(+)-MENTHOL

Synonym(s):(+)-Menthol;(1S,2R,5S)-2-Isopropyl-5-methylcyclohexanol

CAS NO.：15356-60-2
Empirical Formula: C10H20O
Molecular Weight: 156.27
MDL number: MFCD00062983
EINECS: 239-387-8
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 20:33:22

What is (+)-MENTHOL?

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

The Uses of (+)-MENTHOL

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

The Uses of (+)-MENTHOL

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

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.

Properties of (+)-MENTHOL

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)
Flash point:	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 to Low-Melting
Odor	mentholic
optical activity	[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）
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 information for (+)-MENTHOL

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.