laevo-menthol

L-menthol

CAS: 2216-51-5 C10 H20 O MW: 156.26860000 mentholic cooling

Identification

Namelaevo-menthol
IUPAC(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
CAS Number2216-51-5
EINECS218-690-9
FDA UNIIBZ1R15MTK7
Molecular FormulaC10 H20 O
Molecular Weight156.26860000
MDL NumberMFCD00062979
Nikkaji NumberJ9.251G
Beilstein1902293

Regulatory

FEMA Number2665
FDANo longer provide for the use of these seven synthetic flavoring substances

Physical Properties

Appearance colorless crystals (est)
Assay 99.00 to 100.00
Heavey Metals <1.00ppm
Food Chemicals Codex Listed Yes
Optical Rotation -1.00 to +2.00
Melting Point 41.00 to 44.00 °C. @ 760.00 mm Hg
Boiling Point 212.00 to 216.00 °C. @ 760.00 mm Hg, 111.00 to 112.00 °C. @ 20.00 mm Hg
Vapor Pressure 0.032000 mmHg @ 25.00 °C. (est)
Flash Point 190.00 °F. TCC ( 87.78 °C. )
logP (o/w) 3.400
Soluble in alcohol
Insoluble in water
Stability bath foam

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesperfuming agents

Organoleptic Properties

Odor Strength high ,
Substantivity 32 hour(s) at 20.00 % in dipropylene glycol
Odor Description
at 10.00 % in dipropylene glycol.
typical-minty, fresh, cool
Mint-like odor with cooling feel
cool, peppermint
typical minty, fresh, cool
Taste Description
cooling camphoreous minty clean spicy
cool, fresh, peppermint-like
cold, sweet, mint
cool, fresh, peppermint-like

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 3300 mg/kg
Dermal Toxicityskin-rabbit LD50 > 5000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION\nBEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\nBEHAVIORAL: GENERAL ANESTHETIC']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
maximum skin levels for fine fragrances0.5800 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2006)
Recommendation for laevo-menthol usage levels up to8.0000 % in the fragrance concentrate.
use level in formulae for use in cosmetics0.4000 %
Dermal Systemic Exposure in Cosmetic Products0.0102 mg/kg/day (IFRA, 2006)
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
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

FL cooling FR fern FR geranium FR herbal FR lavender lifter FR lime FR mint FL/FR pennyroyal FR peppermint FR rose FR spice FR spring rain FR wintergreen

Natural Occurrence

basil oil basil plant cabbage leaf coconut fruit coriander leaf corn silk cornmint leaf cornmint oil cornmint plant elder black elder flower oil guava leaf oil horsemint shoot lovage root marjoram oil melon bitter melon seed oil mint plant pennyroyal oil peppermint leaf peppermint oil sage leaf sage plant spearmint leaf spearmint oil sunflower flower oil tarragon oil tarragon shoot tea leaf water mint leaf water mint shoot

Synonyms

cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,3R,4S)- L- hexahydrothymol laevo- hexahydrothymol levomenthol L- menthacamphor laevo- menthacamphor (1R,3R,4S)-4- menthan-3-ol (-)-trans-p- menthan-cis-ol (-)-trans-para- menthan-cis-ol (1R,3R,4S)-4- menthane-3-ol (-)-trans-p- menthane-cis-ol (-)-trans-para- menthane-cis-ol (-)-(1R,2S,5R)- menthol (1R,2S,5R)-(-)- menthol D-(-)- menthol L- menthol L-(-)- menthol nat.L- menthol (-)- menthol (GC) ≥99% (sum of enantiomers) laevo- menthol (molten 99.5%) laevo- menthol (natural) L- menthol (pellets) synth. FCC L- menthol 98% up, japan pharmacopeia grade L- menthol cryst. nat. menthol crystal Ip/Bp/Usp/Ep/Jp L- menthol crystal, natural, chinese L- menthol crystals organic menthol crystals menthol crystals (codex) (ex mint) menthol crystals chinese menthol crystals indian L- menthol crystals USP natural laevo- menthol crystals USP select FCC (natural) L- menthol crystals USP synthetic L- menthol crystals USP/BP/EP/JP natural menthol ex mint arvensis india organic menthol flake menthol flakes FCC synthetic menthol L- 99.7% synth. menthol L- natural natural menthol large crystals BP/USP natural menthol medium crystals L- menthol natural spray dried menthol natural menthol powder 97.00%.min menthol powder dry BP/USP natural menthol small crystals natural menthol small crystals BP/USP laevo- menthol USP/NF/FCC natural menthol-L dist. menthol-L freeflow menthol-L pellets (US production) menthol-L pellets PH menthol, (1R,3R,4S)-(-)- menthol, natural crystals USP laevo- menthol(USP/BP/NF) (-)-trans-p- methan-cis-3-ol (-)-trans-p- methane-cis-3-ol (1R-(1-alpha,2-beta,5-alpha))-5- methyl-2-(1-methyl ethyl) cyclohexanol (1R-(1-alpha,2-beta,5-alpha))-5- methyl-2-(1-methylethyl)cyclohexanol (1R,2S,5R)-5- methyl-2-(1-methylethyl)cyclohexanol [1R-(1a,2b,5a)]-5- methyl-2-(1-methylethyl)cyclohexanol (1R,2S,5R)-5- methyl-2-(propan-2-yl)cyclohexan-1-ol (1R,2S,5R)-5- methyl-2-(propan-2-yl)cyclohexanol (1R-(1alpha,2beta,5alpha))-5- methyl-2-isopropyl cyclohexanol (1R,2S,5R)-5- methyl-2-propan-2-yl-cyclohexan-1-ol (1R,2S,5R)-5- methyl-2-propan-2-ylcyclohexan-1-ol L- peppermint camphor 1-iso propyl-4-methyl cyclohexan-2-ol (1R,2S,5R)-2-iso propyl-5-methyl-cyclohexanol (1R,2S,5R)-2-iso propyl-5-methylcyclohexanol Info: menthol PubMed: Influence of repeated daily menthol exposure on human temperature regulation and perception. PubMed: A Green and Sustainable Approach: Celebrating the 30th Anniversary of the Asymmetric l-Menthol Process. PubMed: Formulation and evaluation of floating tablet of H2-receptor antagonist. PubMed: Spraying with 0.20% L-menthol does not enhance 5 km running performance in the heat in untrained runners. PubMed: A continuous tri-phase transition effect for HIFU-mediated intravenous drug delivery. PubMed: Somatosensory and vasomotor manifestations of individual and combined stimulation of TRPM8 and TRPA1 using topical L-menthol and trans-cinnamaldehyde in healthy volunteers. PubMed: Prevention of colonic spasm using L-menthol in colonoscopic examination. PubMed: L-menthol improves adenoma detection rate during colonoscopy: a randomized trial. PubMed: Mechanistic investigation and reversible effect of 2-isopropyl-5-methylcyclohexyl heptanoate on the in vitro percutaneous absorption of indomethacin. PubMed: Synthesis and quantitative analysis of diastereomeric linked ester conjugates with remote stereocenters using high-field NMR and chiral HPLC. PubMed: A combination of site-directed mutagenesis and chemical modification to improve diastereopreference of Pseudomonas alcaligenes lipase. PubMed: A review of topical high-concentration L-menthol as a translational model of cold allodynia and hyperalgesia. PubMed: Structure-activity relationships of monoterpenes and acetyl derivatives against Aedes aegypti (Diptera: Culicidae) larvae. PubMed: A novel animal model of dysphagia following stroke. PubMed: TRPM8 is the principal mediator of menthol-induced analgesia of acute and inflammatory pain. PubMed: Enantioselective hydrolysis of dl-menthyl benzoate by cell-free extract of newly isolated Acinetobacter sp. ECU2040. PubMed: Efficacy of spraying l-menthol solution during endoscopic treatment of early gastric cancer: a phase III, multicenter, randomized, double-blind, placebo-controlled study. PubMed: The effect of inhaled menthol on upper airway resistance in humans: a randomized controlled crossover study. PubMed: The effects of menthol on cold allodynia and wind-up-like pain in upper limb amputees with different levels of phantom limb pain. PubMed: Thermal grill-evoked sensations of heat correlate with cold pain threshold and are enhanced by menthol and cinnamaldehyde. PubMed: Menthosomes, novel ultradeformable vesicles for transdermal drug delivery: optimization and characterization. PubMed: Topical hindpaw application of L-menthol decreases responsiveness to heat with biphasic effects on cold sensitivity of rat lumbar dorsal horn neurons. PubMed: Lack of effect of menthol level and type on smokers' estimated mouth level exposures to tar and nicotine and perceived sensory characteristics of cigarette smoke. PubMed: Multicenter phase II randomized study evaluating dose-response of antiperistaltic effect of L-menthol sprayed onto the gastric mucosa for upper gastrointestinal endoscopy. PubMed: A dual catalyst system provides the shortest pathway for L-menthol synthesis. PubMed: Reduction of misleading ("false") positive results in mammalian cell genotoxicity assays. I. Choice of cell type. PubMed: Optimization and validation of liquid chromatography and headspace-gas chromatography based methods for the quantitative determination of capsaicinoids, salicylic acid, glycol monosalicylate, methyl salicylate, ethyl salicylate, camphor and l-menthol in a topical formulation. PubMed: Body regional influences of L-menthol application on the alleviation of heat strain while wearing firefighter's protective clothing. PubMed: Properties of gastroretentive sustained release tablets prepared by combination of melt/sublimation actions of L-menthol and penetration of molten polymers into tablets. PubMed: Direct GC analysis of the fatty acid compositions of conjugated linoleic acid and its L-menthyl esters. PubMed: An open-label, single-arm study assessing the efficacy and safety of L: -menthol sprayed onto the gastric mucosa during upper gastrointestinal endoscopy. PubMed: A phase I study evaluating tolerability, pharmacokinetics, and preliminary efficacy of L-menthol in upper gastrointestinal endoscopy. PubMed: Proteomics indicates modulation of tubulin polymerization by L-menthol inhibiting human epithelial colorectal adenocarcinoma cell proliferation. PubMed: Topical high-concentration (40%) menthol-somatosensory profile of a human surrogate pain model. PubMed: The stereoisomers of menthol in selected tobacco products. A brief report. PubMed: Antiperistaltic effect and safety of L-menthol sprayed on the gastric mucosa for upper GI endoscopy: a phase III, multicenter, randomized, double-blind, placebo-controlled study. PubMed: Effect of (E)-2-isopropyl-5-methylcyclohexyl octadec-9-enoate on transdermal delivery of Aconitum alkaloids. PubMed: Different effects of l- and d-menthol on the microstructure of ceramide 5/cholesterol/palmitic acid bilayers. PubMed: A statistical approach to the development of a transdermal delivery system for ondansetron. PubMed: Feasibility of transdermal delivery of prochlorperazine. PubMed: An efficient bioprocess for enzymatic production of L-menthol with high ratio of substrate to catalyst using whole cells of recombinant E. coli. PubMed: The influence of menthol on thermoregulation and perception during exercise in warm, humid conditions. PubMed: Topical application of L-menthol induces heat analgesia, mechanical allodynia, and a biphasic effect on cold sensitivity in rats. PubMed: Lidocaine/L-menthol binary system: cocrystallization versus solid-state immiscibility. PubMed: Efficacy and safety profile of a topical methyl salicylate and menthol patch in adult patients with mild to moderate muscle strain: a randomized, double-blind, parallel-group, placebo-controlled, multicenter study. PubMed: Infrared spectroscopic study of lipid interaction in stratum corneum treated with transdermal absorption enhancers. PubMed: Dual response surface-optimized synthesis of L-menthyl conjugated linoleate in solvent-free system by Candida rugosa lipase. PubMed: Erythema multiforme-like generalized contact dermatitis to l-menthol contained in anti-inflammatory medical compresses as an ingredient. PubMed: The effects of swilling an L(-)-menthol solution during exercise in the heat. PubMed: Skin disposition of d-camphor and l-menthol alone and together. PubMed: Effect of l-menthol on the thermotropic behavior of ceramide 2/cholesterol mixtures as a model for the intercellular lipids in stratum corneum. PubMed: Transdermal delivery of tolterodine by O-acylmenthol: In vitro/in vivo correlation. PubMed: Effect of penetration enhancers on transdermal delivery of propofol. PubMed: Menthol and geraniol biotransformation and glycosylation capacity of Levisticum officinale hairy roots. PubMed: Design and in vivo evaluation of an indapamide transdermal patch. PubMed: Formulation optimization of an indomethacin-containing photocrosslinked polyacrylic acid hydrogel as an anti-inflammatory patch. PubMed: Identification of degradation products in loxoprofen sodium adhesive tapes by liquid chromatography-mass spectrometry and dynamic pressurized liquid extraction-solid-phase extraction coupled to liquid chromatography-nuclear magnetic resonance spectroscopy. PubMed: [Advantages of the L-menthol test in assessing chronic nasal obstruction]. PubMed: Impact of menthol inhalation on nasal mucosal temperature and nasal patency. PubMed: Fragrance material review on l-menthol. PubMed: Fragrance material review on d,l-menthol. PubMed: Essential oil of lavender inhibited the decreased attention during a long-term task in humans. PubMed: Differential transfer of dietary flavour compounds into human breast milk. PubMed: Transdermal delivery of valsartan: I. Effect of various terpenes. PubMed: Enhancement in skin permeation of 5-aminolevulinic acid using l-menthol and its derivatives. 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: Expression of Fos protein in brainstem after application of l-menthol to the rat nasal mucosa. PubMed: Insecticidal activity of menthol derivatives against mosquitoes. PubMed: Transdermal delivery of penetrants with differing lipophilicities using O-acylmenthol derivatives as penetration enhancers. PubMed: Effect of O-acylmenthol on transdermal delivery of drugs with different lipophilicity. PubMed: Fragrance release from the surface of branched poly (amide)s. PubMed: Effects of dimethylformamide and L-menthol permeation enhancers on transdermal delivery of quercetin. PubMed: Effects of ethanol/l-menthol on the dynamics and partitioning of spin-labeled lipids in the stratum corneum. PubMed: Characteristic component odors emerge from mixtures after selective adaptation. PubMed: Thermal and nociceptive sensations from menthol and their suppression by dynamic contact. PubMed: Efficient asymmetric synthesis of novel gastrin receptor antagonist AG-041R via highly stereoselective alkylation of oxindole enolates. PubMed: Combined effects of ethanol and L-menthol on hairless rat stratum corneum investigated by synchrotron X-ray diffraction. PubMed: Enhanced skin permeation of salicylate by ion-pair formation in non-aqueous vehicle and further enhancement by ethanol and l-menthol. PubMed: Psychophysical study of the effects of topical application of menthol in healthy volunteers. PubMed: Formulation and evaluation of ethylene-vinyl acetate copolymer matrix patches containing formoterol fumarate. PubMed: Effects of solvents on skin permeation of formoterol fumarate. PubMed: Cold sensitivity in axotomized fibers of experimental neuromas in mice. PubMed: Effects of upper airway anaesthesia on respiratory-related evoked potentials in humans. PubMed: Enzymatic synthesis of l-menthyl alpha-maltoside and l-menthyl alpha-maltooligosides from l-menthyl alpha-glucoside by cyclodextrin glucanotransferase. PubMed: Alpha-anomer-selective glucosylation of menthol with high yield through a crystal accumulation reaction using lyophilized cells of Xanthomonas campestris WU-9701. PubMed: TRPM8 protein localization in trigeminal ganglion and taste papillae. PubMed: Psychophysical isolation of the modality responsible for detecting multimodal stimuli: a chemosensory example. PubMed: [Synthetical evaluation of promoting effect of some kinds of transdermal enhancers with grey relational cluster method]. PubMed: The effect of solvent interactions on alpha-, beta-, and gamma-cyclodextrin/flavor molecular inclusion complexes. PubMed: Effect of L-menthol and 1,8-cineole on phase behavior and molecular organization of SC lipids and skin permeation of zidovudine. PubMed: Synthesis and characterization of fluorescent poly(aromatic amide) dendrimers. PubMed: Evaluation of percutaneous absorption of midazolam by terpenes. PubMed: Synthesis, absolute configuration and biological activities of both enantiomers of 2-(5,7-Dichloro-3-indolyl)propionic acid: a novel dichloroindole auxin and antiauxin. PubMed: Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions. PubMed: Flavor release and perception in hard candy: influence of flavor compound-compound interactions. PubMed: Origin of chiral induction in radical reactions with the diastereoisomers (5R)- and (5S)-5-l-menthyloxyfuran-2[5H]-one. PubMed: Topical menthol--a human model for cold pain by activation and sensitization of C nociceptors. PubMed: Effect of mixed micelle formulations including terpenes on the transdermal delivery of diclofenac. PubMed: Comparison of skin permeation enhancement by 3-l-menthoxypropane-1,2-diol and l-menthol: the permeation of indomethacin and antipyrine through Yucatan micropig skin and changes in infrared spectra and X-ray diffraction patterns of stratum corneum. PubMed: Lytic activity of l-menthol derivatives against the snow blight disease fungus, Micronectriella nivalis. PubMed: Autonomic nervous system responses to odours: the role of pleasantness and arousal. PubMed: Elevation of plasma levels of L-dopa in transdermal administration of L-dopa-butylester in rats. PubMed: In vitro skin permeation of morphine hydrochloride during the finite application of penetration-enhancing system containing water, ethanol and l-menthol. PubMed: Molecular-imprinted, polymer-coated quartz crystal microbalances for the detection of terpenes. PubMed: Effect of pH on skin permeation enhancement of acidic drugs by l-menthol-ethanol system. PubMed: Oral irritant properties of menthol: sensitizing and desensitizing effects of repeated application and cross-desensitization to nicotine. PubMed: [Does the inhalation of a 1% L-menthol solution in the premedication of fiberoptic bronchoscopy affect coughing and the sensation of dyspnea?]. PubMed: Preparation of griseofulvin for topical application using N-methyl-2-pyrrolidone. PubMed: Physicochemical studies of lidocaine-menthol binary systems for enhanced membrane transport. PubMed: Effect of l-menthol-ethanol-water system on the systemic absorption of flurbiprofen after repeated topical applications in rabbits. PubMed: Cyclodextrin encapsulation to prevent the loss of l-menthol and its retention during drying. PubMed: Whisker growth of l-menthol in coexistence with various excipients. PubMed: l-Menthol-induced [Ca2+]i increase and impulses in cultured sensory neurons. PubMed: Effects of branched cyclodextrins on the solubility and stability of terpenes. PubMed: Effect of synthesized cyclohexanol derivatives using L-menthol as a lead compound on the percutaneous absorption of ketoprofen. PubMed: Transbuccal permeation of a nucleoside analog, dideoxycytidine: effects of menthol as a permeation enhancer. PubMed: Analysis of skin disposition of flurbiprofen after topical application in hairless rats. PubMed: Disposition kinetics and effects of menthol. PubMed: Effect of chiral enhancers on the permeability of optically active and racemic metoprolol across hairless mouse skin. PubMed: The posterior nasal nerve plays an important role on cardiopulmonary reflexes to nasal application of capsaicin, distilled water and l-menthol in anesthetized dogs. PubMed: Effects of removal of stratum corneum, delipidization and addition of enhancers, ethanol and l-menthol, on skin permeation of benzoic acid and its 4-n-alkyl substituents in excised guinea pig dorsal skin. PubMed: The anti-inflammatory activity of L-menthol compared to mint oil in human monocytes in vitro: a novel perspective for its therapeutic use in inflammatory diseases. PubMed: Transdermal absorption of L-dopa from hydrogel in rats. PubMed: Development and in vitro evaluation of nimodipine transdermal formulations using factorial design. PubMed: Determination of l-menthol in pharmaceutical products by high performance liquid chromatography with polarized photometric detection. PubMed: Anomer-selective glucosylation of l-menthol by yeast alpha-glucosidase. PubMed: Racemate and enantiomers of ketoprofen: phase diagram, thermodynamic studies, skin permeability, and use of chiral permeation enhancers. PubMed: Effect of several hydrophilic polymers on the permeation of morphine and salicylic acid through excised hairless rat skin. PubMed: Identification of the L-menthol binding site in guinea-pig lung membranes. PubMed: Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. PubMed: Skin permeation of parabens in excised guinea pig dorsal skin, its modification by penetration enhancers and their relationship with n-octanol/water partition coefficients. PubMed: 13-week inhalation toxicity study of menthol cigarette smoke. PubMed: Nasal inhalation of l-menthol reduces respiratory discomfort associated with loaded breathing. PubMed: The effect of L-menthol stimulation of the major palatine nerve on subjective and objective nasal patency. PubMed: Nasal receptors responding to cold and l-menthol airflow in the guinea pig. PubMed: Sensitization and desensitization to capsaicin and menthol in the oral cavity: interactions and individual differences. PubMed: l-Menthol, oleic acid and lauricidin in absorption enhancement of free and sodium salt of diclofenac using ethanol treated silicone membrane as model for skin. PubMed: Preparation and stability testing of a hydrogel for topical analgesia. PubMed: [Antinociceptive effects of counterirritants]. PubMed: Metabolic fate of [3H]-l-menthol in the rat. PubMed: The antitussive effects of menthol, camphor and cineole in conscious guinea-pigs. PubMed: Determination of menthol in honey by gas chromatography. PubMed: Influence of composition of l-menthol-ethanol-water ternary solvent system on the transdermal delivery of morphine hydrochloride. PubMed: Effect of pretreatment of skin with cyclic monoterpenes on permeation of diclofenac in hairless rat. PubMed: Feasibility of use of several cardiovascular agents in transdermal therapeutic systems with l-menthol-ethanol system on hairless rat and human skin. PubMed: Effect of l-menthol on the permeation of indomethacin, mannitol and cortisone through excised hairless mouse skin. PubMed: Menthol in the upper airway depresses ventilation in newborn dogs. PubMed: The sensory effects of l-menthol on human skin. PubMed: Effects of l-menthol and dl-camphor on the penetration and hydrolysis of methyl salicylate in hairless mouse skin. PubMed: Combined effect of cyclic monoterpenes and ethanol on percutaneous absorption of diclofenac sodium. PubMed: Upper airway cooling and l-menthol reduce ventilation in the guinea pig. PubMed: Effect of l-menthol on laryngeal receptors. PubMed: The effect of L-menthol stimulation of the major palatine nerve on nasal patency. PubMed: Effect of cyclic monoterpenes on percutaneous absorption in the case of a water-soluble drug (diclofenac sodium). PubMed: Immobilization of lipase from Candida cylindraceae and its use in the synthesis of menthol esters by transesterification. PubMed: Percutaneous absorption enhancing effect and skin irritation of monocyclic monoterpenes. PubMed: Two-phase system membrane reactor with cofactor recycling. PubMed: The effects of menthol on reaction time and nasal sensation of airflow in subjects suffering from the common cold. PubMed: Olfactory and trigeminal thresholds and nasal resistance to airflow. PubMed: Chromosomal aberrations and sister chromatid exchange tests in Chinese hamster ovary cells in vitro. IV. Results with 15 chemicals. PubMed: Studies on the metabolism of l-menthol in rats. PubMed: The effects of D and L isomers of menthol upon nasal sensation of airflow. PubMed: The effects of menthol isomers on nasal sensation of airflow. PubMed: Menthol inhibits the perception of warmth. PubMed: Menthol modulates oral sensations of warmth and cold. PubMed: Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes. PubMed: Receptor cell responses to odorants: similarities and differences among odorants. PubMed: Demonstration that limonene is the first cyclic intermediate in the biosynthesis of oxygenated p-menthane monoterpenes in Mentha piperita and other Mentha species. PubMed: Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves. PubMed: Demonstration of the Intercellular Compartmentation of l-Menthone Metabolism in Peppermint (Mentha piperita) Leaves. PubMed: Metabolism of Monoterpenes : EVIDENCE FOR COMPARTMENTATION OF l-MENTHONE METABOLISM IN PEPPERMINT (MENTHA PIPERITA) LEAVES. PubMed: Electronic properties of the nitrosamine function. PubMed: Separation of l-menthol from racemic menthol U.S.P.