US3185629A - Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal - Google Patents
Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- propanal
- methyl
- methylenedioxyphenyl
- oils containing
- perfume oils
- 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 - Lifetime
Links
- 239000002304 perfume Substances 0.000 title description 9
- 239000003921 oil Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 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
- IDCKZBGINKOTOL-UHFFFAOYSA-N 3,4-Methylenedioxyphenyl-1-propanal Chemical compound O=CCCC1=CC=C2OCOC2=C1 IDCKZBGINKOTOL-UHFFFAOYSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UZFLPKAIBPNNCA-UHFFFAOYSA-N alpha-ionone Natural products CC(=O)C=CC1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-UHFFFAOYSA-N 0.000 description 2
- 229940007550 benzyl acetate Drugs 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 description 2
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
- -1 Alpha ionone Geranyl acetate Aldehyde Chemical class 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000612152 Cyclamen hederifolium Species 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 244000032014 Java citronella Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-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
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000010632 citronella oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003581 cosmetic carrier Substances 0.000 description 1
- 229930186364 cyclamen Natural products 0.000 description 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940067137 musk ketone Drugs 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
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.
Landscapes
- 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.
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 |
Family
ID=9776262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US98998A Expired - Lifetime US3185629A (en) | 1958-02-11 | 1961-01-19 | Perfume oils containing 2-methyl-3-(3', 4'-methylenedioxyphenyl)-propanal |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3185629A (en) |
| CH (1) | CH379035A (en) |
| GB (1) | GB841921A (en) |
Cited By (6)
| 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 |
| WO2008017820A1 (en) * | 2006-08-05 | 2008-02-14 | Givaudan Nederland Services B.V. | Perfume compositions |
| WO2008009926A3 (en) * | 2006-07-17 | 2008-10-09 | Flexitral Inc | Safrole replacements |
| 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)
| 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)
| 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 |
-
1958
- 1958-02-11 GB GB4390/58A patent/GB841921A/en not_active Expired
-
1959
- 1959-02-10 CH CH6933959A patent/CH379035A/en unknown
-
1961
- 1961-01-19 US US98998A patent/US3185629A/en not_active Expired - Lifetime
Patent Citations (1)
| 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 (10)
| 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 |
| 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 |
|---|---|
| CH379035A (en) | 1964-06-30 |
| GB841921A (en) | 1960-07-20 |
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