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]] [[da:Borneol]] [[de:Borneol]] [[hu:Borneol]] [[ja:ボルネオール]] [[pl:Borneol]] [[pt:Borneol]] [[ru:Борнеол]] [[fi:Borneoli]] [[uk:Борнеол]] [[zh:冰片]]