Basic information
- CAS
50373-36-9- Standard SMILES
C=C(C)[C@@H]1CC[C@@H](C)C[C@H]1O- InChIKey
ZYTMANIQRDEHIO-KXUCPTDWSA-N- Molecular formula
- C10H18O
- Average molar mass
- 154.25 g/mol
Overview
Isopulegol is a p-menthane monoterpenoid. It has a role as a metabolite.
Names & identifiers
- Preferred name
- (-)-Isopulegol
- IUPAC
- (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
- English name
- ISOPULEGOL
- Molecular formula
- C10H18O
- Molecular weight
- 154.25
Names & synonyms
(-)-IsopulegolIsopulegol89-79-2l-Isopulegolcoolact P(1R,2S,5R)-5-METHYL-2-(PROP-1-EN-2-YL)CYCLOHEXAN-1-OLFEMA No. 29623TH92O3BXN(1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-olNSC-231369DTXSID5047116RefChem:792269
Show more names
DL-ISOPULEGOL(?)-IsopulegolFEMA 2962(-)-Isopulegol 99%ISOPULEGOL 99+%ISOPULEGOL, (-)-
DTXCID501764296201-940-6p-Menth-8-en-3-ol50373-36-9Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-(-)-L-Isopulegol(1R,2S,5R)-2-Isopropenyl-5-methylcyclohexanolNVG8YK55NL
Database identifiers
- CAS
50373-36-9、59905-53-2、89-79-2- PubChem CID
- 170833
- DTXSID
DTXSID5047116- ChEMBL
CHEMBL237994- ChEBI
CHEBI:70479- UNII
- 3TH92O3BXN、NVG8YK55NL
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 151
Experimental & physicochemical properties
FragrancesFragrance Ingredient (Isopulegol) -> IFRA transparency List
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.904-0.913
Flavoring AgentsEU Flavoring substances
Solubility
slightly soluble in water; soluble in oils
miscible (in ethanol)
Boiling Point
216.00 to 218.00 °C. @ 760.00 mm Hg
218 °C
Melting Point78 °C
Refractive Index1.468-1.477
Physical Description
Liquid
Solid
Colourless liquid, minty-herbaceous, bitter-sweet, harsh, camphoraceous odour
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for < 0.1% (1 of 1823) of reports.
Warning
H302 (> 99.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1823 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
Hazard information
Regulatory Information
Chemical: Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, [1R-(1.alpha.,2.beta.,5.alpha.)]-
Regulation (EC) No 1831/2003 (amended)
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 16-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11447
Isopulegol: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Pulegone and related substances: Human health tier II assessment
Hazard Classes and Categories
Acute Tox. 4 (> 99.9%)
Flam. Liq. 3 (100%)
Carcinogenicity - category 2
Safety data
- F
- 10-23
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
Chemistry & industry
Pharmacology
Cellular LocationsExtracellular
Uses & manufacturing
U.S. Production2023: 15,884 lb
Consumer UsesOther
Industry UsesFragrance
Household Products
Information on 2 consumer products that contain Isopulegol in the following categories is provided:
Information on 1 consumer products that contain Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel- in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Other (requires additional information)
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-: ACTIVE
Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)-rel-: ACTIVE
Applications
DescriptionSynthesis: Several stereoisomers are possible; only l-isopulegol and d-α-isopulegol have been isolated from mixtures of alcohols obtained by cyclization of d-citronellal.
Description(–)-Isopulegol is a monoterpene that has been found in the essential oils of several aromatic plants, including Cannabis, with diverse biological activities. It has antibacterial activity against S. aureus, E. faecium, E. coli, and M. smegmatis (MICs = 0.78, 12.5, 0.78, and 1.56 μl/ml, respectively, in an agar diffusion assay) and antifungal activity against C. albicans and A. niger (MIC = 1.56 μl/ml for both in an agar diffusion assay). (–)-Isopulegol inhibits C. albicans morphogenesis, adhesion, and biofilm formation (MICs = 0.125, 4, and 0.25 mg/ml, respectively). In vivo, (–)-isopulegol (50 mg/kg, i.p.) increases immobility time in the forced swim and tail suspension tests and increases the number of head dips in a hole board test and time spent in the open arms of the elevated plus maze in mice, indicating depressant- and anxiolytic-like activity. It reduces the size of ulcerated lesions in the stomach in mouse models of ethanol- and indomethacin-induced gastric lesions when administered at a dose of 100 mg/kg.
Related reactions
25 records
Compound notes
Loading…