Farnesol

Title: Farnesol
CAS Registry Number: 4602-84-0
CAS Name: 3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
Molecular Formula: C15H26O
Molecular Weight: 222.37
Percent Composition: C 81.02%, H 11.79%, O 7.19%
Literature References: Found in oils of citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam Peru, and tolu. Isoln: Elge, Chem. Ztg. 34, 857 (1910); 37, 1422 (1913); Kerschbaum, Ber. 46, 1732 (1913); Naves, Helv. Chim. Acta 32, 1798, 2181 (1949); LaFace, ibid. 33, 249 (1950). Synthesis: Ruzicka, ibid. 6, 492 (1923); Ruzicka, Firmenich, ibid. 22, 392 (1939); Nazarov et al., Zh. Obshch. Khim. 28, 1444 (1958); Shvarts, Petrov, ibid. 30, 3598 (1960); Popjak et al., J. Biol. Chem. 237, 56 (1962). Four possible stereoisomers. Stereochemistry: Bates et al., Chem. Ind. (London) 1961, 1907; J. Org. Chem. 28, 1086 (1963). trans-trans-Farnesol is the only stereoisomer present in many essential oils but occurs mixed with cis-trans-farnesol in petitgrain oil and several other oils: Naves, Compt. Rend. 251, 900 (1960). Stereospecific synthesis of trans-trans-farnesol: Corey et al., J. Am. Chem. Soc. 92, 6637 (1970).
Derivative Type: trans-trans-Farnesol
Properties: Liquid. bp0.35 111°. nD25 1.4872. uv max: 192-196 nm (e 28,500).
Boiling point: bp0.35 111°
Index of refraction: nD25 1.4872
Absorption maximum: uv max: 192-196 nm (e 28,500)
Derivative Type: Commercial farnesol
Properties: bp0.2 110-113°. d420 0.8871. nD20 1.4870.
Boiling point: bp0.2 110-113°
Index of refraction: nD20 1.4870
Density: d420 0.8871
Use: In perfumery, to emphasize the odor of sweet floral perfumes, such as lilac and cyclamen.
Faropenem Fasciculins Fasidotril Fasudil Fazadinium Bromide

Farnesol
Skeletal formula of farnesol
Ball-and-stick model
Identifiers
CAS number 4602-84-0 YesY
PubChem 3327, 445070 (2E,6E)-
ChemSpider 3210 YesY, 392816 (2E,6E)-
UNII X23PI60R17 YesY
DrugBank DB02509
KEGG C01493 YesY
ChEBI CHEBI:28600 YesY
ChEMBL CHEMBL25308 N
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C15H26O
Molar mass 222.37 g mol−1
Density 0.887 g/cm3
Boiling point 283-284.00 °C at 760 mmHg
111 °C at 0.35 mmHg
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions it is a colorless liquid. It is insoluble in water, but miscible with oils.

Farnesol is produced from 5-carbon isoprene compounds in both plants and animals. Phosphate activated derivatives of farnesol are the building blocks of most, and possibly all, acyclic sesquiterpenoids. These compounds are doubled to form 30-carbon squalene, which in turn is the precursors for steroids in plants, animals, and fungi. As such, farnesol and its derivatives are important starting compounds for both natural and artificial organic synthesis.