3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||154.253 g·mol−1|
|Appearance||colorless to white lumps|
|Density||1.011 g/cm3 (20 °C)|
|Melting point||208 °C (406 °F; 481 K)|
|Boiling point||213 °C (415 °F; 486 K)|
|slightly soluble (D-form)|
|Solubility||soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin|
|P210, P240, P241, P280, P370+P378|
|NFPA 704 (fire diamond)|
|Flash point||65 °C (149 °F; 338 K)|
|Safety data sheet (SDS)||External MSDS|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. Being chiral, borneol exists as two enantiomers. Both (+)-borneol (older name d-borneol) and (−)-borneol (l-borneol) are found in nature.
Borneol is easily oxidized to the ketone (camphor). One historical name for borneol is Borneo camphor which explains the name.
The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt. Borneol can be found in several species of Heterotheca, Artemisia, Callicarpa, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.
It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.
Borneol can be synthesized by reduction of camphor by the Meerwein–Ponndorf–Verley reduction (a reversible process). Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the diastereomer isoborneol as the kinetically controlled reaction product.
Whereas d-borneol was the enantiomer that used to be the most readily available commercially, the more commercially available enantiomer now is l-borneol, which also occurs in nature.
Borneol from Dipterocarpus spp. is used in traditional Chinese medicine. An early description is found in the Bencao Gangmu.
Borneol is a component of many essential oils and it is a natural insect repellent. It also generates a TRPM8-mediated cooling sensation similar to menthol.
Laevo-borneol is used as an aroma chemical in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets.
Derivatives of isoborneol are used as ligands in asymmetric synthesis:
Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.
Borneol has been shown to have little to no irritation effect when applied to the human skin at a small dose. However, a long term exposure to borneol may cause mild irritation.
Since Borneol does not absorb UV light at 290 nm to 400 nm, it doesn't have any phototoxic or photoallergic potential.
The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl. Isobornyl is the univalent radical C10H17 that is derived from isoborneol. The structural isomer fenchol is also a widely used compound derived from certain essential oils.
Bornyl acetate is the acetate ester of borneol.