isomenthol
DL-isomenthol
Identification
| Name | isomenthol |
| IUPAC | (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol |
| CAS Number | 3623-52-7 |
| EINECS | 222-825-7 |
| FDA UNII | 90E7IB31QH |
| Molecular Formula | C10 H20 O |
| Molecular Weight | 156.26860000 |
| MDL Number | MFCD01941448 |
| Nikkaji Number | J238.499J |
| Beilstein | 3194262 |
Regulatory
| JECFA Food Flavoring | 2249 DL-isomenthol |
| FEMA Number | 4729 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 215.00 to 216.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.032000 mmHg @ 25.00 °C. (est) |
| Flash Point | 200.00 °F. TCC ( 93.30 °C. ) (est) |
| logP (o/w) | 3.216 (est) |
| Soluble in | alcohol |
| Insoluble in | paraffin oil |
Organoleptic Properties
| Odor Description | at 10.00 % in propylene glycol. |
| Taste Description | cooling |
Safety Information
| Oral/Parenteral Toxicity | oral-mouse LD50 3000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for isomenthol usage levels up to | not for fragrance use. |
| baked goods | 30.00000 |
| beverages(nonalcoholic) | 10.00000 |
| beverages(alcoholic) | 10.00000 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 500.00000 |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 20.00000 |
| fruit ices | 20.00000 |
| gelatins / puddings | - |
| granulated sugar | - |
| gravies | - |
| hard candy | 100.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | - |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)-
(±)-iso
menthol
(1)-iso
menthol
cis-1,3-cis-1,4-(±)-
menthol
DL-iso
menthol
(1-alpha,2-beta,5-beta)-(±)-5-
methyl-2-(1-methyl ethyl) cyclohexanol
(1R,2S,5S)-rel-5-
methyl-2-(1-methyl ethyl) cyclohexanol
(1a,2a,5a)-5-
methyl-2-(1-methylethyl)cyclohexanol
(1R,2R,5R)-5-
methyl-2-(propan-2-yl)cyclohexanol
(1R,2R,5R)-5-
methyl-2-propan-2-ylcyclohexan-1-ol
(1R,2R,5R)-2-iso
propyl-5-methylcyclohexanol
Google Patents:
Production of isomenthol isomers
PubMed:
Acaricidal activity of constituents derived from peppermint oil against Tyrophagus putrescentiae.
PubMed:
Phytotoxic activity and chemical composition of aqueous volatile fractions from Eucalyptus species.
PubMed:
Anti-yeast activity of mentha oil and vapours through in vitro and in vivo (real fruit juices) assays.
PubMed:
Antioxidant properties and essential oil composition of Calamintha grandiflora L.
PubMed:
Irradiation depolymerized guar gum as partial replacement of gum Arabic for microencapsulation of mint oil.
PubMed:
Microbial Transformations of (+)-Isomenthol by Fusarium lini and Rhizopus stolonifer.
PubMed:
Menthol shares general anesthetic activity and sites of action on the GABA(A) receptor with the intravenous agent, propofol.
PubMed:
Esters of pyromellitic acid. Part II. Esters of chiral alcohols: para pyromellitate diesters as a novel class of resolving agents and use of pyromellitates as duplicands for chiral purification.
PubMed:
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
PubMed:
Monoterpene metabolism. Cloning, expression, and characterization of menthone reductases from peppermint.
PubMed:
Effect of l-menthol on laryngeal receptors.
PubMed:
The effects of menthol isomers on nasal sensation of airflow.
PubMed:
Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.
PubMed:
Studies in detoxication: The biological reduction of l-menthone to d-neomenthol and of d-isomenthone to d-isomenthol in the rabbit. The conjugation of d-neomenthol with glucuronic acid.
PubMed:
Studies in detoxication: The resolution of dl-isomenthol through its conjugation with glucuronic acid in the rabbit.
PubMed:
Studies in detoxication. II. (a) The conjugation of isomeric 3-menthanols with glucuronic acid and the asymmetric conjugation of dl-menthol and dl-isomenthol in the rabbit. (b) d-isoMenthylglucuronide, a new conjugated glucuronic acid.