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Topic summary

Borneol

Borneol
Names IUPAC name
rel-(1R,2S,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
Other names
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-endo-ol
endo-2-Bornanol, Borneo camphor
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.007.346EC Number
  • 207-352-6
KEGG
UNII
UN number1312
  • 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
    Key: DTGKSKDOIYIVQL-WEDXCCLWSA-N
  • (+/-): 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+/s2
    Key: DTGKSKDOIYIVQL-IUNFSSIHNA-N
  • O[C@H]1C[C@H]2CC[C@]1(C)C2(C)C
Properties C10H18OMolar mass154.253 g·mol Appearance colorless to white lumps Odorpungent, camphor-like Density1.011 g/cm (20 °C) Melting point208 °C (406 °F; 481 K) Boiling point213 °C (415 °F; 486 K) slightly soluble (D-form) Solubilitysoluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin−1.26×10 cm/molHazards GHS labelling: WarningH228P210, P240, P241, P280, P370+P378NFPA 704 (fire diamond)
2
2
0
Flash point65 °C (149 °F; 338 K) Safety data sheet (SDS) External MSDSRelated 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).
checkYverify (  ?)

Borneol is a bicyclicorganic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are found in nature: d-borneol (also written (+)-borneol, dextroborneol, dexborneol) and l-borneol (or (−)-borneol, levoborneol).

Both borneol and isoborneol belong to the category of 2-bornanol, a derivative of bornane. Some sources such as PubChem and CHEBI use the term borneol to refer to the entire category of 2-bornanols while others such as KEGG use the term borneol to refer to the compounds with endo hydroxyl only.

Wikipedia source