EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

dextro-menthol
D-menthol

Supplier Sponsors

Name:(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
CAS Number: 15356-60-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:239-387-8
FDA UNII: C6B1OE8P3W
Beilstein Number:1902292
MDL:MFCD00062983
CoE Number:63
XlogP3-AA:3.00 (est)
Molecular Weight:156.26860000
Formula:C10 H20 O
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
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
FEMA Number:2665 D-menthol
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
Melting Point: 43.00 to 44.00 °C. @ 760.00 mm Hg
Boiling Point: 103.00 to 104.00 °C. @ 9.00 mm Hg
Vapor Pressure:0.032000 mmHg @ 25.00 °C. (est)
Flash Point: 196.00 °F. TCC ( 91.11 °C. )
logP (o/w): 3.216 (est)
Soluble in:
 alcohol
 water, 434.5 mg/L @ 25 °C (est)
Insoluble in:
 paraffin oil
 
Organoleptic Properties:
Odor Description:mentholic
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: perfuming agents
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
D-Menthol 98%
BOC Sciences
For experimental / research use only.
Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-
Coompo
For experimental / research use only.
D-Menthol from Plants ≥98%
Odor: characteristic
Use: The distinct effects of optically active menthols on lipid bilayers were clarified: l-menthol acts on orthorhombic hydrocarbon chain packing with high selectivity, whereas d-menthol has no such specific effect. These findings extend our understanding of the mechanisms by which menthols affect the intercellular lipids in the stratum corneum. Menthol's ability to chemically trigger the cold-sensitive TRPM8 receptors in the skin is responsible for the well-known cooling sensation it provokes when inhaled, eaten, or applied to the skin. Menthol's analgesic properties are mediated through a selective activation of ?-opioid receptors. Menthol also blocks voltage-sensitive sodium channels, reducing neural activity that may stimulate muscles. Menthol also enhances the efficacy of ibuprofen in topical applications via vasodilation, which reduces skin barrier function.
ExtraSynthese
For experimental / research use only.
(+)-Menthol (GC) ≥98%
Penta International
D-MENTHOL
Penta International
MENTHOL LIQUID
Santa Cruz Biotechnology
For experimental / research use only.
(+)-Menthol
Sigma-Aldrich: Aldrich
For experimental / research use only.
(1S,2R,5S)-(+)-Menthol 99%
TCI AMERICA
For experimental / research use only.
(+)-Menthol >99.0%(GC)
 
Safety Information:
Preferred SDS: View
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
maximum skin levels for fine fragrances:
  0.2000 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2006)
use level in formulae for use in cosmetics:
  2.2500 %
Dermal Systemic Exposure in Cosmetic Products:
 0.0573 mg/kg/day (IFRA, 2006)
 
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: 3
Click here to view publication 3
 average usual ppmaverage maximum ppm
baked goods: -130.00000
beverages(nonalcoholic): -35.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -1100.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -68.00000
fruit ices: -68.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -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):15356-60-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :165675
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
Chemidplus:0015356602
RTECS:OT0700000 for cas# 15356-60-2
 
References:
Leffingwell:Chirality or Article
 (1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:15356-60-2
Pubchem (cid):165675
Pubchem (sid):135043092
 
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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2906.11.0000
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%
 
Potential Blenders and core components note
For Odor
anise
anise seed oil colombia
FL/FR
anisic
dihydroanethol
FL/FR
balsamic
amyris wood oil
FL/FR
benzyl salicylate
FL/FR
laevo-
bornyl acetate
FL/FR
iso
bornyl acetate
FL/FR
clover nitrile
FR
camphoreous
camphor tree bark oil
FL/FR
fatty
decanol
FL/FR
floral
iso
amyl salicylate
FL/FR
bois de rose oil brazil
FL/FR
cyclohexyl ethyl alcohol
FL/FR
geranium oil bourbon
FL/FR
heliotropyl diethyl acetal
FR
alpha-
hexyl cinnamaldehyde
FL/FR
ho leaf oil
FR
hyacinth ether
FR
laevo-
linalool
FL/FR
linalool
FL/FR
linalool oxide
FL/FR
methyl dihydrojasmonate
FL/FR
nerol
FL/FR
ocean propanal
FL/FR
herbal
eucalyptus globulus oil
FL/FR
abrialis
lavandin oil
FL/FR
lavender absolute bulgaria
FL/FR
linalyl acetate
FL/FR
nopyl acetate
FR
rosemary oil spain
FL/FR
mentholic
cornmint oil terpeneless
FL/FR
laevo-
menthol
FL/FR
(±)-iso
menthone
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
iso
pulegyl acetate
FL/FR
minty
laevo-
carvone
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
methyl salicylate
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
(-)-iso
pulegol
FL/FR
(R)-(+)-
pulegone
FR
iso
pulegone
FL/FR
spearmint oil america
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
phenolic
methyl benzoate
FL/FR
powdery
para-
anisyl alcohol
FL/FR
spicy
elettaria cardamomum seed oil
FL/FR
pepper tree berry oil
FL/FR
pimenta acris leaf oil
FL/FR
terpenic
alpha-
terpineol
FL/FR
waxy
decyl acetate
FL/FR
woody
(Z)-
woody amylene
FR
For Flavor
No flavor group found for these
(±)-N,N-
dimethyl menthyl succinamide
FL
3-laevo-
menthoxy-2-methyl propane-1,2-diol
FL
menthyl acetate racemic
FL/FR
iso
pulegone
FL/FR
menthyl methyl lactate
FL
anise
anise
anise seed oil colombia
FL/FR
balsamic
benzyl salicylate
FL/FR
laevo-
bornyl acetate
FL/FR
camphoreous
camphor tree bark oil
FL/FR
citrus
linalool
FL/FR
laevo-
linalool
FL/FR
nerol
FL/FR
alpha-
terpineol
FL/FR
cooling
laevo-
menthol
FL/FR
floral
bois de rose oil brazil
FL/FR
geranium oil bourbon
FL/FR
linalyl acetate
FL/FR
methyl dihydrojasmonate
FL/FR
ocean propanal
FL/FR
fruity
para-
anisyl alcohol
FL/FR
green
iso
amyl salicylate
FL/FR
cyclohexyl ethyl alcohol
FL/FR
linalool oxide
FL/FR
herbal
dihydroanethol
FL/FR
eucalyptus globulus oil
FL/FR
abrialis
lavandin oil
FL/FR
lavender absolute bulgaria
FL/FR
rosemary oil spain
FL/FR
mentholic
cornmint oil terpeneless
FL/FR
peppermint cyclohexanone
FL/FR
minty
laevo-
carvone
FL/FR
homo
menthol
FL/FR
(±)-iso
menthone
FL/FR
(-)-
menthone
FL/FR
methyl salicylate
FL/FR
pennyroyal oil
FL/FR
peppermint oil idaho
FL/FR
peppermint oil terpeneless
FL/FR
dextro-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
spearmint oil america
FL/FR
wintergreen oil
FL/FR
WS-23
FL/FR
phenolic
methyl benzoate
FL/FR
spicy
elettaria cardamomum seed oil
FL/FR
pepper tree berry oil
FL/FR
pimenta acris leaf oil
FL/FR
waxy
decanol
FL/FR
decyl acetate
FL/FR
alpha-
hexyl cinnamaldehyde
FL/FR
woody
amyris wood oil
FL/FR
iso
bornyl acetate
FL/FR
iso
pulegyl acetate
FL/FR
 
Potential Uses:
FRmint
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
 cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-
(+)-menthol
(1S,2R,5S)-(+)-menthol
D-menthol
 menthol, (1S,3S,4R)-(+)-
 menthol-d dist.
(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol
 

Articles:

Info:menthol
PubMed:Effects of d-menthol stress on the growth of and microcystin release by the freshwater cyanobacterium Microcystis aeruginosa FACHB-905.
PubMed:The stereoisomers of menthol in selected tobacco products. A brief report.
PubMed:Different effects of l- and d-menthol on the microstructure of ceramide 5/cholesterol/palmitic acid bilayers.
PubMed:Fragrance material review on d-menthol.
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:Identification of the L-menthol binding site in guinea-pig lung membranes.
PubMed:The contribution of cytotoxicity to DNA-effects in the single cell gel test (comet assay).
PubMed:The effects of D and L isomers of menthol upon nasal sensation of airflow.
PubMed:Menthol modulates oral sensations of warmth and cold.
 
Notes:
None found
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