D-Menthol - ≥99% , Activator of TRPM8, CAS No.15356-60-2, Activator of TRPM8

CAS: 15356-60-2 Cat. No.: M105270 Formula: C₁₀H₂₀O Molecular Weight: 156.27 Beilstein Registry Number: 1902292 EC Number: 239-387-8 PubChem CID: 165675

GRADE & PURITY ≥99%

Synonyms

(1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol|(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol|(1S,2R,5S)-Menthol|(1S,2R,5S)-2-Isopropyl-5-methylcyclohexan-1-ol|Menthol, cis-1,3,trans-1,4-|3-p-Menthanol|Menthol, (+)-|(1S,2R,5S)-5-methyl-2-propan-2-yl-cyclohexan-1-ol|(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol|(.+/-.)-Menthol|Cyclohexanol,5-methyl-2-(1-methylethyl)-,(1S,2R,5S)-|MEFENOREX HYDROCHLORIDE, (+/-)-|(+)-(1S,2R,5S)-menthol|5-Methyl-2-(1-methylethyl)cyclohexanol, (1.alpha.,2.beta.,5.alpha.)-|Cyclohexanol, 2-isopropyl-5-methyl-, (1.alpha.,2.beta.,5.alpha.)-|(+/-)-Menthol|(+/-)-Menthol racemic|p-Menthan-3-ol|(1s, 2r, 5s)-(+)-menthol|(1S,2R,5S)-(+)-Menthol|Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)-|Benzeneethanamine, alpha-methyl-N-(2,2,2-trichloroethylidene)-|Fancol menthol|Racemic menthol|(1S,2R,5S)-5-methyl-2-propan-2-yl-1-cyclohexanol|Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S-(1alpha,2beta,5alpha))-|(DL)-Menthol|(+)-Menthol|2-Isopropyl-5-methylcyclohexanol, (1.alpha.,2.beta.,5.alpha.)-|(1S)-(+)-menthol|d-Menthol|5.alpha.-Methyl-2.beta.-(1.alpha.-methylethyl)cyclohexanol|rac-Menthol|Menthol, (1S,3S,4R)-(+)-|(1S,2R,5S)-5-methyl-2-(1-methylethyl)cyclohexanol|Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1.alpha.,2.beta.,5.alpha.)-|MENTHOL, D-|(+)-(1S,3S,4R)-menthol

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

(1S,2R,5S)-(+)-menthol is a chiral secondary alcohol. Its alcohol group can be protected as 2-tetrahydrofuranyl ether by reacting with bromotrichloromethane and tetrahydrofuran.

(1S,2R,5S)-(+)-menthol can undergo acylation with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate to form the corresponding acylated products.

Specifications

Synonyms

(1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol | (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol | (1S,2R,5S)-Menthol | (1S,2R,5S)-2-Isopropyl-5-methylcyclohexan-1-ol | Menthol, cis-1,3,trans-1,4- | 3-p-Menthanol | Menthol, (+)- | (1S,2R,5S)-5-methyl-2-propan-2-yl-cyclohexan-1-ol | (1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol | (.+/-. Show more

Specifications & Purity

≥99%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

ACTIVATOR

Mechanism of action

Activator of TRPM8

Purity

≥99%

Names and Identifiers

Canonical Smiles

CC1CCC(C(C1)O)C(C)C

IUPAC Name

(1S,2R,5S)-5-methyl-2-propan-2-ylcyclohexan-1-ol

InChIKey

NOOLISFMXDJSKH-AEJSXWLSSA-N

INCHI

1S/C10H20O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-11H,4-6H2,1-3H3/t8-,9+,10-/m0/s1

Isomeric SMILES

C[C@H]1CC[C@@H]([C@H](C1)O)C(C)C

WGK Germany

2

RTECS

OT0700000

Alternate CAS

15356-70-4,15356-60-2,89-78-1

PubChem CID

165675

Molecular Weight

156.27

Beilstein

1902292

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-menthan-3-ol

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)

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in methanol (almost transparency), chloroform, alcohols, water (456 mg/l at 25 °C), and ether.
• Specific Rotation[α]: 50 ° (C=10, EtOH)
• Flash Point(°F): 213.8 °F
• Flash Point(°C): 101 °C
• Boil Point(°C): 103-104 °C/9 mmHg
• Melt Point(°C): 42°C
• Molecular Weight: 156.260 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 156.151 Da
• Monoisotopic Mass: 156.151 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 120.000
• 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

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 15356-60-2, the molecular formula is C10H20O, and the molecular weight is 156.27 g/mol. InChIKey NOOLISFMXDJSKH-AEJSXWLSSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.