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

isomenthol
DL-isomenthol

Supplier Sponsors

Name:(1R,2R,5R)-5-methyl-2-propan-2-ylcyclohexan-1-ol
CAS Number: 3623-52-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:222-825-7
FDA UNII:90E7IB31QH
Nikkaji Web:J238.499J
Beilstein Number:3194262
MDL:MFCD01941448
XlogP3-AA:3.00 (est)
Molecular Weight:156.26860000
Formula:C10 H20 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavoring 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
JECFA Food Flavoring:2249 DL-isomenthol
FEMA Number:4729 DL-isomenthol
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 mm/Hg @ 25.00 °C. (est)
Flash Point: 200.00 °F. TCC ( 93.30 °C. ) (est)
logP (o/w): 3.216 (est)
Soluble in:
 alcohol
 water, 434.5 mg/L @ 25 °C (est)
Insoluble in:
 paraffin oil
 
Organoleptic Properties:
Odor Type: mentholic
Odor Strength:medium ,
recommend smelling in a 10.00 % solution or less
mentholic musty woody camphoreous
Odor Description:at 10.00 % in propylene glycol. mentholic musty woody camphoreous
Flavor Type: cooling
cooling
Taste Description: cooling
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
DL-isoMenthol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
 
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
 average usual ppmaverage maximum ppm
baked goods: 30.00000130.00000
beverages(nonalcoholic): 10.0000035.00000
beverages(alcoholic): 10.0000035.00000
breakfast cereal: --
cheese: --
chewing gum: 500.000001100.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 20.0000068.00000
fruit ices: 20.0000068.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 100.00000400.00000
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
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
 
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 2009
(IUPAC):Atomic Weights of the Elements 2009 (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
RSC Learn Chemistry: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
alcoholic
iso
propyl alcohol
FL/FR
balsamic
dextro,laevo-
borneol
FL/FR
laevo-
borneol
FL/FR
iso
bornyl methyl ether
FL/FR
myrrh absolute
FL/FR
earthy
(-)-alpha-
fenchol
FL/FR
floral
bois de rose oil peru
FL/FR
fruity
menthyl isovalerate
FL/FR
herbal
geranic oxide
FL/FR
spike
lavender oil
FL/FR
origanum oil
FL/FR
origanum oil greece
FL/FR
piperitone
FL/FR
rosemary absolute
FL/FR
rosemary oil
FL/FR
rosemary oil africa
FL/FR
rosemary oil morocco
FL/FR
rosemary oil spain
FL/FR
rosemary oil tunisia
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil china
FL/FR
cornmint oil india
FL/FR
cornmint oil terpeneless
FL/FR
dextro,laevo-
menthol
FL/FR
(±)-
menthol
FL/FR
laevo-
menthol
FL/FR
neoiso
menthol
FL/FR
dextro-neo
menthol
FL/FR
dextro,laevo-neo
menthol
FL/FR
(±)-iso
menthone
FL/FR
(+)-
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
menthyl acetate
FL/FR
menthyl acetate racemic
FL/FR
peppermint cyclohexanone
FL/FR
dextro-
piperitone
FL/FR
minty
cornmint oil japan
FL/FR
mentha piperita extract
FL/FR
mentha piperita flower/leaf/stem extract
FL/FR
mentha piperita tincture
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
laevo-
menthyl lactate
FL/FR
2-
methyl cyclohexanone
FL/FR
pennyroyal herb oil america
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil cuba
FL/FR
pennyroyal oil fractions
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil terpenes
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint absolute
FL/FR
peppermint distillates
FL/FR
peppermint oil
FL/FR
peppermint oil america
FL/FR
peppermint oil brazil
FL/FR
peppermint oil china
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil dementholized
FL/FR
peppermint oil england
FL/FR
peppermint oil france
FL/FR
peppermint oil hungary
FL/FR
peppermint oil idaho
FL/FR
peppermint oil india
FL/FR
peppermint oil mongolia
FL/FR
peppermint oil montana
FL/FR
peppermint oil morocco
FL/FR
peppermint oil russia
FL/FR
peppermint oil special fractions
FL/FR
peppermint oil tasmania
FL/FR
peppermint oil terpeneless
FL/FR
peppermint oil willamette
FL/FR
peppermint oil yakima
FL/FR
peppermint water
FL/FR
laevo-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
iso
pulegone
FL/FR
(R)-(+)-
pulegone
FR
musty
ketoiso
phorone
FL/FR
spicy
ginger root oil china
FL/FR
white
sassafras oil
FL/FR
For Flavor
No flavor group found for these
dextro,laevo-
borneol
FL/FR
iso
bornyl methyl ether
FL/FR
dextro,laevo-neo
menthol
FL/FR
neoiso
menthol
FL/FR
menthyl acetate racemic
FL/FR
2-
methyl cyclohexanone
FL/FR
iso
pulegone
FL/FR
white
sassafras oil
FL/FR
alcoholic
alcoholic
iso
propyl alcohol
FL/FR
balsamic
myrrh absolute
FL/FR
camphoreous
laevo-
borneol
FL/FR
(-)-alpha-
fenchol
FL/FR
geranic oxide
FL/FR
rosemary oil tunisia
FL/FR
citrus
ketoiso
phorone
FL/FR
cooling
spike
lavender oil
FL/FR
dextro,laevo-
menthol
FL/FR
laevo-
menthol
FL/FR
menthyl acetate
FL/FR
laevo-
menthyl lactate
FL/FR
peppermint oil america
FL/FR
floral
bois de rose oil peru
FL/FR
fruity
menthyl isovalerate
FL/FR
herbal
origanum oil
FL/FR
origanum oil greece
FL/FR
rosemary absolute
FL/FR
rosemary oil
FL/FR
rosemary oil africa
FL/FR
rosemary oil morocco
FL/FR
rosemary oil spain
FL/FR
mentholic
cornmint oil
FL/FR
cornmint oil terpeneless
FL/FR
(±)-
menthol
FL/FR
dextro-neo
menthol
FL/FR
menthol flavor
FL
(+)-
menthone
FL/FR
peppermint cyclohexanone
FL/FR
minty
cornmint oil china
FL/FR
cornmint oil india
FL/FR
cornmint oil japan
FL/FR
mentha piperita extract
FL/FR
mentha piperita flower/leaf/stem extract
FL/FR
mentha piperita tincture
FL/FR
homo
menthol
FL/FR
(-)-
menthone
FL/FR
(±)-
menthone
FL/FR
(±)-iso
menthone
FL/FR
laevo-
menthyl acetate
FL/FR
mint flavor
FL
pennyroyal herb oil america
FL/FR
pennyroyal oil
FL/FR
pennyroyal oil cuba
FL/FR
pennyroyal oil fractions
FL/FR
pennyroyal oil spain
FL/FR
pennyroyal oil terpenes
FL/FR
pennyroyal oil uruguay
FL/FR
peppermint absolute
FL/FR
peppermint distillates
FL/FR
peppermint oil
FL/FR
peppermint oil brazil
FL/FR
peppermint oil china
FL/FR
peppermint oil CO2 extract
FL/FR
peppermint oil dementholized
FL/FR
peppermint oil england
FL/FR
peppermint oil france
FL/FR
peppermint oil hungary
FL/FR
peppermint oil idaho
FL/FR
peppermint oil india
FL/FR
peppermint oil mongolia
FL/FR
peppermint oil montana
FL/FR
peppermint oil morocco
FL/FR
peppermint oil russia
FL/FR
peppermint oil special fractions
FL/FR
peppermint oil tasmania
FL/FR
peppermint oil terpeneless
FL/FR
peppermint oil willamette
FL/FR
peppermint oil yakima
FL/FR
peppermint water
FL/FR
laevo-
piperitone
FL/FR
piperitone
FL/FR
dextro-
piperitone
FL/FR
(-)-iso
pulegol
FL/FR
spicy
ginger root oil china
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 cabbage leaf
Search Trop Picture
 cornmint oil
Search Trop Picture
 cornmint oil india @ 0.05%
Data GC Search Trop Picture
 geranium oil rwanda @ 0.29%
Data GC Search Trop Picture
 horsemint shoot
Search Trop Picture
 pennyroyal oil @ trace%
Data GC Search Trop Picture
 pennyroyal oil cuba @ 0.30%
Data GC Search Trop Picture
 peppermint leaf
Search Trop Picture
 peppermint oil CO2 extract @ 0.20%
Data GC Search Trop Picture
 stachys obliqua
Search Trop Picture
 sunflower flower
Search Trop Picture
 
Synonyms:
 cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1R,2R,5R)-
(±)-isomenthol
(1)-isomenthol
cis-1,3-cis-1,4-(±)-menthol
DL-isomenthol
(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-isopropyl-5-methylcyclohexanol
 

Articles:

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.
 
Notes:
None found
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