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Odorants And Compositions Comprising Odorants

Abstract: The present invention relates to new classes of odorous oximes and their ketone intermediates (odorants) which are useful as fragrance or flavor materials in particular in providing cassis, catty, tropical, green, coniferous, thuya, floral and/or fruity olfactory notes to perfume, aroma or deodorizing/masking compositions. Figure 1

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Patent Information

Application #
Filing Date
14 April 2020
Publication Number
24/2020
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
patent@depenning.com
Parent Application
Patent Number
Legal Status
Grant Date
2023-12-15
Renewal Date

Applicants

S H KELKAR & COMPANY LIMITED
LBS Marg, Mulund (W), Mumbai, Maharashtra 400 080
POST, Freddy
Sleutelbloemstraat 41 6841 CZ Arnhem

Inventors

1. POST, Freddy
Sleutelbloemstraat 41, 6841 CZ Arnhem
2. POST, Freddy
Sleutelbloemstraat 41, 6841 CZ Arnhem
3. CHAUDHARI, Nitesh
LBS Marg Mulund (W) Mumbai Maharashtra 400 080

Specification

WE CLAIM:
1. Fragrance, flavor and/or deodorizing/masking compositions comprising an oxime
selected from compounds of formula (7) or of formula (8)

wherein R is an alkyl group having from 1 to 9 carbon atoms, an alkenyl group containing only one carbon-carbon double bond (said carbon-carbon double bond being preferably not conjugated with the oxime C=N bond) and having up to 9 carbon atoms, a (substituted) aryl group having up to 8 carbon atoms, an oxo-alkyl group having up to 9 carbon atoms, or an alkoxyaryl group containing up to 9 carbon atoms or (substituted) benzyl group having up to 9 carbon atoms.
2. Fragrance, flavor and/or deodorizing/masking compositions according to claim 1 wherein R is methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, i-butyl, 2-pentyl, 3-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, l-(cyclohexylmethyl), (methoxy)methyl, (ethoxy)methyl, 3-butenyl, 5-(2-methylpent-2-en)yl, 4-pent-2-enyl, 4-pent-1-enyl, 5-(2,5-dimethylhex-2-en)yl, benzyl, phenyl, or 4-methoxyphenyl.
3. Fragrance, flavor and/or deodorizing/masking compositions according to claim 1 wherein the oxime is selected from
Structure Chemical name



4. Fragrance, flavor and/or deodorizing/masking compositions according to any of the preceding claims wherein the content of the compounds of formula (7) and/or of formula (8) is comprised between 0.00001 and 99.9 vvt. %, for example between 0.0001 and 95 wt%.
5. Fragrance, flavor and/or deodorizing/masking compositions according to any of the preceding claims additionally comprising at least one ester and/or one alcohol, preferably at least a mixture of ester and alcohol.
6. Fragrance, flavor and/or deodorizing/masking compositions according to the previous claim wherein the total content of the compound(s) of formula (7) and/or of formula (8) together with the ester(s) and/or alcohol(s) is superior to 25 wt%, preferably superior to 50wt%, for example superior to 75wt%, or even superior to 90wt%.
7. Fragrance, flavor and/or deodorizing/masking compositions according to any of the preceding claims comprising a mixture of oxime compounds according to formula (7) and/or formula (8) wherein the weight ratio between the oxime present in highest weight and the oxime present in the second highest weight in the mixture is comprised between 99.9% and 50%, for example between 99% and 70%.
8. Fragrance, flavor and/or deodorizing/masking compositions according to any of the preceding claims additionally comprising at least one ketone compound of formula (5) and/or(6)


wherein R is an alkyl group having from 1 to 9 carbon atoms, an alkenyl group containing only one carbon-carbon double bond having up to 9 carbon atoms, an (substituted) aryl group having up to 9 carbon atoms, an oxo-alkyl group having up to 9 carbon atoms, an alkoxyaryl group containing up to 9 carbon atoms or a (substituted) benzyl group having up to 9 carbon atoms.
9. Fragrance, flavor and/or deodorizing/masking compositions according to claim 8
wherein the radical R of an oxime compound is identical to the radical R of a ketone
compound,
10. Fragrance, flavor and/or deodorizing/masking compositions according to any of claims
8 or 9 wherein the weight ratio between the oxime(s) and the ketone(s) is comprised
between 0.01% and 99.99%, for example 80% and 99%.
11. Oxime useful in a fragrance, flavor and/or deodorizing/masking composition
according to any of the preceding claims wherein the oxime is selected from compounds of
formula (7) or of formula (8)

wherein R is an alkyl group having from 2 to 9 carbon atoms, an alkenyl group containing only one carbon-carbon double bond (said carbon-carbon double bond being preferably not conjugated with the oxime C=N bond) and having up to 9 carbon atoms, an (substituted) aryl group having up to 9 carbon atoms, an oxo-alkyl group having up to 9 carbon atoms, an alkoxyaryl group containing up to 9 carbon atoms or a (substituted) benzyl group having up to 9 carbon atoms.
12. Oxime according to claim 11 wherein R is ethyl, n-propyl, i-propyl, n-butyl, s-butyl,
t-butyl, i-butyl, 2-pentyl, 3-pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-
(cyclohexylmethyl), (methoxy)methyl, (ethoxy)methyl, 3-butenyl, 5-(2-methylpent-2-en)yl,

4-pent-2-enyl, 4-pent-l-enyl, 5-(2,5-dimethylhex-2-en)yl, benzyl, phenyl, or 4-methoxyphenyl.
13. Oxime according to any of claims 11 to 12 wherein the compounds of formula (8) don't include those wherein R is phenyl.

15. Mixture of oxime compounds according to claims 11 to 14 wherein the weight ratio
between the oxime present in highest weight and the oxime present in the second highest
weight in the mixture is comprised between 99.9% and 50%, for example between 99% and
70%.
16. Process for the preparation of the oximes of formula (7) and/or of formula (8)
according to any of claims 11 to 15 by reacting
the ketones of formula (5) and/or of formula (6)

wherein R is an alkyl group having from 2 to 9 carbon atoms, an alkenyl group containing only one carbon-carbon double bond and having up to 9 carbon atoms, an (substituted) aryl group having up to 9 carbon atoms, an oxo-alkyl group having up to 9 carbon atoms, an alkoxyaryl group containing up to 9 carbon atoms or a (substituted) benzyl group having up to 9 carbon atoms

with a hydroxylamine salt (e.g. hydroxylamine hydrochloride) in the presence of an amine (e.g. pyridine, imidazole) and at a temperature lower than 80°C, preferably lower than 70°C, to form the oximes of formula (7) and/or of formula (8).
17. Process for the preparation of the oximes according to claim 16 wherein the reaction time is more than one day, preferably more than 3 days, for instance more than 7 days.
18. Process for the preparation of the oximes according to any of claims 16 to 17 wherein the compounds of formulae (5), (6), (7) and (8) are characterised in that R is an alkyl group having from 3 to 9 carbon atoms or an aryl group having from 6 to 9 carbon atoms.
19. Process for the preparation of the oximes according to any of claims 16 to 18 wherein
the compounds of formula (5) are prepared by subjecting 2,3-dimethylbutene(s) to an acylation reaction step, optionally followed by either an alkylation or an aldol condensation step, and/or
the compounds of formula (6) are prepared by subjecting 2,3-dimethylbutene(s) to an acylation reaction step, optionally followed by either an alkylation or an aldol condensation step, to form the compounds of formula (5) and by subjecting the said compounds of formula (5) to a hydrogenation reaction step to form the compounds of formula (6).
20. Use of a fragrance, flavor and/or deodorizing/masking composition according to any of claims 1 to 10 in a perfumed or flavored product.
21. Use of an oxime according to any of claims 11 to 15 in a perfumed or flavored product.

Documents

Application Documents

# Name Date
1 202047016093-IntimationOfGrant15-12-2023.pdf 2023-12-15
1 202047016093.pdf 2020-04-14
2 202047016093-PatentCertificate15-12-2023.pdf 2023-12-15
2 202047016093-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [14-04-2020(online)].pdf 2020-04-14
3 202047016093-STATEMENT OF UNDERTAKING (FORM 3) [14-04-2020(online)].pdf 2020-04-14
3 202047016093-Response to office action [15-12-2023(online)].pdf 2023-12-15
4 202047016093-Response to office action [14-12-2023(online)].pdf 2023-12-14
4 202047016093-PRIORITY DOCUMENTS [14-04-2020(online)].pdf 2020-04-14
5 202047016093-Proof of Right [11-12-2023(online)].pdf 2023-12-11
5 202047016093-FORM 1 [14-04-2020(online)].pdf 2020-04-14
6 202047016093-Information under section 8(2) [24-02-2023(online)].pdf 2023-02-24
6 202047016093-DRAWINGS [14-04-2020(online)].pdf 2020-04-14
7 202047016093-DECLARATION OF INVENTORSHIP (FORM 5) [14-04-2020(online)].pdf 2020-04-14
7 202047016093-ABSTRACT [29-04-2022(online)].pdf 2022-04-29
8 202047016093-COMPLETE SPECIFICATION [14-04-2020(online)].pdf 2020-04-14
8 202047016093-CLAIMS [29-04-2022(online)].pdf 2022-04-29
9 202047016093-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [14-04-2020(online)].pdf 2020-04-14
9 202047016093-FER_SER_REPLY [29-04-2022(online)].pdf 2022-04-29
10 202047016093-Information under section 8(2) [29-04-2022(online)].pdf 2022-04-29
10 202047016093-Proof of Right [04-05-2020(online)].pdf 2020-05-04
11 202047016093-Abstract.jpg 2020-06-09
11 202047016093-OTHERS [29-04-2022(online)].pdf 2022-04-29
12 202047016093-PETITION UNDER RULE 137 [29-04-2022(online)].pdf 2022-04-29
12 202047016093-Proof of Right [10-08-2020(online)].pdf 2020-08-10
13 202047016093-FER.pdf 2021-10-29
13 202047016093-FORM-26 [10-08-2020(online)].pdf 2020-08-10
14 202047016093-FORM 18 [05-10-2021(online)].pdf 2021-10-05
14 202047016093-FORM 3 [17-09-2020(online)].pdf 2020-09-17
15 202047016093-FORM 18 [05-10-2021(online)].pdf 2021-10-05
15 202047016093-FORM 3 [17-09-2020(online)].pdf 2020-09-17
16 202047016093-FER.pdf 2021-10-29
16 202047016093-FORM-26 [10-08-2020(online)].pdf 2020-08-10
17 202047016093-Proof of Right [10-08-2020(online)].pdf 2020-08-10
17 202047016093-PETITION UNDER RULE 137 [29-04-2022(online)].pdf 2022-04-29
18 202047016093-Abstract.jpg 2020-06-09
18 202047016093-OTHERS [29-04-2022(online)].pdf 2022-04-29
19 202047016093-Information under section 8(2) [29-04-2022(online)].pdf 2022-04-29
19 202047016093-Proof of Right [04-05-2020(online)].pdf 2020-05-04
20 202047016093-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [14-04-2020(online)].pdf 2020-04-14
20 202047016093-FER_SER_REPLY [29-04-2022(online)].pdf 2022-04-29
21 202047016093-CLAIMS [29-04-2022(online)].pdf 2022-04-29
21 202047016093-COMPLETE SPECIFICATION [14-04-2020(online)].pdf 2020-04-14
22 202047016093-ABSTRACT [29-04-2022(online)].pdf 2022-04-29
22 202047016093-DECLARATION OF INVENTORSHIP (FORM 5) [14-04-2020(online)].pdf 2020-04-14
23 202047016093-DRAWINGS [14-04-2020(online)].pdf 2020-04-14
23 202047016093-Information under section 8(2) [24-02-2023(online)].pdf 2023-02-24
24 202047016093-FORM 1 [14-04-2020(online)].pdf 2020-04-14
24 202047016093-Proof of Right [11-12-2023(online)].pdf 2023-12-11
25 202047016093-Response to office action [14-12-2023(online)].pdf 2023-12-14
25 202047016093-PRIORITY DOCUMENTS [14-04-2020(online)].pdf 2020-04-14
26 202047016093-STATEMENT OF UNDERTAKING (FORM 3) [14-04-2020(online)].pdf 2020-04-14
26 202047016093-Response to office action [15-12-2023(online)].pdf 2023-12-15
27 202047016093-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [14-04-2020(online)].pdf 2020-04-14
27 202047016093-PatentCertificate15-12-2023.pdf 2023-12-15
28 202047016093.pdf 2020-04-14
28 202047016093-IntimationOfGrant15-12-2023.pdf 2023-12-15

Search Strategy

1 SearchStrategy(1)E_29-10-2021.pdf
1 SearchStrategy(2)E_29-10-2021.pdf
2 SearchStrategy(1)E_29-10-2021.pdf
2 SearchStrategy(2)E_29-10-2021.pdf

ERegister / Renewals

3rd: 08 Jan 2024

From 16/10/2020 - To 16/10/2021

4th: 08 Jan 2024

From 16/10/2021 - To 16/10/2022

5th: 08 Jan 2024

From 16/10/2022 - To 16/10/2023

6th: 08 Jan 2024

From 16/10/2023 - To 16/10/2024

7th: 09 Oct 2024

From 16/10/2024 - To 16/10/2025

8th: 09 Oct 2025

From 16/10/2025 - To 16/10/2026