(E, E)-farnesol

(E, E)-farnesol
Compound Structure:
Synonyms: Farnesol;trans,trans-Farnesol;106-28-5;(E,E)-Farnesol;(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol;trans-Farnesol;(2E,6E)-Farnesol;2-trans,6-trans-Farnesol;All-trans-Farnesol;Farnesyl alcohol;3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol
Compound ID: NMPC-051
PubChem ID:

445070
Molecular Formula: C15H26O
Canonical SMILES: CC(=CCCC(=CCCC(=CCO)C)C)C
InChIKey: CRDAMVZIKSXKFV-YFVJMOTDSA-N
About the compound:

Farnesol is a sesquiterpenoid compound belonging to the farnesane group. It is dodeca-2,6,10-triene with methyl groups at positions 3, 7, and 11 and a hydroxy group at position 1. Farnesol serves various roles as a plant metabolite, a fungal metabolite, and an antimicrobial agent. This compound is classified as a farnesanesesquiterpenoid, a primary alcohol, and a polyprenol. Trans,trans-farnesol is a natural product found in organisms like Lonicera japonica and Psidiumguajava. It is an acyclic sesquiterpene alcohol, existing as a colorless liquid under standard conditions. Being hydrophobic, farnesol is insoluble in water but can mix with oils. Farnesol is produced from 5-carbon isoprene compounds in both plants and animals. Phosphate-activated derivatives of farnesol are essential building blocks for various acyclic sesquiterpenoids. These compounds are further processed to form squalene, a 30-carbon compound that serves as a precursor for steroids in plants, animals, and fungi. Farnesol and its derivatives play a crucial role as starting materials in natural and synthetic organic synthesis. Farnesol is present in numerous essential oils, including citronella, neroli, cyclamen, lemon grass, tuberose, rose, musk, balsam, and tolu. It is commonly used in perfumery to enhance the scents of sweet, floral perfumes by acting as a co-solvent that regulates the volatility of odorants. It is especially employed in lilac perfumes. Moreover, farnesol acts as a natural pesticide for mites and functions as a pheromone for several other insects. In addition to its natural sources, farnesol was listed as one of the additives in cigarettes in a 1994 report released by major cigarette companies. It serves as a flavoring ingredient in this context.


https://en.wikipedia.org/wiki/Farnesol

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]
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

2

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Farnesolis a colorless liquid with a delicate floral odor. (NTP, 1992)

Boiling Point

230 to 235 °F at 760 mmHg (NTP, 1992)

Melting Point

< 25 °C

Density

0.8846 at 68 °F (NTP, 1992)

Solubility 

Soluble in three volumes of 70% alcohol

Vapor Pressure

0.0000394 [mmHg]

                                                        

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

Source: PubChem
Source Species: Acalypha segetalis
Plumeria alba
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