US4038270A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Menthol glycoside, process for preparing the same and method for releasing menthol therefrom
Assignee: Toyo Hakka Kogyo Co Ltd
•
Filing: 1975-06-09
•
Granted: 1977-07-26
•
Expires: 1995-06-09
Abstract
Abstract Water-soluble menthol glycosides are prepared by condensing menthol with a mono- or oligosaccharide, preferably a mono- or di-saccharide, i.e., a sugar, or acyl derivative thereof, using a condensing agent or catalyst as needed. These glycosides are hydrolyzed by carbohydrase enzymes, as occur in the human mouth, or common acids, releasing menthol, and provide a more persistent flavor than menthol alone.
Inventors
- 👤 Tatsuo Higashiyama
- 👤 Isao Sakata
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:31
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/207; A; A23; A23L; A23L27/00; A23L27/20; A23L27/203; C07H15/18
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
31 words
A substantially water-soluble menthol glycoside having the general formula: ##STR7## where R is the residue of lactose, maltose or raffinose and n is the number of hydroxyl groups on said residue.
Claim 2
Dependent Claim
31 words
A substantially water-soluble menthol glycoside having the general formula: ##STR7## where R is the residue of lactose, maltose or raffinose and n is the number of hydroxyl groups on said residue.
Claim 3
Independent Claim
127 words
A method of preparing a substantially water-soluble menthol glycoside having the general formula: ##STR8## wherein: R is the residue of a sugar and n is the number of hydroxyl groups, comprising the steps of contacting menthol and a sugar or sugar ester having the formula: ##STR9## wherein: X is hydrogen or carboxylic acyl and R and n have the same significance as above, and Z is a halogen atom or OX, in dimethyl sulfoxide, dimethyl formamide, benzene, or toluene as a reaction medium at a temperature from about room temperature up to about 100° C. in the presence of an acidic condensation catalyst or a condensing agent, recovering the resultant product, and where X is carboxylic acyl hydrolyzing the product with alkali to produce the free glycoside.
Claim 4
Independent Claim
127 words
A method of preparing a substantially water-soluble menthol glycoside having the general formula: ##STR8## wherein: R is the residue of a sugar and n is the number of hydroxyl groups, comprising the steps of contacting menthol and a sugar or sugar ester having the formula: ##STR9## wherein: X is hydrogen or carboxylic acyl and R and n have the same significance as above, and Z is a halogen atom or OX, in dimethyl sulfoxide, dimethyl formamide, benzene, or toluene as a reaction medium at a temperature from about room temperature up to about 100° C. in the presence of an acidic condensation catalyst or a condensing agent, recovering the resultant product, and where X is carboxylic acyl hydrolyzing the product with alkali to produce the free glycoside.
Claim 5
Dependent Claim
19 words
The method of claim 2 wherein said condensation is carried out with mild heating up to about 100° C.
Claim 6
Dependent Claim
17 words
The method of claim 2 where said menthol and said sugar are contacted in generally equi-molar ratios.
Claim 7
Dependent Claim
13 words
The method of claim 2 wherein said carboxylic acyl is lower carboxylic acyl.
Claim 8
Dependent Claim
11 words
The method of claim 2 wherein X is hydrogen or acetyl.
Claim 9
Dependent Claim
31 words
The method of claim 2 wherein said glucoside is recovered by extracting the reaction mixture with a volatile organic solvent, removing said solvent, and re-crystallizing the residue with a polar liquid.
Claim 10
Dependent Claim
19 words
The method of claim 2 wherein said menthol and sugar are contacted from about 1 to about 25 hours.
References Cited (Backward Citations)
US2049758A
Cited
US2218569A
Cited
US2235783A
Cited
US3152115A
Cited
US3219656A
Cited
US3707535A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-25 | 1981-01-24 | 1981-07-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-25 | 1985-01-24 | 1985-07-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-25 | 1989-01-24 | 1989-07-26 | $7700.00 | Window Closed / Lapsed |