isomenthol
DL-isomenthol
 
Notes:
None found
  • BOC Sciences
    • BOC Sciences
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      Product(s):
      3623-52-7 DL-isoMenthol
       
  • CSA
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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
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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:
 alcohol
 water, 434.5 mg/L @ 25 °C (est)
Insoluble in:
 paraffin oil
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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).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
DL-isoMenthol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the CSA
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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: 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 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: --
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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
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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: 3623-52-7
Pubchem (cid): 19244
Pubchem (sid): 134984255
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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%
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Potential Blenders and core components note
 
For Odor
alcoholic
alcoholic
isopropyl alcoholFL/FR
balsamic
laevo-borneolFL/FR
dextro,laevo-borneolFL/FR
isobornyl methyl etherFL/FR
 myrrh absoluteFL/FR
earthy
(-)-alpha-fencholFL/FR
floral
 bois de rose oil peruFL/FR
fruity
 menthyl isovalerateFL/FR
herbal
 geranic oxideFL/FR
spike lavender oilFL/FR
 origanum oilFL/FR
 origanum oil greeceFL/FR
 piperitoneFL/FR
 rosemary absoluteFL/FR
 rosemary oilFL/FR
 rosemary oil africaFL/FR
 rosemary oil moroccoFL/FR
 rosemary oil spainFL/FR
 rosemary oil tunisiaFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil chinaFL/FR
 cornmint oil indiaFL/FR
 cornmint oil terpenelessFL/FR
dextro,laevo-neomentholFL/FR
dextro-neomentholFL/FR
(±)-mentholFL/FR
dextro,laevo-mentholFL/FR
neoisomentholFL/FR
laevo-mentholFL/FR
(+)-menthoneFL/FR
(±)-isomenthoneFL/FR
 menthyl acetateFL/FR
laevo-menthyl acetateFL/FR
 menthyl acetate racemicFL/FR
 peppermint cyclohexanoneFL/FR
dextro-piperitoneFL/FR
minty
 cornmint oil japanFL/FR
 mentha piperita extractFL/FR
 mentha piperita flower/leaf/stem extractFL/FR
 mentha piperita tinctureFL/FR
homomentholFL/FR
(±)-menthoneFL/FR
(-)-menthoneFL/FR
laevo-menthyl lactateFL/FR
2-methyl cyclohexanoneFL/FR
 pennyroyal herb oil americaFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil cubaFL/FR
 pennyroyal oil fractionsFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil terpenesFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint absoluteFL/FR
 peppermint distillatesFL/FR
 peppermint oilFL/FR
 peppermint oil americaFL/FR
 peppermint oil brazilFL/FR
 peppermint oil chinaFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil dementholizedFL/FR
 peppermint oil englandFL/FR
 peppermint oil franceFL/FR
 peppermint oil hungaryFL/FR
 peppermint oil idahoFL/FR
 peppermint oil indiaFL/FR
 peppermint oil mongoliaFL/FR
 peppermint oil montanaFL/FR
 peppermint oil moroccoFL/FR
 peppermint oil russiaFL/FR
 peppermint oil special fractionsFL/FR
 peppermint oil tasmaniaFL/FR
 peppermint oil terpenelessFL/FR
 peppermint oil willametteFL/FR
 peppermint oil yakimaFL/FR
 peppermint waterFL/FR
laevo-piperitoneFL/FR
(-)-isopulegolFL/FR
(R)-(+)-pulegoneFR
isopulegoneFL/FR
musty
ketoisophoroneFL/FR
spicy
 ginger root oil chinaFL/FR
white sassafras oilFL/FR
 
For Flavor
 
No flavor group found for these
dextro,laevo-borneolFL/FR
isobornyl methyl etherFL/FR
dextro,laevo-neomentholFL/FR
neoisomentholFL/FR
 menthyl acetate racemicFL/FR
2-methyl cyclohexanoneFL/FR
isopulegoneFL/FR
white sassafras oilFL/FR
alcoholic
isopropyl alcoholFL/FR
balsamic
 myrrh absoluteFL/FR
camphoreous
laevo-borneolFL/FR
(-)-alpha-fencholFL/FR
 geranic oxideFL/FR
 rosemary oil tunisiaFL/FR
citrus
ketoisophoroneFL/FR
cooling
spike lavender oilFL/FR
dextro,laevo-mentholFL/FR
laevo-mentholFL/FR
 menthyl acetateFL/FR
laevo-menthyl lactateFL/FR
 peppermint oil americaFL/FR
floral
 bois de rose oil peruFL/FR
fruity
 menthyl isovalerateFL/FR
herbal
 origanum oilFL/FR
 origanum oil greeceFL/FR
 rosemary absoluteFL/FR
 rosemary oilFL/FR
 rosemary oil africaFL/FR
 rosemary oil moroccoFL/FR
 rosemary oil spainFL/FR
mentholic
 cornmint oilFL/FR
 cornmint oil terpenelessFL/FR
(±)-mentholFL/FR
dextro-neomentholFL/FR
 menthol flavorFL
(+)-menthoneFL/FR
 peppermint cyclohexanoneFL/FR
minty
 cornmint oil chinaFL/FR
 cornmint oil indiaFL/FR
 cornmint oil japanFL/FR
 mentha piperita extractFL/FR
 mentha piperita flower/leaf/stem extractFL/FR
 mentha piperita tinctureFL/FR
homomentholFL/FR
(±)-isomenthoneFL/FR
(±)-menthoneFL/FR
(-)-menthoneFL/FR
laevo-menthyl acetateFL/FR
 mint flavorFL
 pennyroyal herb oil americaFL/FR
 pennyroyal oilFL/FR
 pennyroyal oil cubaFL/FR
 pennyroyal oil fractionsFL/FR
 pennyroyal oil spainFL/FR
 pennyroyal oil terpenesFL/FR
 pennyroyal oil uruguayFL/FR
 peppermint absoluteFL/FR
 peppermint distillatesFL/FR
 peppermint oilFL/FR
 peppermint oil brazilFL/FR
 peppermint oil chinaFL/FR
 peppermint oil CO2 extractFL/FR
 peppermint oil dementholizedFL/FR
 peppermint oil englandFL/FR
 peppermint oil franceFL/FR
 peppermint oil hungaryFL/FR
 peppermint oil idahoFL/FR
 peppermint oil indiaFL/FR
 peppermint oil mongoliaFL/FR
 peppermint oil montanaFL/FR
 peppermint oil moroccoFL/FR
 peppermint oil russiaFL/FR
 peppermint oil special fractionsFL/FR
 peppermint oil tasmaniaFL/FR
 peppermint oil terpenelessFL/FR
 peppermint oil willametteFL/FR
 peppermint oil yakimaFL/FR
 peppermint waterFL/FR
dextro-piperitoneFL/FR
 piperitoneFL/FR
laevo-piperitoneFL/FR
(-)-isopulegolFL/FR
spicy
 ginger root oil chinaFL/FR
 
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Potential Uses:
None Found
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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
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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
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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.
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