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isomenthol
Isomenthol is a stereoisomer of menthol used as a cooling flavoring agent with a distinct mentholic odor profile.
General Material Description
Isomenthol, also known by synonyms such as DL-isomenthol and cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)-, is a monoterpenoid alcohol with the molecular formula C10H20O. It appears as a clear substance contributing a mentholic, musty, woody, and camphoreous odor. Chemically, it is a stereoisomer of menthol with distinct sensory properties. This compound is referenced in chemical databases such as ChEBI and is obtained via synthesis or isolation from natural essential oils. It is present in various botanical sources including peppermint and cornmint, serving as an important flavoring ingredient.
Occurrence, Applicability & Potential Uses
Isomenthol occurs naturally in plant oils such as cornmint oil and peppermint oil, as well as in other sources like geranium and pennyroyal oils. Biologically, it is involved as a component in these essential oils that contribute to their characteristic aromas and flavors. It finds application chiefly as a flavoring agent in the food industry, providing a cooling effect and menthol-like flavor. Its use level and safety assessments comply with standards such as FEMA (US) which designates it as a flavoring substance under FEMA number 4729.
Physico-Chemical Properties Summary
Isomenthol exhibits a moderate boiling point around 215 to 216°C at standard atmospheric pressure, reflecting adequate volatility for flavor and fragrance applications. Its vapor pressure at 25°C is low (0.032 mmHg), indicating limited volatility at room temperature. The compound is soluble in alcohol and moderately soluble in water (approximately 434.5 mg/L at 25°C), enabling formulation in aqueous and alcoholic solutions. Its estimated logP value of 3.216 suggests moderate lipophilicity, supporting its action in lipid-containing matrices. These physicochemical characteristics influence its use in flavor systems, where controlled release and solubility are critical for sensory impact.
FAQ
What is isomenthol and what are its primary characteristics?
Isomenthol is a stereoisomer of menthol, with chemical formula C10H20O. It is a monoterpene alcohol known for its cooling flavor and a mentholic, musty, woody, and camphorous odor. It appears as a clear compound used extensively in flavoring agents, contributing sensory effects similar to menthol but with distinct nuances.
Where is isomenthol naturally found and how is it typically used?
Isomenthol naturally occurs in essential oils such as cornmint oil, peppermint oil, geranium oil, pennyroyal oil, and others derived from plants like Stachys obliqua and sunflower flowers. It is primarily employed as a flavoring agent in the food industry, valued for its cooling sensation and menthol-like taste. Usage levels are guided by regulatory organizations to ensure safety in consumable products.
What regulations apply to isomenthol and how is it sourced?
Isomenthol is regulated under bodies such as FEMA (US) with FEMA number 4729, recognized as a flavoring substance with established acceptable usage limits in foods. It is sourced both by chemical synthesis and extraction from natural essential oils. Safety data indicate no significant hazard classifications under OSHA standards, and it is approved for flavor use with specified concentrations in various products.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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| Perfumer & Flavorists | Start search |
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| NCBI | Start search |
Literature & References
| (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 3623-52-7 |
| Pubchem (cid): | 19244 |
| Pubchem (sid): | 134984255 |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| HMDB (The Human Metabolome Database): | Search |
| FooDB: | FDB021835 |
| Typical G.C. | |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
| Formulations/Preparations: •some synthetic menthols are not chemical individuals but...mixtures of various isomers...these are designated...l-menthol, dl-menthol, l-isomenthol, d-isomenthol, dl-isomenthol, l-neomenthol, d-neomenthol, l-neoisomenthol, d-neoisomenthol and dl-neoisomenthol. •when mixed with about equal wt of camphor, chloral hydrate, phenol, or thymol, menthol forms "eutectic" mixt liquifying @ room temp. •menthol, usp drug marketed under generic name. •grades: technical; usp; fcc •synthetic menthol is available as the optically active levo-menthol with a purity of 99.9%. synthetic menthol is also commercially available as the racemic mixture •present in cigarettes and pipe tobacco (0.1-0.45%) shaving creams, pre- and aftershave lotions (0.2-0.3%); toothpastes (0.5%); mouthwashes (1-2%); chewing gums (0.5%); cough drops (0.1%); refreshing towels (1%); rubbing alcohol (1-1.2%); and shampoos (2-0.5%) •mentholatum deep heating rub contains 5.9% menthol; mentholatum ointment, 1.35%; mentholatum deep heating lotion, 6% | |
General Material Information
| Preferred name | isomenthol |
| Trivial Name | (E)-1,3, (Z)-1,4-menthol |
| Short Description | DL-isomenthol |
| Formula | C10 H20 O |
| CAS Number | 3623-52-7 |
| Deleted CAS Number | 490-99-3 |
| FEMA Number | 4729 |
| ECHA Number | 222-825-7 |
| FDA UNII | 90E7IB31QH |
| Nikkaji Number | J238.499J |
| Beilstein Number | 3194262 |
| MDL | MFCD01941448 |
| xLogP3-AA | 3.00 (est) |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| JECFA Food Flavoring | 2249 DL-isomenthol |
| FDA Patent | No longer provide for the use of these seven synthetic flavoring substances |
| Synonyms |
|
Suppliers
| BOC Sciences |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 156.26860046387 |
| Boiling Point | 215 to 216°C @ 760 mm Hg |
| Vapor Pressure | 0.032 mmHg @ 25 °C |
| Flash Point TCC Value | 93.3 °C TCC |
| logP (o/w) | 3.216 est |
| Solubility | |
| alcohol | Yes |
| water, 434.5 mg/L @ 25 °C (est) | Yes |
| paraffin oil | No |
Organoleptic Properties
| Odor Type: Mentholic | |
| mentholic, musty, woody, camphoreous | |
| General comment | At 10.00 % in propylene glycol. mentholic musty woody camphoreous |
| Flavor Type: Cooling | |
| cooling | |
| General comment | Cooling |
Occurrences
| (data available) |
Safety Information
Safety information
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| oral-mouse LD50 3000 mg/kg Quarterly Journal of Pharmacy & Pharmacology. Vol. 5, Pg. 233, 1932. | |
| Dermal Toxicity: | |
| Not determined | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| flavoring agents | |||
| Recommendation for isomenthol usage levels up to: | |||
| not for fragrance use. | |||
| Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS). | |||
| The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library | |||
| publication number: 26 | |||
| Click here to view publication 26 | |||
| average usual ppm | average maximum ppm | ||
| baked goods: | 30.00000 | 130.00000 | |
| beverages(nonalcoholic): | 10.00000 | 35.00000 | |
| beverages(alcoholic): | 10.00000 | 35.00000 | |
| breakfast cereal: | - | - | |
| cheese: | - | - | |
| chewing gum: | 500.00000 | 1100.00000 | |
| condiments / relishes: | - | - | |
| confectionery froastings: | - | - | |
| egg products: | - | - | |
| fats / oils: | - | - | |
| fish products: | - | - | |
| frozen dairy: | 20.00000 | 68.00000 | |
| fruit ices: | 20.00000 | 68.00000 | |
| gelatins / puddings: | - | - | |
| granulated sugar: | - | - | |
| gravies: | - | - | |
| hard candy: | 100.00000 | 400.00000 | |
| 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: | - | - | |
Safety references
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA Substance Registry Services (TSCA):3623-52-7 |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :19244 |
| National Institute of Allergy and Infectious Diseases:Data |
| (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol |
| Chemidplus:0003623527 |