ChemicalBook CAS DataBase List 15356-60-2

15356-60-2

Name	(+)-MENTHOL
CAS	15356-60-2
EINECS(EC#)	239-387-8
Molecular Formula	C10H20O
MDL Number	MFCD00062983
Molecular Weight	156.27
MOL File	15356-60-2.mol

Synonyms

(1S,2R,5S)-2-ISOPROPYL-5-METHYLCYCLOHEXANOL (1S,2R,5S)-(+)-MENTHOL D-MENTHOL D-P-MENTHAN-3-OL (+)-MENTHOL MENTHOL, (+)- (+)-P-MENTHAN-3-OL (1S)-(+)-menthol 5-methyl-2-(1-methylethyl)-,[1S-(1.alpha.,2.beta.,5.alpha.)]-Cyclohexanol 5-methyl-2-(1-methylethyl)-,[1s-(1alpha,2beta,5alpha)]-cyclohexano (+)-MENTHOL, TERPENE STANDARD (1S,2R,5S)-(+)-MENTHOL, 99% (96% EE/GLC) (+)-Menthol=D-Menthol Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)- (+)-Menthol, (1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol (1S,3S,4R)-p-Menthane-3-ol (1S,3S,4R)-p-Menthane-3α-ol [1S,2R,5S,(+)]-2-Isopropyl-5-methylcyclohexan-1-ol

Chemical Properties

Melting point	43-44 °C (lit.)
Boiling point	103-104 °C/9 mmHg (lit.)
density	0.890
vapor pressure	0.8 mm Hg ( 20 °C)
refractive index	50 ° (C=10, EtOH)
Fp	196 °F
storage temp.	2-8°C
solubility	Chloroform (Slightly), Methanol (Slightly)
form	Solid
pka	15.30±0.60(Predicted)
color	Colourless to Off-White Oil
Odor	mentholic
Optical Rotation	[α]23/D +48°, c = 10 in ethanol
Water Solubility	Soluble in methanol (almost transparency), chloroform, alcohols, water (456 mg/L at 25°C), and ether.
BRN	1902292
Dielectric constant	3.2（Ambient）
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
SMILES	CC(C)[C@H]1CC[C@H](C)C[C@@H]1O
LogP	3.15 at 25℃
CAS DataBase Reference	15356-60-2(CAS DataBase Reference)
EPA Substance Registry System	Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1S,2R,5S)- (15356-60-2)

Safety Data

Symbol(GHS)	GHS05,GHS07
Signal word	Danger
Hazard statements	H315-H318-H335
Precautionary statements	P261-P280-P305+P351+P338
Hazard Codes	Xi
Risk Statements	R37/38:Irritating to respiratory system and skin . R41:Risk of serious damage to eyes. less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S39:Wear eye/face protection . less more
RIDADR	UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany	2
RTECS	OT0700000
TSCA	Yes
REACH Registrations	Active
HS Code	29061100
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Raw materials And Preparation Products

Hazard Information

Description

(+)-Menthol is a monoterpene alcohol that has been found in Cannabis and has antifungal activity. It inhibits the growth of F. verticillioides (MIC = 1.5 mM). Unlike (–)-menthol, (+)-menthol does not exhibit analgesia, antibacterial, anticancer, or cholinesterase inhibitory activities.

Chemical Properties

(+)-MENTHOL is white low melting solid

Uses

(+)-MENTHOL is used for oral gel patch or film containing herb extracts or Chinese medicine, fruit extract, spearmint, and menthol for smoking cessation.

Uses

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

Definition

ChEBI: (+)-menthol is a p-menthan-3-ol which has (1S,2R,5S)-stereochemistry. In contrast to (-)-menthol, the (+)-enantiomer occurs only rarely in nature. It is an enantiomer of a (-)-menthol.

General Description

(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.

Synthesis

Prod.: by Meerwein-Ponndorf-Verley reduction of l-Menthone, resuhing in approximately two-thirds d-Neomenthol plus one-third i-Menthol. It can also be produced by reduction of d-Menthone.

References

[1] JOSé S. DAMBOLENA . Effects of menthol stereoisomers on the growth, sporulation and fumonisin B1 production of Fusarium verticillioides[J]. Food Chemistry, 2010, 123 1: Pages 165-170. DOI: 10.1016/j.foodchem.2010.04.024
[2] GUY P.P. KAMATOU . Menthol: A simple monoterpene with remarkable biological properties[J]. Phytochemistry, 2013, 96: Pages 15-25. DOI: 10.1016/j.phytochem.2013.08.005

Spectrum Detail

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