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

• ChemBase ID: 704
• Molecular Formular: C10H20O
• Molecular Mass: 156.2652
• Monoisotopic Mass: 156.15141526
• SMILES: O[C@H]1[C@@H](CC[C@H](C1)C)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-/m1/s1
• InChIKey: NOOLISFMXDJSKH-KXUCPTDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol
• IUPAC Traditional name: menthol
• Synonyms: (1R,2S,5R)-2-isopropyl-5-methylcyclohexanol; L-Menthol; (1R,2S,5R)-5-Methyl-2-(1-methylethyl)cyclohexanol; [1R-(1α,2β,5α)]-5-Methyl-2-(1-methylethyl)cyclohexanol; (-)-(1R,3R,4S)-Menthol; (-)-Menthyl Alcohol; (-)-trans-p-Methan-cis-3-ol; (1R)-(-)-Menthol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexan-1-ol; (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexanol; 1R-Menthol; L-Mentholum; Minclea; NSC 62788; (1R,2S,5R)-(-)-Menthol; (1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexan-1-ol; (-)-menthol; L-menthol; L-(-)-menthol; (r)-(-)-menthol; Levomenthol; Menthol; 5-Methyl-2-(1-methylethyl)-cyclohexanol; L-MENTHOL; (1R,2S,5R)-(-)-Menthol; (1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol; 5-Methyl-2-(1-methylethyl)cyclohexanol; L-Menthol crystals; 3-p-Menthanol; Hexahydrothymol; Menthomenthol; peppermint camphor; (-)-Menthol; (1R,2S,5R)-(-)-Menthol; (-)-薄荷醇; (1R,2S,5R)-2-异丙基-5-甲基环己醇; 5-甲基-2-异丙基环己醇; L-薄荷醇; L-薄荷醇晶体; 5-甲基-2-(1-甲基乙基)环己醇; (-)-薄荷醇; L-薄荷醇

Database IDs

• CAS Number: 89-78-1; 2216-51-5
• EC Number: 218-690-9
• MDL Number: MFCD00062979
• Beilstein Number: 1902293
• PubChem SID: 24896767; 24881231; 24849703; 24901228; 46506513; 160964167; 24882791; 24901227; 24901229
• PubChem CID: 16666
• CHEBI ID: 15409
• CHEMBL: 470670
• Chemspider ID: 15803
• DrugBank ID: DB00825
• FEMA ID: 2665
• Unique Ingredient Identifier: YS08XHA860
• Wikipedia Title: Menthol
• Council of Europe Number: 65c

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 2.68
• LOG S: -2.45
• Solubility (Water): 5.58e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.49 mg/mL at 25 oC [CHEM INSPECT TEST INST (1992)]; Slightly soluble, (−)-isomer
• Apperance: White or colorless; crystalline solid
• Melting Point: ~43 °C; 36–38 °C (311 K), racemic; 42–45 °C (318 K), (−)-form (α); 35-33-31 °C, (−)-isomer; 41-44 °C; 41-45 °C(lit.); 43°C
• Boiling Point: 212 °C(lit.); 212°C; 212 °C (485 K)
• Flash Point: 101 °C; 213.8 °F; 93 °C
• Density: 0.89 g/mL at 25 °C(lit.); 0.890 g·cm^−3, solid; (racemic or (−)-isomer)
• Vapor Pressure: 0.8 mmHg ( 20 °C)
• Optical Rotation: [α]20/D -48 to -51°, c = 10% in ethanol; [α]20/D -49°, c = 10 in 95% ethanol; [α]20/D -50±1°, c = 10% in ethanol; [α]20/D -50°, c = 10 in ethanol; [α]20/D -50°, c = 10% in ethanol; [α]22/D -49°, c = 10 in 95% ethanol
• Hydrophobicity(logP): 3.2; 3.233
• Organoleptic: camphoraceous; tobacco; minty; minty; camphoraceous; minty; woody; camphoraceous; tobacco

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: OT0350000, racemic; OT0700000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 37/38-41; R:36/37/38; R37/38, R41
• Safety Statements: 26-39; S:20-25-26-37/39; S26, S36
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• Main Hazard: Irritant, flammable
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Regulation Compliance: FCC

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, GC); 95%; 95+%; 99%
• Grade: analytical standard, for terpene analysis; Halal; Kosher; natural; NI; primary reference standard; puriss.; ReagentPlus®
• Optical Purity: ee: 99% (GLC); enantiomeric ratio: ≥99:1 (GC)
• Suitability: in accordance for appearance of solution
• Description: L-isomer
• Impurities: ≤0.05% non-volatile matter; acidity or alcalinity, complies; chromatographic purity (GC), complies; related subst., complies; residual solvents, complies
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: meets analytical specification of Ph. Eur., BP, USP
• Empirical Formula (Hill Notation): C10H20O
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05214994

MP Biomedicals Rare Chemical collection

DrugBank - DB00825

• Drug Groups: approved
• Description: Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (-)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation.
• Indication: Used to treat occasional minor irritation, pain, sore mouth, and sore throat as well as cough associated with a cold or inhaled irritants.
• Pharmacology: Menthol is a covalent organic compound made synthetically or obtained from peppermint or other mint oils. Menthol's ability to chemically trigger cold-sensitive receptors in the skin is responsible for the well known cooling sensation that it provokes when inhalated, eaten, or applied to the skin. It should be noted that menthol does not cause an actual drop in temperature.
• Toxicity: Menthol, DL: ORAL (LD50): Acute: 2900 mg/kg [Rat], 3100 mg/kg [Mouse]. DERMAL (LD50): Acute: 5001 mg/kg [Rabbit].
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - 588733

Packaging
1 g in glass bottle

Sigma Aldrich - W266558

Biochem/physiol Actions
Taste at 25 ppm
General description
Natural Occurrence: Mentha species.

Sigma Aldrich - W266590

Biochem/physiol Actions
Taste at 25 ppm
General description
Natural Occurrence: Mentha species.
Packaging
1 kg in poly bottle
1 sample in glass bottle
4, 9, 25 kg in fiber drum

Sigma Aldrich - W266523

Biochem/physiol Actions
Taste at 25 ppm
Other Notes
Natural occurrence: Mentha species.
Packaging
1 kg in glass bottle
1 sample in glass bottle
100 g in glass bottle
4 kg in fiber drum

Sigma Aldrich - 63660

Other Notes
Important resolving agent for acids, recent applications include1; Crystallization-induced asymmetric transformation of malonates 2; Chiral auxiliary 3,4

Sigma Aldrich - M2780

Packaging
25, 100, 500 g in poly bottle
Application
Used to prepare reagents for chiral vinylogous Darzens and Reformatsky reactions.1 Important chiral auxiliary employed in the resolution of acids and for stereocontrolled synthesis.2
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M218875

(1R,2S,5R)-(-)-Menthol (L-Menthol) is the natural form of Menthol. L-Menthol is used as: refreshing agent, food flavor, cool and antipruritic drug, carminative drug. Menthol crystals is used for personal care and cosmetics.

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)
• Costa, S., et al.: Toxicology, 252, 40 (2000)