para-menthane-3,8-diol
2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
 
Notes:
derived from the leaves of the lemon eucalyptus, corymbia citriodora; a leech repellent.
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2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol (Click)
CAS Number: 42822-86-6Picture of molecule
ECHA EINECS - REACH Pre-Reg: 255-953-7
Nikkaji Web: J309.978D
Beilstein Number: 2552262
MDL: MFCD00191551
XlogP3-AA: 2.20 (est)
Molecular Weight: 172.26780000
Formula: C10 H20 O2
NMR Predictor: Predict (works with chrome or firefox)
EFSA/JECFA Comments: Racemate.
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
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 1416  p-menthane-3,8-diol
Flavis Number: 02.246 (Old)
DG SANTE Food Flavourings: 02.246  p-menthane-3,8-diol
FEMA Number: 4053  p-menthane-3,8-diol
FDA Mainterm: P-MENTHANE-3,8-DIOL
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Physical Properties:
Appearance: white crystals (est)
Assay: 99.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.97600 to 0.98200 @  25.00 °C.
Pounds per Gallon - (est).: 8.121 to  8.171
Melting Point: 34.00 to  35.00 °C. @ 760.00 mm Hg
Boiling Point: 266.00 to  268.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.001000 mm/Hg @ 25.00 °C. (est)
Flash Point: 248.00 °F. TCC ( 120.00 °C. )
logP (o/w): 1.374 (est)
Soluble in:
 alcohol
 water, slightly
 water, 670.7 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Type: herbal
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
 minty  herbal  eucalyptus  
Odor Description:
at 10.00 % in dipropylene glycol. 
minty herbal eucalyptus
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: hair conditioning
oral care agents
skin conditioning
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Suppliers:
BOC Sciences
For experimental / research use only.
p-Menthane-3,8-diol 99%
Lipo Chemicals
Coolact® 38D
Odor: characteristic
Use: Coolact® 38D is a sensory agent that provides a cooling effect to the skin. The product functions by directly stimulating the receptors at the nerve endings of the skin to produce a cooling sensation.
Parchem
para-menthane-3,8-diol
Sigma-Aldrich: Aldrich
For experimental / research use only.
(+)-CIS-P-MENTHANE-3,8-DIOL
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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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
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Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for para-menthane-3,8-diol usage levels up to:
  5.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 39.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 18.00 (μg/capita/day)
Structure Class: I
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: 21. Update in publication number(s): 25
Click here to view publication 21
 average usual ppmaverage maximum ppm
baked goods: 100.00000120.00000
beverages(nonalcoholic): 48.0000050.00000
beverages(alcoholic): 40.0000050.00000
breakfast cereal: 20.0000050.00000
cheese: 50.0000075.00000
chewing gum: 1500.000002000.00000
condiments / relishes: 50.00000100.00000
confectionery froastings: 200.00000350.00000
egg products: --
fats / oils: 100.00000500.00000
fish products: --
frozen dairy: 5.0000025.00000
fruit ices: 5.0000025.00000
gelatins / puddings: 150.00000200.00000
granulated sugar: 5.0000025.00000
gravies: 35.0000040.00000
hard candy: 500.00000800.00000
imitation dairy: 75.00000100.00000
instant coffee / tea: 25.0000050.00000
jams / jellies: 150.00000175.00000
meat products: --
milk products: 75.00000100.00000
nut products: 15.0000050.00000
other grains: --
poultry: --
processed fruits: 20.00000150.00000
processed vegetables: 20.0000075.00000
reconstituted vegetables: 20.0000025.00000
seasonings / flavors: 15.0000030.00000
snack foods: 15.0000030.00000
soft candy: 500.00000750.00000
soups: 15.0000025.00000
sugar substitutes: --
sweet sauces: 25.00000300.00000
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Safety References:
European Food Safety Athority(efsa): Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...
European Food Safety Authority (EFSA) reference(s):
Flavouring Group Evaluation 9, Revision 1: (FGE.09 Rev1)[1] - Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical groups 8 and 30, and an ester of a phenol carboxylic acid from chemical group 25 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf
Flavouring Group Evaluation 9, Revision 2 (FGE.09Rev2): Secondary alicyclic saturated and unsaturated alcohols, ketones and esters containing secondary alicyclic alcohols from chemical group 8 and 30, and an ester of a phenol derivative from chemical group 25
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 96 (FGE.96): Consideration of 88 flavouring substances considered by EFSA for which EU production volumes / anticipated production volumes have been submitted on request by DG SANCO. Addendum to FGE. 51, 52, 53, 54, 56, 58, 61, 62, 63, 64, 68, 69, 70, 71, 73, 76, 77, 79, 80, 83, 84, 85 and 87.
View page or View pdf
EPI System: View
ClinicalTrials.gov: search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 556998
National Institute of Allergy and Infectious Diseases: Data
 2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
Chemidplus: 0042822866
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References:
 2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 556998
Pubchem (sid): 135251241
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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
FDA Everything Added to Food in the United States (EAFUS): View
CHEBI: View
HMDB (The Human Metabolome Database): HMDB36145
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
Read: Under the conditions of intended use - New developments in the FEMA GRAS program and the safety assessment of flavor ingredients
Read: A GRAS assessment program for flavor ingredients
Read: Sensory testing for flavorings with modifying properties. Food Technology
Read: Criteria for the safety evaluation of flavoring substances
Read: A procedure for the safety evaluation of natural flavor complexes used as ingredients in food: essential oils
Read: FEMA Expert Panel: 30 Years of safety evaluation for the flavor industry
Read: Consumption ratio and food predominance of flavoring materials
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Potential Blenders and core components note
 
For Odor
anisic
 estragoleFL/FR
camphoreous
 herbal ethanoneFR
citrus
 petitgrain combava oilFR
floral
 menthadienyl formateFR
1,8-cineoleFL/FR
ortho-cresyl salicylateFL/FR
isodihydrolavandulolFR
(Z)-isodihydrolavandulyl acetateFR
 herbal undecaneFR
 herbal undecanolFR
 hyssop oilFL/FR
spike lavender oilFL/FR
spike lavender oil spainFL/FR
 melaleuca leucadendron cajaputi oilFL/FR
 niaouli oilFR
 piperitoneFL/FR
 rosemary absoluteFL/FR
 sabinene hydrateFL/FR
mentholic
 cornmint oilFL/FR
laevo-menthyl acetateFL/FR
minty
homomenthyl acetateFL/FR
spicy
 elettaria cardamomum seed oilFL/FR
 marjoram oil (thymus mastichina) spainFL/FR
thujonic
 sage oil dalmatianFL/FR
 
For Flavor
 
No flavor group found for these
ortho-cresyl salicylateFL/FR
 melaleuca leucadendron cajaputi oilFL/FR
 piperitenone oxideFL
 piperitoneFL/FR
cooling
spike lavender oilFL/FR
homomenthyl acetateFL/FR
 sabinene hydrateFL/FR
herbal
2-acetoxy-1,8-cineoleFL
1,8-cineoleFL/FR
 hyssop oilFL/FR
spike lavender oil spainFL/FR
 rosemary absoluteFL/FR
licorice
 estragoleFL/FR
mentholic
 cornmint oilFL/FR
minty
laevo-menthyl acetateFL/FR
spicy
 elettaria cardamomum seed oilFL/FR
 marjoram oil (thymus mastichina) spainFL/FR
thujonic
 sage oil dalmatianFL/FR
 
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Potential Uses:
 hair conditioning 
 herbalFR
 mintFR
 oral care agents 
 skin conditioning 
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Occurrence (nature, food, other): note
 litsea cubeba
Search Trop  Picture
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Synonyms:
 citriodiol
 cubebaol
 cyclohexanemethanol, 2-hydroxy-a,a,4-trimethyl-
 cyclohexanol, 2-(2-hydroxy-2-propyl)-5-methyl-
2-(1-hydroxy-1-methyl ethyl)-5-methyl cyclohexanol
2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanol
1-hydroxy-2-(1-methyl-1-hydroxyethyl)-5-methyl cyclohexane
2-hydroxy-a,a,4-trimethylcyclohexane methanol
2-(2-hydroxypropan-2-yl)-5-methylcyclohexan-1-ol
2-(2-hydroxypropan-2-yl)-5-methylcyclohexanol
(1alpha,3beta,4beta)-p-menthan-3,8-diol
(1alpha,3beta,4beta)-para-menthan-3,8-diol
p-menthan-3,8-diol
para-menthan-3,8-diol
(1alpha,3beta,4beta)-p-menthane-3,8-diol
(1alpha,3beta,4beta)-para-menthane-3,8-diol
p-menthane-3,8-diol
isopulegol hydrate
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Articles:
PubMed: Assessing the efficacy of candidate mosquito repellents against the background of an attractive source that mimics a human host.
PubMed: A push-pull system to reduce house entry of malaria mosquitoes.
PubMed: The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. - a literature review.
PubMed: [Field efficacy of repellent formulation containing para-menthane-3,8-diol and lemongrass against Culicoides pachymerus (Diptera: Ceratopogonidae) in Colombia].
PubMed: Efficacy testing of several Ixodes ricinus tick repellents: different results with different assays.
PubMed: Repellents and acaricides as personal protection measures in the prevention of tick-borne diseases.
PubMed: Efficacy of DEET and non-DEET-based insect repellents against bites of Simulium damnosum vectors of onchocerciasis.
PubMed: [Studies on anti-tumor metastatic constituents from Lindera glauca].
PubMed: Metabolism of (+)- and (-)-menthols by CYP2A6 in human liver microsomes.
PubMed: Patent literature on mosquito repellent inventions which contain plant essential oils--a review.
PubMed: [Personal protection measures against blood-sucking insects and ticks].
PubMed: Efficacy and safety of catnip (Nepeta cataria) as a novel filth fly repellent.
PubMed: Dihydronepetalactones deter feeding activity by mosquitoes, stable flies, and deer ticks.
PubMed: Percutaneous absorption of an insect repellent p-menthane-3,8-DIOL: a model for human dermal absorption.
PubMed: Effective insect repellent formulation in both surfactantless and classical microemulsions with a long-lasting protection for human beings.
PubMed: Acaricidal effects of Corymbia citriodora oil containing para-menthane-3,8-diol against nymphs of Ixodes ricinus (Acari: Ixodidae).
PubMed: Repellency of MyggA Natural spray (para-menthane-3,8-diol) and RB86 (neem oil) against the tick Ixodes ricinus (Acari: Ixodidae) in the field in east-central Sweden.
PubMed: PMD, a registered botanical mosquito repellent with deet-like efficacy.
PubMed: Repellency of oils of lemon eucalyptus, geranium, and lavender and the mosquito repellent MyggA natural to Ixodes ricinus (Acari: Ixodidae) in the laboratory and field.
PubMed: Efficacy of repellent products against caged and free flying Anopheles stephensi mosquitoes.
PubMed: [Extraction and determination of volatile constituents in leaves of Eucalyptus citriodora].
PubMed: Laboratory and field tests of the effectiveness of the lemon-eucalyptus extract, Citridiol, as a repellent against land leeches of the genus Haemadipsa (Haemadipsidae).
PubMed: Laboratory evaluation of mosquito repellents against Aedes albopictus, Culex nigripalpus, and Ochierotatus triseriatus (Diptera: Culicidae).
PubMed: Enhancement effect of p-menthane-3,8-diol on in vitro permeation of antipyrine and indomethacin through Yucatan micropig skin.
PubMed: Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and deet to black salt marsh mosquitoes (Diptera: Culicidae) in the Everglades National Park.
PubMed: Repellent activities of stereoisomers of p-menthane-3,8-diols against Anopheles gambiae (Diptera: Culicidae).
PubMed: Efficacy of three insect repellents against the malaria vector Anopheles arabiensis.
PubMed: Evaluation of a eucalyptus-based repellent against Anopheles spp. in Tanzania.
PubMed: Studies on the metabolism of l-menthol in rats.
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