JPS60136553A - ２―アルキリデン―３―メチルチオプロパナール類 - Google Patents
２―アルキリデン―３―メチルチオプロパナール類Info
- Publication number
- JPS60136553A JPS60136553A JP58242162A JP24216283A JPS60136553A JP S60136553 A JPS60136553 A JP S60136553A JP 58242162 A JP58242162 A JP 58242162A JP 24216283 A JP24216283 A JP 24216283A JP S60136553 A JPS60136553 A JP S60136553A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- methylbutylidene
- methylthiopropanal
- alkylidene
- aroma
- 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.)
- Granted
Links
- 239000000796 flavoring agent Substances 0.000 claims abstract description 33
- 235000019634 flavors Nutrition 0.000 claims abstract description 31
- -1 2-methylbutylidene Chemical group 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 230000002085 persistent effect Effects 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 13
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 230000002045 lasting effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000003607 modifier Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 8
- 239000003205 fragrance Substances 0.000 description 8
- 239000002537 cosmetic Substances 0.000 description 7
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 230000002688 persistence Effects 0.000 description 5
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 241001632576 Hyacinthus Species 0.000 description 4
- 235000013361 beverage Nutrition 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000005923 long-lasting effect Effects 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- IBSLHWQWKUNIJE-UHFFFAOYSA-N 2-(methylsulfanylmethyl)but-2-enal Chemical compound CSCC(=CC)C=O IBSLHWQWKUNIJE-UHFFFAOYSA-N 0.000 description 2
- DNOUKPGPAUUCPC-UHFFFAOYSA-N 2-methylsulfanylpropanal Chemical compound CSC(C)C=O DNOUKPGPAUUCPC-UHFFFAOYSA-N 0.000 description 2
- GQFPHBQLLUTFPC-UHFFFAOYSA-N 4-methyl-2-(methylsulfanylmethyl)hex-2-enal Chemical compound CCC(C)C=C(C=O)CSC GQFPHBQLLUTFPC-UHFFFAOYSA-N 0.000 description 2
- FHZUYUPNOHOVIC-UHFFFAOYSA-N 5-methyl-2-(methylsulfanylmethyl)hex-2-enal Chemical compound CSCC(C=O)=CCC(C)C FHZUYUPNOHOVIC-UHFFFAOYSA-N 0.000 description 2
- 241000951471 Citrus junos Species 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- 240000000560 Citrus x paradisi Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 244000269722 Thea sinensis Species 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
- 229940079593 drug Drugs 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 229940100595 phenylacetaldehyde Drugs 0.000 description 2
- 235000013606 potato chips Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001730 (5R)-5-butyloxolan-2-one Substances 0.000 description 1
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 1
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 1
- FNHVKVSDWQLOEU-UHFFFAOYSA-N 4-methyl-2-(methylsulfanylmethyl)pent-2-enal Chemical compound CSCC(C=O)=CC(C)C FNHVKVSDWQLOEU-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 240000009088 Fragaria x ananassa Species 0.000 description 1
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 1
- KNVYLIIBQXVDKC-UHFFFAOYSA-N Guaicyl phenylacetate Chemical compound COC1=CC=CC=C1OC(=O)CC1=CC=CC=C1 KNVYLIIBQXVDKC-UHFFFAOYSA-N 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 240000006909 Tilia x europaea Species 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- UZFLPKAIBPNNCA-BQYQJAHWSA-N alpha-ionone Chemical compound CC(=O)\C=C\C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-BQYQJAHWSA-N 0.000 description 1
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000020279 black tea Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- GXANMBISFKBPEX-ARJAWSKDSA-N cis-3-hexenal Chemical compound CC\C=C/CC=O GXANMBISFKBPEX-ARJAWSKDSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000001877 deodorizing effect Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 239000001299 ferula galbaniflua resinoid Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- IFYYFLINQYPWGJ-VIFPVBQESA-N gamma-Decalactone Natural products CCCCCC[C@H]1CCC(=O)O1 IFYYFLINQYPWGJ-VIFPVBQESA-N 0.000 description 1
- IPBFYZQJXZJBFQ-UHFFFAOYSA-N gamma-octalactone Chemical compound CCCCC1CCC(=O)O1 IPBFYZQJXZJBFQ-UHFFFAOYSA-N 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- GXANMBISFKBPEX-UHFFFAOYSA-N hex-3c-enal Natural products CCC=CCC=O GXANMBISFKBPEX-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- GYBMSOFSBPZKCX-UHFFFAOYSA-N sodium;ethanol;ethanolate Chemical compound [Na+].CCO.CC[O-] GYBMSOFSBPZKCX-UHFFFAOYSA-N 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012438 synthetic essential oil Substances 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Seasonings (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58242162A JPS60136553A (ja) | 1983-12-23 | 1983-12-23 | ２―アルキリデン―３―メチルチオプロパナール類 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58242162A JPS60136553A (ja) | 1983-12-23 | 1983-12-23 | ２―アルキリデン―３―メチルチオプロパナール類 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3332829A Division JPH05255690A (ja) | 1991-11-22 | 1991-11-22 | 持続性香気香味賦与乃至変調剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60136553A true JPS60136553A (ja) | 1985-07-20 |
| JPH0430390B2 JPH0430390B2 (enrdf_load_stackoverflow) | 1992-05-21 |
Family
ID=17085250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58242162A Granted JPS60136553A (ja) | 1983-12-23 | 1983-12-23 | ２―アルキリデン―３―メチルチオプロパナール類 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60136553A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820840A (en) * | 1987-01-23 | 1989-04-11 | Appleton Papers Inc. | Process for producing fluorene compounds |
| JP2023508866A (ja) * | 2019-12-20 | 2023-03-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 芳香化学物質としてのドデカンジエン－１－オール及びドデセン－１－オール又はそれらの混合物 |
-
1983
- 1983-12-23 JP JP58242162A patent/JPS60136553A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820840A (en) * | 1987-01-23 | 1989-04-11 | Appleton Papers Inc. | Process for producing fluorene compounds |
| JP2023508866A (ja) * | 2019-12-20 | 2023-03-06 | ビーエーエスエフ ソシエタス・ヨーロピア | 芳香化学物質としてのドデカンジエン－１－オール及びドデセン－１－オール又はそれらの混合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0430390B2 (enrdf_load_stackoverflow) | 1992-05-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS60136553A (ja) | ２―アルキリデン―３―メチルチオプロパナール類 | |
| JPH05255690A (ja) | 持続性香気香味賦与乃至変調剤 | |
| JP3415678B2 (ja) | シクロヘキセン誘導体 | |
| JPH0737633B2 (ja) | ホツプ精油の香気改良方法 | |
| JP2818511B2 (ja) | テトラヒドロフルフリル３−メルカプトプロピオネートおよび香料組成物 | |
| JPS6028950A (ja) | シス−３−アルケン酸類、その製法および利用 | |
| JPS6150960A (ja) | メチルチオ酢酸エステル及びその利用 | |
| JPS60149592A (ja) | ２−アルキル−チアゾリジノ〔３，４−ｂ〕チアゾリジン類及びその利用 | |
| JPS6251636A (ja) | γ−シクロラバンジユラ−ル | |
| JPS58183668A (ja) | 持続性香気香味賦与乃至変調剤 | |
| JPS60184034A (ja) | 香料組成物 | |
| JPH0464B2 (enrdf_load_stackoverflow) | ||
| JPS6383018A (ja) | 香料組成物 | |
| JP3133200B2 (ja) | ４−（６，６−ジメチル−２−メチレンシクロヘキシル）−２−メチル−２−ブテナールの香料組成物 | |
| JPH0481639B2 (enrdf_load_stackoverflow) | ||
| JPH049345A (ja) | ８―メチル―４（ｚ）―ノネン誘導体 | |
| JPS6081164A (ja) | α−もしくはβ−モノシクロホモフアルネシル酸の製法 | |
| JPH02196740A (ja) | 脂肪族ケトン類および脂肪族アルコール類 | |
| JPS60149574A (ja) | ２−アルコキシ−４−エチル−３−メチル−２−ブテン−４，１−オリド類 | |
| JPS61263913A (ja) | 香料組成物 | |
| JPS60209562A (ja) | （±）−シス−ｒ−イロンの製法及びその利用 | |
| JPS62292778A (ja) | ４，７，７，１１−テトラメチル−１２−オキサ−ビシクロ（９，４，０）−４，８，１３−ペンタデカトリエン | |
| JPS62292739A (ja) | フムレン誘導体 | |
| JPH02152958A (ja) | γ―モノシクロネロリドール | |
| JPS6045540A (ja) | エチレングリコ−ル誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |