EP1613611A1 - Novel sesquiterpene oxides as perfuming and flavouring agents - Google Patents
Novel sesquiterpene oxides as perfuming and flavouring agentsInfo
- Publication number
- EP1613611A1 EP1613611A1 EP03816443A EP03816443A EP1613611A1 EP 1613611 A1 EP1613611 A1 EP 1613611A1 EP 03816443 A EP03816443 A EP 03816443A EP 03816443 A EP03816443 A EP 03816443A EP 1613611 A1 EP1613611 A1 EP 1613611A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- mixture
- acid
- products
- formula
- 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.)
- Withdrawn
Links
- 239000002304 perfume Substances 0.000 title claims abstract description 5
- 229930004725 sesquiterpene Natural products 0.000 title abstract description 11
- 150000004354 sesquiterpene derivatives Chemical class 0.000 title abstract description 10
- 239000000796 flavoring agent Substances 0.000 title abstract description 4
- 235000013355 food flavoring agent Nutrition 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- GFJIQNADMLPFOW-UHFFFAOYSA-N cis-Elemol Natural products CC(=C)C1CC(C(C)(C)O)CCC1(C)C=C GFJIQNADMLPFOW-UHFFFAOYSA-N 0.000 claims abstract description 8
- LLKXNMNOHBQSJW-UHFFFAOYSA-N Elemol Natural products CCC(=C)C1CC(C=CC1(C)C)C(C)(C)O LLKXNMNOHBQSJW-UHFFFAOYSA-N 0.000 claims abstract description 7
- GFJIQNADMLPFOW-VNHYZAJKSA-N elemol Chemical compound CC(=C)[C@@H]1C[C@H](C(C)(C)O)CC[C@@]1(C)C=C GFJIQNADMLPFOW-VNHYZAJKSA-N 0.000 claims abstract description 7
- 150000004965 peroxy acids Chemical class 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000002781 deodorant agent Substances 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 244000147568 Laurus nobilis Species 0.000 claims description 5
- 235000017858 Laurus nobilis Nutrition 0.000 claims description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 235000005212 Terminalia tomentosa Nutrition 0.000 claims description 5
- 235000007303 Thymus vulgaris Nutrition 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 239000002386 air freshener Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 239000001585 thymus vulgaris Substances 0.000 claims description 5
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical group C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 235000009411 Rheum rhabarbarum Nutrition 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 229940093499 ethyl acetate Drugs 0.000 claims description 4
- 235000019439 ethyl acetate Nutrition 0.000 claims description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 239000000741 silica gel Substances 0.000 claims description 3
- 229910002027 silica gel Inorganic materials 0.000 claims description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 2
- 239000003570 air Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229960004132 diethyl ether Drugs 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims description 2
- 239000002453 shampoo Substances 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 230000002195 synergetic effect Effects 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 244000299790 Rheum rhabarbarum Species 0.000 claims 1
- 240000002657 Thymus vulgaris Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- MRUXRHZVXCSIKW-UHFFFAOYSA-N ethaneperoxoic acid;perchloric acid Chemical compound CC(=O)OO.OCl(=O)(=O)=O MRUXRHZVXCSIKW-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- OKQJPMSNSZSSMN-UHFFFAOYSA-N 1,3,3,7a-tetramethyl-1-propan-2-yl-4,7-dihydro-3ah-2-benzofuran Chemical compound C1C=CCC2(C)C(C(C)C)(C)OC(C)(C)C21 OKQJPMSNSZSSMN-UHFFFAOYSA-N 0.000 abstract 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 241000246358 Thymus Species 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241000219061 Rheum Species 0.000 description 3
- OPFTUNCRGUEPRZ-UHFFFAOYSA-N (+)-beta-Elemen Natural products CC(=C)C1CCC(C)(C=C)C(C(C)=C)C1 OPFTUNCRGUEPRZ-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- QDUJKDRUFBJYSQ-UHFFFAOYSA-N alpha-elemene Natural products CC(C)C1=CC(=C(C)C)CCC1(C)C=C QDUJKDRUFBJYSQ-UHFFFAOYSA-N 0.000 description 2
- GFJIQNADMLPFOW-UMVBOHGHSA-N beta-elemol Chemical compound CC(=C)[C@H]1C[C@H](C(C)(C)O)CC[C@@]1(C)C=C GFJIQNADMLPFOW-UMVBOHGHSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MXDMETWAEGIFOE-CABCVRRESA-N delta-elemene Chemical compound CC(C)C1=C[C@H](C(C)=C)[C@@](C)(C=C)CC1 MXDMETWAEGIFOE-CABCVRRESA-N 0.000 description 2
- QDUJKDRUFBJYSQ-OAHLLOKOSA-N elemene Chemical compound CC(C)C1=CC(=C(C)C)CC[C@@]1(C)C=C QDUJKDRUFBJYSQ-OAHLLOKOSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- -1 sesquiterpene alcohols Chemical class 0.000 description 2
- DWIOZLHIFRRJII-UHFFFAOYSA-N 1,3,3a,4,5,6-hexahydro-2-benzofuran Chemical compound C1CCC2COCC2=C1 DWIOZLHIFRRJII-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101000737296 Pisum sativum Chlorophyll a-b binding protein AB96 Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- RVOXATXFYDNXRE-UHFFFAOYSA-N gamma-elemene Natural products CC(=C1CCC(C)(C(C1)C(=C)C)C(=C)C)C RVOXATXFYDNXRE-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- MXDMETWAEGIFOE-UHFFFAOYSA-N rac-delta-elemene Natural products CC(C)C1=CC(C(C)=C)C(C)(C=C)CC1 MXDMETWAEGIFOE-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Definitions
- the present inventions deals with a novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl-- 1,1,3,3 a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) and its process for preparation having odoriferous character.
- mixture of diastereoisomers of compound, of formula (1) in the ratio of 75:25 possesses multiodorant being a combination of rubarb, laurel, thyme and florex.
- a Japanese patent JP 54084551 by Nagakura et al, published on 5 th July, 1979 describes the use in perfumery, for cosmetics and flavor for food, of substances, specifically of an oily and multi-component oxidation product obtained by treating a mixture, consisting of alpha elemene and delta elemene, resulting from heat dehydration of beta elemol or an alpha elemene mixture separated from the dehydration product, with a peracid.
- a main objective of the present invention provides a novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) and its process for preparation.
- An object of the present invention provides compound of formula (1) having perfuming and flavoring property.
- Still another object of the present invention is to provide a mixture of stereoisomers of compund of formula (1) having multuioderant being the combination of rhubarb, laurel, thyme and florex.
- Still yet another object of the present invention provides the use of a compound of formula (1) alone or in combination with other perfuming ingredients, solvents, or additives to obtain desired olfactory effect.
- Yet another object of the present invention provides an incorporation of different proportions of compound of formula (1) into various products depending upon the nature of the products used and to obtain desired olfactory effect.
- the present invention describes the process for the preparation of novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) by the reaction of elemol with per acid at a temperature range of 20 to 30°C.
- the invention also deals with the use of compound of formula (1) as a perfuming and flavouring agent.
- FORMULA 1 represents basic structure of novel sesquiterpene oxides
- SCHEME-1 represents formation of elemene alcohols 2 & 3, probable products expected from reaction of elemenes, as per the reaction conditions given in JP 54084551.
- the present invention provides a compound named 3S, 3aR, 7aR-6-iso ⁇ ropyl-l,l,3,3a-tetramethyl-l,3,3,9,4,7,7a-hexahydroisobenzofuran of formula (1).
- An embodiment of the present invention provides a compound having following characteristics: Light yellow oil, [ ⁇ ] D -57.2 ( EtOH)
- Still another embodiment of the present invention provides a compound having isobenzofuran ring responsible for olfactory characteristics.
- Yet another embodiment of the present invention provides a compound used in fine perfumery, colognes, hygiene products, batch gels, hair care products, deodorants, air- freshener and cosmetic preparation.
- Another embodiment of the present invention provides a compound as a single or as a mixture of isomers that can be used to impart fragrance to consumer products.
- Still another embodiment of the present invention provides a process for the preparation of compound (1), the said process comprising steps of: a) dissolving elemol in glacial acetic acid to obtain a solution, b) adding perchloric acid to the step (a) solution at a temperature range of 20 to 30° C to obtain a reaction mixture, c) stirring the reaction mixture of step (b) at an ambient temperature for a period of 60 h to 80h, d) diluting with water the reaction mixture of step (d) extracting with the aqueous solution an organic solvent, separating the organic and the aqueous layer, e) washing the organic layer of step (d) with aqueous sodium bicarbonate followed by water, f) drying the washed organic layer over anhydrous sodium sulphate, filtering, and removing the solvent from the filtrate to obtain crude product, and g) pur
- step (b) provides a process, wherein in step (b), the peracid used is selected from a group consisting of peracetic acid, perchloric acid or perbenzoic acid.
- step (d) provides a process, wherein in step (d) the organic solvent used is selected from diethylether, methylene, chloride, chloroform or ethylacetate.
- Still another embodiment of the present invention provides a process, wherein in step (g) the mixture of organic solvent used is ethylacetate petroleum ether (4:96).
- Yet another embodiment of the present invention provides a process having isobenzofuran ring responsible for olfactory characteristics.
- Still another embodiment of the present invention provides a process wherein the compound is used in fine perfumery, colognes, hygeine products, batch gels, hair care products, deodorants, air freshness or cosmetic preparation.
- This compound can be used as an additive and when used in the applications, the products accepted to the users and it has not shown any adverse effect.
- Yet another embodiment of the present invention provides a synergistic composition containing an effective amount of compound (I) or mixture of its isomers, the said composition being useful in perfuming the soaps, shower or bath gels, hygiene products, hair care products such as shampoos, body deodorants, air fresheners or cosmetic preparation.
- This compound can be used as an additive and when used in the applications, the
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention describes the process for the preparation of novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl 1,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) by the reaction of elemol with per acid at a temperature range of 20 to 30°C. The invention also deals with the use of compound of formula (1) as a perfuming and flavouring agent.
Description
NOVEL SESQUITERPENE OXIDES AS PERFUMING AND FLAVORING
AGENTS
Filed of the invention
The present inventions deals with a novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl-- 1,1,3,3 a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) and its process for preparation having odoriferous character. In addition, mixture of diastereoisomers of compound, of formula (1) in the ratio of 75:25 possesses multiodorant being a combination of rubarb, laurel, thyme and florex. Background of Prior Art The compounds as defined in formula 1, have been detected, among other reaction products, during the course of studies on peracid dehydration of the sesquiterpene elemol.
A Japanese patent JP 54084551 by Nagakura et al, published on 5th July, 1979 describes the use in perfumery, for cosmetics and flavor for food, of substances, specifically of an oily and multi-component oxidation product obtained by treating a mixture, consisting of alpha elemene and delta elemene, resulting from heat dehydration of beta elemol or an alpha elemene mixture separated from the dehydration product, with a peracid.
It is important to point out that this document of prior art neither specifies structure nor stereochemistry of any component of the mixture except giving the infrared and NMR spectra of the mixture. Without doubt, on the basis of the experimental conditions described in the abstract of the document, for the preparation of mixtures of diastereomers of elemenes oxides derived each from alpha and delta elemenes one may, theoretically expect the sesquiterpene alcohols, 2 and 3 as shown in the scheme-I.
Compound of formula (1) is neither prepared synthetically nor isolated from a natural product and reported the prior art. Its use as a perfuming or flavoring ingredient is also not known in the prior art.
During the synthesis of a reference compound, dehydration of elemol was carried out. The pleasant smelling novel sesquiterpene oxides, compounds of the present invention, were obtained as side products during the reaction. Object of the invention
A main objective of the present invention provides a novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) and its process for preparation.
An object of the present invention provides compound of formula (1) having perfuming and flavoring property.
Still another object of the present invention is to provide a mixture of stereoisomers of compund of formula (1) having multuioderant being the combination of rhubarb, laurel, thyme and florex.
Yet another object of the present invention is to provide stereo isomers of compound of formula (1) having pronounced differences in their odoriferous properties. Still another object of the present invention is to utilise the compound of formula (1) in fine perfumery, colognes, hygiene products, hair care products, body deodorants, air fresheners and cosmetic preparations.
Still yet another object of the present invention, provides the use of a compound of formula (1) alone or in combination with other perfuming ingredients, solvents, or additives to obtain desired olfactory effect.
Yet another object of the present invention provides an incorporation of different proportions of compound of formula (1) into various products depending upon the nature of the products used and to obtain desired olfactory effect. Summary of the invention
Accordingly, the present invention describes the process for the preparation of novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl l,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) by the reaction of elemol with per acid at a temperature range of 20 to 30°C. The invention also deals with the use of compound of formula (1) as a perfuming and flavouring agent. BRIEF DESCRIPTION OF THE DRAWINGS: FORMULA 1 represents basic structure of novel sesquiterpene oxides SCHEME-1 represents formation of elemene alcohols 2 & 3, probable products expected from reaction of elemenes, as per the reaction conditions given in JP 54084551. DETAILED DESCRIPTION OF THE INVENTION
In accordance to the objects, the present invention provides a compound named 3S, 3aR, 7aR-6-isoρropyl-l,l,3,3a-tetramethyl-l,3,3,9,4,7,7a-hexahydroisobenzofuran of formula (1).
An embodiment of the present invention provides a compound having following characteristics: Light yellow oil, [ α ]D -57.2 ( EtOH)
Infrared: 2964, 1377,1184, 950, 808, 777 cm-1
1H NMR (CDC13): δ 5.36 (lH,d,J= 6.12 Hz ); 3.55 (lH,q,J=7.2 Hz); 2.26 (lH,m ); 1.24 (3H,s); 1.16 ( 3H,s );0.77 ( 3H,s ); 1.03 (6H,d, J=7.92 Hz); 1.13 (3H, d, J=7.2 Hz);1.9,1.72,1.89,1.75. 13C NMR: 78.7; 81.2; 42.7; 37.7; 117.0; 143.4; 23.9; 54.3; 14.4; 12.6; 24.8; 30.6;
35.2; 21.4; 21.9 ppm.
MS: 222 (14), 207 (30), 178 (14), 163 (32), 149 (10), 135 (75), 93 (100), 79(18) Still another embodiment of the present invention provides a compound having isobenzofuran ring responsible for olfactory characteristics. Yet another embodiment of the present invention provides a compound used in fine perfumery, colognes, hygiene products, batch gels, hair care products, deodorants, air- freshener and cosmetic preparation.
Another embodiment of the present invention provides a compound as a single or as a mixture of isomers that can be used to impart fragrance to consumer products. Still another embodiment of the present invention provides a process for the preparation of compound (1), the said process comprising steps of: a) dissolving elemol in glacial acetic acid to obtain a solution, b) adding perchloric acid to the step (a) solution at a temperature range of 20 to 30° C to obtain a reaction mixture, c) stirring the reaction mixture of step (b) at an ambient temperature for a period of 60 h to 80h,
d) diluting with water the reaction mixture of step (d) extracting with the aqueous solution an organic solvent, separating the organic and the aqueous layer, e) washing the organic layer of step (d) with aqueous sodium bicarbonate followed by water, f) drying the washed organic layer over anhydrous sodium sulphate, filtering, and removing the solvent from the filtrate to obtain crude product, and g) purifying the crude product of step (f) over silica gel column eluting with a mixture of organic solvent to obtain the compound of formula (1).
Still another embodiment of the present invention provides a process, wherein in step (b), the peracid used is selected from a group consisting of peracetic acid, perchloric acid or perbenzoic acid.
Yet another embodiment of the present invention provides a process, wherein in step (d) the organic solvent used is selected from diethylether, methylene, chloride, chloroform or ethylacetate.
Still another embodiment of the present invention provides a process, wherein in step (g) the mixture of organic solvent used is ethylacetate petroleum ether (4:96).
Yet another embodiment of the present invention provides a process having isobenzofuran ring responsible for olfactory characteristics.
Still another embodiment of the present invention provides a process wherein the compound is used in fine perfumery, colognes, hygeine products, batch gels, hair care products, deodorants, air freshness or cosmetic preparation. This compound can be used as an additive and when used in the applications, the products accepted to the users and it has not shown any adverse effect.
Yet another embodiment of the present invention provides a synergistic composition containing an effective amount of compound (I) or mixture of its isomers, the said composition being useful in perfuming the soaps, shower or bath gels, hygiene products, hair care products such as shampoos, body deodorants, air fresheners or cosmetic preparation.
Still another embodiment of the present invention provides a composition that can be used alone or in combination with other perfuming agents, solvents or additives.
Yet another embodiment of the present invention provides a composition, wherein the mixture of isomers of compound (I) in the ratio 75:25 is a multiodorant being a combination of rhubarb, laurel, thyme and florex.
The invention is illustrated with references to the examples, which should not be 5 construed to limit the scope of the present invention.
EXAMPLE 1
Preparation of the compounds of formula 1:
To a solution of elemol (3.5-gm) in glacial acetic acid (42 ml) was added perchloric acid (0.7 ml, 60%). The reaction mixture was allowed to stand at room 10 temperature (25-27° C) for 72 hours with continuous stining, The reaction product was diluted with water and extracted with ether. The ethereal extract washed with sodium bicarbonate, then with water and dried over anhydrous sodium sulfate. Removal of the solvent gave a crude product containing, besides elemenes (major product of the reaction) all the stereoisomers of sesquiterpene oxide. The preferred compound is a major 15 component of the stereoisomeric mixture.
EXAMPLE 2
Purification of the preferred compound, 3S, 3aR, 7aR -6 isopropyl- 1,1, 3, 3 a- tetramethyl l,3,3a,4,7,7a, hexahydro isobenzofuran:
The crude product was flash column chromatographed over silica gel with ethyl 20 acetate in petroleum ether (4:96) to yield the preferred compound. Rf of the compound in the same solvent system as the eluent is 0.6.Yield: 0.28 g.
Analytical data:
Llight yellow oil, [α]D-57.2 ( EtOH)
Infrared: 2964, 1377,1184, 950, 808, 777 cm-1 25 1H NMR (CDC13): δ 5.36 (lH,d,J= 6.12 Hz ); 3.55 (lH,q,J=7.2 Hz); 2.26 (lH,m ); 1.24
(3H,s); 1.16 ( 3H,s );0.77 ( 3H,s ); 1.03 (6H,d, J=7.92 Hz); 1.13 (3H, d, J=7.2
Hz);1.9,1.72,1.89,1.75.
13C NMR: 78.7; 81.2; 42.7; 37.7; 117.0; 143.4; 23.9; 54.3; 14.4; 12.6; 24.8; 30.6; 35.2;
21.4; 21.9 ppm. 30 MS: 222 (14), 207 (30), 178 (14), 163 (32), 149 (10), 135 (75), 93 (100), 79(18)
ADVANTAGES OF THE PRESENT INVENTION
1. The molecule is novel with the novel application
2. It is multi-odorant with the tonalities of rhubarb, laurel, thyme and florex.
3. This compound can be used as an additive and when used in the applications, the
"3^ TvrnrlπH-c arrpwrprl tn tVip π<!f»r<! and it has nnt shn n anv adverse effect
Claims
1. A compound 3S, 3aR, 7aR-6-isopropyl-l,l,3,3a-tetramethyl-l,3,3,9,4,7,7a- hexahydroisobenzofuran of formula (1).
2. A compound of claim 1 has following characteristics:
Llight yellow oil, [ α ]D-57.2 ( EtOH)
Infrared: 2964, 1377,1184, 950, 808, 777 cm
1H NMR (CDC13): δ 5.36 (lH,d,J= 6.12 Hz ); 3.55 (lH,q,J=7.2 Hz); 2.26 (lH,m ); 1.24 (3H,s); 1.16 ( 3H,s );0.77 ( 3H,s ); 1.03 (6H,d, J=7.92 Hz); 1.13 (3H, d, J=7.2 Hz);1.9,1.72,1.89,1.75.
13C NMR: 78.7; 81.2; 42.7; 37.7; 117.0; 143.4; 23.9; 54.3; 14.4; 12.6; 24.8; 30.6; 35.2; 21.4; 21.9 ppm.
MS: 222 (14), 207 (30), 178 (14), 163 (32), 149 (10), 135 (75), 93 (100), 79(18)
3. A compound of claim 1 has isobenzofuran ring responsible for olfactory characteristics.
4. A compound of claim 1 is used in fine perfumery, colognes, hygiene products, batch gels, hair care products, deodorants, air freshener or cosmetic preparation.
5. A compound of claim 1 as single or as a mixture of isomers can be used to impart fragrance to consumer products.
6. A process for the preparation of compound (1) of claim 1, the said process comprising steps of: a) dissolving elemol in glacial acetic acid to obtain a solution, b) adding perchlorid acid to the step (a) solution at a temperature in the range of 20 to 30° C to obtain a reaction mixture, c) stirring the reaction mixture of step (b) at an ambient temperature for a period of 60 h to 80h, d) diluting with water the reaction mixture of step (d) extracting with the aqueous solution an organic solvent, separating the organic and the aqueous layer, e) washing the organic layer of step (d) with aqueous sodium bicarbonate followed by water, f) drying the washed organic layer over anhydrous sodium sulphate, filtering, and removing the solvent from the filtrate to obtain crude product, and g) purifying the crude product of step (f) over silica gel column eluting with a mixture of organic solvent to obtain the compound of formula ( 1 ).
7. A process of claim 6, wherein in step (b) the per acid used is selected from a group consisting of peracetic acid perchloric acid or perbenzoic acid.
8. A process of claim 6, wherein in step (d) the organic solvent used, is selected from diethylether, methylene, chloride, chloroform or ethylacetate.
9. A process of claim 6, wherein in step (g) the mixture of organic solvent used, is ethylacetate petroleum ether (4:96),
10. A process of claim 6, wherein in step (g) the compound obtained, has isobenzofuran ring responsible for olfactory characteristics. 11. A process of claim 6 wherein the compound obtained is used in fine perfumery, colognes, hygiene products, batch gels, hair care products, deodorants, air freshness or cosmetic preparation.
12. A synergistic composition containing an effective amount of compound (I) or mixture of its isomers, the said composition is useful in perfuming the soaps, shower or bath gels, hygiene products, hair care products such as shampoos, body deodorants, air fresheners or cosmetic preparation.
13. A composition of claim 12 can be used alone or in combination with other perfuming agents, solvents or additives.
4. A composition of claim 8, wherein the mixture of isomers of compound (I) in the ratio 75:25 is multiodorant being a combination of rhubarb, laurel, thyme and florex.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2003/000083 WO2004085417A1 (en) | 2003-03-26 | 2003-03-26 | Novel sesquiterpene oxides as perfuming and flavouring agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1613611A1 true EP1613611A1 (en) | 2006-01-11 |
Family
ID=34385756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP03816443A Withdrawn EP1613611A1 (en) | 2003-03-26 | 2003-03-26 | Novel sesquiterpene oxides as perfuming and flavouring agents |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP1613611A1 (en) |
| JP (1) | JP4551225B2 (en) |
| AU (1) | AU2003226618A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2804939B1 (en) * | 2012-01-18 | 2018-04-04 | The Procter and Gamble Company | Perfume systems |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5484551A (en) * | 1977-12-19 | 1979-07-05 | Takasago Corp | Elemene oxides |
-
2003
- 2003-03-26 JP JP2004569894A patent/JP4551225B2/en not_active Expired - Lifetime
- 2003-03-26 AU AU2003226618A patent/AU2003226618A1/en not_active Abandoned
- 2003-03-26 EP EP03816443A patent/EP1613611A1/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2004085417A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4551225B2 (en) | 2010-09-22 |
| JP2006521285A (en) | 2006-09-21 |
| AU2003226618A1 (en) | 2004-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0507190B1 (en) | Compositions with physiological cooling effect and active compounds suitable for such compositions | |
| JPS6133005B2 (en) | ||
| CN107250090A (en) | Method for preparing 1-[(1R,4R/S,8S)-10,10-dimethyl-7-methylene-4-bicyclo[6.2.0]decyl]ethanone | |
| JPH08319250A (en) | Perfume | |
| DE69028755T2 (en) | Use of unsaturated macrocyclic ketones and perfume ingredients | |
| DE69717612T2 (en) | PERFUMED MACROCYCLIC LACTON | |
| EP0584477B1 (en) | Use of a cyclopentadecenone as a perfuming ingredient | |
| US7138368B2 (en) | Sesquiterpene oxides as perfuming and flavoring agents | |
| KR20230121826A (en) | Method for producing 2-(4'-diethylamino-2'-hydroxybenzoyl)benzoic acid hexyl ester | |
| EP0004968B1 (en) | Norbornene(-ane) derivatives, process for their preparation and their use as perfuming agents | |
| EP1613611A1 (en) | Novel sesquiterpene oxides as perfuming and flavouring agents | |
| EP2801571B1 (en) | Novel diethyl-methyl-hexahydro-isobenzofurans and their use in perfume compositions | |
| JPS6020364B2 (en) | long lasting fragrance | |
| JP3009404B2 (en) | Compounded fragrances containing 2-methoxy-4-propyl-1-cyclohexanol, perfumed products containing the compounded fragrances, and methods for enhancing, improving or changing the odor characteristics of the compounded fragrances | |
| EP2904077B1 (en) | Flavor and fragrance formulation (iv) | |
| EP0151521A2 (en) | Perfumery compositions | |
| JP2590254B2 (en) | New fragrance mixture | |
| EP0306529A1 (en) | Perfume composition | |
| DE19702279B4 (en) | 3,5,5-trimethylcyclohexanone | |
| EP2772527B1 (en) | Novel decenal mixtures and their use in perfume compositions | |
| JPH0211591B2 (en) | ||
| JPS6233169A (en) | 2-acyl-5-methylfuran, manufacture and use | |
| DE60207974T2 (en) | Cyclohexenylcyclopropylketon | |
| WO2024096037A1 (en) | Fragrance composition and consumer product | |
| EP2209389B1 (en) | Bicyclic campholenic derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20051026 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LI LU MC NL PT SE SI SK TR |
|
| AX | Request for extension of the european patent |
Extension state: AL LT LV MK |
|
| RIC1 | Information provided on ipc code assigned before grant |
Ipc: A61Q 13/00 00000000ALI20051202BHEP Ipc: C07D 307/87 19850101AFI20051202BHEP |
|
| DAX | Request for extension of the european patent (deleted) | ||
| 17Q | First examination report despatched |
Effective date: 20061123 |
|
| GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20070710 |