Borneol


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borneol

[′bȯr·nē‚ȯl]
(organic chemistry)
C10H17OH White lumps with camphor odor; insoluble in water, soluble in alcohol; melting point 203°C; used in perfumes, medicine, and chemical synthesis.

Borneol

 

bornyl alcohol, a secondary alcohol of the bicyclic terpene group. Borneol has an endo configuration; its isomer, called isoborneol, has an exo configuration. [The (CH3)2C group is located outside the plane of the ring.]

Borneol and isoborneol contain an asymmetric carbon atom (denoted by an asterisk), and therefore each of them exists in two optically active forms and one inactive racemic form (−, +, and ±). Borneo camphor, (+)-borneol, is contained in the secretions of the tree Dryobanalops camphora, which grows on the islands of Borneo and Sumatra, as well as in rosemary, lavender, and camphor oils. The acetate form, ( − )-borneol, is contained in the coniferous needle of the Siberian pine. Both (+)-borneol and (−)-borneol have a melting point Tm = 208.5° C, boiling point Tb = 212° C, and angle of rotation of the plane of polarization [α]D20 = ±37.9°; and both sublimate. The racemate (±)-borneol melts at 210.3° C. Both (−)-borneol and (±)-borneol are components of valerian oil.

Borneol is converted into camphor upon oxidation and catalytic dehydrogenation; the dehydration of borneol leads to camphene. The primary method of obtaining borneol is the hydration of pinene, which is contained in turpentine. Borneol is used in the production of camphor.

Isoborneol (Tm= 214° C) is not found in nature; it is obtained from camphene.

References in periodicals archive ?
The healing properties of borneol are attributed to the properties such as Analgesia, putridity elimination, and flesh regeneration, and repair of damaged cells.
(26.) Liu D, Gao Y, Wang H, Zi J, Huang H (2010) Evaluation of the effects of cytochrome P450 nonsynonymous single-nucleotide polymorphisms on tanshinol borneol ester metabolism and inhibition potential.
Wang, [41] investigated the toxicity of 1,8-cineole, camphor, eugenol, linalool, carvacrol, thymol, borneol, bornyl acetate and linalyl acetate against adults of S.
The antinociceptive activity of several monoterpenes such as borneol (Almeida et al., 2013), linalool (Quintans-Junior et al., 2013) and citronellol (Brito et al., 2012) have been described.
Rosemary also contains borneol and other volatile oils that are known to exert antispasmodic activity upon the heart and other smooth-muscle tissues.
By the process of steam distillation an essential oil is obtained (5.8%) from rhizomes having compounds borneol (0.5%), cineol (1%), sabinene (0.6%), sesquiterpenes (53%), zingiberene (25%) and a-phellandrene (1%).
The major constituents of the oil are linalool, linalyl acetate, cineol, pinene, limonene, geranial, borneol and some tannin [5].
Among the other substances positively identified in the study were nicotine, myristic acid and isopropyl myristate, cocaine, cinnamaldehyde, vanillin, quinolene and butyl quinone, borneol and other forms of camphor, pyrene, phenol, toluene and naphthalene.
The main components of these fractions were alpha-pinene, 1-8-cineole, camphor, verbenone and borneol constituting 80% of the total oil.
Its essential oil contains cineol, borneol, and thujone.
In the other study, borneol, [alpha]-terpinene, linolool, and geranyl proprionate were found as major constituents in the L.
It contains 1-4% volatile oil containing cineole, zingiberene, borneol, and resins like gingerol and shogaol.