(-)-isopulegol

1R,2S,5R-isopulegol

CAS: 89-79-2 C10 H18 O MW: 154.25266000 minty minty

Identification

Name(-)-isopulegol
IUPAC(1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
CAS Number89-79-2
EINECS201-940-6
FDA UNII3TH92O3BXN
Molecular FormulaC10 H18 O
Molecular Weight154.25266000
MDL NumberMFCD00134655
Nikkaji NumberJ1.523.142D
Beilstein1906573
CoE Number2033

Regulatory

JECFA Food Flavoring755 isopulegol
DG SANTE Food Flavourings02.067 1R,2S,5R-isopulegol
FEMA Number2962
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)89-79-2 ; ISOPULEGOL
FDA RegulationFDA 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 Yes
Specific Gravity 0.90400 to 0.91300 @ 25.00 °C.
Pounds per Gallon - (est). 7.522 to 7.597
Refractive Index 1.46800 to 1.47700 @ 20.00 °C.
Melting Point 78.00 °C. @ 760.00 mm Hg
Boiling Point 216.00 to 218.00 °C. @ 760.00 mm Hg, 91.00 °C. @ 12.00 mm Hg
Acid Value 1.00 max. KOH/g
Vapor Pressure 0.099000 mmHg @ 25.00 °C. (est)
Flash Point 195.00 °F. TCC ( 90.56 °C. )
logP (o/w) 2.724 (est)
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesfragrance

Organoleptic Properties

Odor Strength medium ,
Substantivity 28 hour(s) at 100.00 %
Odor Description at 10.00 % in dipropylene glycol.
Odor sample from Sigma-Aldrich
Taste Description
minty cooling mentholic peppermint grassy herbal tropical
minty, cooling, slightly fruity

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Human Experience8 % solution: no irritation or sensitization.
Oral/Parenteral Toxicityoral-rat LD50 1030 ul/kg
Dermal Toxicityskin-rabbit LD50 3 ml/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
Recommendation for (-)-isopulegol usage levels up to6.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU)850.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)3300.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)3900 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
baked goods14.00000
beverages(nonalcoholic)50.00000
beverages(alcoholic)50.00000
breakfast cereal-
cheese-
chewing gum500.00000
condiments / relishes-
confectionery froastings100.00000
egg products-
fats / oils-
fish products-
frozen dairy12.00000
fruit ices-
gelatins / puddings50.00000
granulated sugar-
gravies-
hard candy100.00000
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 candy100.00000
soups-
sugar substitutes-
sweet sauces-
Dairy products, excluding products of category 02.0 (01.0)12.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)-
Processed fruit (04.1)-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)10.00000
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)50.00000
Bakery wares (07.0)5.00000
Meat and meat products, including poultry and game (08.0)14.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)-
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)-
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)-

Augustus Oils Ltd

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Berje Inc.

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Indukern, S.A. F&F Ingredients Division

Commitment to quality

Idukern F&F Ingredients is your partner for the fragrance and flavor ingredients.

View All Website +34 93 506 91 00 info@indukern.es

Lluch Essence S.L.

A family company dedicated to sales and distribution

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Natural Advantage

Manufacturer of natural flavor ingredients

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OQEMA

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Penta International Corporation

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Riverside Aromatics Ltd.

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Sigma-Aldrich

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Synerzine, Inc.

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Vigon International

Passion for Simplicity

Manufacturer and supplier of high quality flavor and fragrance ingredients.

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Potential Uses

FR apricot FL caramel FR cherry FR citronella FR eucalyptus oil replacer FR geranium FR herbal FR lemongrass FR mandarin FR mint oral care agents FR peach FL/FR pennyroyal FR peppermint FR plum FR raspberry FL/FR rose leaf FR spearmint FR tuberose

Natural Occurrence

cornmint oil eucalyptus citriodora hesperozygis rhododon hesperozygis ringens lemon balm shoot lemon leaf oil lemongrass plant mandarin fruit oregano shoot pepper black pepper fruit pepper black pepper seed petitgrain lemon oil rosemary plant

Synonyms

coolact P (Takasago) koolada-OBMA synthetic (1R,3R,4S)-p- menth-8-en-3-ol (1R,3R,4S)-para- menth-8-en-3-ol p-8,9- menthen-3-ol p-8(9)- menthen-3-ol para-8,9- menthen-3-ol para-8(9)- menthen-3-ol (1R-(1alpha,2beta,5alpha))-5- methyl-2-(1-methyl ethenyl) cyclohexanol (1R,2S,5R)-5- methyl-2-(1-methyl ethenyl) cyclohexanol (1R-(1alpha,2beta,5alpha))-5- methyl-2-(1-methylethenyl)cyclohexanol (1R,2S,5R)-5- methyl-2-(1-methylethenyl)cyclohexanol (1R,2R,5S)-5- methyl-2-prop-1-en-2-ylcyclohexan-1-ol (1R,2R,5S)-2-iso propenyl-5-methyl cyclohexanol (-)-L-iso pulegol (-)-laevo-iso pulegol 1R,2S,5R-iso pulegol L-iso pulegol laevo-iso pulegol iso pulegol purified PubMed: Lewis acid catalysis and Green oxidations: sequential tandem oxidation processes induced by Mn-hyperaccumulating plants. 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.