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Borneol

 
Wikipedia: Borneol
Borneol
Borneol
Borneol-3D-balls.png
IUPAC name
Identifiers
CAS number 507-70-0 Yes check.svgY
PubChem 6552009
SMILES
InChI
InChI key DTGKSKDOIYIVQL-WEDXCCLWBQ
ChemSpider ID 5026296
Properties
Molecular formula C10H18O
Molar mass 154.25 g mol−1
Density 1.011 g/cm3 @ 20 °C
Melting point

208 °C, 481 K, 406 °F

Boiling point

sublimes

Hazards
MSDS External MSDS
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Borneol is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position. Isoborneol is its exo isomer.

Isoborneol

Borneol is easily oxidized to the ketone yielding 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. The same reduction but then fast and irreversible with sodium borohydride gives isoborneol as the kinetically controlled reaction product.

Reduction of camphor to isoborneol

Borneol exists as two enantiomers which have two different CAS numbers. Naturally occurring d-(+)-borneol is optically active. It can be found in several species of Artemisia and Dipterocarpaceae.

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,[1] and it is a natural insect repellent.[2]

Contents

Use in organic chemistry

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

Similar chemicals

List of plants that contain the chemical

Toxicology

Borneol is an eye, skin, and respiratory irritant; and is harmful if swallowed.[6]

Notes & References

  1. ^ Plants containing borneol (Dr. Duke's Phytochemical and Ethnobotanical Databases)]
  2. ^ "Chemical Information". sun.ars-grin.gov. http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL. Retrieved 2008-03-02. 
  3. ^ Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent Organic Syntheses, Vol. 82, p.87 (2005) Article
  4. ^ James D. White, Duncan J. Wardrop, and Kurt F. Sundermann Organic Syntheses, Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) Article.
  5. ^ Wong, K. C. et al. (2006). "Compositon of the essential oil of rhizomes of kaempferia galanga L.". Flavour and Fragrance Journal 7 (5): 263–266. doi:10.1002/ffj.2730070506. 
  6. ^ Material Safety Data Sheet, Fisher Scientific

External links


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camphol
terpene alcohol (organic chemistry)
cardamon oil (materials)

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Why does the gem-dimethyl groups appear as separate peaks in the proton NMR spectrum of isoborneol although they almost overlap in borneol?

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Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Borneol" Read more