Menthol Oil - Directory & Reference Resources


Menthol Oil - Directory & Reference Resources

Menthol-From Wikipedia, the free encyclopedia

Menthol

 

General

Systematic name 2-(2-Propyl)-5-

methylcyclohexanol

Stereochemical

configuration (2S,5R,1R)

Other names 3-p-Menthanol,

Hexahydrothymol,

Menthomenthol,

peppermint camphor

Molecular formula C10H20O

SMILES CC1CCC(C(C1)O)C(C)C

Molar mass 156.27 g·mol−1

Appearance White or colorless

crystalline solid

CAS number [89-78-1], racemic

[2216-51-5], (−)-isomer

Properties

Density and phase 0.890 g·cm−3, solid

(racemic or (−)-isomer)

Solubility in water Slightly soluble, (−)-isomer

In ethanol, diethyl ether,

acetone, chloroform

acetic acid, hexane Soluble

Melting point 36-38 °C (311 K), racemic

42-45 °C (318 K), (−)-form (α)

35-33-31 °C, (−)-isomer

Boiling point 212 °C (485 K)

Chiral rotation [α]D -50° at 18 °C, 10% in EtOH

Hazards

MSDS External MSDS

Main hazards Irritant, flammable

NFPA 704

210 

Flash point 93 °C

R/S statement R37/38, R41 S26, S36

RTECS number OT0350000, racemic

OT0700000, (−)-enantiomer

Supplementary data page

Structure & properties n, εr, etc.

Thermodynamic data Phase behavior

Solid, liquid, gas

Spectral data UV, IR, NMR, MS

Related compounds

Related alcohols Cyclohexanol, Pulegol,

Dihydrocarveol, Piperitol

Related compounds Menthone, Menthene,

Thymol, p-Cymene,

Citronellal

Except where noted otherwise, data are given for

materials in their standard state (at 25 °C, 100 kPa)

Infobox disclaimer and references

Menthol is a covalent organic compound made synthetically or obtained from 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.

Contents

1 History and occurrence

2 Structure

3 Applications

4 Synthesis

5 Natural menthol

6 Chemical properties

7 Biological properties

8 Notes

9 References

10 External links

 History and occurrence

There is evidence[1] that menthol has been known in Japan for more than 2000 years, but in the west it was not isolated until 1771, by Gambius.[2] (-)-Menthol (also called l-menthol or (1R,2S,5R)-menthol) occurs naturally in peppermint oil (along with a little menthone, the ester menthyl acetate and other compounds), obtained from mentha x piperita. Japanese menthol also contains a small percentage of the 1-epimer, (+)-neomenthol.

Structure

Natural menthol exists as one pure enantiomer, nearly always the (1R,2S,5R) form (bottom left of diagram below). The other seven stereoisomers are:

In the natural compound, the isopropyl group is oriented trans- orientation to both the methyl and alcohol groups. Thus it can be drawn in any of the ways shown:

In the ground state all three bulky groups in the chair are equatorial, making (-)-menthol and its enantiomer the most stable two isomers out of the eight.

There are two crystal forms for racemic menthol; these have melting points of 28 °C and 38 °C. Pure (-)-menthol has four crystal forms, of which the most stable is the α form, the familiar broad needles.

 Applications

Menthol is included in many products for a variety of reasons. These include:

In non-prescription 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 to relieve minor aches and pains such as muscle cramps, sprains, headaches and similar conditions, alone or combined with products like Camphor 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 IcyHot patches or knee/elbow sleeves

In decongestants for chest and sinuses (cream, patch or nose inhaler)

Examples: Vicks Vaporub

In certain medications used to treat sunburns, as it provides a cooling sensation (then often associated with Aloe)

As an additive in certain cigarette brands, for flavor, to reduce the throat and sinus irritation caused by smoking and arguably to reduce the bad-breath smokers experience and possibly improve the smell of second-hand smoke.

Commonly used in oral hygiene products and bad-breath remedies like mouthwash, toothpaste, mouth and tongue-spray, and more generally as a food flavor agent e.g. in chewing-gum, candy

In a soda as well as in a syrup to be mixed with water to obtain a very low alcohol drink or (brand Riclès in France). The syrup is/was 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 honeybees

In perfumery, menthol is used to prepare menthyl esters to emphasise 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, esp. Japan: some variety use `functional protrusion' i.e. 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 (ex: St Ives)

Some supporters of the homeopathic theory of pharmacology believe that menthol interferes with the effects of homeopathic remedies. Its use is strongly discouraged for those seeking homeopathic cures, to the point of prohibiting the use of mint-flavored toothpaste. Currently no other reported nutrient or herb interactions involve menthol. It is used in Eastern medicine to treat indigestion, nausea, sore throat, diarrhea, colds, and headaches. (-)-Menthol has low toxicity: Oral (rat) LD50: 3300 mg·kg−1; Skin (rabbit) LD50: 15800 mg·kg−1).

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 is also used for classical resolution of chiral carboxylic acids, via the menthyl esters.

Synthesis

As with many widely-used natural products, the demand for menthol greatly exceeds the supply from natural sources. Menthol is manufactured as a single enantiomer (94% ee) by Takasago International Co. on a scale of 400 000 tonnes per year. The process involves an asymmetric synthesis developed by a team led by Ryoji Noyori:

The process begins by forming an allylic amine from myrcene, which undergoes asymmetric isomerisation in the presence of a BINAP rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal. This is cyclised by a carbonyl-ene-reaction initiated by zinc bromide to isopulegol which is then hydrogenated to give pure (1R,2S,5R)-menthol.

Racemic menthol can be prepared simply by hydrogenation of thymol, and menthol is also formed by hydrogenation of pulegone. For preparation of other isomers such as neomenthol, see ref. 1.

 Natural menthol

Mentha arvensis is the primary species of mint used to make natural menthol crystals and natural menthol flakes. This species is primarily grown in the Uttar Pradesh region in India.

 Chemical properties

Menthol reacts in many ways like a normal secondary alcohol. It is oxidised to menthone by oxidising agents such as chromic acid, though under some conditions the oxidation can go further and break open the ring. Menthol is easily dehydrated to give mainly 3-menthene, by the action of 2% sulfuric acid. PCl5 gives menthyl chloride.

 Biological properties

Menthol's ability to chemically trigger cold-sensitive receptors in the skin is responsible for the well known cooling sensation that it provokes when inhaled, eaten, or applied to the skin. Menthol does not cause an actual drop in temperature.[3] In this sense it is similar to capsaicin, the chemical responsible for the spiciness of hot peppers (which stimulates heat sensors, also without causing actual temperature rise).

 Notes

^ J. L. Simonsen, The Terpenes Volume I (2nd edition), Cambridge University Press, 1947, p230-249.

^ Adversoriorum varii argumentii, Liber unus, Leiden, 1771, p99.

^ R. Eccles, Menthol and Related Cooling Compounds, Journal of Pharm. Pharmacol. 1994 46: 618-630

 References

E. E. Turner, M. M. Harris, Organic Chemistry, Longmans, Green & Co., London, 1952.

Handbook of Chemistry and Physics, 71st edition, CRC Press, Ann Arbor, Michigan, 1990.

The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.

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