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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
Molecular Weight:
156.27
MDL Number:
MFCD00001484
MOL File:
15356-70-4.mol
MSDS File:
SDS
Last updated:2024-11-29 16:50:29

MENTHOL Properties

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)
FEMA 2665 | MENTHOL RACEMIC
refractive index 1.4615
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)
EWG's Food Scores 1
FDA UNII YS08XHA860

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H302-H315-H319-H331-H336-H351-H361d-H372
Precautionary statements  P202-P301+P312-P302+P352-P304+P340+P311-P305+P351+P338-P308+P313
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

MENTHOL price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich CRM40467 D,L-Menthol solution certified reference material, 2000?μg/mL in methanol, ampule of 1?mL 15356-70-4 1mL $75 2024-03-01 Buy
JR MediChem JR8-N0276 DL-Menthol 98% 15356-70-4 20mg $100 2021-12-16 Buy
Arctom CFN99160 DL-Menthol ≥98% 15356-70-4 20mg $30 2021-12-16 Buy
Product number Packaging Price Buy
CRM40467 1mL $75 Buy
JR8-N0276 20mg $100 Buy
CFN99160 20mg $30 Buy

MENTHOL Chemical Properties,Uses,Production

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.

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

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

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.

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.

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.

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

Global( 225)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8808 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12834 58
Shandong Juchuang Chemical Co., LTD
+undefined15030412209 admin@juchuangchem.com China 387 58
Aurora Industry Co., Ltd.
+86-13591747876 +86-13591747876 alex1_auco@126.com China 299 58
Hebei Zhuanglai Chemical Trading Co Ltd
+86-16264648883 +86-16264648883 niki@zlchemi.com China 2691 58
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806 sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 FandaChem@Gmail.com China 9087 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679 +8618949832763 info@tnjchem.com China 2986 55
career henan chemical co
+86-0371-86658258 +8613203830695 sales@coreychem.com China 29880 58

View Lastest Price from MENTHOL manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
MENTHOL pictures 2024-12-23 MENTHOL
15356-70-4
US $50.00 / kg 1kg 99 5000 Hebei Zhuanglai Chemical Trading Co Ltd
DL-Menthol pictures 2024-12-20 DL-Menthol
15356-70-4
US $0.00 / kg 1kg ≥98% HPLC 1000kg Changsha Staherb Natural Ingredients Co., Ltd.
MENTHOL pictures 2024-11-19 MENTHOL
15356-70-4
US $10.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
  • MENTHOL pictures
  • MENTHOL
    15356-70-4
  • US $50.00 / kg
  • 99
  • Hebei Zhuanglai Chemical Trading Co Ltd
  • DL-Menthol pictures
  • DL-Menthol
    15356-70-4
  • US $0.00 / kg
  • ≥98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • MENTHOL pictures
  • MENTHOL
    15356-70-4
  • US $10.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd
3-p-Menthol 4-Isopropyl-1-methylcyclohexan-3-ol mentholracemique NCI-C50000 MENTHOL, DL- (+/-)-MENTHOL MENTHOL HEXAHYDROTHYMOL 2-ISOPROPYL-5-METHYLCYCLOHEXANOL 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 D,L-Menthol solution mentholracemic Menthol, cis-1,3,trans-1,4-(.+/-.)- Menthol, cis-1,3,trans-1,4-(± Menthol, (± Menthol racemique dl-3-p-Menthanol d,1-menthol cyclohexanol,5-methyl-2-(1-methylethyl)-,(1-alpha,2-beta,5-alpha) Cyclohexanol, 5-methyl-2-(1-methylethyl)-, (1alpha,2beta,5alpha)-(± cis-1,3-trans-1,4-(+-)-mentho 5-methyl-2-(1-methylethyl)-,(1alpha,2beta,5alpha)-(+/-)-cyclohexano 5-methyl-2-(1-methylethyl)-,(1.alpha.,2.beta.,5.alpha.)-(+-)-Cyclohexanol (+/-)-p-Menthan-3-ol Menthol cristal racementhol FEMA 2665 2-Isopropyl-5-methylcyclohexanol D-Menthol Menthol racemic 15356-70-4 Building Blocks Terpenes Monocyclic Monoterpenes Organic Building Blocks Oxygen Compounds C9 to C30 Alcohols MEA - MESAnalytical Standards Alphabetic M NMR Reference Standards NMRStable Isotopes Spectroscopy Biochemistry Monocyclic Monoterpenes Terpenes