量优选为0.03质量％以上、更优选0.05质量％以上，另外优选为3质量％以下、更优选1质量％以下。
本发明的醛组合物通过少量含有式(6)所示的醇，可以对香味进一步赋予海风感。
具有以上组成的本发明的醛组合物，由于具有有新鲜的海风感的花、植物样的香味，作为香料是有用的。另外，如以下说明那样，作为调和香料(香料组合物)的原料也是有用的，可以用作各种产品的香气成分。
[香料组合物]
本发明的香料组合物含有前述醛组合物。
即，本发明的香料组合物含有醛组合物，该醛组合物含有下述式(1)所示的醛和下述式(2)所示的醛，式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03。
将前述醛组合物配混于调和香料的情况下，花感、香水草的甜味增强。
进而，本发明的香料组合物可以含有下述式(6)所示的醇。
进而，本发明的醛组合物优选实质上不含有式(5)所示的不饱和醛。
本发明的香料组合物中的前述醛组合物的含量，若根据香料组合物的种类、目标的香气的种类和香气的强度等适当调整即可，优选为0.01～90质量％、更优选0.1～50质量％。
本发明的香料组合物中，作为可以与前述醛组合物组合来使用的香料成分，不限于以下，可列举出例如聚氧化亚乙基月桂基硫酸醚等表面活性剂；一缩二丙二醇、邻苯二甲酸二乙酯、乙二醇、丙二醇、肉豆蔻酸甲酯、柠檬酸三乙酯等溶剂；柠檬烯、α-蒎烯、β-蒎烯、萜品烯、香松烯、长叶烯、朱栾萜烯等烃类；里哪醇、香茅醇、香叶醇、橙花醇、松油醇、二氢月桂烯醇、乙基里哪醇、金合欢醇、橙花叔醇、顺式-3-己烯醛、雪松醇、薄荷脑、龙脑、β-苯基乙醇、苯甲醇、苯基己醇、2,2,6-三甲基环己基-3-己醇、1-(2-叔丁基环己氧基)-2-丁醇、4-异丙基环己烷甲醇、4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、异莰基环己醇、3,7-二甲基-7-甲氧基辛烷-2-醇等醇类；丁子香酚、百里酚、香草醛等酚类；里哪醇甲酸酯、甲酸香茅酯、甲酸香叶酯、乙酸正己酯、乙酸顺式-3-己烯酯、乙酸里哪醇酯、乙酸香茅酯、乙酸香叶酯、乙酸橙花酯、乙酸萜品酯、乙酸诺卜酯、乙酸冰片酯、乙酸异冰片酯、乙酸邻叔丁基环己酯、乙酸对叔丁基环己酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苏合香酯、乙酸肉桂酯、乙酸二甲基苄基甲酯、乙酸3-戊基四氢吡喃-4-基酯、丙酸香茅酯、丙酸三环癸烯酯、丙酸烯丙基环己酯、丙酸乙基2-环己酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基甲酯、异丁酸三环癸烯酯、2-壬烯酸甲酯、苯甲酸甲酯、苯甲酸苄酯、肉桂酸甲酯、水杨酸甲酯、水杨酸正己酯、水杨酸顺式-3-己烯酯、惕各酸香叶酯、惕各酸顺式-3-己烯酯、茉莉酮酸甲酯、二氢茉莉酮酸甲酯、甲基-2,4-二羟基-3,6-二甲基苯甲酸酯、缩水甘油酸乙基甲基苯酯、邻氨基苯甲酸甲酯、果香酯等酯类；正辛醛、正癸醛、正十二醛、2-甲基十一醛、10-十一烯醛、香茅醛、柠檬醛、羟基香茅醛、二甲基四氢苯甲醛、4(3)-(4-羟基-4-甲基戊基)-3-环己烯-1-甲醛、2-环己基丙醛、对叔丁基-α-甲基氢化肉桂醛、对异丙基-α-甲基氢化肉桂醛、对乙基-α,α-二甲基氢化肉桂醛、α-戊基肉桂醛、α-己基肉桂醛、胡椒醛、α-甲基-3,4-亚甲基二氧基氢化肉桂醛等醛类；甲基庚烯酮、4-亚甲基-3,5,6,6-四甲基-2-庚酮、戊基环戊酮、3-甲基-2-(顺式-2-戊烯-1-基)-2-环戊烯-1-酮、甲基环戊酮醇、玫瑰酮、γ-甲基紫罗兰酮类、α-紫罗兰酮类、香芹酮、薄荷酮、樟脑、诺卡酮、苄基丙酮、茴香基丙酮、甲基β-萘基酮、2,5-二甲基-4-羟基-3(2H)-呋喃酮、麦芽醇、7-乙酰基-1,2,3,4,5,6,7,8-八氢-1,1,6,7-四甲基萘、麝香酮、香猫酮、环十五酮、环十六烯酮等酮类；乙醛乙基苯基丙基缩醛、柠檬醛二乙基缩醛、苯基乙醛甘油缩醛、乙基乙酰乙酸酯乙二醇缩酮类的缩醛类和缩酮类；茴香脑、β-萘基甲基醚、β-萘基乙基醚、氧化柠檬烯、玫瑰氧化物、1,8-桉树脑、外消旋体或光学活性的十二氢-3a,6,6,9a-四甲基萘并[2,1-b]呋喃等醚类；香茅腈等腈类；γ-壬内酯、γ-十一烷酸内酯、σ-癸内酯、γ-茉莉内酯、香豆素、环十五内酯、环十六内酯、麝香梨内脂、十三烷二酸环乙撑酯、11-氧杂十六内酯等内酯类；橘子、柠檬、香柠檬、柑橘、薄荷、留兰香、熏衣草、甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉花、依兰依兰、茴香、丁香、姜、肉豆蔻、小豆蔻、香柏、扁柏、岩兰草、广藿香、赖百当等天然精油、天然提取物等其他香料物质等。该其他香料物质可以单独配混或配混多种。
为了赋予香气、以及为了进行配混对象物的香气的改良，本发明的香料组合物可以用作香妆品、健康卫生材料、杂货、饮料、食品、准药物、药物等各种产品的香气成分。
本发明的香料组合物例如可以用作香水、花露水类等香味产品；洗发剂、护发素、生发油、发乳、摩丝、定型发胶、发蜡、喷雾液等毛发用化妆品；化妆水、美容液、乳膏、乳液、润肤膏、粉底、香粉、口红、彩妆化妆品等皮肤用化妆品；餐具洗涤用洗涤剂、衣物洗涤用洗涤剂、居住用洗涤剂、玻璃清洁剂、柔软剂、漂白剂、芳香剂、杀虫剂等卫生用产品；牙膏、漱口剂、沐浴剂、止汗剂、烫发剂等准药物；纸产品等杂货；药物；食品等的香气成分。
上述产品中的本发明的香料组合物的含量，若根据各产品所需要的香气的强度等适当调整即可，优选为0.001～50质量％、更优选0.01～20质量％。
另外，本发明的其他的实施方式的香料组合物含有前述式(1)所示的醛。前述式(1)所示的醛作为香料也是有用的，香料组合物中的式(1)所示的醛的含量优选为0.01～90质量％、更优选0.1～50质量％，作为可以与式(1)所示的醛组合来使用的香料成分的例子，可列举出前述例子。
进而这些产品中的该香料组合物的含量分别优选为0.001～50质量％、更优选0.01～20质量％。
[醛的制造方法、和醛组合物的制造方法]
构成本发明的醛组合物的醛可以利用任意制造方法得到，优选通过依次具有使下述通式(3)所示的二甲基苯甲醛与丙醛进行醇醛缩合的醇醛缩合工序、和氢化工序，得到下述通式(4)所示的醛的制造方法得到。
作为构成本发明的醛组合物的醛，至少为式(1)所示的醛和式(2)所示的醛，利用前述的制造方法制造它们时的反应通过下式表示。以下对本制造方法进行说明。
本发明的醛组合物以式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03含有式(1)所示的醛和式(2)所示的醛。可以以利用前述式子的方法分别得到式(1)所示的醛和式(2)所示的醛后，将它们混合，而形成前述质量比的方式进行调整，也可以以在前述的原料、中间体的阶段混合、而形成前述质量比的方式进行调整。
特别是若在作为原料的前述式(3a)所示的3,4-二甲基苯甲醛的市售品中含有前述式(3b)所示的2,3-二甲基苯甲醛的情况下，并且将它们作为原料，则所得到的最终产物的质量比[(1)/(2)]处于前述范围内时，直接使用3,4-二甲基苯甲醛的市售品是简便的，因此优选。
＜醇醛缩合工序＞
本发明的醛的制造方法，作为最初的工序，具有使式(3)所示的醛和丙醛进行醇醛缩合的醇醛缩合工序。
本工序的醇醛缩合反应优选使用碱性化合物作为催化剂。
对于作为催化剂使用的碱性化合物，可例示出氢氧化钠、氢氧化钾、碳酸氢钠、或它们的混合物等。碱性化合物的量相对于作为原料的二甲基苯甲醛1当量，优选为0.05当量以上、更优选0.1当量以上、进一步优选0.2当量以上、并且优选为3当量以下、更优选1当量以下、进一步优选0.5当量以下。
丙醛的添加量相对于作为原料的二甲基苯甲醛1当量，优选为0.5当量以上、更优选0.8当量以上、并且优选为1.5当量以下、更优选1.1当量以下。丙醛的添加优选依次或连续地花费时间进行。例如优选通过滴加来加入。
本工序的醇醛缩合反应优选在溶剂中进行。
作为溶剂，可例示出水混合性的各种有机溶剂，具体而言，优选例示出甲醇、乙醇、1-丙醇、2-丙醇、叔丁醇、烯丙醇、乙二醇、丙二醇、二甘醇等醇，更优选为甲醇、乙醇、1-丙醇、2-丙醇、叔丁醇、乙二醇、丙二醇、二甘醇。
本工序的醇醛缩合反应中的反应温度没有特别限定，但是从反应速度的观点考虑，优选为0℃以上、更优选10℃以上，并且从抑制副反应的观点考虑，优选为50℃以下、更优选40℃以下、进一步优选30℃以下。
另外，反应时间没有特别限定，若为充分进行缩合的时间即可，但是优选为10分钟以上、更优选30分钟以上、进一步优选1小时以上，并且优选为24小时以下、更优选12小时以下、进一步优选6小时以下、更进一步优选3小时以下。
反应的停止若通过中和进行即可，例如通过添加乙酸等酸、可以停止反应。
另外，从反应结束后的溶液将前述式(5)所示的中间体和前述式(5b)所示的中间体(3-(二甲基苯基)-2-甲基丙烯醛)分离的方法没有特别限定，若将分液和提取操作、蒸馏纯化适当组合来进行即可。
例如向反应结束后的溶液添加低极性或非极性的有机溶剂、将前述中间体移相到油相、将所得到的油相例如利用硫酸镁干燥后、将通过过滤得到的滤液浓缩、进而蒸馏纯化，由此可以分离。
＜氢化工序＞
本发明的醛的制造方法在醇醛缩合工序之后具有氢化工序、得到前述式(4)所示的醛。
本工序为将通过醇醛缩合反应得到的前述式(5)所示的中间体和前述式(5b)所示的中间体氢化，而得到作为目的物的式(1)所示的醛和式(2)所示的醛的工序。氢化的方法没有特别限定，可以通过使用了氢化催化剂的公知的方法进行。
作为氢化催化剂，没有特别限定，可以使用公知的催化剂，例如可以使用将Ni、Pt、Pd、Ru等金属负载于碳、二氧化硅、氧化铝、硅藻土等而成的负载型不均匀系氢化催化剂；使用Ni、Co、Fe、Cr等的有机酸盐或乙酰丙酮盐等过渡金属盐和有机铝等还原剂的、所谓的齐格勒型氢化催化剂；Ti、Ru、Rh、Zr等的有机金属化合物等所谓的有机金属络合物等均匀系氢化催化剂等。
本工序中的氢化反应的温度从抑制反应性和副反应的观点考虑，优选为0℃以上、更优选10℃以上、进一步优选20℃以上、并且优选为150℃以下、进一步优选100℃以下。
氢化反应中使用的氢的压力优选为0.01MPaG以上、更优选0.03MPaG以上、进一步优选0.05MPaG以上、并且优选为10MPaG以下、更优选3MPaG以下、进一步优选1MPaG以下、更进一步优选0.5MPaG以下。
反应时间没有特别限定，优选为3分钟以上、更优选10分钟以上、进一步优选30分钟以上、并且优选为24小时以下、更优选12小时以下、进一步优选8小时以下。
氢化反应可以在溶剂的存在下进行。作为所使用的溶剂，只要不会抑制氢化反应则没有特别限定，可例示出戊烷、己烷、异戊烷、庚烷、辛烷、异辛烷等脂肪族烃；环戊烷、甲基环戊烷、环己烷、甲基环己烷、乙基环己烷等脂环式烃；苯、甲苯、乙基苯、二甲苯等芳香族烃等烃溶剂。它们可以单独使用1种或组合2种以上来使用。
从反应结束后的溶液将作为目的物的式(1)所示的醛、式(2)所示的醛、或它们的混合物分离纯化的方法没有特别限定，若适当选择公知的方法进行即可。具体而言，可例示出过滤、色谱、蒸馏纯化等，通过将它们适当组合来纯化，可以得到纯度高的目标的醛、或醛组合物。
含有如此得到的式(1)所示的醛和式(2)所示的醛这两者的醛组合物，具有有新鲜的海风感的花、植物样的香味，作为香料是有用的，进而作为调和香料(香料组合物)的原料也是有用的。另外，式(1)所示的醛作为香料也是有用的、作为调和香料原料也是有用的。
需要说明的是，通过进一步进行本工序中的氢化反应，如下述反应式所示那样也可以得到下述式(6)所示的醇。通过在所得到的醛或组合物中少量含有式(6)所示的醇，可以对香味进一步赋予海风感。
＜其他的制造方法＞
下述式(1)所示的醛、和含有下述式(1)所示的醛和下述式(2)所示的醛的醛组合物也可以利用前述的制造方法以外的方法得到。例如可以如下述反应式表示那样，使用通过邻二甲苯与2-甲基-3,3-二乙酰氧基丙烯的反应合成乙酰氧基烯醇中间体后、利用水解来合成的方法。
根据该方法，如下述反应式所示那样，在邻二甲苯与2-甲基-3,3-二乙酰氧基丙烯的反应中，起因于烯醇中间体的异构体的生成，也副生成下述式(2)所示的醛，因此通过一次的反应，也可以得到含有式(1)所示的醛和式(2)所示的醛的醛组合物。
实施例
基于以下所示的实施例对本发明进行具体说明，但是本发明不被这些实施例限制。
＜组成的分析＞
后述的各工序中的组成、产物的组成、和组合物的组成，通过使用气相色谱(GC-2010Plus、株式会社岛津制作所制)、将正癸烷(试剂等级、FUJIFILMWako Pure ChemicalCorporation制)作为内标物质制成标准曲线来求出。
需要说明的是，作为毛细管柱，使用Agilent Technologies,Inc.制的HR-1701(内径0.32mmφ、长度30m)。对于升温程序，由100℃以5℃/分钟的比率升温至280℃、保持30分钟。
＜NMR光谱分析＞
装置：Varian NMR System PS600 600MHz
溶剂：氘代氯仿(CDCl3)
测定模式：1H、13C
内标物质：四甲基硅烷(TMS)
＜香味/香调的评价＞
实施例和比较例中得到的醛组合物、和香料组合物的香味和香调，通过浸渗于宽度8mm、长度15cm的滤纸，专家闻嗅的方法评价。
＜原料＞
实施例和比较例使用以下的原料。
3,4-二甲基苯甲醛：Mitsubishi Gas Chemical Company,Inc.制
2,3-二甲基苯甲醛：东京化成工业株式会社制
丙醛：FUJIFILMWako Pure Chemical Corporation制
甲醇：FUJIFILMWako Pure Chemical Corporation制特级试剂
庚烷：FUJIFILMWako Pure Chemical Corporation制特级试剂
50％氢氧化钠：FUJIFILMWako Pure Chemical Corporation制
乙酸：FUJIFILMWako Pure Chemical Corporation制
碳酸钠：FUJIFILMWako Pure Chemical Corporation制
10％钯-碳催化剂：N.E.CHEMCAT CORPORATION制、含水品、PE类型
正癸烷：FUJIFILMWako Pure Chemical Corporation制
＜醛的制造＞
实施例1(3-(3,4-二甲基苯基)-2-甲基丙醛(式(1)))
(醇醛缩合工序)
向具备搅拌装置、温度计、滴液漏斗的内容积500mL的圆底烧瓶投入甲醇(100.0g)、50％氢氧化钠水溶液(14.3g)、3,4-二甲基苯甲醛(纯度99.95质量％、2,3-二甲基苯甲醛含量0.01质量％、100.0g)，搅拌的同时冷却到15℃后，花费1小时滴加丙醛(43.6g)。滴加结束后，15℃下保持1小时，完成反应。添加乙酸(10.8g)中和后，加入水、庚烷，利用分液将水相分离。接着将庚烷蒸馏去除，得到粗中间体溶液。将该粗中间体溶液简单蒸馏(116～120℃/2torr)，得到作为中间体、含有3-(3,4-二甲基苯基)-2-甲基丙烯醛(式(5))的中间体溶液。
(氢化工序)
将通过醇醛缩合工序得到的中间体溶液(64.0g)、5％碳酸钠水溶液(30.0g)、10％钯-碳催化剂(N.E.CHEMCAT CORPORATION制、含水品、PE类型、1.0g)投入到具备磁力诱导式搅拌机、可以利用夹套控制内部温度的200mL的不锈钢制高压釜，在75℃、氢压0.4MPa下搅拌6小时进行氢化反应。将反应液过滤而去除催化剂，加入庚烷，利用分液将水相分离。接着将庚烷蒸馏去除，得到粗组合物。对粗组合物使用理论塔板数20层塔板的精馏塔在10torr下进行精馏，作为125～126℃的馏分，得到3-(3,4-二甲基苯基)-2-甲基丙醛(式(1))(21.0g、含有3-(2,3-二甲基苯基)-2-甲基丙醛(式(2))0.01质量％)。以下示出NMR光谱测定的结果。所得到的醛的香味/香调评价的结果如表1所示。
[3-(3,4-二甲基苯基)-2-甲基丙醛(式(1))的NMR光谱测定的结果]
1H NMR(600MHz,CDCl3)δ1.08(3H,d,J＝7.2Hz),2.23(3H,s),2.24(3H,s),2.54(1H,dd,J＝13.8Hz,8.4Hz),2.63-2.67(1H,m),3.01(1H,dd,J＝13.8Hz,6.0Hz),6.90(1H,dd,J＝7.5Hz,1.5Hz),6.94(1H,s),7.05(1H,d,J＝7.8),9.71(1H,s)
13C NMR(150MHz,CDCl3)δ13.3,19.3,19.8,36.3,48.1,126.3,129.7,130.3,134.6,136.1,136.7,204.7
制造例1(3-(2,3-二甲基苯基)-2-甲基丙醛(式(2)))
替代3,4-二甲基苯甲醛，使用2,3-二甲基苯甲醛(纯度99.0％、25.0g)，除此之外与实施例1同样地获得3-(2,3-二甲基苯基)-2-甲基丙醛(式(2))(9.0g、含有3-(3,4-二甲基苯基)-2-甲基丙醛(式(1))0.08质量％)。以下示出NMR光谱的测定的结果。所得到的醛香味/香调评价的结果如表1所示。
[3-(2,3-二甲基苯基)-2-甲基丙醛(式(2))的NMR光谱测定的结果]
1H NMR(600MHz,CDCl3)δ1.10(3H,d,J＝7.2Hz),2.21(3H,s),2.28(3H,s),2.56-2.65(2H,m),3.14(1H,dd,J＝13.8Hz,6.0Hz),6.97(1H,dd,J＝6.3Hz,2.1Hz),7.02-7.05(2H,m),9.72(1H,s)
13C NMR(150MHz,CDCl3)δ13.5,15.3,20.8,34.6,47.1,125.4,127.9,128.3,134.6,136.9,137.2,204.6
制造例2(3-(3,4-二甲基苯基)-2-甲基丙烯醛(式(5)))
(醇醛缩合工序)
向具备搅拌装置、温度计、滴液漏斗的内容积500mL的圆底烧瓶投入甲醇(100.0g)、50％氢氧化钠水溶液(14.3g)、3,4-二甲基苯甲醛(纯度99.2质量％、2,3-二甲基苯甲醛含量0.69质量％、100.0g)，搅拌的同时冷却到15℃后，花费1小时滴加丙醛(43.6g)。滴加结束后，15℃下保持1小时，完成反应。添加乙酸(10.8g)中和后，加入水、庚烷，利用分液将水相分离。接着将庚烷蒸馏去除，得到粗中间体溶液。将该粗中间体溶液简单蒸馏(116～120℃/2torr)，进而使用理论塔板数20层塔板的的精馏塔进行精馏，得到3-(3,4-二甲基苯基)-2-甲基丙烯醛(式(5))(10.0g、纯度98.08质量％)。
＜醛组合物的制造＞
实施例2
(醇醛缩合工序)
向具备搅拌装置、温度计、滴液漏斗的内容积500mL的圆底烧瓶投入甲醇(100.0g)、50％氢氧化钠水溶液(14.3g)、3,4-二甲基苯甲醛(纯度99.2质量％、2,3-二甲基苯甲醛含量0.69质量％、100.0g)，搅拌的同时冷却到15℃后，花费1小时滴加丙醛(43.6g)。滴加结束后，15℃下保持1小时，完成反应。添加乙酸(10.8g)中和后，加入水、庚烷，利用分液将水相分离。接着将庚烷蒸馏去除，得到粗中间体溶液。将该粗中间体溶液简单蒸馏(116～120℃/2torr)，得到作为中间体、含有3-(3,4-二甲基苯基)-2-甲基丙烯醛(式(5))92.2％、3-(2,3-二甲基苯基)-2-甲基丙烯醛(式(5b))0.7％的中间体溶液。
(氢化工序)
将通过醇醛缩合工序得到的中间体溶液(64.0g)、5％碳酸钠水溶液(30.0g)、10％钯-碳催化剂(N.E.CHEMCAT CORPORATION制、含水品、PE类型、1.0g)投入到具备磁力诱导式搅拌机、可以利用夹套控制内部温度的200mL的不锈钢制高压釜，在75℃、氢压0.4MPa下搅拌6小时进行氢化反应。将反应液过滤而去除催化剂，加入庚烷，利用分液将水相分离。接着将庚烷蒸馏去除，得到粗组合物(3-(3,4-二甲基苯基)-2-甲基丙醛纯度91.0％)。对粗组合物使用理论塔板数20层塔板的精馏塔在10torr下进行精馏，作为125～126℃的馏分，得到含有3-(3,4-二甲基苯基)-2-甲基丙醛(式(1))和3-(2,3-二甲基苯基)-2-甲基丙醛(式(2))的醛组合物(20.0g)。所得到的醛组合物的组成和香味/香调评价的结果如表1所示。
实施例3～4及比较例1
在实施例2中得到的醛组合物中添加制造例1中得到的醛、制造例2中得到的醛，使各成分形成表1所示的比率而得到各醛组合物。所得到的醛组合物的组成和香味/香调评价的结果如表1所示。
[表1]
表1
实施例5及比较例2(花水果样的香料组合物(面向洗涤剂))
对于表2所示的调和香料基质，分别以3.5质量％添加实施例2中得到的醛组合物、和铃兰醛(Lilial、3-(对叔丁基苯基)-2-甲基丙醛)，进行香味/香调评价。
[表2]
表2 (质量％)
| 实施例5 | 比较例2 | |
| 铃兰醛(LILIAL)(3-(对叔丁基苯基)-2-甲基丙醛) | - | 3.5 |
| 实施例2的醛组合物((1)/(2)＝99.03/0.97) | 3.5 | - |
| 醛(ALDEHYDE)C-14 | 2 | 2 |
| 庚酸烯丙酯(ALLYL OENANTHATE) | 1.6 | 1.6 |
| 龙涎酮(ISO E SUPER) | 2.5 | 2.5 |
| 降龙涎香醚(AMBROXAN) | 0.1 | 0.1 |
| 香茅醇(CITRONELLOL) | 2.5 | 2.5 |
| 丙酸三环癸烯酯(CYCLAPROP) | 8.5 | 8.5 |
| 水杨酸环己酯(CYCLO HEXYL sALICYLATE) | 1 | 1 |
| 3，6-二甲基-3-环己烯-1-甲醛(CYCLVERTAL＝VERTOLIFF) | 0.4 | 0.4 |
| 大马酮(DAMASCENONE) | 0.3 | 0.3 |
| 2，6-二甲基-7-辛烯-2-醇(DIHYDRO MYRCENOL) | 2 | 2 |
| 1，2-双棕榈酸甘油酯(DPG) | 8.45 | 8.45 |
| 1-(5，5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮(DYNASCONE)10DPG | 0.7 | 0.7 |
| 苯甲酸乙酯(ETHYL BENZOATE) | 0.15 | 0.15 |
| 2-甲基丁酸乙酯(ETHYL 2-METHYL BUTYRATE) | 1 | 1 |
| 环十五内酯(EXALTOLIDE TOTAL) | 2.5 | 2.5 |
| 乙酸香叶酯(GERANYL ACETATE) | 2 | 2 |
| 环十五烯内酯(HABANOLDE) | 4 | 4 |
| 胡椒醛(HELIOTROPINE) | 0.5 | 0.5 |
| 己基肉桂醛(HEXYL CINNAMIC ALDEHYDE) | 1.2 | 1.2 |
| 丁酸异戊酯(ISO AMYL BUTYRATE) | 0.3 | 0.3 |
| 里哪醇(LINALOOL) | 8 | 8 |
| 3，5，5-三甲基-己酸乙酯(MELUSAT) | 2.8 | 2.8 |
| α-异甲基紫罗兰酮(METHYL IONONE GAMMA) | 4 | 4 |
| 甲基柑青醛B(MYRAC ALDEHYDE) | 0.2 | 0.2 |
| 5倍瓦伦西亚橙油(0RANGE OIL VALENCIA 5-FOLD) | 2 | 2 |
| PHENOSANOL | 2.5 | 2.5 |
| 苯乙醇(PHENYL ETHYL ALCOHOL) | 3.5 | 3.5 |
| 环己基丙酸乙酯(POIRENATE) | 4.5 | 4.5 |
| 梨醇酯(PRENYL ACETATE) | 0.6 | 0.6 |
| 4-甲基-3-癸烯-5-醇(UNDECAVERTOL) | 0.2 | 0.2 |
| 乙酸邻叔丁基环己酯(VERDOX) | 12 | 12 |
| 4-叔丁基环己基乙酸酯(VERTENEX) | 9 | 9 |
| 三环癸烷羧酸乙酯(FRUITATE) | 5.5 | 5.5 |
| 总计 | 100 | 100 |
与比较例2的香料组合物相比，实施例5的香料组合物的天芥菜(Heliotrope)样的甜味和花(Floral)感升高。
实施例6及比较例3(水果/花样的香料组合物(面向身体护理))
对于表3所示的调和香料基质，分别以2.5质量％添加实施例2中得到的醛组合物、和新洋茉莉醛(Helional、3-(3，4-亚甲基二氧基苯基)-2-甲基丙醛)，进行香味/香调评价。
[表3]
表3 (质量％)
| 实施例6 | 比较例3 | |
| 新洋茉莉醛(Helional、3-(3，4-亚甲基二氧基苯基)-2-甲基丙醛) | - | 2.5 |
| 实施例2的醛组合物((1)/(2)＝99.03/0.97) | 2.5 | - |
| 醛(ALDEHYDE)C-14 | 0.3 | 0.3 |
| 环己基丙酸烯丙酯(Allyl cyclohexyl propionate) | 0.3 | 0.3 |
| 庚酸烯丙酯(Allyl oenanthate) | 0.1 | 0.1 |
| 极品龙涎醇10％(Ambermax 10tec) | 0.7 | 0.7 |
| Amberose | 3 | 3 |
| 降龙涎香醚(Ambroxan) | 0.1 | 0.1 |
| 乙酸苄酯(Benzy l acetate) | 0.5 | 0.5 |
| 蓝莓基质(Blueberry base) | 0.2 | 0.2 |
| 顺式-茉莉酮(Cis-jasmone) | 0.1 | 0.1 |
| 乙酸-顺式-3-己烯酯(Cis-3-hexenyl acetate) | 0.1 | 0.1 |
| 水杨酸-顺式-3-己烯酯(Cis-3-hexenyl salicylate) | 2.8 | 2.8 |
| 香茅醇(Citronellol) | 1.3 | 1.3 |
| 乙酸香茅酯(Citronellyl acetate) | 0.6 | 0.6 |
| α-大马酮(Damascone alpha) | 0.16 | 0.16 |
| Y-癸内酯(Decalactone gamma) | 0.3 | 0.3 |
| 1，2-双棕榈酸甘油酯(DPG) | 17.4 | 17.4 |
| 乙酰乙酸乙酯(Ethyl acetoacetate) | 0.2 | 0.2 |
| 丁酸乙酯(Ethyl butyrate) | 0.04 | 0.04 |
| 乙基芳樟醇(Ethyl linalool) | 2.2 | 2.2 |
| 乙基麦芽酚(Ethyl maltol) | 0.14 | 0.14 |
| 麝香T(Ethylene brassylate) | 12.5 | 12.5 |
| 铃兰吡喃(Florol) | 8 | 8 |
| 环十五烯内酯(Habanolide) | 7 | 7 |
| 二氢茉莉酮酸甲酯(Hedione) | 26 | 26 |
| 乙酸己酯(Hexyl acetate) | 0.5 | 0.5 |
| β-紫罗酮(lonone beta) | 1 | 1 |
| 女贞醛(Ligustral) | 0.1 | 0.1 |
| 曼可罗兰(Magnolan) | 2 | 2 |
| 2-甲基戊酸乙酯(Manzanate) | 0.04 | 0.04 |
| α-异甲基紫罗兰酮(Methyl ionone gamma) | 2 | 2 |
| Y-壬内酯(Nonalactone gamma) | 0.1 | 0.1 |
| 佛罗里达橙油(Orange oil florida) | 2 | 2 |
| 苯乙醛(Phenyl acetaldehyde)50PEA | 0.04 | 0.04 |
| 苯乙醇(Phenylethylalcohol) | 0.5 | 0.5 |
| 覆盆子酮(Raspberry ketone) | 0.2 | 0.2 |
| 玫瑰氧化物(Rose oxide) | 0.06 | 0.06 |
| 檀香醇(Sandela) | 0.7 | 0.7 |
| 乙酸苏合香酯(Styrallyl acetate) | 0.3 | 0.3 |
| 4-甲基-3-癸烯-5-醇(Undecavertol) | 0.6 | 0.6 |
| 2，2，5-三甲基-5-戊基环戊酮(Veloutone) | 0.32 | 0.32 |
| 乙酸邻叔丁基环己酯(Veerdox) | 3 | 3 |
| 总计 | 100 | 100 |
与比较例3的香料组合物相比，实施例6的香料组合物的效力强，花(Floral)感增加，有分量。
实施例7及比较例4(花/植物样的香料组合物(面向身体护理))
对于表4所示的调和香料基质，分别以3质量％添加实施例2中得到的醛组合物、和波吉洪醛(Bourgeonal、3-(4-叔丁基苯基)丙醛)，进行香味/香调评价。
[表4]
表4 (质量％)
| 实施例7 | 比较例4 | |
| 波吉洪醛(Bourgeonal、3-(4-叔丁基苯基)丙醛) | - | 3 |
| 实施例2的醛组合物((1)/(2)＝99.03/0.97) | 3 | - |
| 醛(ALDEHYDE)C-14 | 0.5 | 0.5 |
| 醛(ALDEHYDE)C-16 | 0.5 | 0.5 |
| 环己基丙酸烯丙酯(Allyl cyclohexyl propionate) | 1 | 1 |
| 戊基肉桂醛(Amyl cinnamic aldehyde) | 8 | 8 |
| 茴香醛(Anisaldehyde) | 0.5 | 0.5 |
| 乙酸苄酯(Benzyl acetate) | 2.6 | 2.6 |
| 顺式-3-己烯醇(Cis-3-Hexenol) | 0.6 | 0.6 |
| 香茅醇(Citronellol) | 2 | 2 |
| 香茅腈(Citronellyl nitrile) | 0.2 | 0.2 |
| 兔耳草醛(Cyclamen aldehyde) | 1.5 | 1.5 |
| δ-大马酮(Damascone delta) | 0.1 | 0.1 |
| γ-癸内酯(Decalactone gamma) | 0.4 | 0.4 |
| 1，2-双棕榈酸甘油酯(DPG) | 3.6 | 3.6 |
| 乙基香兰素(Ethyl vanillin) | 0.05 | 0.05 |
| 2-甲基丁酸乙酯(Ethyl-2-methyl butyrate) | 0.3 | 0.3 |
| 钤兰吡喃(Florol) | 9 | 9 |
| 乙酸香叶酯(Geranyl acetate) | 0.3 | 0.3 |
| 二氢茉莉酮酸甲酯(Hedione) | 25 | 25 |
| 乙酸己酯(Hexyl acetate) | 0.6 | 0.6 |
| 水杨酸己酯(Hexyl salicylate) | 5 | 5 |
| 女贞醛(Ligustral) | 0.2 | 0.2 |
| 里哪醇(Linalool) | 8 | 8 |
| 乙酸芳樟酯(Linalyl acetate) | 3 | 3 |
| 2，6-二甲基-5-庚烯醛(Melonal) | 0.1 | 0.1 |
| 邻氨基苯甲酸甲酯(Methyl anthranilate) | 0.1 | 0.1 |
| α-异甲基紫罗兰酮(Methyl ionone gamma) | 5 | 5 |
| 辛炔羧酸甲酯(Methyl octyne carbonate) | 0.15 | 0.15 |
| Musk 50BB | 12 | 12 |
| 佛罗里达橙油(0range oil florida) | 4 | 4 |
| 梨醇酯(Prenyl acetate) | 0.2 | 0.2 |
| 覆盆子酮(Raspberry ketone) | 0.2 | 0.2 |
| 乙酸苏合香酯(styrallyl acetate) | 0.8 | 0.8 |
| 松油醇(Terpineol) | 1.5 | 1.5 |
| 总计 | 100 | 100 |
与比较例4的香料组合物相比，实施例7的香料组合物的有清洁感的白花(WhiteFloral)感增加，香味有影响力。
实施例8及比较例5(花/植物样的香料组合物(面向织物护理))
对于表5所示的调和香料基质，分别以12质量％添加实施例2中得到的醛组合物、和波吉洪醛(Bourgeonal、3-(4-叔丁基苯基)丙醛)，进行香味/香调评价。
[表5]
表5 (质量％)
| 实施例8 | 比较例5 | |
| 波吉洪醛(Bourgeonal、3-(4-叔丁基苯基)丙醛) | - | 12 |
| 实施例2的醛组合物((1)/(2)＝99.03/0.97) | 12 | - |
| Amberone | 20 | 20 |
| 水杨酸戊酯(Amyl salicylate) | 1.8 | 1.8 |
| 茴香醛(Anisaldehyde) | 1.8 | 1.8 |
| 苯甲醛(Benzaldehyde) | 0.04 | 0.04 |
| 乙酮苄酯(Benzyl acetate) | 2 | 2 |
| 乙酸-顺式-3-己烯酯(Cis-3-Hexenyl acetate) | 0.04 | 0.04 |
| 兔耳草醛(Cyclamen aldehyde) | 0.35 | 0.35 |
| 丙酸三环癸烯酯(Cyclaprop) | 2.5 | 2.5 |
| δ-大马酮(Damascone delta) | 0.13 | 0.13 |
| 1，2-双棕榈酸甘油酯(DPG) | 6.51 | 6.51 |
| 海风醛(Floralozone) | 0.1 | 0.1 |
| 铃兰吡喃(Florol) | 8.5 | 8.5 |
| 二氢茉莉酮酸甲酯(Hedione) | 4.5 | 4.5 |
| 新洋茉莉醛(Helional) | 3.5 | 3.5 |
| α-紫罗酮(lonone alpha) | 2.5 | 2.5 |
| 乙酸三环癸烯酯(Jasmacyclene) | 8 | 8 |
| 可艾酮(Koavone) | 1.3 | 1.3 |
| 女贞醛(Ligustral) | 0.5 | 0.5 |
| 里哪醇(Linalool) | 2.5 | 2.5 |
| 邻氨基苯甲酸甲酯(Methyl anthranilate) | 0.27 | 0.27 |
| α-异甲基紫罗兰酮(Methyl ionone gamma) | 15 | 15 |
| 2-萘乙酮(0ranger crystals) | 0.53 | 0.53 |
| 乙酸苯乙酯(Phenyl ethyl acetate) | 2.5 | 2.5 |
| 苯乙醇(phenyl ethyl alcohol) | 2.5 | 2.5 |
| 梨醇酯(Prenyl acetate) | 0.1 | 0.1 |
| 4-甲基-3-癸烯-5-醇(undecavertol) | 0.17 | 0.17 |
| 紫罗兰香馜(Violiff) | 0.36 | 0.36 |
| 总计 | 100 | 100 |
比较例5的香料组合物的醛(Aldehyde)感强，与此相对地，实施例8的香料组合物的白花(White Floral)感增加，香味一致、为非常优雅的香味。
由实施例的结果可知，本发明的醛组合物具有有新鲜的海风感的花、植物样的香味，因此作为香料是有用的。进而可知配混于调和香料的情况下，花感、香水草样的甜味增强，作为调和香料的原料也是有用的。
另外可知，本发明的式(1)所示的醛由于也具有有海风感的花的香味，因此作为香料也是有用的。
Claims (5)
1.一种醛组合物，其含有下述式(1)所示的醛和下述式(2)所示的醛，
式(1)所示的醛和式(2)所示的醛的质量比[(1)/(2)]为96/4～99.97/0.03，
2.一种香料组合物，其含有权利要求1所述的醛组合物。
3.下述式(1)所示的醛，
4.一种香料组合物，其含有权利要求3所述的醛。
5.一种醛的制造方法，其依次具有使下述通式(3)所示的二甲基苯甲醛与丙醛进行醇醛缩合的醇醛缩合工序、和氢化工序，得到下述通式(4)所示的醛，
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| PCT/JP2021/040326 WO2022102465A1 (ja) | 2020-11-12 | 2021-11-02 | アルデヒド組成物 |
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| EP (1) | EP4245748A4 (zh) |
| JP (1) | JPWO2022102465A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3703584A1 (de) * | 1987-02-06 | 1988-08-18 | Consortium Elektrochem Ind | Aldehyde und alkohole mit 3-methyl- oder 3,5-dimethylphenylgruppen, deren herstellung und verwendung als duftstoffe |
| DE69516036T2 (de) | 1994-05-31 | 2000-12-21 | Firmenich & Cie | Aromatische Verbindungen und ihre Verwendung in der Parfümerie |
| GB201308236D0 (en) * | 2013-05-08 | 2013-06-12 | Givaudan Sa | Improvements in or relating to organic compounds |
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