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Open Access Articles- Top Results for Borneol

Borneol

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Borneol

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This page is a soft redirect. Names

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IUPAC name
endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
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507-70-0 7pxY ChEBI CHEBI:15393 7pxY ChEMBL ChEMBL486208 7pxY ChemSpider 5026296 7pxY Jmol-3D images Image KEGG C01411 7pxY PubChem Template:Chembox PubChem/format Template:Chembox UNII colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

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C10H18O Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance colorless to white lumps Odor pungent, camphor-like Density 1.011 g/cm3 (20 °C)[1] Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". slightly soluble (D-form) Solubility soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Hazards

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SDS External MSDS NFPA 704

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This page is a soft redirect. Related compounds

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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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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

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.

File:Synthesis of isoborneol from camphor.svg
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. 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]" (PDF). Org. Synth. 82: 87. ; Coll. Vol. 11, p. 702 
  7. ^ White, J. D.; Wardrop, D. J.; Sundermann, K. F. (2002). "(2S)-(−)-3-exo-(DIMETHYLAMINO)ISOBORNEOL [(2S)-(−)-DAIB]" (PDF). Org. Synth. 79: 130. ; Coll. Vol. 10, p. 305 
  8. ^ Material Safety Data Sheet, Fisher Scientific

External links