piperitol
p-menth-1-en-3-ol
 
Notes:
Flavouring material with a pungent taste
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3-methyl-6-propan-2-ylcyclohex-2-en-1-ol (Click)
CAS Number: 491-04-3Picture of molecule
ECHA EINECS - REACH Pre-Reg: 207-725-3
FDA UNII: 7UM0ILT6I7
Nikkaji Web: J6.049F
CoE Number: 10248
XlogP3-AA: 2.10 (est)
Molecular Weight: 154.25266000
Formula: C10 H18 O
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
IBM Patents: Obtain
Pubchem Patents: Search
PubMed: Search
NCBI: Search
JECFA Food Flavoring: 434  p-menth-1-en-3-ol
Flavis Number: 02.083 (Old)
DG SANTE Food Flavourings: 02.083  p-menth-1-en-3-ol
FEMA Number: 3179  p-menth-1-en-3-ol
FDA Mainterm: P-MENTH-1-EN-3-OL
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Physical Properties:
Appearance: white to pale amber crystals (est)
Assay: 97.00 to 100.00 % 
Food Chemicals Codex Listed: No
Specific Gravity: 0.93000 to 0.93600 @  25.00 °C.
Pounds per Gallon - (est).: 7.739 to  7.788
Refractive Index: 1.47620 @  25.00 °C.
Melting Point: 96.00 to  97.00 °C. @ 760.00 mm Hg
Boiling Point: 230.00 to  232.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.020000 mm/Hg @ 25.00 °C. (est)
Flash Point: 193.00 °F. TCC ( 89.44 °C. )
logP (o/w): 2.919 (est)
Soluble in:
 alcohol
 water, 360.2 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
Odor Strength: medium ,
recommend smelling in a 10.00 % solution or less
Odor Description:
at 10.00 % in dipropylene glycol. 
herbal
  
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
6-(isopropyl)-3-methylcyclohex-2-en-1-ol
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
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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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavoring agents
Recommendation for piperitol usage levels up to:
 not for fragrance use.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.02 (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: 4
Click here to view publication 4
 average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): -20.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -20.00000
fruit ices: -20.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -20.00000
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:
Flavor & Extract Manufacturers Association (FEMA) reference(s):
The FEMA GRAS assessment of alicyclic substances used as flavor ingredients.View pdf
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 212: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 212 Revision 1 (FGE.212Rev1): alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19.
View page or View pdf
Scientific Opinion on Flavouring Group Evaluation 212 Revision 3 (FGE.212Rev3): a,-unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf
EPI System: View
NLM Hazardous Substances Data Bank: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 491-04-3
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 10282
National Institute of Allergy and Infectious Diseases: Data
 3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
Chemidplus: 0000491043
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References:
 3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 491-04-3
Pubchem (cid): 10282
Pubchem (sid): 134976467
Flavornet: 491-04-3
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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
HMDB (The Human Metabolome Database): HMDB35838
FooDB: FDB014609
Haz-Map: View
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
No odor group found for these
 calamenene 
balsamic
 bornyl formateFL/FR
 frankincense absoluteFL/FR
floral
(Z)-3-hexen-1-yl salicylateFL/FR
 terpinyl isobutyrateFL/FR
green
sec-butyl-3-methyl but-2-ene thioateFL/FR
 privet dioxaneFR
herbal
 carvacryl methyl etherFL/FR
 herbal acetalFR
1-para-menthen-9-yl acetateFL/FR
T-muurololFL/FR
3-octanon-1-olFL/FR
 rosemary absoluteFL/FR
 saffron indenoneFL/FR
 safranalFL/FR
 thymyl methyl etherFL/FR
woody
 cistus twig/leaf absoluteFR
 patchouli absoluteFR
 woody acetateFR
 
For Flavor
 
No flavor group found for these
 bornyl formateFL/FR
sec-butyl-3-methyl but-2-ene thioateFL/FR
 calamenene 
 carvacryl methyl etherFL/FR
T-muurololFL/FR
3-octanon-1-olFL/FR
 saffron indenoneFL/FR
 terpinyl isobutyrateFL/FR
fruity
1-para-menthen-9-yl acetateFL/FR
green
(Z)-3-hexen-1-yl salicylateFL/FR
herbal
 rosemary absoluteFL/FR
medicinal
 frankincense absoluteFL/FR
musty
 thymyl methyl etherFL/FR
woody
 safranalFL/FR
 
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Potential Uses:
 balsam 
 herbalFL
 oriental 
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Occurrence (nature, food, other): note
 artemisia deserti krasch. oil iran @ 1.40%
Data  GC  Search Trop  Picture
 cascarilla bark oil @ 0.10%
Data  GC  Search Trop  Picture
 cumin seed
Search Trop  Picture
 dill leaf
Search Trop  Picture
 eucalyptus camaldulensis dehn. leaf oil jerusalem @ 0.10%
Data  GC  Search Trop  Picture
 horsemint plant
Search Trop  Picture
 mentha longifolia plant
Search Trop  Picture
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Synonyms:
3-carvomenthenol
2-cyclohexen-1-ol, 3-methyl-6-(1-methylethyl)-
3-hydroxy-4-isopropyl-1-methyl cyclohexene
3-hydroxy-4-isopropyl-1-methylcyclohexene
p-menth-1-en-3-ol
para-menth-1-en-3-ol
1-p-menthen-3-ol
1-para-menthen-3-ol
1-methyl-4-isopropyl-1-cyclohexen-3-ol
3-methyl-6-(1-methyl ethyl)-2-cyclohexen-1-ol
3-methyl-6-(1-methylethyl)-2-cyclohexen-1-ol
3-methyl-6-propan-2-yl cyclohex-2-en-1-ol
3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
6-isopropyl-3-methylcyclohex-2-en-1-ol
6-(isopropyl)-3-methyl cyclohex-2-en-1-ol
6-(isopropyl)-3-methylcyclohex-2-en-1-ol
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Articles:
PubMed: Anti-inflammatory, antinociceptive activity of an essential oil recipe consisting of the supercritical fluid CO2 extract of white pepper, long pepper, cinnamon, saffron and myrrh in vivo.
PubMed: Is differential use of Juniperus monosperma by small ruminants driven by terpenoid concentration?
PubMed: Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer.
PubMed: Effect of unsaturated menthol analogues on the in vitro penetration of 5-fluorouracil through rat skin.
PubMed: An expedient approach to the total synthesis of (+)-5-epi-eudesm-4(15)-ene-1β,6β-diol.
PubMed: Comparative study of volatile oil compositions of two Plectranthus species from northern India.
PubMed: Identification of methanol-soluble compounds in sesame and evaluation of antioxidant potential of its lignans.
PubMed: Quantitative determination of 10 phenylpropanoid and lignan compounds in Lancea tibetica by high-performance liquid chromatography with UV detection.
PubMed: Secondary metabolites and cytotoxic activities from the stem bark of Zanthoxylum nitidum.
PubMed: Lignan derivatives from the stem bark of Syzygium cumini (L.) Skeels.
PubMed: Composition and antifungal activity of the essential oil of the Brazilian Chenopodium ambrosioides L.
PubMed: Fragrance material review on 4-carvomenthenol.
PubMed: Hinokinin biosynthesis in Linum corymbulosum Reichenb.
PubMed: Anti-inflammatory and analgesic activities of the ethanolic extracts from Zanthoxylum riedelianum (Rutaceae) leaves and stem bark.
PubMed: Formation of two methylenedioxy bridges by a Sesamum CYP81Q protein yielding a furofuran lignan, (+)-sesamin.
PubMed: Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin.
PubMed: Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare L.: determination of optimal extraction parameters.
PubMed: Cinnamylphenols from Phyllodium pulchellum.
PubMed: Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.
PubMed: Chemical constituents and biological activities of Zanthoxylum usambarense.
PubMed: [GC-MS analysis of supercritical carbon dioxide extraction products from pericarp of Zanthoxylum bungeanum].
PubMed: Separation and NMR studies on lignans of Raulinoa echinata.
PubMed: Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum.
PubMed: Evaluation of the trypanocidal activity of lignans isolated from the leaves of Zanthoxylum naranjillo.
PubMed: Insecticidal activity of monoterpenoids to western corn rootworm (Coleoptera: Chrysomelidae), twospotted spider mite (Acari: Tetranychidae), and house fly (Diptera: Muscidae).
PubMed: Isolation and identification of house fly,Musca domestica L., repellents from pepper tree,Schinus molle L.
PubMed: (+)-Piperitol from Paulownia tomentosa.
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