US3859366A - 2-alkyl-oct-5-en-2-ols and their esters - Google Patents
2-alkyl-oct-5-en-2-ols and their esters Download PDFInfo
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- US3859366A US3859366A US211789A US21178971A US3859366A US 3859366 A US3859366 A US 3859366A US 211789 A US211789 A US 211789A US 21178971 A US21178971 A US 21178971A US 3859366 A US3859366 A US 3859366A
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- US
- United States
- Prior art keywords
- alkyl
- compounds
- oct
- ols
- esters
- Prior art date
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- 150000002148 esters Chemical class 0.000 title abstract description 7
- 239000003205 fragrance Substances 0.000 abstract description 17
- 239000000203 mixture Substances 0.000 abstract description 17
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 235000019568 aromas Nutrition 0.000 abstract description 5
- 230000005923 long-lasting effect Effects 0.000 abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- 239000000126 substance Substances 0.000 description 13
- 239000002304 perfume Substances 0.000 description 8
- -1 for example Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000402754 Erythranthe moschata Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
Definitions
- ABSTRACT 2-Alky1-oct-5-en-2-o1s and their esters characterized by the structural formula 1 CH CH2CH CHCHzCH2CCHa wherein R represents alkyl, having from 1 to 8 carbon atoms and R represents hydroxyl or'R COO-, wherein R represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl.
- R represents alkyl, having from 1 to 8 carbon atoms and R represents hydroxyl or'R COO-, wherein R represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl.
- rosy aromas and are useful as fragrances or as components in fragrance compositions.
- the principal object of the present invention is to provide a new class of aroma chemicals consisting of 2-alkyl-oct-5-en-2-ols and their esters.
- Another object of the present invention is to provide a specific class of compounds having a characteristic aroma which is utilized in the preparation of fragrances and fragrance compositions.
- fragrances have very pleasant, strong and long lasting green, floral, rosy aromasand are useful as fragrances or as components fragrance compositions.
- alkyl groups characterized by R and R in the above formula include methyl, ethyl, npropyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-aniyl, iamyl, tert-amyl, n-octyl.
- Groups other than alkyl characterized by R in the above formula include phenyl, naphthyl and phenylalkyl and the like.
- the scope of the present invention encompasses both the cis and trans forms, as well as mixtures thereof, of the novel compounds of this invention.
- the precursor compounds can be the cis, trans or mixtures of both as desired to provide the compounds of this invention.
- R has the same meaning as defined hereinbefore, with 3-hexenyl magnesium halides as illustrated in the following equation (wherein X represents a halogen; chlorine, bromine or iodine):
- the reaction conditions are not critical but should be such as to facilitate the preparation of the products.
- the Grignard reaction is normally conducted at a temperature of from ambient temperatures up to about C. and the esterification reaction is'normally conducted within this same range.
- novel compounds of this invention are useful as fragrances in the preparation and formulation of, fragrance compositions'such as perfumes and perfumed products due to their pleasing, strong and long lasting aroma.
- perfume compositions and the use thereof in cosmetic, detergent and bar soap formulations and the like are exemplary of the utility thereof.
- these novel compounds can be utilized as the primary fragrance .in many such compositions.
- the compounds of this invention are used in concentrations of from trace amounts up to about 50 percent of the fragrance composition into which they are incorporated. As will be expected, the concentration of the compound will vary depending on the particular fragrance desired in the composition and even within the same, composition when compounded by different perfumers.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
2-Alkyl-oct-5-en-2-ols and their esters characterized by the structural formula
WHEREIN R represents alkyl having from 1 to 8 carbon atoms and R1 represents hydroxyl or R2COO-, wherein R2 represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have very pleasant, strong and long lasting green, floral, rosy aromas and are useful as fragrances or as components in fragrance compositions.
WHEREIN R represents alkyl having from 1 to 8 carbon atoms and R1 represents hydroxyl or R2COO-, wherein R2 represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have very pleasant, strong and long lasting green, floral, rosy aromas and are useful as fragrances or as components in fragrance compositions.
Description
United States Patent [191 Schleppnik' [451 Jan. 7, 1975 1 1 Z-ALKYL-IOCT-S-EN-Z-OLS AND THEIR ESTERS [52] U.S. Cl. 260/632 R, 252/522, 260/469,
260/476 R, 260/488 R, 260/638 R, 260/665 [51] Int. Cl. C07c 33/02 [58] Field of Search 260/632 R [56] References Cited UNITED STATES PATENTS 2,837,569 6/1958 Verley 260/6315 2,902,510 9/1959 Webb 260/632 R 2,919,290 12/1959 Webb 260/632 R 3,344,171 9/1967 Lemberg 260/631.5
OTHER PUBLICATIONS Awell et al., C. A., Vo1. 52 (1958), 17211 Barlot et al., C. A., Vol. 75, (1971), 35055X (p. 434), QD1A51.
Takei et al., C. A., Vol. 31 (1937), 6815, QD1A51.
Primary Examiner-Joseph E. Evans Attorney, Agent, or Firm-Howard C. Stanley; John E. Maurer; Neal E. Willis [57] ABSTRACT 2-Alky1-oct-5-en-2-o1s and their esters characterized by the structural formula 1 CH CH2CH=CHCHzCH2CCHa wherein R represents alkyl, having from 1 to 8 carbon atoms and R represents hydroxyl or'R COO-, wherein R represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl. These compounds can be in the cis or trans forms or mixtures thereof. The compounds have 4 very pleasant, strong and long lasting green, floral,
rosy aromas and are useful as fragrances or as components in fragrance compositions.
1 Claim, No Drawings Z-ALKYL-OCT-S-EN-Z-OLS AND THEIR ESTERS and until comparatively recently, the perfumer has uti- I lized natural perfume chemicals of animal and vegetable origin. Thus, natural perfume chemicals such as the essential oils, for example, oil of rose and oil of cloves, and animal secretions such as musk, have been manipulated by the perfumer to achieve a variety of fragrances. In more recent years, however, research perfume chemists have developed alarge number of synthetic odoriferous chemicals possessing aroma characteristics particularly desired in the art. These synthetic aroma chemicals have added a new dimension to the ancient art ofthe perfumer, since the compounds prepared are usually of a stable chemical nature, are inexpensive as compared with the natural perfume chemicals and lend themselves more easily to manipulation than natural perfume chemicals since such natural perfume chemicals are usually a complex mixture of substances which defy chemical analysis. In contrast thereto, the synthetic aroma chemicals possess a known chemical structure and may therefore be manipulated by the perfumer to suit specific needs. Accordingly, there isa great need in the art of fragrance com-' positions for new compounds possessing specific char acteristic aromas.
The principal object of the present invention is to provide a new class of aroma chemicals consisting of 2-alkyl-oct-5-en-2-ols and their esters.
Another object of the present invention is to provide a specific class of compounds having a characteristic aroma which is utilized in the preparation of fragrances and fragrance compositions.
These and other objects, aspects and advantages of this invention will become apparent from a consideration of the accompanying specification and claims.
In accordance with the above objects, there is provided by the present invention a novel class of compounds characterized by the structural formula wherein R represents alkyl having from to 8 carbon atoms and R represents hydroxyl or R COO-, wherein R represents alkyl having from 1 to 8 carbon atoms, aryl or aralkyl.
These compounds have very pleasant, strong and long lasting green, floral, rosy aromasand are useful as fragrances or as components fragrance compositions.
Representative alkyl groups characterized by R and R in the above formula include methyl, ethyl, npropyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-aniyl, iamyl, tert-amyl, n-octyl.
Groups other than alkyl characterized by R in the above formula include phenyl, naphthyl and phenylalkyl and the like.
It should be understood that the scope of the present invention encompasses both the cis and trans forms, as well as mixtures thereof, of the novel compounds of this invention. The precursor compounds can be the cis, trans or mixtures of both as desired to provide the compounds of this invention.
The novel alcohols of this invention are prepared by reacting a methyl ketone characterized by the structural formula ll RCCII:
wherein R has the same meaning as defined hereinbefore, with 3-hexenyl magnesium halides as illustrated in the following equation (wherein X represents a halogen; chlorine, bromine or iodine):
ll (JUaUllzOlk-OIICIIzClIzCCH; RMgX ()ll CIIaCIIrCH==CHOH2CH=+ CH1 R cmo1r=o1I=oIIomoH=JJ-oIIi wherein R and R have the same meaning as defined hereinabove.
The reaction conditions are not critical but should be such as to facilitate the preparation of the products. Thus, the Grignard reaction is normally conducted at a temperature of from ambient temperatures up to about C. and the esterification reaction is'normally conducted within this same range.
The novel compounds of this invention are useful as fragrances in the preparation and formulation of, fragrance compositions'such as perfumes and perfumed products due to their pleasing, strong and long lasting aroma. Perfume compositions and the use thereof in cosmetic, detergent and bar soap formulations and the like are exemplary of the utility thereof. Likewise, these novel compounds can be utilized as the primary fragrance .in many such compositions.
The compounds of this invention are used in concentrations of from trace amounts up to about 50 percent of the fragrance composition into which they are incorporated. As will be expected, the concentration of the compound will vary depending on the particular fragrance desired in the composition and even within the same, composition when compounded by different perfumers.
The following examples willserve to illustrate certain specific embodiments within the scope of this invention and are not to be construed as limiting the scope thereof.
EXAMPLE 1 cis-2-methyl-oct-5-en-2-ol 12.2 grams of magnesium were mixed with 50 ml. of I anhydrous tetrahydrofuran and activated with 0.5 ml. of methyl iodide. To this massa solution of 59.3 grams (0.5 moles) of cis-l-chloro-3-hexene in 150 ml. of tetrahydrofuran was added drop-wise with stirring. A
greenish turbid solution formed and an exothermic re- 1.4435 was obtained. After fractional distillation 48.2 grams of a product which had a boiling point of 88 to 89C. at 20 mm. of Hg. was obtained which had an n,, 1.4425 and was found to be cis-2-methyl-oct-5-en-2- 01. The material was submitted to a fragrance panel for aroma characterization and it was described as havin green, grass, sweet, floral and lavender aromas.
- which had a boiling point of 90 to 91C. at ml. of
continued for' 15 hours and the complex was decomposed with ice-concentrated ammonium chloride solution. 68.1 Grams of a crude product with an n,,
Hg. and which had an n 1.4325 which was found to be cis-2-methyl-oct-5-en 2-yl acetate. The material was submitted to a fragrance panel for aroma characterization and it was described as having green, leafy,
' earthy, ozone and greenhouse aromas.
While the invention has been described herein with regard to certain specific embodiments, it is not so limited. It is to be understood that variations and modifications thereof may be made by those skilled in the art without departing from the spirit and scope of the invention.
The embodiments of this invention in which an exclusive property or privilege is claimed are defined as follows:'
g l. Cis-2-methyl-oct-5-en-2-ol.
Claims (1)
1. CIS-2-METHYL-OCT-5-EN-2-OL
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US211789A US3859366A (en) | 1971-12-23 | 1971-12-23 | 2-alkyl-oct-5-en-2-ols and their esters |
| US05/432,012 US3966648A (en) | 1971-12-23 | 1974-01-09 | 2-Alkyl-oct-5-en-2-ols in fragrance compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US211789A US3859366A (en) | 1971-12-23 | 1971-12-23 | 2-alkyl-oct-5-en-2-ols and their esters |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/432,012 Division US3966648A (en) | 1971-12-23 | 1974-01-09 | 2-Alkyl-oct-5-en-2-ols in fragrance compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3859366A true US3859366A (en) | 1975-01-07 |
Family
ID=22788381
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US211789A Expired - Lifetime US3859366A (en) | 1971-12-23 | 1971-12-23 | 2-alkyl-oct-5-en-2-ols and their esters |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3859366A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006109A (en) * | 1974-03-15 | 1977-02-01 | Givaudan Corporation | Trimethyl nonene alcohols and perfume compositions |
| US4045475A (en) * | 1975-01-27 | 1977-08-30 | Hoffmann-La Roche Inc. | Optically active alcohols and lower esters thereof |
| US4126585A (en) * | 1976-06-11 | 1978-11-21 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2-Methyl-2-ethyl-hexanoate ester perfume compositions |
| US4585662A (en) * | 1980-07-31 | 1986-04-29 | Givaudan Corporation | Acyclic alcohol odorant and/or flavoring substances |
| US5087612A (en) * | 1989-09-25 | 1992-02-11 | Firmenich Sa | Oxygenated alicyclic compounds and their use in perfumery |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837569A (en) * | 1953-04-27 | 1958-06-03 | Verley Albert | Method of fixing lower alkyl radicals on ethylenic double bonds of terpenes |
| US2902510A (en) * | 1956-04-09 | 1959-09-01 | Glidden Co | 2-substituted-2,6-dimethyl-7-octenes and process for preparing same |
| US2919290A (en) * | 1955-11-07 | 1959-12-29 | Glidden Co | Acyclic carbinols and esters and method of preparation of the esters |
| US3344171A (en) * | 1964-09-23 | 1967-09-26 | Int Flavors & Fragrances Inc | Isomerization of terpenes with a noble metal catalyst in the presence of hydrogen chloride |
-
1971
- 1971-12-23 US US211789A patent/US3859366A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2837569A (en) * | 1953-04-27 | 1958-06-03 | Verley Albert | Method of fixing lower alkyl radicals on ethylenic double bonds of terpenes |
| US2919290A (en) * | 1955-11-07 | 1959-12-29 | Glidden Co | Acyclic carbinols and esters and method of preparation of the esters |
| US2902510A (en) * | 1956-04-09 | 1959-09-01 | Glidden Co | 2-substituted-2,6-dimethyl-7-octenes and process for preparing same |
| US3344171A (en) * | 1964-09-23 | 1967-09-26 | Int Flavors & Fragrances Inc | Isomerization of terpenes with a noble metal catalyst in the presence of hydrogen chloride |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4006109A (en) * | 1974-03-15 | 1977-02-01 | Givaudan Corporation | Trimethyl nonene alcohols and perfume compositions |
| US4045475A (en) * | 1975-01-27 | 1977-08-30 | Hoffmann-La Roche Inc. | Optically active alcohols and lower esters thereof |
| US4126585A (en) * | 1976-06-11 | 1978-11-21 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2-Methyl-2-ethyl-hexanoate ester perfume compositions |
| US4585662A (en) * | 1980-07-31 | 1986-04-29 | Givaudan Corporation | Acyclic alcohol odorant and/or flavoring substances |
| US5087612A (en) * | 1989-09-25 | 1992-02-11 | Firmenich Sa | Oxygenated alicyclic compounds and their use in perfumery |
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