Farnesol

Farnesol

Names
IUPAC name (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
Identifiers
CAS Number	4602-84-0 Y
3D model (Jmol)	Interactive image (2E,6E)-: Interactive image
ChEBI	CHEBI:28600 Y
ChEMBL	ChEMBL25308 N
ChemSpider	3210 Y 392816 (2E,6E)- N
DrugBank	DB02509 Y
ECHA InfoCard	100.022.731
IUPHAR/BPS	3215
KEGG	C01493 Y
PubChem	3327 445070 (2E,6E)-
UNII	EB41QIU6JL N
InChI InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3 Y Key: CRDAMVZIKSXKFV-UHFFFAOYSA-N Y (2E,6E)-: InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+ Key: CRDAMVZIKSXKFV-YFVJMOTDSA-N
SMILES OCC=C(CCC=C(CC\C=C(/C)C)C)C (2E,6E)-: OC/C=C(/CC/C=C(/CC\C=C(/C)C)C)C
Properties
Chemical formula	C15H26O
Molar mass	222.37 g/mol
Appearance	Clear colorless liquid
Odor	Floral
Density	0.887 g/cm3
Boiling point	283 to 284.00 °C (541.40 to 543.20 °F; 556.15 to 557.15 K) at 760 mmHg 111 °C at 0.35 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
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 hydrophobic, and thus 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.

Farnesol is present in many essential oils such as citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam and tolu. It is used in perfumery to emphasize the odors of sweet floral perfumes. Its method of action for enhancing perfume scent is as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes.

Farnesol is a natural pesticide for mites and is a pheromone for several other insects.

In a 1994 report released by five top cigarette companies, farnesol was listed as one of 599 additives to cigarettes. It is a flavoring ingredient.

Farnesol is produced from isoprene compounds in both plants and animals. When geranyl pyrophosphate reacts with isopentenyl pyrophosphate, the result is the 15-carbon farnesyl pyrophosphate, which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene. Oxidation can then provide sesquiterpenoids such as farnesol.