Borneol

Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. There are two different enantiomers of borneol. Both d-(+)-borneol and l-(–)-borneol are found in nature.

Borneol
Borneol
Names
IUPAC name
endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.685
KEGG
UNII
Properties
C10H18O
Molar mass 154.253 g·mol−1
Appearance colorless to white lumps
Odor pungent, camphor-like
Density 1.011 g/cm3 (20 °C)[1]
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
−1.26×10−4 cm3/mol
Hazards
Safety data sheet External MSDS
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 65 °C (149 °F; 338 K)
Related compounds
Related compounds
 Bornane (hydrocarbon)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Reactions

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.[2]) 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 isomer isoborneol as the kinetically controlled reaction product.

Synthesis of the borneol isomer isoborneol via reduction of camphor.

Natural occurrences

Borneol can be found in several species of Heterotheca,[3] Artemisia, Callicarpa[4], Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.[5]

It is one of the chemical compounds found in castoreum. This compound is gathered from the beaver's plant food.[6]

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 is used in traditional Chinese medicine. An early description is found in the Bencao Gangmu.

Borneol is a component of many essential oils[7] and it is a natural insect repellent.[8]

Use in organic chemistry

Derivatives of isoborneol are used as chiral ligands in asymmetric synthesis:

Toxicology

Borneol is an eye, skin, and respiratory irritant; it is harmful if swallowed.[11]

Derivatives

The bornyl group is a univalent radical C10H17 derived from borneol by removal of hydroxyl and is also known as 2-bornyl.[12] Isobornyl is the univalent radical C10H17 that is derived from isoborneol.[13]

Bornyl acetate is the acetate ester of borneol.

Notes and references
  1. Lide, D. R., ed. (2005). CRC Handbook of Chemistry and Physics (86th ed.). Boca Raton (FL): CRC Press. p. 3.56. ISBN 0-8493-0486-5.
  2. C. Gerhardt (1842) "Sur la transformation de l'essence de valériane en camphre de Bornéo et en camphre des laurinées" (On the transformation of the essence of valerian into Borneo camphor and into laurel camphor), Comptes rendus, 14 : 832-835. 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.)
  3. Lincoln, D.E., B.M. Lawrence. 1984. "The volatile constituents of camphorweed, Heterotheca subaxillaris". Phytochemistry 23(4): 933-934
  4. "Species Information". sun.ars-grin.gov. Retrieved 2008-03-02.
  5. Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the essential oil of rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
  6. The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
  7. Plants containing borneol Archived 2015-09-23 at the Wayback Machine (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
  8. "Chemical Information". sun.ars-grin.gov. Archived from the original on 2004-11-07. Retrieved 2008-03-02.
  9. Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005). "(2S)-(–)-3-exo-(MORPHOLINO)ISOBORNEOL [(–)-MIB]" (PDF). Organic Syntheses. 82: 87.; Collective Volume, 11, p. 702
  10. White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]" (PDF). Organic Syntheses. 79: 130.; Collective Volume, 10, p. 305
  11. Material Safety Data Sheet, Fisher Scientific
  12. "Definition of BORNYL". www.merriam-webster.com.
  13. "Definition of ISOBORNYL". www.merriam-webster.com.
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