TWI821449B - 羧酸酯化合物、其製造方法、以及香料組成物 - Google Patents
羧酸酯化合物、其製造方法、以及香料組成物 Download PDFInfo
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- TWI821449B TWI821449B TW108140578A TW108140578A TWI821449B TW I821449 B TWI821449 B TW I821449B TW 108140578 A TW108140578 A TW 108140578A TW 108140578 A TW108140578 A TW 108140578A TW I821449 B TWI821449 B TW I821449B
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- carboxylic acid
- ester compound
- reaction
- acid ester
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- -1 Carboxylate ester compound Chemical class 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 239000002304 perfume Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 18
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 239000002994 raw material Substances 0.000 abstract description 16
- 239000000126 substance Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000003205 fragrance Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 238000005810 carbonylation reaction Methods 0.000 description 16
- JURLNXPXCMWCHE-KRXBUXKQSA-N (3e)-3-ethylidenebicyclo[2.2.1]heptane Chemical compound C1CC2C(=C/C)/CC1C2 JURLNXPXCMWCHE-KRXBUXKQSA-N 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000032050 esterification Effects 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- 239000003599 detergent Substances 0.000 description 6
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- 239000000796 flavoring agent Substances 0.000 description 5
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- 238000004817 gas chromatography Methods 0.000 description 5
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- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
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- 239000004615 ingredient Substances 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
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- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
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- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
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- 239000005457 ice water Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 235000013599 spices Nutrition 0.000 description 3
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- BGCIAWBDYRWKEK-UHFFFAOYSA-N (1-butylcyclohexyl) acetate Chemical group CCCCC1(OC(C)=O)CCCCC1 BGCIAWBDYRWKEK-UHFFFAOYSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- FLUWAIIVLCVEKF-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 description 2
- DEMFSGPWYVAINM-UHFFFAOYSA-N 3-ethylbicyclo[2.2.1]heptane Chemical compound C1CC2C(CC)CC1C2 DEMFSGPWYVAINM-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 2
- 241000271309 Aquilaria crassna Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- DZNVIZQPWLDQHI-UHFFFAOYSA-N Citronellyl formate Chemical compound O=COCCC(C)CCC=C(C)C DZNVIZQPWLDQHI-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000005792 Geraniol Substances 0.000 description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical group CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- 241000220317 Rosa Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1s,4s,6r)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 229960002903 benzyl benzoate Drugs 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
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- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
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- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
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- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 2
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- VNYPXKJMCADQLD-UHFFFAOYSA-N ethyl 2-ethylbicyclo[2.2.1]heptane-2-carboxylate Chemical compound CCC1(CC2CCC1C2)C(=O)OCC VNYPXKJMCADQLD-UHFFFAOYSA-N 0.000 description 2
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- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
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- 150000002576 ketones Chemical class 0.000 description 2
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Abstract
本發明之課題係提供作為調合香料原料為有用之具有水果香氣的羧酸酯化合物及其製造方法、以及含有該羧酸酯化合物之香料組成物。
本發明之羧酸酯化合物係以式(1)表示。
Description
本發明係關於新穎的羧酸酯化合物及其製造方法、以及含有該羧酸酯化合物之香料組成物，尤其係關於作為調合香料原料而言為有用的羧酸酯化合物及其製造方法、以及含有該羧酸酯化合物之香料組成物。
已知酯類之中，有作為香料為有用的化合物。例如：具有玫瑰般之香氣之乙酸香葉酯、具有茉莉花般之甘甜香氣之茉莉酸甲酯、具有水果香調(note)之Fruitate(參環[5.2.1.02,6
]癸烷-2-甲酸乙酯)、具有強烈乾燥水果香調之苯甲酸甲酯等，作為調合香料原料為有用。又，專利文獻1中，記載為莰烯之衍生物之羧酸酯化合物具有清爽的松(pine)般之香氣。
[先前技術文獻]
[專利文獻]
[專利文獻1]國際公開第2012/063433號
[發明所欲解決之課題]
本發明欲解決之課題，係提供作為調合香料原料為有用的具有水果香氣之新穎的羧酸酯化合物及其製造方法、以及含有該羧酸酯化合物之香料組成物。
[解決課題之手段]
本案發明者在合成各種化合物並針對其香氣進行探討後，發現特定的羧酸酯化合物具有水果的香氣，並完成了本發明。
本發明係提供以下>1>～>4>。
>1>式(1)表示之羧酸酯化合物。
[化1]
(式中，R係碳數2～6之烷基。)
>2>如>1>之羧酸酯化合物，其中，R係乙基、正丙基、或異丙基。
>3>一種香料組成物，含有式(1)表示之羧酸酯化合物。
[化2]
(式中，R係碳數2～6之烷基。)
>4>一種羧酸酯化合物之製造方法，係式(1)表示之羧酸酯化合物之製造方法，係在氟化氫之存在下，使式(2)表示之化合物與一氧化碳進行反應後，進一步使其與碳數2～6之醇進行反應。
[化3]
(式中R係碳數2～6之烷基。)
[化4]
[發明之效果]
本發明之羧酸酯化合物具有水果的香氣，作為用在盥洗用品、肥皂、衣物用洗劑等範圍廣泛的製品中之賦予香氣成分而言為有用。此外，依據本發明之羧酸酯化合物之製造方法，可利用於工業上為有利的方法來製造該羧酸酯化合物。
以下，利用實施形態針對本發明進行說明。又，以下說明中，表示數值範圍之「A～B」的記載，係代表「A以上且B以下」(A>B時)，或「A以下且B以上」(A>B時)。亦即，代表包含為端點之A及B之數值範圍。
又，質量份及質量%各自與重量份及重量%同義。
[羧酸酯化合物]
本發明之羧酸酯化合物係以下式(1)表示。
[化5]
(式中，R係碳數2～6之烷基。)
式(1)中，R係碳數2～6之烷基。就碳數2～6之烷基而言，宜為直鏈狀或分支狀之烷基，可列舉：乙基、正丙基、異丙基、正丁基、異丁基、三級丁基、戊基、己基等。該等之中，考量香氣性之觀點，宜為乙基、正丙基、異丙基，更宜為乙基。
式(1)表示之羧酸酯化合物具有立體異構物，可為外型(Exo)亦可為內型(Endo)，又，亦可為依任意的比率混合外型及內型，並無特別限定。
該等之中，考量製造容易性及香氣性之觀點，宜為外型。
[羧酸酯化合物之製造方法]
本發明之羧酸酯化合物(式(1)表示之羧酸酯化合物)，可利用在氟化氫(以下亦稱作「HF」)之存在下，使式(2)表示之化合物與一氧化碳進行反應後，進一步使其與碳數2～6之醇進行反應的方法來在工業上有利地製造。
具體而言，在氟化氫(HF)之存在下，使式(2)表示之化合物與一氧化碳進行反應並羰基化，獲得式(3)表示之醯氯。然後，在氟化氫之存在下，使式(3)表示之醯氯與碳數2～6之醇進行反應並酯化。
[化6]
(式中，R係碳數2～6之烷基。)
(式(2)表示之化合物)
式(2)表示之化合物係2-亞乙基降莰烷，可將5-亞乙基-2-降莰烯(ENB)予以氫化來獲得。又，已知ENB係作為乙烯-丙烯-二烯(EPDM)橡膠之原料。
(一氧化碳)
本發明中使用之一氧化碳，亦可含有氮、甲烷等鈍性氣體。反應時之一氧化碳分壓宜為0.5～5MPaG，更宜為1～3MPaG之範圍內。一氧化碳分壓若高於0.5MPaG，則羰基化反應充分地進展，可不併發歧化、聚合等副反應而以高產率獲得目的物之脂環族羰基化合物。又，考量設備負荷之觀點，一氧化碳分壓宜在5MPaG以下。
(氟化氫)
本發明中使用的HF，係反應的溶劑，也係觸媒，且會成為原料，因此宜使用實質上無水者。HF之使用量，相較於為原料之式(2)表示之化合物，宜為4～25莫耳倍、更宜為6～15莫耳倍。HF之莫耳比若係4莫耳倍以上，羰基化反應會以良好效率進展，可抑制歧化、聚合等副反應，且能以高產率獲得為目的物之羰基化合物。又，考量原料成本及生產性之觀點宜使用25莫耳倍以下之HF。
(反應溶劑)
羰基化反應中，亦可使用良好地溶解原料且對HF為非活性的溶劑。例如可使用已烷、庚烷、癸烷等飽和烴化合物。溶劑之使用的有無及量並無特別限定，適當選擇即可，考量抑制聚合反應並使產率改善之觀點，相較於為原料之式(2)之化合物宜為0.2～2.0質量倍，考量生產性及能源效率之觀點宜為0.5～1.2質量倍。
(羰基化反應之反應條件)
羰基化反應之形式並無特別限制，可為批次式、半連續式、連續式等之任一種方法。
羰基化反應之反應溫度宜為-50℃～30℃，更宜為-30℃～20℃之範圍。考量反應速度之觀點宜於-50℃以上進行。又，考量抑制異構物生成量之觀點宜於30℃以下進行。
羰基化反應之反應時間，考量使反應充分進展之觀點，宜為1小時以上，並且，考慮反應效率之觀點，宜為5小時以下。反應終點並無特別限定，可例示一氧化碳之吸收停止之時點。
羰基化反應中，利用HF與一氧化碳生成醯氯(式(3))。生成而得之醯氯反應液(羰基化反應液)，可在將過剩的HF餾去之後，利用蒸餾等常法進行精製，並使用作為接續步驟之酯化步驟的原料，但通常係採用使仍含有HF觸媒之羰基化反應液直接與醇進行反應來製造羧酸酯化合物之方法。
(醇)
本發明中使用之醇係碳數2～6之醇。
就碳數2～6之醇而言，並無特別限制，可因應目的而適當選擇，可舉例如：乙醇、正丙醇、異丙醇、正丁醇、異丁醇、三級丁基、戊醇、己醇。該等之中，宜為乙醇、正丙醇、異丙醇、正丁醇、異丁醇，更宜為乙醇、正丙醇、異丙醇，又更宜為乙醇。
碳數2～6之醇的使用量，並無特別限制，可因應目的而適當選擇，相對於為原料之式(2)之化合物，宜為0.5～2.0莫耳倍，更宜為0.8～1.7莫耳倍，又更宜為1.0～1.7莫耳倍。
(酯化反應之反應條件)
酯化反應之反應溫度，考量改善產率之觀點宜為-20℃以上，並且，考量抑制酯之分解、添加之醇之脫水反應等副反應之觀點，宜為20℃以下。
酯化反應之反應時間，考量使反應充分進展之觀點宜為0.5小時以上，並且，考量反應效率之觀點宜為3小時以下。反應終點並無特別限定，可例示認為反應熱已不再上升之時點。
如此般獲得之酯化產物係羧酸酯-HF錯合物溶液。藉由加熱羧酸酯-HF錯合物溶液，羧酸酯與HF之鍵結分解，可將HF氣化分離、回收、再利用。該錯合物之分解操作有儘量迅速地進行並避免產物之加熱變質、異構化等之必要。為了迅速地進行錯合物之熱分解，宜在例如對HF為非活性之溶劑(例如庚烷等飽和脂肪族烴、甲苯等芳香族烴)之回流下進行分解。又，將反應液抽出至冰水中時，例如從高壓釜底部抽出至冰水中，使油相與水相分離後，宜將油相利用2質量%氫氧化鈉水溶液清洗2次、利用蒸餾水清洗2次，並利用無水硫酸鈉進行脫水。此外，對獲得之液利用蒸發器將低沸點成分等去除後，使用理論板數約20板之精餾塔進行精餾，藉此可獲得經精製之羧酸酯化合物。
又，本發明之羧酸酯化合物亦可利用上述以外之方法來製造。例如，如下述圖解所示，使由環戊二烯與2-乙基丙烯醛之狄耳士-阿德爾反應而獲得之醛化合物(式(4))氧化而獲得羧酸化合物(式(5))，使該該羧酸化合物與碳數2～6之醇進行反應而獲得酯化合物(式(6))，使該酯化合物氫化，藉此可獲得本發明之羧酸酯化合物(式(1)表示之羧酸酯化合物)。又，式(5)表示之羧酸化合物，亦可藉由環戊二烯與2-乙基丙烯酸(2-亞甲基丁酸)之狄耳士-阿德爾反應而獲得。
[化7]
(式中，R係碳數2～6之烷基。)
本發明之羧酸酯化合物，由於具有水果的香氣，因此可單獨或與其他成分組合而使用作為肥皂、沐浴乳、潤髮乳、洗劑、化妝品、噴霧製品、芳香劑、香水、入浴劑等賦香成分。又，可期待使用作為食品、醫藥、農藥、液晶等的合成中間體。
[香料組成物]
本發明之香料組成物含有前述式(1)表示之羧酸酯化合物。
本發明之香料組成物係在通常使用之其他香料成分或所期望組成之調合香料中，混合單獨或2種以上之前述式(1)表示之羧酸酯化合物並摻合而獲得。前述式(1)表示之羧酸酯化合物之摻合量，依據調合香料的種類、目的之香氣的種類及香氣的強度等而有所不同，宜在調合香料中添加0.01～90質量%，更宜添加0.1～50質量%。
就可與本發明之羧酸酯化合物組合並使用之其他香料成分而言，並無特別限制，可因應目的來適當選擇。可舉例如：
檸檬烯、α-蒎烯、β-蒎烯、萜品烯、雪松烯(cedrene)、長葉烯(longifolene)、瓦倫西亞橘烯(valencene)等烴類；
沉香醇(linalool)、香茅醇、香葉醇(Geraniol)、橙花醇(Nerol)、萜品醇(Terpineol)、二氫月桂烯醇(Dihydromyrcenol)、乙基沉香醇(Ethyllinalool)、菌綠烯醇(Farnesol)、橙花三級醇(Nerolidol)、順-3-己烯醇、雪松醇(Cedrol)、薄荷醇(Menthol)、冰片(Borneol)、β-苯基乙醇、苯甲醇、苯基已醇、2,2,6-三甲基環己基-3-已醇、1-(2-三級丁基環己氧基)-2-丁醇、4-異丙基環己甲醇、4-甲基-2-(2-甲基丙基)四氫-2H-吡喃-4-醇、2-甲基-4-(2,2,3-三甲基-3-環戊烯-1-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-環戊烯-1-基)-2-丁烯-1-醇、異樟腦基環已醇(Isocamphyl cyclohexanol)、3,7-二甲基-7-甲氧基辛烷-2-醇等醇類；
丁香酚、瑞香酚(Thymol)、香草精等酚類；
甲酸沉香酯、甲酸香茅酯、甲酸香葉酯、乙酸正己酯、乙酸順-3-己烯酯、乙酸沉香酯、乙酸香茅酯、乙酸香葉酯、乙酸橙花酯、乙酸萜品酯、乙酸諾甫酯(Nopyl acetate)、乙酸莰酯(Bornyl acetate)、乙酸異莰酯(Isobornyl acetate)、乙酸鄰三級丁基環己酯、乙酸對三級丁基環己酯、乙酸三環癸烯酯、乙酸苄酯、乙酸蘇合香酯(Styrallyl acetate)、乙酸桂皮酯(Cinnamyl acetate)、乙酸二甲基苄基原酯(Dimethyl benzyl carbinyl acetate)、乙酸3-戊基四氫吡喃-4-酯、丙酸香茅酯、丙酸三環癸烯酯、丙酸烯丙基環己酯、丙酸乙基2-環己酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基原酯、異丁酸三環癸烯酯、2-壬酸甲酯、苯甲酸甲酯、苯甲酸苄酯、桂皮酸甲酯、水楊酸甲酯、水楊酸正己酯、水楊酸順-3-己烯酯、惕恪酸香葉酯(Geranyl tiglate)、惕恪酸順-3-己烯酯、茉莉酸甲酯、二氫茉莉酸甲酯、2,4-二羥基-3,6-二甲基苯甲酸甲酯、甲基苯基環氧丙酸乙酯、鄰胺苯甲酸甲酯、果香酯(fruitate)等酯類；
正辛醛、正癸醛、正十二醛、2-甲基十一醛、10-十一烯醛、香茅醛、檸檬醛、羥基香茅醛、二甲基四氫苯甲醛、4(3)-(4-羥基-4-甲基戊基)-3-環己烯-1-甲醛、2-環己基丙醛、對三級丁基-α-甲基氫桂皮醛、對異丙基-α-甲基氫桂皮醛、對乙基-α,α-二甲基氫桂皮醛、α-戊基桂皮醛、α-己基桂皮醛、向日葵醛(piperonal)、α-甲基-3,4-亞甲基二氧基氫桂皮醛等醛類；
甲基庚烯酮、4-亞甲基-3,5,6,6-四甲基-2-庚酮、戊基環戊酮、3-甲基-2-(順-2-戊烯-1-基)-2-環戊烯-1-酮、甲基環戊烯醇酮(methyl cyclopentenolone)、玫瑰酮(rose ketone)、γ-甲基紫羅酮、α-紫羅酮、香旱芹酮、薄荷酮、樟腦、諾卡酮、苄基丙酮、茴香酮(Anisylacetone)、甲基-β-萘基酮、2,5-二甲基-4-羥基-3(2H)-呋喃酮、麥芽醇、7-乙醯基-1,2,3,4,5,6,7,8-八氫-1,1,6,7-四甲基萘、麝香酮、靈貓酮、環十五酮、環十六烯酮等酮類；
乙醛乙基苯基丙基縮醛、檸檬醛二乙基縮醛、苯乙醛甘油縮醛、乙醯乙酸乙酯乙二醇縮酮類之縮醛類及縮酮類；
大茴香腦、β-萘基甲基醚、β-萘基乙基醚、氧化檸檬烯、玫瑰醚(Rose oxide)、1,8-桉醚、外消旋混合物或光學活性之十二氫-3a,6,6,9a-四甲基萘并[2,1-b]呋喃等醚類；
香茅腈等腈類；
γ-壬內酯、γ-十一內酯、σ-癸內酯、γ-茉莉內酯、香豆素、環十五內酯、環十六內酯、黃葵内酯(Ambrettolide)、巴西酸乙二酯(Ethylene brassylate)、11-氧雜十六內酯等內酯類；
柳橙、檸檬、香檸檬(Bergamot orange)、橘、胡椒薄荷、綠薄荷、薰衣草、洋甘菊、迷迭香、桉樹、鼠尾草、羅勒、玫瑰、天竺葵、茉莉、依蘭、大茴香、丁香、薑、肉豆蔻、小豆蔻、雪松、檜木、香根草、廣藿香、勞丹脂等之天然精油或天然萃取物；
等。又，該其他香料成分可單獨使用亦可摻合多種。
前述含有式(1)表示之羧酸酯化合物之香料組成物，由於式(1)表示之羧酸酯化合物會賦予水果般的優良香氣，因此可使用作為用以改良摻合對象物之香氣之香妝品類、健康衛生材料、雜貨、食品、準醫藥品、醫藥品等各種製品中之香氣成分。
前述含有式(1)表示之羧酸酯化合物之香料組成物，可使用作為例如：香水、古龍水類等香氣製品；洗髮精、潤絲精類、養髮液、護髮霜類、髮慕斯、髮膠、髮蠟、髮噴霧、其他毛髪用化妝料；化妝水、美容液、乳霜、乳液、面膜、粉底、化妝用白粉、口紅、各種化妝類等皮膚用化妝料；洗碗用洗劑、洗滌用洗劑、柔軟劑類、消毒用洗劑類、消臭洗劑類、室內芳香劑、家具保養劑、玻璃清潔劑、家具清潔劑、地板清潔劑、消毒劑、殺蟲劑、漂白劑、其他各種健康衛生用洗劑類；牙膏、漱口水、入浴劑、止汗製品、燙髮液等準醫藥品；衛生紙、面紙等雜貨；醫藥品等；食品等之製品的香氣成分。
又，就相對於製品之本發明之香料組成物的摻合量而言，並無特別限制，可因應目的適當選擇，就前述式(1)表示之羧酸酯化合物之相對於製品的摻合量而言，宜為0.001～50質量%，更宜為0.01～20質量%。
[實施例]
以下，利用實施例及比較例更具體地說明本發明，但本發明並不受這些實施例所限制。
>氣相層析分析條件>
氣相層析係使用氣相層析儀(島津製作所股份有限公司製、「GC-2010Plus」)及毛細管柱(信和化工股份有限公司製、「HR-1」(0.32mmφ×25m))。升溫條件係以5℃/分之條件從100℃升溫至310℃為止。
>GC-MS>
使用日本電子股份有限公司製之GC-MS質譜儀JMS-T100GCV。
>1
H-NMR、13
C-NMR光譜分析>
利用以下條件進行測定。
裝置：日本電子股份有限公司製之NMR頻譜裝置JNM-ECA500
內部標準物質：四甲基矽烷(TMS)
>羧酸酯化合物產率、異構物比>
・羧酸酯化合物產率(莫耳%)=(羧酸酯化合物之莫耳數)/(2-亞乙基降莰烷之莫耳數)×100
・異構物比(%)=(2-乙基降莰烷-Exo-2-羧酸酯之莫耳數)/(羧酸酯化合物合計之莫耳數)×100
合成例1
(利用5-亞乙基-2-降莰烯(ENB)之氫化所為之2-亞乙基降莰烷之製備)
在具備磁感應式攪拌機、頂部有3個入口噴嘴、底部有1個抽吸噴嘴，且可利用夾套控制內部溫度之內容積200mL的不銹鋼製高壓釜中，添加Cu-Cr系觸媒(日揮觸媒化成股份有限公司製，「N-203S」)2.0g、庚烷(和光純藥工業股份有限公司製，特級)30g，於170℃、氫氣壓力1MPaG下進行1小時之活性化。冷卻後，添加5-亞乙基-2-降莰烯(東京化成工業股份有限公司製)100g，於90℃、氫氣壓力2MPaG下攪拌2小時進行氫化反應。將反應液過濾並去除觸媒，餾去為溶劑之庚烷，獲得含有2-亞乙基降莰烷濃度95質量%、2-乙基降莰烷濃度5質量%之液狀的反應產物(以下亦稱作「反應液」)89g(產率88莫耳%(又，產率係由2-亞乙基降莰烷及2-乙基降莰烷之合計莫耳數相對於為原料之5-亞乙基-2-降莰烯之莫耳數而算出))。又，2-亞乙基降莰烷之產率為84莫耳%(由2-亞乙基降莰烷之莫耳數相對於為原料之5-亞乙基-2-降莰烯之莫耳數而算出)。
反應式示於下。
[化8]
實施例1
(利用2-亞乙基降莰烷之羰基化及酯化所為之2-乙基降莰烷-2-甲酸乙酯之製造)
使用具備磁感應式攪拌機、頂部有3個入口噴嘴、底部有1個抽吸噴嘴，且可利用夾套控制內部溫度之內容積500mL的不銹鋼製高壓釜進行實驗。
首先，將高壓釜內部以一氧化碳取代後，導入氟化氫158g(7.9莫耳)，使液溫成為0℃後，以一氧化碳加壓至2MPaG。
將反應溫度保持於0℃，且將反應壓力保持於2MPaG，同時費時60分鐘從高壓釜頂部供給合成例1中製備而得之反應液(2-亞乙基降莰烷濃度95質量%、2-乙基降莰烷濃度5質量%)82g與庚烷(和光純藥工業股份有限公司製，特級)82g之混合液，並進行羰基化反應。原料之供給結束後，持續攪拌20分鐘，直到無法察覺有一氧化碳之吸收為止。
接著，將反應溫度保持於0℃，費時15分鐘從高壓釜頂部供給乙醇46g(1.0莫耳，相對於為原料之2-亞乙基降莰烷為1.6莫耳倍)，於攪拌下進行酯化1小時。將反應液從高壓釜底部抽出到冰水中，使油相與水相分離後，將油相以2質量%氫氧化鈉水溶液100mL清洗2次、以蒸餾水100mL清洗2次，並利用無水硫酸鈉10g進行脫水。
獲得之液體利用蒸發器去除低沸點成分後，使用理論板數20板之精餾塔進行精餾(餾出溫度150℃、真空度60torr)後，利用內部標準法以氣相層析進行分析。其結果，羧酸酯化合物(Exo型與Endo型之混合物)之產率為94.1莫耳%(2-亞乙基降莰烷基準)。又，為主產物之2-乙基降莰烷-2-exo-甲酸乙酯之產率為84.9莫耳%(2-亞乙基降莰烷基準，異構物比90.3%)。
針對主產物利用GC-MS(CI+
)進行分析之結果，相對於目的物之分子量196.29呈現出197.15([M+
H]+
)。又，氘代氯仿溶劑中之1
H-NMR之化學位移值、及13
C-NMR之化學位移值(δppm，TMS基準)係如以下所示，由此結果，鑑定其為2-乙基降莰烷-2-甲酸乙酯。又，NMR之鑑定中，在下列化學式中[2]係代表標記了2之符號的碳原子或鍵結於該碳原子之氫原子。以下相同。
[化9]
1
H NMR(500MHz, CDCl3
) δ(ppm)：0.76(t, J=7.5Hz, 3H, [9]), 0.90(dd, J=12.5, 3.0Hz, 1H, [5a>endo>]), 1.06-1.11(m, 1H, [7a>endo>]), 1.19-1.21(m, 1H, [3b]), 1.23(t, J=7.0Hz, 3H, [13]), 1.28-1.32(m, 1H, [3a]), 1.33-1.41(m, 1H, [6a>endo>]), 1.45-1.50(m, 1H, [7b>exo>]), 1.51-1.58(m, 1H, [6b>exo>]), 1.58-1.64(m, 2H, [8]), 2.17-2.19(m, 1H, [4]), 2.20-2.24(m, 1H, [5b>exo>]), 2.54(br d, J=4.0, 1H, [2]), 4.09-4.13(m, 2H, [12])
[化10]
13
C NMR(126MHz, CDCl3
) δ(ppm)：10.55 [9], 14.37 [13], 23.15 [6], 29.05 [7], 29.60 [8], 36.81 [4], 38.81 [3], 41.29 [5], 42.78 [2], 54.35 [1], 60.27 [12], 178.06 [10]
2-乙基降莰烷-2-甲酸乙酯具有水果、草本植物、木本植物般(fruity-herbal-woody)的香氣。
實施例2
(利用2-亞乙基降莰烷之羰基化及酯化所為之2-乙基降莰烷-2-甲酸正丙酯之製造)
除了將實施例1中之酯化中使用之醇代替為正丙醇以外，以與實施例1相同之方式進行羰基化及酯化及反應生成液之處理。
利用氣相層析進行分析之結果，羧酸酯化合物之產率為92.9莫耳%(2-亞乙基降莰烷基準)，為主產物之2-乙基降莰烷-exo-2-甲酸正丙酯之產率為83.0莫耳%(2-亞乙基降莰烷基準，異構物比89.4%)。
針對主產物進行GC-MS(CI+
)分析之結果，相對於目的物之分子量210.32呈現出211.13([M+
H]+
)。又，氘代氯仿溶劑中之1
H-NMR之化學位移值、及13
C-NMR之化學位移值(δppm，TMS基準)係如以下所示，由此結果，鑑定其為2-乙基降莰烷-2-甲酸正丙酯。
[化11]
1
H NMR(500MHz, CDCl3
) δ(ppm)：0.76(t, J=7.5Hz, 3H, [9]), 0.89-0.92(m, 1H, [5b>endo>]), 0.93(t, J=7.0Hz, 3H, [14]), 1.05-1.11(m, 1H, [7a>endo>]), 1.18-1.22(m, 1H, [3b]), 1.27-1.32(m, 1H, [3a]), 1.33-1.40(m, 1H, [6b>endo>]), 1.45-1.51(m, 1H, [7b>exo>]), 1.52-1.59(m, 1H, [6a>exo>]), 1.60-1.67(m, 4H, [13], [8]), 2.17-2.19(m, 1H, [4]), 2.20-2.24(m, 1H, [5a>exo>]), 2.54(br d, J=3.5Hz, 1H, [2]), 4.98-4.05(m, 2H, [12])
[化12]
13
C NMR(126MHz, CDCl3
) δ(ppm)：10.59 [9, 14], 22.16 [13], 23.16 [6], 29.06 [7], 29.64 [8], 36.82 [4], 38.82 [3], 41.30 [5], 42.80 [2], 54.52 [1], 65.98 [12], 178.14 [10]
又，2-乙基降莰烷-2-甲酸正丙酯具有水果、木本植物、草本植物般(fruity-woody-herbal)的香氣。
實施例3
(利用2-亞乙基降莰烷之羰基化及酯化所為之2-乙基降莰烷-2-甲酸異丙酯之製造)
除了將實施例1中之酯化中使用的醇代替為異丙醇以外，以與實施例1相同之方式進行羰基化及酯化及反應生成液之處理。
利用氣相層析進行分析之結果，羧酸酯化合物之產率為92.4莫耳%(2-亞乙基降莰烷基準)，為主產物之2-乙基降莰烷-2-exo-甲酸異丙酯之產率為81.2莫耳%(2-亞乙基降莰烷基準，異構物比87.9%)。
針對主產物以GC-MS(CI+
)進行分析之結果，相對於目的物之分子量210.32呈現出211.12([M+
H]+
)。又，氘代氯仿溶劑中之1
H-NMR之化學位移值、及13
C-NMR之化學位移值(δppm，TMS基準)係如以下所示，由此結果，鑑定其為2-乙基降莰烷-2-甲酸異丙酯。
[化13]
1
H NMR(500MHz, CDCl3
) δ(ppm)：0.76(t, J=7.0Hz, 3H, [9]), 0.87-0.90(m, 1H, [5b>endo>]), 1.05-1.11(m, 1H, [7a>endo>]), 1.19-1.21(m, 7H, [3b], [13], [15]), 1.29-1.30(m, 1H, [3a]), 1.33-1.39(m, 1H, [6b>endo>]), 1.45-1.51(m, 1H, [7b>exo>]), 1.51-1.56(m, 1H, [6a>exo>]), 1.56-1.64(m, 2H, [8]), 2.16-2.19(m, 1H, [4]), 2.19-2.22(m, 1H, [5a>exo>]), 2.54(br d, J=4.0Hz, 1H, [2]), 4.96-5.01(m, 1H, [12])
[化14]
13
C NMR(126MHz, CDCl3
) δ(ppm)：10.47 [9], 21.85-21.88 [13], [15], 23.16 [6], 29.08 [7], 29.53 [8], 36.80 [4], 38.74 [3], 41.25 [5], 42.79 [2], 54.25 [1], 67.22 [12], 177.49 [10]
又，2-乙基降莰烷-2-甲酸異丙酯具有草本植物、水果、蘋果、木本植物般(herbal-fruity-apple-woody)的香氣。
實施例4
(香料組成物)
依循下表1之配方，使用實施例1中獲得之羧酸酯化合物來製備花香-水果香調香料組成物。
[表1]
| 配方 | 質量份 |
| 苯甲醛 | 3 |
| 香茅醇 | 70 |
| CYCLACET(註冊商標) (International Flavors & Fragrances, Inc.製) | 140 |
| γ-癸內酯 | 10 |
| 乙酸二甲基苄基原酯(Dimethyl benzyl carbinyl acetate) | 80 |
| 苯基乙酸乙酯 | 6 |
| GALAXOLIDE(註冊商標) (International Flavors & Fragrances, Inc.製) (50BB:50% in benzyl benzoate) | 180 |
| 香葉醇(Geraniol) | 85 |
| 沉香醇(Linalool) | 80 |
| 甲基紫羅酮 | 30 |
| 苯基乙醇 | 155 |
| 玫瑰醚(Rose oxide) | 6 |
| TRIPLAL(註冊商標) (International Flavors & Fragrances, Inc.製) | 5 |
| VERTENEX(註冊商標) (International Flavors & Fragrances, Inc.製) | 100 |
| 實施例1之化合物 | 50 |
| 合計 | 1000 |
官能性評價由具5年以上經驗之4名專門感官品評員進行，其結果，全員判斷含有實施例1之化合物之花香-果香調香料組成物，具有強烈的水果香調香氣，嗜好性高，此外擴散性亦優良。
[產業上利用性]
本發明之新穎羧酸酯化合物具有水果的香氣、優異的香氣性，因此作為用在盥洗用品、肥皂、衣物用洗劑等範圍廣泛的製品之賦予香氣成分而言為有用。此外，依據本發明之羧酸酯化合物之製造方法，可利用於工業上為有利的方法來製造該羧酸酯化合物。
Claims (4)
- 一種羧酸酯化合物，係以下式(1)表示；
- 如申請專利範圍第1項之羧酸酯化合物，其中，R係乙基、正丙基、或異丙基。
- 一種香料組成物，含有式(1)表示之羧酸酯化合物；
- 一種羧酸酯化合物之製造方法，係式(1)表示之羧酸酯化合物之製造方法，係在氟化氫之存在下，使式(2)表示之化合物與一氧化碳進行反應後，進一步使其與以ROH表示之碳數2~6之醇進行反應；
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|---|---|---|---|
| JP2018216004 | 2018-11-16 | ||
| JP2018-216004 | 2018-11-16 |
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| Country | Link |
|---|---|
| US (1) | US11725161B2 (zh) |
| EP (1) | EP3882233B1 (zh) |
| JP (1) | JP7351313B2 (zh) |
| KR (1) | KR20210092727A (zh) |
| CN (1) | CN113015717B (zh) |
| ES (1) | ES2936714T3 (zh) |
| TW (1) | TWI821449B (zh) |
| WO (1) | WO2020100708A1 (zh) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037644A1 (en) * | 1980-03-25 | 1981-10-14 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Carbonyl norbornanes, organoleptic uses thereof and processes for preparing same |
| TW541341B (en) * | 2000-11-13 | 2003-07-11 | Rhodia Cons Spec Ltd | Tannages |
| EP2639218A1 (en) * | 2010-11-12 | 2013-09-18 | Mitsubishi Gas Chemical Company, Inc. | Novel carboxylic acid ester compound and production therefor, and perfume composition thereof |
| WO2018051776A1 (ja) * | 2016-09-15 | 2018-03-22 | 三菱瓦斯化学株式会社 | 香料組成物 |
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| US4374054A (en) | 1980-03-25 | 1983-02-15 | International Flavors & Fragrances Inc. | Use in perfumery of carboalkoxy alkyl norbornanes |
| US4350823A (en) | 1980-03-25 | 1982-09-21 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes |
| US4312888A (en) | 1980-03-25 | 1982-01-26 | International Flavors & Fragrances Inc. | Flavoring with carboalkoxy alkyl norbornanes |
| US4357246A (en) | 1980-03-25 | 1982-11-02 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornanes, organoleptic uses thereof and process for preparing same |
| US4347858A (en) | 1980-03-25 | 1982-09-07 | International Flavors & Fragrances Inc. | Use of carboalkoxy alkyl norbornanes for augmenting or enhancing the aroma or taste of a smoking tobacco composition or at least a portion of a smoking tobacco article |
| US4319036A (en) * | 1980-03-25 | 1982-03-09 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornanes and process for preparing same |
| US4395366A (en) | 1980-03-25 | 1983-07-26 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes, organoleptic uses thereof and process for preparing same |
| US4386064A (en) | 1980-03-25 | 1983-05-31 | International Flavors & Fragrances Inc. | Flavoring with carbomethoxy methyl norbornanes |
| US4310681A (en) | 1980-03-25 | 1982-01-12 | International Flavors & Fragrances Inc. | Carboalkoxy alkyl norbornane derivatives and process for preparing same |
| US4367158A (en) * | 1980-10-23 | 1983-01-04 | International Flavors & Fragrances Inc. | Use of norbornyl ethers in augmenting or enhancing the aroma of detergents |
| US4357253A (en) | 1980-11-13 | 1982-11-02 | International Flavors & Fragrances Inc. | Process of enhancing or augmenting the aroma of detergents using norbornyl esters |
| US4431577A (en) | 1981-07-16 | 1984-02-14 | International Flavors & Fragrances Inc. | Carbomethoxy methyl norbornanes, organoleptic uses thereof and process for preparing same |
| JPS60190738A (ja) * | 1984-03-09 | 1985-09-28 | Kao Corp | 香料組成物 |
| EP2690086B1 (en) * | 2011-03-25 | 2015-12-30 | Mitsubishi Gas Chemical Company, Inc. | Carboxylic acid ester compound, method for producing the compound, and fragrance composition comprising the compound |
-
2019
- 2019-11-07 JP JP2020555581A patent/JP7351313B2/ja active Active
- 2019-11-07 ES ES19884807T patent/ES2936714T3/es active Active
- 2019-11-07 US US17/291,022 patent/US11725161B2/en active Active
- 2019-11-07 KR KR1020217013041A patent/KR20210092727A/ko unknown
- 2019-11-07 EP EP19884807.9A patent/EP3882233B1/en active Active
- 2019-11-07 CN CN201980074605.6A patent/CN113015717B/zh active Active
- 2019-11-07 WO PCT/JP2019/043662 patent/WO2020100708A1/ja active Application Filing
- 2019-11-08 TW TW108140578A patent/TWI821449B/zh active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0037644A1 (en) * | 1980-03-25 | 1981-10-14 | INTERNATIONAL FLAVORS & FRAGRANCES INC. | Carbonyl norbornanes, organoleptic uses thereof and processes for preparing same |
| TW541341B (en) * | 2000-11-13 | 2003-07-11 | Rhodia Cons Spec Ltd | Tannages |
| EP2639218A1 (en) * | 2010-11-12 | 2013-09-18 | Mitsubishi Gas Chemical Company, Inc. | Novel carboxylic acid ester compound and production therefor, and perfume composition thereof |
| WO2018051776A1 (ja) * | 2016-09-15 | 2018-03-22 | 三菱瓦斯化学株式会社 | 香料組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3882233B1 (en) | 2023-01-11 |
| CN113015717A (zh) | 2021-06-22 |
| EP3882233A1 (en) | 2021-09-22 |
| EP3882233A4 (en) | 2022-03-30 |
| ES2936714T3 (es) | 2023-03-21 |
| WO2020100708A1 (ja) | 2020-05-22 |
| US20220041955A1 (en) | 2022-02-10 |
| US11725161B2 (en) | 2023-08-15 |
| TW202033488A (zh) | 2020-09-16 |
| KR20210092727A (ko) | 2021-07-26 |
| CN113015717B (zh) | 2024-04-30 |
| JP7351313B2 (ja) | 2023-09-27 |
| JPWO2020100708A1 (ja) | 2021-10-14 |
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