GB1057360A - Derivatives of dihydrocinnamaldehyde useful in perfumery - Google Patents

Derivatives of dihydrocinnamaldehyde useful in perfumery

Info

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
Application number
GB4772065A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhone Poulenc SA
Original Assignee
Rhone Poulenc SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Rhone Poulenc SA filed Critical Rhone Poulenc SA
Publication of GB1057360A publication Critical patent/GB1057360A/en
Expired legal-status Critical Current

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.
GB4772065A 1964-11-13 1965-11-10 Derivatives of dihydrocinnamaldehyde useful in perfumery Expired GB1057360A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
JPWO2023243499A1 (en) * 2022-06-17 2023-12-21

Cited By (30)

* Cited by examiner, † Cited by third party
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
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
JP2016523828A (en) * 2013-05-08 2016-08-12 ジボダン エス エー Improvements in or relating to organic compounds
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
NL6514604A (en) 1966-05-16
FR1460826A (en) 1966-01-07
FR1443997A (en) 1966-07-01
CH447440A (en) 1967-11-30
DE1467511A1 (en) 1969-02-27
FR1430164A (en) 1966-03-04
BE672280A (en) 1966-05-12
NL149778B (en) 1976-06-15

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