Borneol

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Borneol
Borneol Borneol-3D-balls.png
Identifiers
CAS number 507-70-0 YesY
PubChem 6552009
ChemSpider 5026296 YesY
UNII M89NIB437X YesY
KEGG C01411 YesY
ChEBI CHEBI:15393 YesY
ChEMBL CHEMBL486208 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H18O
Molar mass 154.25 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)
Solubility in water slightly soluble (D-form)
Solubility soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
Hazards
MSDS External MSDS
NFPA 704
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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 65 °C (149 °F; 338 K)
Related compounds
Related compounds Bornane (hydrocarbon)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Borneol is a bicyclic organic compound and a terpene. 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.

Reactions[edit]

Borneol is easily oxidized to the ketone (camphor). One historical name for borneol is Borneo camphor which explains the name. 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[edit]

Borneol can be found in several species of Artemisia, Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.[2]

It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver plant food.[3]

Uses[edit]

Whereas d-borneol was the antipode that formerly was the most readily available commercially, the currently more commercially available antipode is l-borneol, which also occurs in nature.

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

Borneol is a component of many essential oils,[4] and it is a natural insect repellent.[5]

Use in organic chemistry[edit]

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

Toxicology[edit]

Borneol is an eye, skin, and respiratory irritant; and is harmful if swallowed.[8]

Notes and references[edit]

  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. ^ 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. 
  3. ^ The Beaver: Its Life and Impact. Dietland Muller-Schwarze, 2003, page 43 (book at google books)
  4. ^ Plants containing borneol (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
  5. ^ "Chemical Information". sun.ars-grin.gov. Retrieved 2008-03-02. 
  6. ^ Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. (2005), "(2S)-(–)-3-exo-(MORPHOLINO)ISOBORNEOL [(–)-MIB]", Org. Synth. 82: 87 ; Coll. Vol. 11: 702 
  7. ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002), "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]", Org. Synth. 79: 130 ; Coll. Vol. 10: 305 
  8. ^ Material Safety Data Sheet, Fisher Scientific

External links[edit]