Borneol
Template:Short description Template:Chembox Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are found in nature: d-borneol (also written (+)-borneol) and l-borneol (or (−)-borneol).
Reactions
Borneol is oxidized to the ketone (camphor).
Occurrence
The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt.[1] Borneol can be found in several species of Heterotheca,[2] Artemisia, Rosmarinus officinalis (rosemary)[3] Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.[4]
It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.[5]
Synthesis
Borneol can be synthesized by reduction of camphor by the Meerwein–Ponndorf–Verley reduction (a reversible process). Industrially, a racemic mixture of camphor is used, leading to a racemic mixture of borneol and isoborneol. The chirality can be controlled by changing the chirality of camphor: (+)-camphor gives (−)-isoborneol and (+)-borneol.[6]
Reduction of camphor with sodium borohydride (fast and irreversible) gives instead the diastereomer isoborneol.
Natural sources
Industrially, natural (+)-borneol is produced from Cinnamomum burmanni (one specific chemotype)[7] and Cinnamomum camphora.[8][9]
Natural (-)-borneol occurs in Blumea balsamifera.[9]
Biosynthesis
Borneol is synthesized using DMAPP as the starting material. DMAPP is then converted to GPP, which is acted upon by a bornyl diphosphate synthase to yield a bornyl diphosphate. A phosphatase then removes the phosphate groups, yielding borneol.[10]
The chirality of borneol in a plant depends on the preferred chirality of the bornyl diphosphate synthase. Synthases for either chirality have been sequenced.[10][11]
A downstream product is camphor of either chirality, a reaction catalyzed by (+)-borneol dehydrogenase or (−)-borneol dehydrogenase.
Uses
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[12] and it is a natural insect repellent.[13] It also generates a TRPM8-mediated cooling sensation similar to menthol.[14]
Laevo-borneol is used in perfumery. It has a balsamic odour type with pine, woody and camphoraceous facets.
Dextro-borneol (dexborneol) is used in edaravone/dexborneol, a drug approved in China for stroke.[15]
Toxicology
Borneol may cause eye, skin, and respiratory irritation; it is harmful if swallowed.[16] Acute exposure may cause headache, nausea, vomiting, dizziness, lightheadedness, and syncope. Exposure to higher levels or over a longer period of time may cause restlessness, difficulty concentrating, irritability, and seizures.[17]
Skin irritation
Borneol has been shown to have little to no irritation effect when applied to the human skin at doses used in fine fragrance formulation.[18] Skin exposure can lead to sensitization and a future allergic reaction even to small quantities.[17]
Derivatives
The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl.[19] Isobornyl is the univalent radical C10H17 that is derived from isoborneol.[20] The structural isomer fenchol is also a widely used compound derived from certain essential oils.
Bornyl acetate is the acetate ester of borneol.
Notes and references
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From p. 834: "Je donne, par cette raison, à l'hydrogène carboné de l'essence de valériane, le nom de bornéène, et, au camphre lui-même, celui de bornéol." (I give, for this reason [namely, that the compound that Gerhardt had obtained from valerian oil was identical to that obtained by Pelouze from camphor from Borneo], to the hydrocarbon from valerian essence, the name bornéène, and, to camphor itself, that of borneol.) - ↑ Script error: No such module "Citation/CS1".
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- ↑ The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
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- ↑ a b Script error: No such module "citation/CS1". 右旋 (+) Template:Webarchive 左旋 (-) Template:Webarchive 合成 (racemic synthetic) Template:Webarchive
- ↑ a b Script error: No such module "Citation/CS1".
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- ↑ Plants containing borneol Template:Webarchive (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
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- ↑ Material Safety Data Sheet. Fisher Scientific.
- ↑ a b HAZARDOUS SUBSTANCE FACT SHEET (PDF)
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