Borneol

Borneol

Names
IUPAC name endo-1,7,7-Trimethyl- bicyclo[2.2.1]heptan-2-ol
Identifiers
CAS Number	507-70-0 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15393 Y
ChEMBL	ChEMBL486208 Y
ChemSpider	5026296 Y
ECHA InfoCard	100.007.346
IUPHAR/BPS	6413
KEGG	C01411 Y
PubChem	6552009
UNII	M89NIB437X Y
InChI InChI=1S/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 Y Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N Y 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 Key: DTGKSKDOIYIVQL-WEDXCCLWBQ
SMILES O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C
Properties
Chemical formula	C10H18O
Molar mass	154.25 g·mol−1
Appearance	colorless to white lumps
Odor	pungent, camphor-like
Density	1.011 g/cm3 (20 °C)
Melting point	208 °C (406 °F; 481 K)
Boiling point	213 °C (415 °F; 486 K)
Solubility in water	slightly soluble (D-form)
Solubility	soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
Magnetic susceptibility (χ)	-126·10−6 cm3/mol
Hazards
Safety data sheet	External MSDS
NFPA 704	2 2 0
Flash point	65 °C (149 °F; 338 K)
Related compounds
Related compounds	Bornane (hydrocarbon)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Borneol is a bicyclic organic compound and a terpene derivative. 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.

Borneol is easily oxidized to the ketone (camphor). One historical name for borneol is Borneo camphor which explains the name. (The compound was named in 1842 by the French chemist Charles Frédéric Gerhardt.) 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.

Borneol can be found in several species of Heterotheca,Artemisia, Callicarpa", Dipterocarpaceae, Blumea balsamifera and Kaempferia galanga.

It is also one of the chemical compounds found in castoreum. This compound is gathered from the beaver plant food.

Whereas d-borneol was the enantiomer that used to be the most readily available commercially, the more commercially available enantiomer now is l-borneol, which also occurs in nature.