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Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-(CAS No. 2216-51-5)

Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)- C10H20O (cas 2216-51-5) Molecular Structure

2216-51-5 Structure

Identification and Related Records

【Name】
Cyclohexanol,5-methyl-2-(1-methylethyl)-, (1R,2S,5R)-
【CAS Registry number】
2216-51-5
【Synonyms】
Cyclohexanol,5-methyl-2-(1-methylethyl)-, [1R-(1a,2b,5a)]-
Menthol, (1R,3R,4S)-(-)- (8CI)
(-)-Menthol
(-)-Menthylalcohol
(-)-trans-p-Methan-cis-3-ol
(1R)-(-)-Menthol
(1R,2S,5R)-(-)-Menthol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexan-1-ol
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol
(R)-(-)-Menthol
L-Menthol
Levomenthol
NSC 62788
【EINECS(EC#)】
218-690-9
【Molecular Formula】
C10H20O (Products with the same molecular formula)
【Molecular Weight】
156.26
【Inchi】
InChI=1/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-AEJSXWLSSA-N
【Canonical SMILES】
CC1CCC(C(C1)O)C(C)C
【Isomers smiles】
C[C@@H]1CC[C@H]([C@@H](C1)O)C(C)C
【MOL File】
2216-51-5.mol

Chemical and Physical Properties

【Appearance】
white crystals
【Density】
0.89
【Melting Point】
41-43℃
【Boiling Point】
212℃
【Refractive Index】
1.46
【Flash Point】
93℃
【Alpha】
-51 o (589NM, C=10, ETOH)
【Water】
insoluble
【Solubilities】
slight
【Color/Form】
Crystals or granules
COLORLESS, HEXAGONAL, USUALLY NEEDLE-LIKE CRYSTALS, OR FUSED MASSES, OR CRYSTALLINE POWDER
【Stability】
Stable.
【HS Code】
29061100
【Storage temp】
?20°C
【Spectral properties】
Index of refraction: 1.58 @ 25 deg C/D; Specific optical rotation: -50 deg @ 18 deg C/D (10% alc soln) /D- form/
MASS: 966 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:156.2652 [g/mol]
Molecular Formula:C10H20O
XLogP3-AA:3
H-Bond Donor:1
H-Bond Acceptor:1
Rotatable Bond Count:1
Exact Mass:156.151415
MonoIsotopic Mass:156.151415
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Formal Charge:0
Complexity:120
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:2.2
Conformer Sampling RMSD:0.6
CID Conformer Count:4

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38;R41
【Safety Statements 】
S26;S37/39
【Skin, Eye, and Respiratory Irritations】
MODERATE IRRITANT TO MUCOUS MEMBRANES ON INHALATION.
【Fire Potential】
FIRE HAZARD: SLIGHT
Combustible liquid.
【Formulations/Preparations】
SOME SYNTHETIC MENTHOLS ARE NOT CHEMICAL INDIVIDUALS BUT...MIXTURES OF VARIOUS ISOMERS...THESE ARE DESIGNATED...L-MENTHOL, DL-MENTHOL, L-ISOMENTHOL, D-ISOMENTHOL, DL-ISOMENTHOL, L-NEOMENTHOL, D-NEOMENTHOL, L-NEOISOMENTHOL, D-NEOISOMENTHOL AND DL-NEOISOMENTHOL.
WHEN MIXED WITH ABOUT EQUAL WT OF CAMPHOR, CHLORAL HYDRATE, PHENOL, OR THYMOL, MENTHOL FORMS "EUTECTIC" MIXT LIQUIFYING @ ROOM TEMP.
MENTHOL, USP DRUG MARKETED UNDER GENERIC NAME.
Grades: Technical; USP; FCC
Synthetic menthol is available as the optically active levo-menthol with a purity of 99.9%. Synthetic menthol is also commercially available as the racemic mixture
/Present in/ cigarettes and pipe tobacco (0.1-0.45%) shaving creams, pre- and aftershave lotions (0.2-0.3%); toothpastes (0.5%); mouthwashes (1-2%); chewing gums (0.5%); cough drops (0.1%); refreshing towels (1%); rubbing alcohol (1-1.2%); and shampoos (2-0.5%)
Mentholatum Deep Heating Rub /contains/ 5.9% Menthol; Mentholatum ointment, 1.35%; Mentholatum Deep Heating Lotion, 6%
【Exposure Standards and Regulations】
Essential oils, oleoresins (solvent-free), and natural extractives (including distillates) that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Menthol is included on this list.
【Reactivities and Incompatibilities】
Incompatible with phenol; beta-naphthol; resorcinol or thymol in trituration; potassium permanganate; chromium trioxide; pyrogallol.
【Protective Equipment and Clothing】
MODERATE IRRITANT TO MUCOUS MEMBRANES ON INHALATION.
【Octanol/Water Partition Coefficient】
log Kow = 3.3
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

NATURAL MENTHOL, KNOWN ALSO AS PEPPERMINT CAMPHOR MAY BE OBTAINED FROM PEPPERMINT OIL WHETHER AMERICAN, CHINESE, OR JAPANESE EITHER BY COOLING THE OIL TO POINT OF CRYSTALLIZATION OF MENTHOL OR BY FRACTIONAL DISTILLATION OF THE OIL.
BEING A HEXAHYDROTHYMOL, MENTHOL MAY BE PREPD BY HYDROGENATION (REDUCTION) OF THYMOL. OTHER SUBSTANCES, ALSO TERPENE DERIVATIVES, FROM WHICH MENTHOL MAY BE SYNTHESIZED ARE PULEGONE, PIPERITONE, MENTHONE, & CERTAIN CITRONELLA OILS.
Obtained from peppermint oil or other mint oils, or prepd synthetically by hydrogenation of thymol. Chromatographic sepn from mint oils.
A synthetic process for menthol involves the hydrogenation of thymol or 3-hydroxy-p-cymene which can be obtained from essential oils or produced synthetically from p-cymene (isopropyltoluene) or meta-cresol
U.S. Imports

(1972) 6.96X10+8 GRAMS
(1975) 7.7X10+8 GRAMS
(1984) 1.46X10+9 g
U.S. Production

(1972) 2.5X10+8 GRAMS
(1974) 1.3X10+8 GRAMS
(1980) 2.63X10+8 g
Consumption Patterns

Cigarettes and Tobacco, 60%; Salves and lotions, 15%; Oral products, 12%; Shaving products, 5%; Confectionary, 3%, Misc, 5% (1981)
【Usage】

Medication: topical antipruritic, medication (vet): has been used as a mild local anesthetic, antiseptic & internally as a carminative & gastric sedative menthol.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents, usually topical, that relieve itching (pruritus).
【Therapeutic Uses】
Antipruritics
MENTHOL MAY BE INCORPORATED INTO THERAPEUTIC LOTIONS OR OINTMENTS IN A 0.25 TO 2% CONCN FOR RELIEF OF PRURITUS. OINTMENTS OF CAMPHOR AND MENTHOL OR MENTHOL AND METHYL SALICYLATE ARE ALSO USED.
MENTHOL HAS BEEN WIDELY USED IN 1 OR 2 PERCENT SOLUTION IN LIQUID PETROLATUM AND ALSO IN INHALERS, FOR TREATMENT OF UPPER RESPIRATORY INFECTIONS.
MENTHOL IS ONE OF MOST WIDELY USED ANTIPRURITICS IN DERMATOLOGIC THERAPY OF VARIOUS DISEASES ACCOMPANIED BY ITCHING. ...IT IS ALSO FREQUENTLY OF SERVICE IN NAUSEA AND GASTRODYNIA. ...HAS BEEN USED TO CONTROL SUPERFICIAL INFLAMMATIONS...
INHALERS CONTAINING MENTHOL COMPRESSED INTO BLOCKS OR CONES ARE COMMONLY USED FOR RELIEF OF NASAL CONGESTION, HEADACHE, & NEURALGIA. ... IT IS NOW RARELY ADMIN INTERNALLY.
MEDICATION (VET): ITS VAPORS HAVE BEEN USED CLINICALLY IN RESP SYNDROMES OF HORSES, SWINE, & POULTRY. ... PARENTERALLY, IT IS USED IN STIMULANT EXPECTORANT MIXTURE...
MEDICATION (VET): TOPICALLY (0.1-2.0% CONCN), AS LOCAL SKIN ANESTHETIC IN MAMMARY OINTMENTS, WOUND TREATMENTS, & DERMATITIS THERAPY, WHERE IT MAY ALSO SERVE AS GERMICIDE OR ADJUVANT TO OTHER ANTIMICROBIALS OR AS COUNTERIRRITANT. ... IT IS ANTIFOAMING AGENT IN PRESENCE OF MUCUS OR SERUM.
MEDICATION: (VET): HAS BEEN USED AS MILD LOCAL ANESTHETIC, ANTISEPTIC; INTERNALLY AS CARMINATIVE & GASTRIC SEDATIVE
【Biomedical Effects and Toxicity】
NOT ALL GLUCURONIDES ARE EXCRETED BY TUBULAR SECRETION... CONJUGATES OF HIGHER MOL WT SUCH AS GLUCURONIDES OF ANDROSTERONE...ARE ELIMINATED BY GLOMERULAR FILTRATION ALONE, WHEREAS THOSE OF MENTHOL...OF LOWER MOL WT...BY TUBULES IN ADDITION TO GLOMERULAR FILTRATION...
MANY SUBSTANCES WITH DIVERSE STRUCTURES ARE KNOWN TO BE EXCRETED INTO BILE; THESE INCL GLUCURONIDES OF MENTHOL...
ABSORPTION CAN OCCUR FROM TOPICAL USE.

Supplier Location

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