GB1057360A - Derivatives of dihydrocinnamaldehyde useful in perfumery - Google Patents
Derivatives of dihydrocinnamaldehyde useful in perfumeryInfo
- Publication number
- GB1057360A GB1057360A GB4772065A GB4772065A GB1057360A GB 1057360 A GB1057360 A GB 1057360A GB 4772065 A GB4772065 A GB 4772065A GB 4772065 A GB4772065 A GB 4772065A GB 1057360 A GB1057360 A GB 1057360A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- cyclohexyl
- alkenyl
- optionally
- 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.)
- Expired
Links
Classifications
-
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/23—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
- C07C47/232—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/235—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Cleansing materials such as soap cakes and an alkyl aryl sulphonate/phosphate detergent contain as a perfume ingredient a dihydrocinnamaldehyde, optionally a -Me substituted, which contains as a nuclear substituent 3,4-(CH2)4, or-in the 2- or 4-position-cyclohexyl or primary C4-6 alkyl or alkenyl, but excluding 4-isobutyldihydrocinnamaldehyde.ALSO:The invention comprises dihydrocinnamaldehydes, optionally a -Me substituted, containing as nuclear substituents 3,4-(CH2)4, or-in the 2- or 4-position-cyclohexyl or primary C4- 6 alkyl or alkenyl; 4-isobutyldihydrocinnamal dehyde is specifically excluded. These compounds are made by a Friedel-Crafts reaction of the corresponding substituted benzene with acrolein, methacrolein or a diacylate thereof; where a diacylate is used, the product is hydrolysed to the aldehyde. Ortho- and para-isomers of the aldehydes are separated by reaction with NaHSO3 in MeOH and cooling to precipitate the p-bisulphate complex which is then separated, the o-isomer being recovered from the mother liquor.ALSO:Perfumes and cosmetic preparations contain a dihydrocinannamaldehyde, optionally a -Me substituted, which contains as a nuclear substituent 3,4-(CH2)4, or in the 2- or 4- position-cyclohexyl or primary C4-6 alkyl or alkenyl, but excluding 4-isobutyldihydrocinnamaldehyde. Examples of perfume compositions, talcum powder, antiperspirant lotion and cold cream are given.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR994846A FR1430164A (en) | 1964-11-13 | 1964-11-13 | Aldehyde p. isobutyl alpha-methyldihydrocinnamic |
FR14857A FR1443997A (en) | 1964-11-13 | 1965-04-27 | Aldehyde o. isobutyl alpha-methyl dihydrocinnamic |
FR35495A FR1460826A (en) | 1964-11-13 | 1965-10-19 | Substituted dihydrocinnamic aldehydes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1057360A true GB1057360A (en) | 1967-02-01 |
Family
ID=27242118
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4772065A Expired GB1057360A (en) | 1964-11-13 | 1965-11-10 | Derivatives of dihydrocinnamaldehyde useful in perfumery |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE672280A (en) |
CH (1) | CH447440A (en) |
DE (1) | DE1467511A1 (en) |
FR (3) | FR1430164A (en) |
GB (1) | GB1057360A (en) |
NL (1) | NL149778B (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0043526A1 (en) * | 1980-07-04 | 1982-01-13 | L. GIVAUDAN & CIE Société Anonyme | Process for the preparation of dihydrocinnamaldehyde derivatives |
WO2014180945A1 (en) * | 2013-05-08 | 2014-11-13 | Givaudan Sa | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
CN105218395A (en) * | 2015-11-04 | 2016-01-06 | 杨海霞 | A kind of synthetic method of azo-compound |
WO2016074698A1 (en) * | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
JP2016523828A (en) * | 2013-05-08 | 2016-08-12 | ジボダン エス エー | Improvements in or relating to organic compounds |
CN106365968A (en) * | 2016-08-30 | 2017-02-01 | 安徽华业香料股份有限公司 | Synthesis method of silver aldehyde spice |
CN106478391A (en) * | 2016-08-30 | 2017-03-08 | 安徽华业香料股份有限公司 | A kind of synthetic method to isobutyl group β chlorine α methyl cinnamaldehyde |
US9708570B2 (en) * | 2013-06-28 | 2017-07-18 | Givaudan, S.A. | Organic compounds |
WO2019122236A1 (en) | 2017-12-21 | 2019-06-27 | Firmenich Sa | Method for identifying positive allosteric modulators for odorant receptors |
WO2020127325A2 (en) | 2018-12-19 | 2020-06-25 | Firmenich Sa | Use of volatile compounds to modulate the perception of floral muguet |
US10760033B2 (en) | 2014-11-12 | 2020-09-01 | Givaudan Sa | Process of forming 2-(4-isobutyl-2-methylphenyl) propanal |
WO2022207619A1 (en) * | 2021-04-01 | 2022-10-06 | Basf Se | 2-(2-(3-methylbut-2-en-1yl)phenyl) propanal and mixtures thereof as aroma ingredient |
USRE49502E1 (en) * | 2014-11-10 | 2023-04-25 | Givaudan Sa | Phenyl based compounds substituted with aldehyde moieties and their use in perfumery |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0392258B1 (en) * | 1989-04-12 | 1995-04-19 | Firmenich Sa | Aromatic aldehydes, their derivatives and their use as ingredients in perfumes, herbicides and fungicides |
CN117980454A (en) | 2021-09-29 | 2024-05-03 | 三菱瓦斯化学株式会社 | Aldehyde composition |
WO2023243499A1 (en) * | 2022-06-17 | 2023-12-21 | 三菱瓦斯化学株式会社 | Aldehyde composition |
-
0
- BE BE672280D patent/BE672280A/xx unknown
-
1964
- 1964-11-13 FR FR994846A patent/FR1430164A/en not_active Expired
-
1965
- 1965-04-27 FR FR14857A patent/FR1443997A/en not_active Expired
- 1965-10-19 FR FR35495A patent/FR1460826A/en not_active Expired
- 1965-11-10 GB GB4772065A patent/GB1057360A/en not_active Expired
- 1965-11-10 NL NL6514604A patent/NL149778B/en not_active IP Right Cessation
- 1965-11-12 DE DE19651467511 patent/DE1467511A1/en not_active Withdrawn
- 1965-11-12 CH CH1564265A patent/CH447440A/en unknown
Cited By (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0043526A1 (en) * | 1980-07-04 | 1982-01-13 | L. GIVAUDAN & CIE Société Anonyme | Process for the preparation of dihydrocinnamaldehyde derivatives |
US4389527A (en) * | 1980-07-04 | 1983-06-21 | Givaudan Corporation | Process for the preparation of dihydrocinnamaldehyde derivatives |
CN105208999B (en) * | 2013-05-08 | 2019-05-10 | 奇华顿股份有限公司 | 3- (4- isobutyl group -2- aminomethyl phenyl) propionic aldehyde as fragrance component |
WO2014180945A1 (en) * | 2013-05-08 | 2014-11-13 | Givaudan Sa | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
US10457891B2 (en) | 2013-05-08 | 2019-10-29 | Givaudan S.A. | Organic compounds |
KR20160006690A (en) * | 2013-05-08 | 2016-01-19 | 지보당 에스아 | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
CN105208999A (en) * | 2013-05-08 | 2015-12-30 | 奇华顿股份有限公司 | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
JP2016523828A (en) * | 2013-05-08 | 2016-08-12 | ジボダン エス エー | Improvements in or relating to organic compounds |
JP2016523827A (en) * | 2013-05-08 | 2016-08-12 | ジボダン エス エー | 3- (4-Isobutyl-2-methylphenyl) propanal as a perfume ingredient |
AU2014264609B2 (en) * | 2013-05-08 | 2018-03-08 | Givaudan Sa | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
JP2018138550A (en) * | 2013-05-08 | 2018-09-06 | ジボダン エス エー | Improvements in or relating to organic compounds |
US9656938B2 (en) | 2013-05-08 | 2017-05-23 | Givaudan S.A. | Organic compounds |
RU2662835C2 (en) * | 2013-05-08 | 2018-07-31 | Живодан Са | 3-(4-isobutyl-2-methylphenyl)propanal as perfume ingredient |
US9988592B2 (en) | 2013-05-08 | 2018-06-05 | Givaudan, S.A. | Organic compounds |
KR102353588B1 (en) | 2013-05-08 | 2022-01-19 | 지보당 에스아 | 3-(4-isobutyl-2-methylphenyl) propanal as perfume ingredient |
US9708570B2 (en) * | 2013-06-28 | 2017-07-18 | Givaudan, S.A. | Organic compounds |
JP2017534650A (en) * | 2014-11-10 | 2017-11-24 | ジボダン エス エー | Improvements in or related to organic compounds |
US10138195B2 (en) | 2014-11-10 | 2018-11-27 | Givaudan, S.A. | Organic compounds |
WO2016074698A1 (en) * | 2014-11-10 | 2016-05-19 | Givaudan Sa | Improvements in or relating to organic compounds |
USRE49502E1 (en) * | 2014-11-10 | 2023-04-25 | Givaudan Sa | Phenyl based compounds substituted with aldehyde moieties and their use in perfumery |
CN107074714A (en) * | 2014-11-10 | 2017-08-18 | 奇华顿股份有限公司 | In organic compound or associated improvement |
CN107074714B (en) * | 2014-11-10 | 2020-11-06 | 奇华顿股份有限公司 | Improvements in or relating to organic compounds |
US10760033B2 (en) | 2014-11-12 | 2020-09-01 | Givaudan Sa | Process of forming 2-(4-isobutyl-2-methylphenyl) propanal |
CN105218395B (en) * | 2015-11-04 | 2017-07-07 | 滁州品之达电器科技有限公司 | A kind of synthetic method of azo-compound |
CN105218395A (en) * | 2015-11-04 | 2016-01-06 | 杨海霞 | A kind of synthetic method of azo-compound |
CN106478391A (en) * | 2016-08-30 | 2017-03-08 | 安徽华业香料股份有限公司 | A kind of synthetic method to isobutyl group β chlorine α methyl cinnamaldehyde |
CN106365968A (en) * | 2016-08-30 | 2017-02-01 | 安徽华业香料股份有限公司 | Synthesis method of silver aldehyde spice |
WO2019122236A1 (en) | 2017-12-21 | 2019-06-27 | Firmenich Sa | Method for identifying positive allosteric modulators for odorant receptors |
WO2020127325A2 (en) | 2018-12-19 | 2020-06-25 | Firmenich Sa | Use of volatile compounds to modulate the perception of floral muguet |
WO2022207619A1 (en) * | 2021-04-01 | 2022-10-06 | Basf Se | 2-(2-(3-methylbut-2-en-1yl)phenyl) propanal and mixtures thereof as aroma ingredient |
Also Published As
Publication number | Publication date |
---|---|
CH447440A (en) | 1967-11-30 |
FR1430164A (en) | 1966-03-04 |
NL6514604A (en) | 1966-05-16 |
FR1443997A (en) | 1966-07-01 |
DE1467511A1 (en) | 1969-02-27 |
NL149778B (en) | 1976-06-15 |
FR1460826A (en) | 1966-01-07 |
BE672280A (en) | 1966-05-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1057360A (en) | Derivatives of dihydrocinnamaldehyde useful in perfumery | |
US6133228A (en) | Slow release of fragrant compounds in perfumery using 2-benzoyl benzoates, 2-alkanoyl benzoates or α-keto esters | |
SU814283A3 (en) | Aromatizing composition | |
US3636113A (en) | Novel fragrance materials chemical intermediates and processes | |
US4459224A (en) | Perfume compositions as well as perfumed articles and materials containing alkyl substituted benzyl cyanides as a fragrance | |
NL153522B (en) | PROCESS FOR THE PREPARATION OF NITRILES USED AS A ODOR, METHOD FOR THE PREPARATION OF ODOR MIXTURES, PERFUME COMPOSITIONS AND PERFUMED PRODUCTS AND MOLDED OBJECTS CONTAINING THESE SUBSTANCES. | |
SE7500526L (en) | ||
GB1300970A (en) | Indane compounds, processes of making same and their use as fragrance material | |
GB988502A (en) | New aldehyde useful in perfumery | |
US3660311A (en) | Novel fragrance methods and compositions | |
GB1401950A (en) | Odoriferous composition | |
JP2005529194A (en) | Compounds for the controlled release of active aldehydes | |
GB1168673A (en) | Method for Prolonging the Odor of Perfumed Materials | |
JPS61178944A (en) | 4-(2,2,3-trimethylcyclopent-3-en-1-yl)-but-3-en-1-ols, manufacture and use as aromatics | |
US4040986A (en) | Preparation of 4-methoxybenzonitrile perfume compositions | |
GB1289805A (en) | ||
US4904640A (en) | 2-alkylidene-3,3,5(3,5,5)-trimethyl cyclopentanones | |
US3679750A (en) | Hexahydro-1,4,9,9-tetramethyl-4,7-methano-azulenones | |
ES2259697T3 (en) | FRAGRANCE COMPOSITION CONTAINING 3- (3-HEXENIL) -2-CYCLOPENTENONE | |
US3869493A (en) | Novel odorants | |
US4396523A (en) | 1-Phenyl-and-benzyl-2,2-dichloro-cyclopropanes | |
JPS6212735A (en) | (2z,4e(or 4z))-2,4,11-dodecatrienal and perfumery composition containing same | |
US3907873A (en) | Novel fragrance materials and process | |
US4594183A (en) | Perfume compositions and perfumed articles containing one or more tetramethyl-tri-cycloundecyl-alkyl ketones as perfume base | |
US3745130A (en) | Perfume composition |