Farnesol

Farnesol
Compound Structure:
Synonyms: 3,7,11-trimethyldodeca-2,6,10-trien-1-ol; Farnesyl alcohol; Nikkosome; Trimethyl dodecatrienol; trans,trans-Farnesol; 2,6,10-Trimethyl-2,6,10-dodecatrien-12-ol
Compound ID: NMPC-1048
PubChem ID:

3327

Molecular Formula: C15H26O
Canonical SMILES: CC(=CCCC(=CCCC(=CCO)C)C)C
InChIKey: CRDAMVZIKSXKFV-UHFFFAOYSA-N
About the compound:

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 possibly all acyclic sesquiterpenoids. These compounds are doubled to form 30-carbon squalene, which is the precursor for steroids in plants, animals, and fungi. Farnesol and its derivatives are important starting compounds for 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. It enhances perfume scent by acting as a co-solvent that regulates the volatility of the odorants. It is especially used in lilac perfumes. 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

GHS Hazard Statements

H315 (99.41%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (83.95%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (84.94%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H400 (12.46%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

H410 (13.64%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

First Aid

In case of exposure:

EYES: Remove contact lenses, flush with water or saline for 20-30 minutes, seek medical help, transport to hospital immediately.

SKIN: Flood with water, wash with soap, seek medical help if symptoms develop.

INHALATION: Leave contaminated area, seek medical help if symptoms arise, provide respiratory protection.

INGESTION: Do not induce vomiting. Give water if conscious, call hospital or poison control, transport to hospital if advised, ensure airway if unconscious (NTP, 1992).

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

222.37 g/mol

XLogP3-AA

4.8

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

7

Exact Mass

222.198365449 g/mol

Monoisotopic Mass

222.198365449 g/mol

Topological Polar Surface Area

20.2Ų

Heavy Atom Count

16

Formal Charge

0

Complexity

265

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

2

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Slightly yellow to colourless liquid; mild, oily, floral aroma

Boiling Point

110-113 °C

Density

0.884-0.889

Solubility 

Insoluble in water; soluble in oils

Vapor Pressure

0.0000394 [mmHg]

Source: PubChem                   

Source Species: Artocarpus altilis.
Cymbopogon citratus
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