isopulegol
p-menth-8-en-3-ol
Identification
| Name | isopulegol |
| IUPAC | 5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol |
| CAS Number | 7786-67-6 |
| EINECS | 232-102-8 |
| FDA UNII | Search |
| Molecular Formula | C10 H18 O |
| Molecular Weight | 154.25266000 |
| Nikkaji Number | J36.816D |
Regulatory
| FEMA Number | 2962 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 89-79-2 ; ISOPULEGOL |
| FDA Regulation | FDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION |
Physical Properties
| Appearance | colorless clear liquid (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 197.00 to 198.00 °C. @ 760.00 mm Hg (est) |
| Vapor Pressure | 0.099000 mmHg @ 25.00 °C. (est) |
| Flash Point | 173.00 °F. TCC ( 78.30 °C. ) (est) |
| logP (o/w) | 2.724 (est) |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | fragrance |
Organoleptic Properties
| Odor Strength | medium , |
| Substantivity | 28 hour(s) at 100.00 % |
| Odor Description |
at 10.00 % in dipropylene glycol. Minty, cooling, medicinal, woody with a green herbaceous undernote
|
| Odor sample from | Givaudan Corporation |
| Taste Description |
minty cooling herbal eucalyptus grassy peppermint weedy earthy at 30.00 ppm.
|
Safety Information
| Preferred SDS | View |
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | oral-rat LD50 1030 ul/kg |
| Dermal Toxicity | skin-rabbit LD50 3 ml/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavor and fragrance agents |
| RIFM Fragrance Material Safety Assessment | Search |
| maximum skin levels for fine fragrances | 0.0500 % and are based on the assumption that the fragrance mixture is used at 20% in a consumer product (IFRA Use Level Survey). (IFRA, 2004) |
| Recommendation for isopulegol usage levels up to | 6.0000 % in the fragrance concentrate. |
| Dermal Systemic Exposure in Cosmetic Products | 0.0007 mg/kg/day (IFRA, 2004) |
| baked goods | 14.00000 |
| beverages(nonalcoholic) | 50.00000 |
| beverages(alcoholic) | 50.00000 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 500.00000 |
| condiments / relishes | - |
| confectionery froastings | 100.00000 |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 12.00000 |
| fruit ices | - |
| gelatins / puddings | 50.00000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 100.00000 |
| 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 | 100.00000 |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
p-
menth-8-en-3-ol
para-
menth-8-en-3-ol
8(9)-p-
menthen-3-ol
8(9)-para-
menthen-3-ol
5-
methyl-2-(1-methyl vinyl) cyclohexan-1-ol
5-
methyl-2-(1-methylvinyl)cyclohexan-1-ol
5-
methyl-2-prop-1-en-2-ylcyclohexan-1-ol
1-
methyl-4-isopropenyl cyclohexan-3-ol
iso
pulegol extra FCC
PubMed:
Intramolecular Hydrogen Transfer Reaction: Menthon from Isopulegol.
PubMed:
Airborne Antituberculosis Activity of Eucalyptus citriodora Essential Oil.
PubMed:
Saturated Long-Chain Esters of Isopulegol as Novel Permeation Enhancers for Transdermal Drug Delivery.
PubMed:
In Vivo Potential Anti-Inflammatory Activity of Melissa officinalis L. Essential Oil.
PubMed:
GABA(A) receptor modulation by terpenoids from Sideritis extracts.
PubMed:
β-Cyclodextrin as the suitable molecular container for isopulegol enantiomers.
PubMed:
Effect of unsaturated menthol analogues on the in vitro penetration of 5-fluorouracil through rat skin.
PubMed:
Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans.
PubMed:
Olfactory discrimination ability of South African fur seals (Arctocephalus pusillus) for enantiomers.
PubMed:
Revision of the stereochemistry of elisabethatriene, a putative biosynthetic intermediate of pseudopterosins.
PubMed:
Prokaryotic squalene-hopene cyclases can be converted to citronellal cyclases by single amino acid exchange.
PubMed:
MOFs as multifunctional catalysts: one-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst.
PubMed:
Activation-independent cyclization of monoterpenoids.
PubMed:
A DFT analysis of thermal decomposition reactions important to natural products.
PubMed:
Bioactivity against Tribolium castaneum Herbst (Coleoptera: Tenebrionidae) of Cymbopogon citratus and Eucalyptus citriodora essential oils grown in Colombia.
PubMed:
Characterization and antioxidant activity of essential oils from fresh and decaying leaves of Eucalyptus tereticornis.
PubMed:
Silylene-mediated ring contraction of homoallylic ethers to form allylic silanes.
PubMed:
Effects of isopulegol on pentylenetetrazol-induced convulsions in mice: possible involvement of GABAergic system and antioxidant activity.
PubMed:
Gastroprotective activity of isopulegol on experimentally induced gastric lesions in mice: investigation of possible mechanisms of action.
PubMed:
Reactivity in the confined spaces of zeolites: the interplay between spectroscopy and theory to develop structure-activity relationships for catalysis.
PubMed:
Cyclisation of citronellal over heterogeneous inorganic fluorides--highly chemo- and diastereoselective catalysts for (+/-)-isopulegol.
PubMed:
Zr-zeolite beta: a new heterogeneous catalyst system for the highly selective cascade transformation of citral to (+/-)-menthol.
PubMed:
A cavitand with a fluorous rim acts as an amine receptor.
PubMed:
Synthesis of a dialuminum-substituted silicotungstate and the diastereoselective cyclization of citronellal derivatives.
PubMed:
Fragrance Material Review on isopulegol.
PubMed:
Menthol shares general anesthetic activity and sites of action on the GABA(A) receptor with the intravenous agent, propofol.
PubMed:
Sedative effect of monoterpene alcohols in mice: a preliminary screening.
PubMed:
Central nervous system activity of acute administration of isopulegol in mice.
PubMed:
Synthesis of +-dihydro-epi-deoxyarteannuin B.
PubMed:
Probing the Lewis acidity and catalytic activity of the metal-organic framework [Cu3(btc)2] (BTC=benzene-1,3,5-tricarboxylate).
PubMed:
Enantioselective organocatalytic formal [3 + 3]-cycloaddition of alpha,beta-unsaturated aldehydes and application to the asymmetric synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
PubMed:
The essential oils from Zanthoxylum schinifolium pericarp induce apoptosis of HepG2 human hepatoma cells through increased production of reactive oxygen species.
PubMed:
The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.
PubMed:
The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel.
PubMed:
Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
PubMed:
Sn-Beta zeolite as diastereoselective water-resistant heterogeneous Lewis-acid catalyst for carbon-carbon bond formation in the intramolecular carbonyl-ene reaction.
PubMed:
Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations.
PubMed:
About the stereoelectronics of the intramolecular addition of allylsilanes to aldehydes.
PubMed:
Changes in essential oil during enzyme-assisted ensiling of lemongrass (Cymbopogon citratus Stapf.) and lemon eucalyptus (Eucalyptus citriodora Hook).
PubMed:
A short route to (-)-mintlactone by thallium(III)-mediated cyclization of (-)-isopulegol.
PubMed:
Ethnobotany, volatile oils and secretion tissues of werneria poposa from Argentina.
PubMed:
Comparison of antimicrobial properties of monoterpenes and their carbonylated products.
PubMed:
Pheromone syntheses: a tropical approach. Enantioselective synthesis of the (2R,6S,10S) and (2S,6S,10S) isomers of methyl 2,6,10-trimethyldodecanoate.