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(E,E)-Farnesol

CAS106-28-5

MFC15H26O

MW222.37

EINECS679-283-3

Chemical Properties

Melting point	61-63 °C
Boiling point	149 °C4 mm Hg(lit.)
Density	0.886 g/mL at 20 °C(lit.)
refractive index	n20/D 1.490(lit.)
Flash point	205 °F
storage temp.	Sealed in dry,2-8°C
form	neat
pka	14.42±0.10(Predicted)
Water Solubility	Miscible with alcohol. Immiscible with water.
Sensitive	Light Sensitive
BRN	1723039
InChIKey	CRDAMVZIKSXKFV-YFVJMOTDSA-N
CAS DataBase Reference	106-28-5(CAS DataBase Reference)
NIST Chemistry Reference	2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (E,E)-(106-28-5)
EPA Substance Registry System	(E,E)-Farnesol (106-28-5)

Safety Information

Hazard Codes	Xi
Risk Statements	43
Safety Statements	24/25-36/37
WGK Germany	3
RTECS	JR4979000
F	8
TSCA	Yes
HS Code	29052290

MSDS

Usage And Synthesis

Chemical Properties

Clear Colourless Oil
Uses

Farnesol is a natural organic compound which is present in many essential oils.
Uses

trans,trans-Farnesol is an intermediate used in the biological synthesis of cholesterol from mevalonic acid. It is used in the perfume industry. Further, it is used in the preparation of terpenes such as squalenes, cembranoids and forskolin. It is also used in the synthesis of Cecropia juvenile hormone.
Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 3298, 1980 DOI: 10.1021/ja00529a091
The Journal of Organic Chemistry, 40, p. 3617, 1975 DOI: 10.1021/jo00912a039
General Description

trans,trans-Farnesol is sesquiterpene alcohol, which is commonly found in many essential oils, citrus fruits, propolis, and plant-derived foods and beverages. It is an effective bioactive agent that can be used in pharmaceuticals and cosmetics.
Purification Methods

The main impurity is the cis-trans isomer. Purify it by gas chromatography using a 4ft x 0.125in 3%OV-1 column at 150o. [Corey et al. J Am Chem Soc 92 6637 1970, Popjak et al. J Biol Chem 237 56 1962.] It has also been fractionated through a 14-in Podbielniak column (p 11) at 11o/0.35mm. Alternatively it has been purified by gas chromatography using SF96 silicone on Fluoropak columns or Carbowax 20M on Fluoropak or base-washed 30:60 firebrick (to avoid decomposition, prepared by treating the firebrick with 5N NaOH in MeOH and washed with MeOH to pH 8) at 210o with Helium carrier gas at 60 mL/min flow rate. The diphenylcarbamoyl derivative has m 61-63o (from MeOH) and has an IR band at 3500 cm-1. [Bates et al. J Org Chem 28 1086 1963, Beilstein 1 IV 2335.]

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