(E)-1,3, (Z)-1,4-menthol
trans-1,3, cis-1,4-menthol
 
Notes:
None found
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CAS Number: 490-99-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 207-722-7
FDA UNII: 90E7IB31QH
Nikkaji Web: J238.499J
Beilstein Number: 3194262
XlogP3-AA: 3.00 (est)
Molecular Weight: 156.26860000
Formula: C10 H20 O
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome, Edge or firefox)
Category: flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar: Search
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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:
 water, 434.5 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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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
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Safety in Use Information:
Category: flavor and fragrance agents
 
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 490-99-3
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: 003623527
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References:
 (1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 490-99-3
Pubchem (cid): 19244
Pubchem (sid): 134984255
Pherobase: View
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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
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%
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 cyclotrichium origanifolium
Search Trop  Picture
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Synonyms:
isomenthol
trans-1,3, cis-1,4-menthol
(1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
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Articles:
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.
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