ChemicalBook > CAS DataBase List > MENTHOL

MENTHOL

Product Name
MENTHOL
CAS No.
15356-70-4
Chemical Name
MENTHOL
Synonyms
D-Menthol;Menthol racemic;2-Isopropyl-5-methylcyclohexanol;racementhol;FEMA 2665;MENTHOL;NCI-C50000;3-p-Menthol;d,1-menthol;MENTHOL, DL-
CBNumber
CB7116412
Molecular Formula
C10H20O
Formula Weight
156.27
MOL File
15356-70-4.mol
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MENTHOL Property

Melting point:
34-36 °C(lit.)
Boiling point:
216 °C(lit.)
Density 
0.89 g/mL at 25 °C(lit.)
vapor pressure 
0.8 mm Hg ( 20 °C)
refractive index 
1.4615
FEMA 
2665 | MENTHOL RACEMIC
Flash point:
200 °F
storage temp. 
2-8°C
solubility 
Practically insoluble in water, very soluble in ethanol (96 per cent) and in light petroleum, freely soluble in fatty oils and in liquid paraffin, very slightly soluble in glycerol.
form 
cryst.
color 
White
Dielectric constant
3.2（Ambient）
InChIKey
NOOLISFMXDJSKH-UHFFFAOYSA-N
CAS DataBase Reference
15356-70-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
37/38-41-48/20/22-40-38-22
Safety Statements 
36/37/39-36-26
RIDADR 
UN 1888 6.1/PG 3
WGK Germany 
2
RTECS 
OT0525000
HS Code 
29061100
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H336May cause drowsiness or dizziness

H351Suspected of causing cancer

H372Causes damage to organs through prolonged or repeated exposure

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
CRM40467
Product name
D,L-Menthol solution
Purity
certified reference material, 2000?μg/mL in methanol, ampule of 1?mL
Packaging
1mL
Price
$75
Updated
2024/03/01
Arctom
Product number
CFN99160
Product name
DL-Menthol
Purity
≥98%
Packaging
20mg
Price
$30
Updated
2021/12/16
JR MediChem
Product number
JR8-N0276
Product name
DL-Menthol
Purity
98%
Packaging
20mg
Price
$100
Updated
2021/12/16
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MENTHOL Chemical Properties,Usage,Production

Chemical Properties

Free-flowing or agglomerated, crystalline powder or prismatic or acicular, colourless, shiny crystals

Chemical Properties

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.

Chemical Properties

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.

Physical properties

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, 211.7
rac-neoisomenthol 214.6
rac-menthol, 216.5
rac-isomenthol, 218.6
Other 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.

Occurrence

Has apparently not been reported to occur in nature

Preparation

By hydrogenation of thymol followed by separation from its other isomers.

Indications

Menthol, a cyclic alcohol (derived from peppermint, other mint oils, or prepared synthetically), relieves itching by generating a cool sensation. It is usually used in 0.25% to 2% concentrations but is present in concentrations as high as 16% in some OTC products.

Definition

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.

Production Methods

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.

Toxicity evaluation

The acute oral LD50 in 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 LD50 in cats was reported to be 1500-1600 mg/kg (Flury & Seel, 1926). The sc LD50 in the mouse was reported as 1400-1600 mg/kg (Flury & Seel, 1926) and the ip LD50 as 750 mg/kg in the rat (Herken, 1961) and 1500-1600 mg/kg in the cat (Flury & Seel, 1926). In rabbits, the ip LD50 was reported to be approximately 2000 mg/kg (Herken, 1961), while the acute dermal LD50 exceeded 5000 mg/kg (Levenstein, 1973).

Pharmaceutical Applications

Menthol is widely used in pharmaceuticals, confectionery, and toiletry products as a flavoring agent or odor enhancer. In addition to its characteristic peppermint flavor, l-menthol, which occurs naturally, also exerts a cooling or refreshing sensation that is exploited in many topical preparations. Unlike mannitol, which exerts a similar effect due to a negative heat of solution, l-menthol interacts directly with the body’s coldness receptors. d-Menthol has no cooling effect, while racemic menthol exerts an effect approximately half that of l-menthol.
When used to flavor tablets, menthol is generally dissolved in ethanol (95%) and sprayed onto tablet granules and not used as a solid excipient.
Menthol has been investigated as a skin-penetration enhancer and is also used in perfumery, tobacco products, chewing gum and as a therapeutic agent. When applied to the skin, menthol dilates the blood vessels, causing a sensation of coldness followed by an analgesic effect. It relieves itching and is used in creams, lotions, and ointments. When administered orally in small doses menthol has a carminative action.

Safety Profile

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.

Safety

Almost all toxicological data for menthol relate to its use as a therapeutic agent rather than as an excipient. Inhalation or ingestion of large quantities can result in serious adverse reactions such as ataxia and CNS depression,hypersensitivity reactions, severe abdominal pain, nausea, vomiting, vertigo, drowsiness, and coma.Although menthol is essentially nonirritant there have been some reports of hypersensitivity following topical application. In a Polish study approximately 1% of individuals were determined as being sensitive to menthol.There have been reports of apnea and instant collapse in infants after the local application of menthol to their nostrils.
The WHO has set an acceptable daily intake of menthol at up to 0.4 mg/kg body-weight.
LD50 (rat, IM): 10.0 g/kg
LD50 (rat, oral): 3.18 g/kg

target

GABAA receptor

Metabolism

Rabbits are said to eliminate 59% of dl-menthol as glucuronide (Williams, 1938).

storage

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.

Incompatibilities

Incompatible with: butylchloral hydrate; camphor; chloral hydrate; chromium trioxide; b-naphthol; phenol; potassium permanganate; pyrogallol; resorcinol; and thymol.

Regulatory Status

Included in the FDA Inactive Ingredients Database (dental preparations, inhalations, oral aerosols, capsules, solutions, suspensions, syrups, and tablets; also topical preparations). Included in nonparenteral medicines licensed in the UK. Accepted for use in foods and confectionery as a flavoring agent of natural origin. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

MENTHOL Preparation Products And Raw materials

Raw materials

Preparation Products

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MENTHOL Suppliers

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View Lastest Price from MENTHOL manufacturers

Hebei Zhuanglai Chemical Trading Co Ltd
Product
MENTHOL 15356-70-4
Price
US $50.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-11-29
Hebei Weibang Biotechnology Co., Ltd
Product
MENTHOL 15356-70-4
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-19
Aurora Industry Co., Ltd.
Product
Menthol Crystals natural 15356-70-4
Price
US $15.00/kg
Min. Order
100kg
Purity
99%
Supply Ability
50 tons
Release date
2024-09-05

15356-70-4, MENTHOLRelated Search:

l-Menthol acetate (+)-MENTHOL,MENTHOL, (+)-,(1S)-(+)-mentho menthol,isovalerat Menthol, acetate, cis-1,3,trans-1,4- MENTHOL ACETATE L-Menthol Fancol menthol,Menthol terpine hydrate,Racemic menthol,MENTHOL 99 (+/-)-MENTHOL,MENTHOL,MENTHOL, DL-,1-mentho l-Menthol formate Menthol, fumarate (2:1), (1R,3R,4S)- Menthol octadecanoate Menthol pentanoate Menthol octanoate Menthol hexanoate MENTHOL BOLD CRYSTAL Menthol heptanoate Menthol tridecanoate Silicic acid tetra-menthol ester

  • 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)-(&plusmn
  • cyclohexanol,5-methyl-2-(1-methylethyl)-,(1-alpha,2-beta,5-alpha)
  • d,1-menthol
  • dl-3-p-Menthanol
  • Menthol racemic
  • Menthol racemique
  • Menthol, (&plusmn
  • Menthol, cis-1,3,trans-1,4-(&plusmn
  • Menthol, cis-1,3,trans-1,4-(.+/-.)-
  • mentholracemic
  • mentholracemique
  • NCI-C50000
  • racementhol
  • MENTHOL, DL-
  • (+/-)-MENTHOL
  • MENTHOL
  • HEXAHYDROTHYMOL 2-ISOPROPYL-5-METHYLCYCLOHEXANOL
  • FEMA 2665
  • DL-MENTHAN-3-OL
  • DL-4-MENTHAN-3-OL
  • DL-2-ISOPROPYL-5-METHYLCYCLOHEXANOL
  • 5-METHYL-2-(1-METHYETHYL)CYCLOHEXANOL
  • (1RS,3RS,4SR)-4 MENTHAN-3-OL
  • DL-Menthol, racemic
  • CYCLOHEXANOL,5-METHYL-2-(1-ME
  • Menthol solution
  • DL-MENTHOL USP (RACEMIC) SYNTHETIC
  • 2-Isopropyl-5-methylcyclohexanol
  • D-Menthol
  • D,L-Menthol solution
  • (+/-)-p-Menthan-3-ol
  • Menthol cristal
  • 15356-70-4
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