Sign In to Follow Application
View All Documents & Correspondence

Methyl Menthol Derivative And Cooling Agent Composition Containing Same

Abstract: The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation malodor bitterness or the like it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

Get Free WhatsApp Updates!
Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
19 September 2017
Publication Number
39/2017
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
Parent Application
Patent Number
Legal Status
Grant Date
2020-02-04
Renewal Date

Applicants

TAKASAGO INTERNATIONAL CORPORATION
37-1, Kamata 5-chome, Ota-ku, Tokyo 144-8721

Inventors

1. ITOH, Hisanori
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
2. HORI, Yoji
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
3. OTSUKA, Masashi
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
4. MATSUMOTO, Takaji
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073
5. SATO, Tomoharu
c/o TAKASAGO INTERNATIONAL CORPORATION, 4-11, Nishiyawata 1-chome, Hiratsuka-shi, Kanagawa 254-0073

Specification

[Claim 1]
A cooling agent composition, comprising a methyl menthol derivative represented by the following general formula (1A) or the following general formula (1B):

[in the formulae, a double line composed of a solid line and a dotted line is a double bond or a single bond, and a symbol * is an asymmetric carbon atom,
W is a hydrogen atom, or forms a ring with X via a single bond or an oxygen atom,
X represents -CHO, -CO-Y or -O-Z,
Y is a group represented by the following formula (i) or formula (ii):
(i) NR1R2 or
(ii) OR3
(in the formula (i) and the formula (ii), R1 to R3 are each independently a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent), and
Z is a group represented by the following formula (iii) or formula (vi):
(iii) R4 or
(vi) COR5
(in the formula (iii), R4 is a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent, and
in the formula (vi), R5 is a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group

having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent)]. [Claim 2]
The cooling agent composition according to Claim 1, wherein the methyl menthol derivative is a (2S)-form. [Claim 3]
The cooling agent composition according to Claim 1 or 2, further comprising at least one kind of cool feeling substance other than the methyl menthol derivative. [Claim 4]
The cooling agent composition according to Claim 3, wherein the cool feeling substance other than the methyl menthol derivative is at least one cool feeling substance selected from the group consisting of:
one or more kinds of compounds selected from menthol, menthone, camphor, pulegol, isopulegol, cineole, cubenol, menthyl acetate, pulegyl acetate, isopulegyl acetate, menthyl salicylate, pulegyl salicylate, isopulegyl salicylate, 3-(l-menthoxy)propan-1,2-diol, 2-methyl-3-(l-menthoxy)propan-1,2-diol, 2-(l-menthoxy)ethan-1-ol, 3-(l-menthoxy)propan-1-ol, 4-(l-menthoxy)butan-1-ol, menthyl 3-hydroxybutanoate, menthyl glyoxylate, p-menthane-3,8-diol, 1-(2-hydroxy-4-methylcyclohexyl)ethanone, menthyl lactate, menthone glycerin ketal, menthyl-2-pyrrolidone-5-carboxylate, monomenthyl succinate, alkali metal salts of monomenthyl succinate, alkaline earth metal salts of monomenthyl succinate, monomenthyl glutarate, alkali metal salts of monomenthyl glutarate, alkaline earth metal salts of monomenthyl glutarate, N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine, p-menthane-3-carboxylic acid glycerol ester, menthol propylene glycol carbonate, menthol ethylene glycol carbonate, p-menthane-2,3-diol, 2-isopropyl-N,2,3-trimethylbutanamide, N-ethyl-p-menthane-3-carboxamide, ethyl 3-(p-menthane-3-carboxamide)acetate, N-(4-methoxyphenyl)-p-menthanecarboxamide, N-ethyl-2,2-diisopropylbutanamide, N-cyclopropyl-p-menthanecarboxamide, N-(4-cyanomethylphenyl)-p-menthanecarboxamide, N-(2-pyridin-2-yl)-3-p-menthanecarboxamide, N-(2-hydroxyethyl)-2-isopropyl-2,3-dimethylbutanamide, N-(1,1-dimethyl-2-hydroxyethyl)-2,2-diethylbutanamide, cyclopropanecarboxylic acid (2-isopropyl-5-methylcyclohexyl)amide, N-ethyl-2,2-diisopropylbutanamide, N-[4-(2-amino-2-oxoethyl)phenyl]-p-menthanecarboxamide, 2-[(2-p-menthoxy)ethoxy]ethanol, 2,6-diethyl-5-isopropyl-2-methyltetrahydropyran, and trans-4-tert-butylcyclohexanol;
one or more kinds of sugar alcohols selected from xylitol, erythritol, dextrose, and sorbitol; and
one or more kinds of natural products selected from Japanese mint oil, peppermint oil, spearmint oil, and eucalyptus oil.

[Claim 5]
A sensory stimulant composition, comprising the cooling agent composition described in any one of Claims 1 to 4. [Claim 6]
The sensory stimulant composition according to Claim 5, further comprising at least one kind of warm feeling substance. [Claim 7]
The sensory stimulant composition according to Claim 6, wherein the warm feeling substance is at least one warm feeling substance selected from the group consisting of:
one or more kinds of compounds selected from vanillyl methyl ether, vanillyl ethyl ether, vanillyl propyl ether, vanillyl isopropyl ether, vanillyl butyl ether, vanillyl amyl ether, vanillyl isoamyl ether, vanillyl hexyl ether, isovanillyl methyl ether, isovanillyl ethyl ether, isovanillyl propyl ether, isovanillyl isopropyl ether, isovanillyl butyl ether, isovanillyl amyl ether, isovanillyl isoamyl ether, isovanillyl hexyl ether, ethyl vanillyl methyl ether, ethyl vanillyl ethyl ether, ethyl vanillyl propyl ether, ethyl vanillyl isopropyl ether, ethyl vanillyl butyl ether, ethyl vanillyl amyl ether, ethyl vanillyl isoamyl ether, ethyl vanillyl hexyl ether, vanillin propylene glycol acetal, isovanillin propylene glycol acetal, ethyl vanillin propylene glycol acetal, vanillyl butyl ether acetic acid ester, isovanillyl butyl ether acetic acid ester, ethyl vanillyl butyl ether acetic acid ester, 4-(l-menthoxymethyl)-2-(3’-methoxy-4’-hydroxyphenyl)-1,3-dioxolane, 4-(l-menthoxymethyl)-2-(3’-hydroxy-4’-methoxyphenyl)-1,3-dioxolane, 4-(l-menthoxymethyl)-2-(3’-ethoxy-4’-hydroxyphenyl)-1,3-dioxolane, capsaicin, dihydrocapsaicin, nordihydrocapsaicin, homodihydrocapsaicin, homocapsaicin, biscapsanthin, trishomocapsanthin, nornorcapsanthin, norcapsanthin, capsaicinol, vanillyl caprylamide (octylic acid vanillylamide), vanillyl pelargonamide (nonylic acid vanillylamide), vanillyl caproamide (decylic acid vanillylamide), vanillyl undecamide (undecylic acid vanillylamide), N-trans-feruloyltyramine, N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoylpiperidine, N-trans-feruloylpiperidine, N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoylpiperidine, N-5-(4-hydroxyphenyl)-2E,4E-pentadienoylpiperidine, piperine, isopiperine, chavicine, isochavicine, piperamine, piperettine, piperolein B, retrofractamide A, pipercide, guineenside, piperiline, piperamide C5:1 (2E), piperamide C7:1 (6E), piperamide C7:2 (2E,6E), piperamide C9:1 (8E), piperamide C9:2 (2E,8E), piperamide C9:3 (2E,4E,8E), fagaramide, sanshool-I, sanshool-II, hydroxysanshool, sanshoamide, gingerol, shogaol, zingerone, methylgingerol, paradol, spilanthol, chavicine, polygodial (tadeonal), isopolygodial, dihydropolygodial, and tadeon; and

one or more kinds of natural products selected from capsicum oil, capsicum oleoresin, ginger oleoresin, jambu oleoresin (Spilanthes oleracea extract), sansho (Zanthoxylum piperitum) extract, sanshoamide, black pepper extract, white pepper extract, and polygonum extract. [Claim 8]
A flavor composition and/or a fragrance composition, comprising the sensory stimulant composition described in any one of Claims 5 to 7. [Claim 9]
A flavor composition and/or a fragrance composition, comprising the sensory stimulant composition described in any one of Claims 5 to 7 in an amount of 0.00001 to 90 mass%. [Claim 10]
A product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition described in any one of Claims 5 to 7. [Claim 11]
A product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the sensory stimulant composition described in any one of Claims 5 to 7 in an amount of 0.00001 to 50 mass%. [Claim 12]
A product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, and comprises the flavor composition and/or the fragrance composition described in Claim 8 or 9. [Claim 13]
A product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and

drugs, and comprises the flavor composition and/or the fragrance composition described in Claim 8 or 9 in an amount of 0.00001 to 50 mass%. [Claim 14]
A method for producing a product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, wherein the method comprises blending the sensory stimulant composition described in any one of Claims 5 to 7. [Claim 15]
A method for producing a product, which is any product selected from the group consisting of beverages, foods, fragrances or cosmetics, toiletry products, air care products, daily necessities and household goods, compositions for oral use, hair care products, skin care products, body care products, detergents for clothes, soft finishing agents for clothes, quasi-drugs, and drugs, wherein the method comprises blending the flavor composition and/or the fragrance composition described in Claim 8 or 9. [Claim 16]
A methyl menthol derivative represented by the following general formula (1A):

[in the formula, a double line composed of a solid line and a dotted line is a double bond or a single bond, and a symbol * is an asymmetric carbon atom,
W is a hydrogen atom, or forms a ring with X’ via a single bond or an oxygen atom,
X’ represents -CHO, -CO-Y’ or -O-Z,
Y’ is a group represented by the following formula (i) or formula (ii’):
(i) NR1R2 or
(ii’) OR3’
(in the formula (i), R1 and R2 are each independently a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent,

or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent, and
in the formula (ii’), R3’ is a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent), and
Z is a group represented by the following formula (iii) or formula (vi):
(iii) R4 or
(vi) COR5
(in the formula (iii), R4 is a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent, and
in the formula (vi), R5 is a hydrogen atom, a linear or branched alkyl group having a carbon number of 1 to 10 which may have a substituent, a linear or branched alkenyl group having a carbon number of 2 to 10 which may have a substituent, a cycloalkyl group having a carbon number of 3 to 10 which may have a substituent, an aryl group having a carbon number of 6 to 20 which may have a substituent, or a heterocyclic group having a carbon number of 2 to 15 which may have a substituent)]. [Claim 17]
The methyl menthol derivative according to Claim 16, wherein the methyl menthol derivative is a (2S)-form.

Documents

Application Documents

# Name Date
1 201747033143-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [19-09-2017(online)].pdf 2017-09-19
2 201747033143-STATEMENT OF UNDERTAKING (FORM 3) [19-09-2017(online)].pdf 2017-09-19
3 201747033143-PROOF OF RIGHT [19-09-2017(online)].pdf 2017-09-19
4 201747033143-PRIORITY DOCUMENTS [19-09-2017(online)].pdf 2017-09-19
5 201747033143-POWER OF AUTHORITY [19-09-2017(online)].pdf 2017-09-19
6 201747033143-FORM 1 [19-09-2017(online)].pdf 2017-09-19
7 201747033143-DECLARATION OF INVENTORSHIP (FORM 5) [19-09-2017(online)].pdf 2017-09-19
8 201747033143-COMPLETE SPECIFICATION [19-09-2017(online)].pdf 2017-09-19
9 201747033143-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [19-09-2017(online)].pdf 2017-09-19
10 201747033143.pdf 2017-09-21
11 abstract 201747033143.jpg 2017-09-22
12 Correspondence by Agent_Form 1_29-09-2017.pdf 2017-09-29
13 201747033143-FORM 3 [05-02-2018(online)].pdf 2018-02-05
14 201747033143-FORM 18 [16-03-2018(online)].pdf 2018-03-16
15 201747033143-FER.pdf 2019-05-28
16 201747033143-certified copy of translation (MANDATORY) [20-08-2019(online)].pdf 2019-08-20
17 201747033143-PETITION UNDER RULE 137 [26-09-2019(online)].pdf 2019-09-26
18 201747033143-OTHERS [26-09-2019(online)].pdf 2019-09-26
19 201747033143-MARKED COPIES OF AMENDEMENTS [26-09-2019(online)].pdf 2019-09-26
20 201747033143-FORM-26 [26-09-2019(online)].pdf 2019-09-26
21 201747033143-FORM 3 [26-09-2019(online)].pdf 2019-09-26
22 201747033143-FORM 13 [26-09-2019(online)].pdf 2019-09-26
23 201747033143-FER_SER_REPLY [26-09-2019(online)].pdf 2019-09-26
24 201747033143-CLAIMS [26-09-2019(online)].pdf 2019-09-26
25 201747033143-certified copy of translation (MANDATORY) [26-09-2019(online)].pdf 2019-09-26
26 201747033143-AMMENDED DOCUMENTS [26-09-2019(online)].pdf 2019-09-26
27 201747033143-ABSTRACT [26-09-2019(online)].pdf 2019-09-26
28 Correspondence by Agent_Power of Attorney_09-10-2019.pdf 2019-10-09
29 201747033143-HearingNoticeLetter-(DateOfHearing-12-12-2019).pdf 2019-11-26
30 201747033143-REQUEST FOR ADJOURNMENT OF HEARING UNDER RULE 129A [09-12-2019(online)].pdf 2019-12-09
31 201747033143-ExtendedHearingNoticeLetter-(DateOfHearing-03-01-2020).pdf 2019-12-10
32 201747033143-FORM-26 [24-12-2019(online)].pdf 2019-12-24
33 201747033143-Correspondence to notify the Controller (Mandatory) [24-12-2019(online)].pdf 2019-12-24
34 Correspondence by Agent_Form26_03-01-2020.pdf 2020-01-03
35 201747033143-Written submissions and relevant documents (MANDATORY) [17-01-2020(online)].pdf 2020-01-17
36 201747033143-Retyped Pages under Rule 14(1) (MANDATORY) [17-01-2020(online)].pdf 2020-01-17
37 201747033143-MARKED COPIES OF AMENDEMENTS [17-01-2020(online)].pdf 2020-01-17
38 201747033143-FORM 13 [17-01-2020(online)].pdf 2020-01-17
39 201747033143-2. Marked Copy under Rule 14(2) (MANDATORY) [17-01-2020(online)].pdf 2020-01-17
40 201747033143-Marked up Claims_Granted 331178_03-02-2020.pdf 2020-02-03
41 201747033143-Description_Granted 331178_03-02-2020.pdf 2020-02-03
42 201747033143-Claims_Granted 331178_03-02-2020.pdf 2020-02-03
43 201747033143-Abstract_Granted 331178_03-02-2020.pdf 2020-02-03
44 201747033143-PatentCertificate04-02-2020.pdf 2020-02-04
45 201747033143-Marked up Claims_Granted 331178_04-02-2020.pdf 2020-02-04
46 201747033143-IntimationOfGrant04-02-2020.pdf 2020-02-04
47 201747033143-Description_Granted 331178_04-02-2020.pdf 2020-02-04
48 201747033143-Claims_Granted 331178_04-02-2020.pdf 2020-02-04
49 201747033143-Abstract_Granted 331178_04-02-2020.pdf 2020-02-04
50 201747033143-RELEVANT DOCUMENTS [27-07-2021(online)].pdf 2021-07-27
51 201747033143-RELEVANT DOCUMENTS [14-09-2022(online)].pdf 2022-09-14

Search Strategy

1 201747033143SS_21-05-2019.pdf

ERegister / Renewals

3rd: 27 Feb 2020

From 24/03/2018 - To 24/03/2019

4th: 27 Feb 2020

From 24/03/2019 - To 24/03/2020

5th: 27 Feb 2020

From 24/03/2020 - To 24/03/2021

6th: 27 Feb 2020

From 24/03/2021 - To 24/03/2022