Showing Compound (2Z,6E)-Farnesol (FDB014760)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:27 UTC

Update date

2025-11-19 00:49:27 UTC

Primary ID

FDB014760

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(2Z,6E)-Farnesol

Description

(z)-farnesol, also known as 2-cis,6-trans-farnesol or (z,e)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, (z)-farnesol is considered to be an isoprenoid lipid molecule (z)-farnesol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (z)-farnesol can be found in linden, which makes (z)-farnesol a potential biomarker for the consumption of this food product.

CAS Number

3790-71-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(2-cis,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	ChEBI
(2Z,6E)-Farnesol	ChEBI
(Z,e)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	ChEBI
(Z,e)-Farnesol	ChEBI
2-cis,6-trans-Farnesol	ChEBI
cis,trans-Farnesol	ChEBI
(2-cis,6-trans)-Farnesol	HMDB
(2Z,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	HMDB
(±)-cis,trans-Farnesol	manual
(Z,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	biospider
(Z,E)-Farnesol	biospider
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-, (Z,E)-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	4.84	ALOGPS
logP	4.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.98 m³·mol⁻¹	ChemAxon
Polarizability	28.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C15H26O

IUPAC name

(2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

InChI Identifier

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-

InChI Key

CRDAMVZIKSXKFV-PVMFERMNSA-N

Isomeric SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C/CO

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

Classification

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

farnesol (CHEBI:16774 )
Acyclic farnesane sesquiterpenoids (C03220 )
Farnesenes (C03220 )
Acyclic farnesane sesquiterpenoids (LMPR0103010013 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 81.02%; H 11.78%; O 7.19%	DFC
Melting Point	Not Available
Boiling Point	Bp3 135°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(2Z,6E)-Farnesol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0avr-8930000000-641aa7a0528c963eca89	Spectrum
Predicted GC-MS	(2Z,6E)-Farnesol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05xr-9860000000-2eeca721058a47519afd	Spectrum
Predicted GC-MS	(2Z,6E)-Farnesol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-1590000000-88a1356fe7cab3171954	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avi-7930000000-81c18181dbd66735216a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-9400000000-e44ecbea8a96f84abd43	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0390000000-9beef594142e0da5de92	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-1980000000-3b9708ac6185abaf6d96	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05bf-4910000000-a8db2089f5647c8532ad	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05gi-5930000000-9f54facb49232e1c6a46	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05o0-9600000000-55d109ed92e3da30c7ea	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00l6-9100000000-bcc664ee21d185da076e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0690000000-8a43271c10743cad1e3e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l2-4900000000-7dcaa3b1e66cfbe960c9	2021-09-25	View Spectrum