(−)-Isopulegol - Moligand™, ≥99% , CAS No.89-79-2

CAS: 89-79-2 Cat. No.: I434325 Molecular Weight: 154.25 EC Number: 201-940-6

GRADE & PURITY Moligand™, ≥99%

Synonyms

AS-10358 | EINECS 256-557-7 | Isopulegol | (1R,3R,4S)-P-METH-8-EN-3-OL | 5-Methyl-2-(1-methylethenyl)cyclohexanol, (1R-(1alpha,2beta,5alpha))- | GTPL2462 | NVG8YK55NL | p-8(9)-Menthen-3-ol | Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R,2S,5R)- | DTXSI

Storage

Room temperature

Overview

Isopulegol is monoterpene alcohol, a useful ingredient for the production of fragrances in perfume industries. It is also used as a starting material in the manufacture of menthol by the hydrogenation process. Menthol is an important component in cosmetics, pharmaceuticals, and toothpaste.

Application

(−)-Isopulegol can be used as a starting material for the enantioselective preparation of: 8-arylmenthols by Smiles-Truce rearrangement of aryl sulfonates.,· Stereoisomers of 5,9-dimethylpentadecane. Octahydro-2 H -chromen-4-ol by Prins cyclization with vanillin in the presence of montmorillonite clay as the catalyst. p -menthane-3,8,9-triol by catalytic Sharpless dihydroxylation.

Specifications

Synonyms

AS-10358 | EINECS 256-557-7 | Isopulegol | (1R, 3R, 4S)-P-METH-8-EN-3-OL | 5-Methyl-2-(1-methylethenyl)cyclohexanol, (1R-(1alpha, 2beta, 5alpha))- | GTPL2462 | NVG8YK55NL | p-8(9)-Menthen-3-ol | Cyclohexanol, 5-methyl-2-(1-methylethenyl)-, (1R, 2S, 5R)- | DTXSI

Specifications & Purity

Moligand™, ≥99%

Storage

Room temperature

Grade

Moligand™

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC1CCC(C(C1)O)C(=C)C
• IUPAC Name: (1R,2S,5R)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol
• InChIKey: ZYTMANIQRDEHIO-KXUCPTDWSA-N
• INCHI: 1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-11H,1,4-6H2,2-3H3/t8-,9+,10-/m1/s1
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)O)C(=C)C
• Alternate CAS: 89-79-2,50373-36-9,59905-53-2,7786-67-6
• NSC Number: 1263
• MeSH Entry Terms: isopulegol
• Molecular Weight: 154.25
• Reaxy-Rn: 4128962
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4128962&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Prenol lipids
      • Subclass Monoterpenoids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Prenol lipids
• Subclass: Monoterpenoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Menthane monoterpenoids
• Alternative Parents: Monocyclic monoterpenoids Cyclohexanols Cyclic alcohols and derivatives Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: P-menthane monoterpenoid - Monocyclic monoterpenoid - Cyclohexanol - Cyclic alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Alcohol - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
• External Descriptors: p-menthane monoterpenoid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TRPM8 Tclin Transient receptor potential cation channel subfamily M member 8 (1 Activities)

Discover Target: TRPM8

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Associated Targets(non-human)

Mycobacterium tuberculosis (203094 Activities)

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Plasmodium falciparum (966862 Activities)

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Candida albicans (78123 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 154.250 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 154.136 Da
• Monoisotopic Mass: 154.136 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 151.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1