MENTHOL
-
MENTHOL
structure -
-
CAS No:
15356-70-4
-
Formula:
C10H20O
-
Chemical Name:
MENTHOL
-
Synonyms:
3-p-Menthol;4-Isopropyl-1-methylcyclohexan-3-ol;5-methyl-2-(1-methylethyl)-,(1.alpha.,2.beta.,5.alpha.)-(+-)-Cyclohexanol;5-methyl-2-(1-methylethyl)-,(1alpha,2beta,5alpha)-(+/-)-cyclohexano;cis-1,3-trans-1,4-(+-)-mentho;Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5alpha)-(±;cyclohexanol,5-methyl-2-(1-methylethyl)-,(1-alpha,2-beta,5-alpha);d,1-menthol
- Categories:
-
CAS No:
Description
Free-flowing or agglomerated, crystalline powder or prismatic or acicular, colourless, shiny crystals
Racemic menthol is a mixture of equal parts of the (1R,2S,5R)- and (1S,2R,5S)-isomers of menthol. It is a free-flowing or agglomerated crystalline powder, or colorless, prismatic, or acicular shiny crystals, or hexagonal or fused masses with a strong characteristic odor and taste. The crystalline form may change with time owing to sublimation within a closed vessel. The USP 32 specifies that menthol may be either naturally occurring l-menthol or syntheti-cally prepared racemic or dl-menthol. However, the JP XV and PhEur 6.0, along with other pharmacopeias, include two separate monographs for racemic and l-menthol.
Menthol has three asymmetric carbon atoms in its cyclohexane ring and, therefore, occurs as four pairs of optical isomers.The configurations of four of these isomers are given; the other four are their mirror images.(1R,3R,4S)-()-Menthol,,; (1R,3S,4S)-(+)-neomenthol,; (1R,3S,4R)-(+)- isomenthol,; (1R,3R,4R)-(+)-neoisomenthol,. ()-Menthol is the isomer that occurs most widely in nature. It is the main component of peppermint and cornmint oils obtained from the Mentha piperita and Mentha arvensis species. Esterified menthol also occurs in these oils (e.g., as the acetate and isovalerate).Other menthol stereoisomers may be present in these oils as well.
ChEBI: P-menthan-3-ol is any secondary alcohol that is one of the eight possible diastereoisomers of 5-methyl-2-(propan-2-yl)cyclohexan-1-ol. It has a role as a volatile oil component. It is a p-menthane monoterpenoid and a secondary alcohol.
Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An eye and skin irritant. K%en heated to decomposition it emits acrid smoke and irritating fumes. See also MENTHOL and 1-MENTHOL.
Characteristics
20.2
Physical Properties.The eight optically active menthols differ in their sensory properties. ()-Menthol has a characteristic peppermint odor and also exerts a cooling effect. The other isomers do not possess this cooling effect and are, therefore, not considered to be “refreshing.” Racemic menthol occupies an intermediate position; the cooling effect of the ()-menthol present is distinctly perceptible.The enantiomeric menthols have identical physical properties (apart from their specific rotations), but the racemates differ from the optically active forms in, for example, theirmelting points.Although the differences between the boiling points are small, the (racemic) stereoisomers can be separated by fractional distillation. Boiling points (in °C at 101.3 kPa) are as follows:rac-neomenthol, 211.7rac-neoisomenthol 214.6rac-menthol, 216.5rac-isomenthol, 218.6Other physical constants of commercially available levorotatory and racemic menthols are as follows: ()-menthol, mp 43 °C, [α]20 D 50° (ethanol, 10%); racemic menthol, mp 38 °C.Chemical Properties.Hydrogenation of menthols yields p-menthane; oxidation with chromic acid or catalytic dehydrogenation yields menthones. Dehydration under mild conditions yields 3-p-menthene as the main product. Reaction with carboxylic acids or their derivatives yields menthyl esters, which are used mainly as aroma substances and in pharmaceutical preparations and formulations. The esterification of menthols with benzoic acid is used on an industrial scale in the resolution of racemic menthol.
3.2
0.89 g/mL at 25 °C(lit.)
34-36 °C(lit.)
216 °C(lit.)
200 °F
1.4615
0.42 mg/mL at 25 °C
2-8°C
0.8 mm Hg ( 20 °C)
5.4 (NTP, 1992) (Relative to Air)
The acute oral LD50in rats has been reported as 3180 mg/kg by Jenner, Hagan, Taylor, Cook & Fitzhugh (1964) and as 2900 mg/kg by Herken (1961). The acute oral LD50in cats was reported to be 1500-1600 mg/kg (Flury & Seel, 1926). The sc LD50in the mouse was reported as 1400-1600 mg/kg (Flury & Seel, 1926) and the ip LD50as 750 mg/kg in the rat (Herken, 1961) and 1500-1600 mg/kg in the cat (Flury & Seel, 1926). In rabbits, the ip LD50was reported to be approximately 2000 mg/kg (Herken, 1961), while the acute dermal LD50exceeded 5000 mg/kg (Levenstein, 1973).
2-8°C
Safety Information
UN 1888 6.1/PG 3
2
Xn,Xi
36/37/39-36-26
OT0525000
Xn,Xi
A formulation containing menthol 1% w/w in aqueous cream has been reported to be stable for up to 18 months when stored at room temperature.Menthol should be stored in a well-closed container at a temperature not exceeding 25°C, since it sublimes readily.
Stable under recommended storage conditions.
P264, P280, P302+P352, P321, P332+P313, P362
37/38-41-48/20/22-40-38-22
Incompatible with: butylchloral hydrate; camphor; chloral hydrate; chromium trioxide; b-naphthol; phenol; potassium permanganate; pyrogallol; resorcinol; and thymol.
UN 1888 6.1/PG 3
MENTHOL Use and Manufacturing
Menthol occurs widely in nature as l-menthol and is the principal component of peppermint and cornmint oils obtained from the Mentha piperita and Mentha arvensis species. Commercially, lmenthol is mainly produced by extraction from these volatile oils. It may also be prepared by partial or total synthetic methods.Racemic menthol is prepared synthetically via a number of routes, e.g. by hydrogenation of thymol.
Recommended Suppliers of MENTHOL
-
![China]()
CN
8 YRS
Business licensedDistributor Supplier of Resin,Coating&Ink,Adhesive,Polyurethane,Home&Personal Care,Plastic & Rubber -
![China]()
CN
3 YRS
Business licensedTrader Supplier of Food AdditivesInquiryUnit Price: $1660-1670 /MT FOBCAS No.: 15356-70-4Grade: Food GradeContent: 99% -
![China]()
CN
4 YRS
Business licensedTrader Supplier of Semaglutide,Tirzepatide,API,EnzymeInquiryCAS No.: 15356-70-4Grade: Pharmaceutical GradeContent: 99.5% -
![China]()
CN
4 YRS
Business licensed Certified factoryManufactory Supplier of Flavors & Fragrances,Catalyst & Auxiliary,Intermediates,Dyes & Pigments,Inorganic Chemistry,petro chemicals,Surfactant,Food Additives,Water Treatment Chemicals
Learn More Other Chemicals
-
Menthol
1490-04-6
-
Succinic acid menthol monoester
77341-67-4
-
Menthol propylene glycol carbonate
156324-82-2
-
25-Deoxyecdysone Formula
22005-50-1
-
compoundk Formula
160729-91-9
-
7-[4-[4-(2-bromophenyl)piperazin-1-yl]butoxy]-3,4-dihydro-1H-quinolin-2-one Formula
203395-84-0
-
Moscatilin Structure
108853-14-1
-
beta-sitosterol sulfate Structure
24815-93-8
-
What is Cocoa butter
8002-31-1
-
What is (2β,3β,5β,22S)-22,25-Epoxy-2,3,14,20-tetrahydroxycholest-7-en-6-one
26361-67-1