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

• ChemBase ID: 148769
• Molecular Formular: C10H20O
• Molecular Mass: 156.2652
• Monoisotopic Mass: 156.15141526
• SMILES: C[C@H]1CC[C@@H]([C@H](C1)O)C(C)C
• Canonical SMILES: C[C@H]1CC[C@@H]([C@H](C1)O)C(C)C
• InChI: 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
• InChIKey: NOOLISFMXDJSKH-AEJSXWLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• IUPAC Traditional name: menthol (L)
• Synonyms: (1S,2R,5S)-5-Methyl-2-(1-methylethyl)cyclohexanol; [1S-(1α,2β,5α)]-5-Methyl-2-(1-methylethyl)c; yclohexanol; (1S,3S,4R)-(+)-Menthol; (1S,2R,5S)-(+)-Menthol; (1S,2R,5S)-Menthol; d-Menthol; (1S,2R,5S)-(+)-Menthol; (1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol; L-Menthol; (+)-Menthol; D-Menthol; (+)-Menthol; (1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol; (1S,2R,5S)-(+)-Menthol; L-薄荷醇; (+)-薄荷醇; (+)-薄荷醇; (1S,2R,5S)-2-异丙基-5-甲基环己醇; D-薄荷醇

Database IDs

• CAS Number: 15356-60-2; 2216-51-5
• EC Number: 239-387-8; 218-690-9
• MDL Number: MFCD00062983; MFCD00062979
• Beilstein Number: 1902293; 1902292
• Merck Index: 145837
• PubChem SID: 24853440; 162242944
• PubChem CID: 165675

CALCULATED PROPERTIES

• Acid pKa: 19.549648
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.664273
• LogD (pH = 7.4): 2.6642733
• Log P: 2.6642733
• Molar Refractivity: 47.4453 cm^3
• Polarizability: 19.046404 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Low Melting Solid
• Melting Point: ~43 °C; 39-41°C; 41-44°C; 42-45°C; 43 - 44°C; 43-44 °C(lit.)
• Boiling Point: 103-104 °C/9 mmHg(lit.); 104-105°C/10mm; 212-216°C
• Flash Point: 101 °C; 213.8 °F; 91°C(195°F); 93°C(199°F)
• Density: 0.89; 0.890
• Vapor Pressure: 0.8 mmHg ( 20 °C)
• Optical Rotation: [α]20/D +49±1°, c = 10% in ethanol; [α]23/D +48°, c = 10 in ethanol; +49 (c=10 in ethanol); -50 (c=10 in ethanol)
• Hydrophobicity(logP): 3.233

Safety Information

• RTECS: OT0350000; OT0700000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 37/38-41
• Safety Statements: 26-37/39; 26-37/39-60; 26-39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335; H318-H315-H335; H318-H315-H335-H303
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... UGT1A4(54657)

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95%; 99%
• Grade: puriss. p.a.; terpene standard for GC
• Optical Purity: ee: 96% (GLC); enantiomeric ratio: ≥98.5:1.5 (GC)
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C10H20O

DETAILS

Sigma Aldrich - 224464

Packaging
10, 50 g in glass bottle

Toronto Research Chemicals - M218885

D-Menthol is used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation.

REFERENCES

• Ikaheimo, I., et al.: J. Antimicrob. Chemother., 46, 287 (2000)
• Gillet, Y., et al.: Lancet, 359, 753 (2000)
• Turos, E., et al.: Bioorg. Med. Chem. Lett., 2002, 12, 2229 (2000)
• The L-menthyl ester of succinic acid has been used in a chiral synthesis of (1S,2S)-cyclopropanedicarboxylic acid: Org. Synth. Coll., 8, 141 (1993):
  
• One recrystallization gives the pure enantiomer.