This article needs additional citations for verification. Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (July 2009)

Borneol
IUPAC name	endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
CAS number	507-70-0 Y
PubChem	6552009
SMILES	O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C
InChI	1/C10H18O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7-8,11H,4-6H2,1-3H3/t7-,8+,10+/m1/s1
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
Y (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.

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]

[edit] Use in organic chemistry

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

• (2S)-(−)-3-exo-(morpholino)isoborneol or MIB^[3] with a morpholine substituent in the α-hydroxyl position
• (2S)-(−)-3-exo-(dimethylamino)isoborneol or DAIB^[4] with a dimethylamino substituent in the α-hydroxyl position

[edit] Similar chemicals

• (+)-Borneol^{[citation needed]}
• (−)-Borneol^{[citation needed]}

[edit] List of plants that contain the chemical

• Kaempferia galanga ^{[5][clarification needed]}

[edit] Toxicology

This section requires expansion.

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

[edit] Notes & References

[edit] External links

• NIST datasheet including full spectroscopic data
• Dynamic 3D model borneol
• Dynamic 3D model isoborneol
• Borneol in Chinese medicine