(-)-Menthol, 3-p-Menthol, Hexahydrothymol,
Menthomenthol, peppermint camphor, is an organic compound made synthetically or obtained from cornmint, peppermint or other mint oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1R,2S,5R) configuration. Menthol has local anesthetic and counterirritant qualities, and it is widely used to relieve minor throat irritation. Menthol also acts as a weak kappa opioid receptor agonist.
Natural menthol exists as one pure stereoisomer, nearly always the (1R,2S,5R) form (bottom left corner of the diagram below). The eight possible stereoisomers are:
In the natural compound, the isopropyl group is in the trans orientation to both the methyl and hydroxyl groups. Thus, it can be drawn in any of the ways shown:
In nonprescription products for short-term relief of minor sore throat and minor mouth or throat irritation Examples: lip balms and cough medicines;
As an antipruritic to reduce itching;
As a topical analgesic, it is used to relieve minor aches and pains, such as muscle cramps, sprains, headaches and similar conditions, alone or combined with chemicals such as camphor, eucalyptus oil or capsaicin. In Europe, it tends to appear as a gel or a cream, while in the US, patches and body sleeves are very frequently used. Examples: Tiger Balm, or IcyHot patches or knee/elbow sleeves;
In decongestants for chest and sinuses (cream, patch or nose inhaler) Examples: Vicks Vaporub, Mentholatum, vapoRem;
In certain medications used to treat sunburns, as it provides a cooling sensation (then often associated with aloe);
In aftershave products to relieve razor burn;
As an additive in certain cigarette brands, for flavor, to reduce the throat and sinus irritation caused by smoking;
Commonly used in oral hygiene products and bad-breath remedies, such as mouthwash, toothpaste, mouth and tongue-spray, and more generally as a food flavor agent; e.g., in chewing gum, candy;
In a soda to be mixed with water it is used to obtain a very low alcohol drink or pure (brand Ricqlès which contains 80% alcohol in France); the alcohol is also used to alleviate nausea, in particular motion sickness, by pouring a few drops on a lump of sugar.
As a pesticide against tracheal mites of honey bees;
In perfumery, menthol is used to prepare menthyl esters to emphasize floral notes (especially rose).
In first aid products such as "mineral ice" to produce a cooling effect as a substitute for real ice in the absence of water or electricity (pouch, body patch/sleeve or cream);
In various patches ranging from fever-reducing patches applied to children's foreheads to "foot patches" to relieve numerous ailments (the latter being much more frequent and elaborate in Asia, especially Japan: some varieties use "functional protrusions", or small bumps to massage ones feet as well as soothing them and cooling them down);
In some beauty products such as hair conditioners, based on natural ingredients (e.g. St. Ives).
As an antispasmodic and smooth muscle relaxant in upper gastrointestinal endoscopy In organic chemistry, menthol is used as a chiral auxiliary in asymmetric synthesis. For example, sulfinate esters made from sulfinyl chlorides and menthol can be used to make enantiomerically pure sulfoxides by reaction with organolithium reagents or Grignard reagents. Menthol reacts with chiral carboxylic acids to give diastereomic menthyl esters, which are useful for chiral resolution.
Package & Transporttt
Package Size: 25kg/drum
UN Number: 3080
Hazard Class: 6.1
1. Store in a cool, dry place.
2. Keep container closed when not in use. Corrosives area.
3. Keep containers tightly closed.
|Molar massss||156.27 g/mol|
|RTECS number||OT0350000, racemic|
|PubChem||3690, 16666 (racemic)|
|Jmol-3D images||Image 1|
|Appearance||White or Colorless Crystalline solid|
|Melting point||36–38℃, racemic
42–45℃, (−)-form (α)
|Vapour pressure||0.0637 mmHg|
|Solubility in water||Slightly soluble|