US3185629A - Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal - Google Patents

Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal Download PDF

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Publication number
US3185629A
US3185629A US98998A US9899861A US3185629A US 3185629 A US3185629 A US 3185629A US 98998 A US98998 A US 98998A US 9899861 A US9899861 A US 9899861A US 3185629 A US3185629 A US 3185629A
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United States
Prior art keywords
propanal
methyl
methylenedioxyphenyl
oils containing
perfume oils
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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 - Lifetime
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US98998A
Inventor
Muus G J Beets
Harm Van Essen
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.)
International Flavors and Fragrances IFF Nederland NV
International Flavors and Fragrances Inc
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International Flavors and Fragrances Inc
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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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

Definitions

  • a composition consisting of a perfume oil, a fragrance-imparting proportion of 2-methyl-3-(3',4'-methylenedioxyphenyl)-propanal and perfume diluents.
  • a composition consisting of a perfume oil having exceptional tenacity and a sulficient amount of 2-methyl-3- (3 ,4-methylenedioxyphenyl) -propanal to impart the fragrance of the propanal to the oil, and a cosmetic carrier compatible with the propanal.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)

Description

United States Patent 4,3 3 V 3 Claims. (Cl. 167-94) This is a division of application No. 789,795, filed January 29, 195 9, new Patent No. 3,008,968.
We have discovered that 2-methyl-3- (3',4-methylenedioxyphenyl)-propanal of structure I is an outstanding olfactory ingredient in perfume-containing compositions:
It shows an exceptional tenacity. A strip of filter paper was moistened with 2-methyl-3- (3',4'-methylenedioxyphenyl)-propanal to which 10/00 of a normal anti-oxidant, e.g. hydroquinone, had been added and kept for two months in contact with air at room temperature. After this period the odor was still strong and undegenerated.
It hasan excellent stability in pure form and in perfume compositions as well as in articles in which such compositions are used, such as soaps, cosmetics, powders and aerosol products. Although 2-methy1-3-(3',4'-methylenedioxyphenyl)-propanal has a very strong, interesting and definite odor, it is easy to blend into specific and widely varying types of perfumes in relatively large amounts. This is clearly demonstrated by the examples given below.
2-methyl-3-(3,4'-methylenedi0xyphenyl) -propanal has not been described in the literature. Its lower homologue, piperonyl-ethanal or 3-( 3,4-methylenedioxyphenyl) -propanal (II) is far less interesting. It has been obtained in small quantities by some authors (Fourneau and Tideneau, Comptes rendus 141 (1905), 663; V. Paolini, Gazz 42, I (1912), 30 and Atti della R. Accad. dei Lincei (5), 20 (1911), 940; E. mosettig, Ber. 62 (1929), 1274, but none of them mentions the odor.
Pure 2-methyl-3-(3'-4-methylenedioxyphenyl) propanal as an olfactory ingredient, admixture with the indicated additional components in the given amounts:
Example I A perfume oil having a cyclamen character was made by mixing together the following ingredients:
Parts by weight 2-methyl-3-(3',4,-methylenedioxyphenol)-propanal 50 Hydroxyeitronellal 12 Linalool 4 Alpha ionone 5 Linalyl acetate 4 Geraniol ex Java citronella oil 3 Phenyl ethyl alcohol 5 Musk ketone 2 Amyl cinamic aldehyde 5 Benzyl acetate 5 Terpineol t 5 Example II A perfume oil having a jasmin character was mixed from the following ingredients:
Parts by weight 2-methyl-3-(3',4-methylenedioxypheny1)-propanal 50 Amyl cinnamic aldehyde 13 Benzyl acetate 10 Linalool 5 Linalyl acetate 5 Hydroxy citronallal 5 Heliotropin 4 Phenyl ethyl alcohol 8 Example 111 Alpha ionone Geranyl acetate Aldehyde C undecylenic What we claim is l. A composition consisting ofperfume oil and Z-methy1-3- 3 ',4'-methylene dioxyphenyl) -prop anal.
2. A composition consisting of a perfume oil, a fragrance-imparting proportion of 2-methyl-3-(3',4'-methylenedioxyphenyl)-propanal and perfume diluents.
3. A composition consisting of a perfume oil having exceptional tenacity and a sulficient amount of 2-methyl-3- (3 ,4-methylenedioxyphenyl) -propanal to impart the fragrance of the propanal to the oil, and a cosmetic carrier compatible with the propanal.
References Cited by the Examiner UNITED STATES PATENTS 3,008,968 11/61 Beets 1679'4 X OTHER REFERENCES Bogert et al.: J. Am. Chem. Soc., vol. 53, pages 2747-2755 (1931).
Moncrief: The Chem. of Perf. Materials, United Trade Press, London, 1949, pp. 38, 39, 84.
FRANK CACCIAPAGLIA, 111., Primary Examiner.
IRVING MARCUS, LEWIS GOTTS, Examiners.

Claims (1)

1. A COMPOSITION CONSISTING OF PERFUME OIL AND 2-METHYL-3-(3'',4''-METHYLENEDIOXYPHENYL)-PROPANAL.
US98998A 1958-02-11 1961-01-19 Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal Expired - Lifetime US3185629A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4390/58A GB841921A (en) 1958-02-11 1958-02-11 2-piperonyl-propanal, a new perfume, and process for making same

Publications (1)

Publication Number Publication Date
US3185629A true US3185629A (en) 1965-05-25

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US98998A Expired - Lifetime US3185629A (en) 1958-02-11 1961-01-19 Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal

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US (1) US3185629A (en)
CH (1) CH379035A (en)
GB (1) GB841921A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04305575A (en) * 1990-09-27 1992-10-28 Hoechst Ag Method of manufacturing perfume
WO2006095200A1 (en) * 2005-03-10 2006-09-14 Quest International Services B.V. Perfume compositions
WO2008009926A2 (en) * 2006-07-17 2008-01-24 Flexitral, Inc Safrole replacements
WO2008017820A1 (en) * 2006-08-05 2008-02-14 Givaudan Nederland Services B.V. Perfume compositions
US20100121085A1 (en) * 2007-02-15 2010-05-13 Ube Industries, Ltd. 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof
CN101622238B (en) * 2007-03-07 2013-05-29 宇部兴产株式会社 Method of retaining the quality of 2-methyl-3-(3,4-methylenedioxyphenyl)propanal and process for producing the same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2975283B1 (en) 2011-05-17 2019-04-05 V. Mane Fils SENSORY USE OF 6-CYCLOPENTYLIDENEHEXANE DERIVATIVES

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3008968A (en) * 1958-02-11 1961-11-14 Int Flavors & Fragrances Inc Process for making 2-methyl-3-(3'-4'-methylenedioxyphenyl)-propanal

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3008968A (en) * 1958-02-11 1961-11-14 Int Flavors & Fragrances Inc Process for making 2-methyl-3-(3'-4'-methylenedioxyphenyl)-propanal

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04305575A (en) * 1990-09-27 1992-10-28 Hoechst Ag Method of manufacturing perfume
WO2006095200A1 (en) * 2005-03-10 2006-09-14 Quest International Services B.V. Perfume compositions
US20080108542A1 (en) * 2005-03-10 2008-05-08 Perring Keith D Perfume Compositions
WO2008009926A2 (en) * 2006-07-17 2008-01-24 Flexitral, Inc Safrole replacements
WO2008009926A3 (en) * 2006-07-17 2008-10-09 Flexitral Inc Safrole replacements
WO2008017820A1 (en) * 2006-08-05 2008-02-14 Givaudan Nederland Services B.V. Perfume compositions
US9011829B2 (en) 2006-08-05 2015-04-21 Givaudan Nederland Services B.V. Perfume compositions
US10722607B2 (en) 2006-08-05 2020-07-28 Givaudan S.A. Perfume compositions
US20100121085A1 (en) * 2007-02-15 2010-05-13 Ube Industries, Ltd. 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof
US8168809B2 (en) 2007-02-15 2012-05-01 Ube Industries, Ltd. 2-methyl-3-(3,4-methylenedioxyphenyl)propanal, and method for production thereof
CN101622238B (en) * 2007-03-07 2013-05-29 宇部兴产株式会社 Method of retaining the quality of 2-methyl-3-(3,4-methylenedioxyphenyl)propanal and process for producing the same

Also Published As

Publication number Publication date
GB841921A (en) 1960-07-20
CH379035A (en) 1964-06-30

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