Borneol
2963034
218579624
2008-06-11T07:59:48Z
147.46.241.87
{{Chembox new
| Name = Borneol
| ImageFileL1 = Borneol_Structure.png
| ImageSizeL1 = 120px
| ImageNameL1 = Borneol
| ImageFileR1 = Borneol-3D-balls.png
| ImageSizeR1 = 140px
| IUPACName = ''endo''-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
| Section1 = {{Chembox Identifiers
| CASOther = [507-70-0] (+)<br\> [464-45-9] (-)
| SMILES = CC1(C2(C)C)C(O)CC2CC1
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>10</sub>H<sub>18</sub>O
| MolarMass = 154.25 g/mol
| Density = 1.011 g/cm<sup>3</sup> @ 20<sup>o</sup>C
| MeltingPt = 208 °C
| BoilingPt = sublimes
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://physchem.ox.ac.uk/MSDS/BO/borneol.html External MSDS]}}
}}
'''Borneol''' is a [[bicyclic]] [[organic compound]] and a [[terpene]]. The [[hydroxyl]] group in this compound is placed in an [[Endo-exo isomerism|endo]] position. '''Isoborneol''' is its [[exo isomer]].
: [[Image:Isoborneol Structure.png|thumb|left|100px|Isoborneol]]<br style="clear:left;"/>
Borneol is easily [[organic oxidation|oxidized]] to the [[ketone]] yielding [[camphor]]. One historical name for borneol is '''Borneo camphor''' which explains the name. Borneol can be synthesized by [[organic reduction|reduction]] of [[camphor]] by the [[Meerwein-Ponndorf-Verley Reduction]]. The same reduction but then fast and irreversible with [[sodium borohydride]] gives [[isoborneol]] as the [[kinetic reaction control|kinetically controlled]] reaction product.
: [[Image:Camphortoborneolreaction.png|Reduction of camphor to isoborneol]]
Borneol exists as two [[enantiomer]]s 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 [[moxibustion|moxa]]. An early description is found in the [[Bencao Gangmu]].
Borneol is a component of many [[essential oil]]s, <ref>[http://www.ars-grin.gov/cgi-bin/duke/highchem.pl?chem=borneol&allchems=x Plants containing borneol] (Dr. Duke's Phytochemical and Ethnobotanical Databases)]</ref> and it is a natural [[insect repellent]].<ref>
{{cite web
|url=http://sun.ars-grin.gov:8080/npgspub/xsql/duke/chemdisp.xsql?chemical=BORNEOL
|title=Chemical Information
|publisher=sun.ars-grin.gov
|accessdate=2008-03-02
|last=
|first=
}}
</ref>
== Use in organic chemistry ==
Derivatives of isoborneol are used as chiral [[ligand]]s in [[asymmetric synthesis]]:
* (2S)-(−)-3-exo-(morpholino)isoborneol or '''MIB'''<ref>Young K. Chen, Sang-Jin Jeon, Patrick J. Walsh, and William A. Nugent [[Organic Syntheses]], Vol. 82, p.87 (2005) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v82p0087 Article]</ref> with a [[morpholine]] [[substituent]] in the α-hydroxyl position
* (2S)-(−)-3-exo-(dimethylamino)isoborneol or '''DAIB'''<ref>James D. White, Duncan J. Wardrop, and Kurt F. Sundermann [[Organic Syntheses]], Coll. Vol. 10, p.305 (2004); Vol. 79, p.130 (2002) [http://www.orgsynth.org/orgsyn/prep.asp?prep=v79p0130 Article].</ref> with a [[amine|dimethylamino]] [[substituent]] in the α-hydroxyl position
== External links ==
* [http://webbook.nist.gov/cgi/cbook.cgi?ID=507-70-0&Units=SI&Mask=100 NIST datasheet including full spectroscopic data]
* [http://www.flavornet.org/info/507-70-0.html Dynamic 3D model borneol]
* [http://www.flavornet.org/info/124-76-5.html Dynamic 3D model isoborneol]
* [http://www.itmonline.org/arts/borneol.htm Borneol in Chinese medicine]
== References ==
<references/>
[[Category:alcohols]]
[[Category:Terpenes and terpenoids]]
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[[ja:ボルネオール]]
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