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Borneol

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Title: Borneol  
Author: World Heritage Encyclopedia
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Subject: Camphor, Kaempferia galanga, 5β-Dihydroprogesterone, Nutmeg oil, 2-Methylisoborneol
Collection: Gabaa Receptor Positive Allosteric Modulators, Monoterpenes, Secondary Alcohols
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Borneol

Borneol
Borneol
Names
IUPAC name
endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
 Y
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
Jmol-3D images Image
KEGG  Y
PubChem
UNII  Y
Properties
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)
slightly soluble (D-form)
Solubility soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
Hazards
Safety data sheet External MSDS
NFPA 704
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).
 Y  (: Y/N?)

Borneol is 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.

Contents

  • Reactions 1
  • Natural occurrences 2
  • Uses 3
    • Use in organic chemistry 3.1
  • Toxicology 4
  • Notes and references 5
  • External links 6

Reactions

Borneol is easily 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 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

Whereas d-borneol was the enantiomer that formerly was the most readily available commercially, the currently more commercially available enantiomer 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

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

Toxicology

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

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.  
  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.  
  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]" (PDF).  
  7. ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]" (PDF).  
  8. ^ Material Safety Data Sheet, Fisher Scientific

External links

  • NIST datasheet including full spectroscopic data
  • Borneol in Chinese medicine


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