Showing Compound Farnesol (FDB014891)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:32 UTC

Update date

2019-11-26 03:10:53 UTC

Primary ID

FDB014891

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Farnesol

Description

Component of many flower absolutes [CCD] Farnesol is a natural organic compound which is an acyclic sesquiterpene alcohol found as a colorless liquid. It is insoluble in water, but miscible with oils. It is the building block of most, and possibly all, acyclic sesquiterpenoids and is an important starting compound for organic synthesis. [Wikipedia]. Farnesol is found in many foods, some of which are ginger, cumin, sweet basil, and highbush blueberry.

CAS Number

4602-84-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2-trans,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	ChEBI
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	ChEBI
(2E,6E)-Farnesol	ChEBI
(e)-Farnesol	ChEBI
(e,e)-Farnesol	ChEBI
2-trans,6-trans-Farnesol	ChEBI
all-trans-Farnesol	ChEBI
trans,trans-alpha-Farnesol	ChEBI
trans,trans-Farnesol	ChEBI
trans-Farnesol	ChEBI
Ditrans,polycis-polyprenol	Kegg
trans,trans-a-Farnesol	Generator
trans,trans-Α-farnesol	Generator
2-cis,6-trans-Farnesol	HMDB
3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	HMDB
Farnesyl alcohol	HMDB
FCI 119a	HMDB
Nikkosome	HMDB
Farnesol	MeSH
(E)-beta-Farnesol	PhytoBank
(E)-β-Farnesol	PhytoBank
(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	PhytoBank
(E,E)-Farnesyl alcohol	PhytoBank
(t,t)-Farnesol	PhytoBank
2,6-Di-trans-farnesol	PhytoBank
2,6-trans,trans-Farnesol	PhytoBank
3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol	PhytoBank
all-E-Farnesol	PhytoBank
trans-1-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatriene	PhytoBank
trans-2,trans-6-Farnesol	PhytoBank
3,7,11-Trimethyl-2,6,10-dodecen-1-ol	PhytoBank
2,6,10-Dodecatrien-1-ol, 3,7,11-trimethyl-	biospider
3,7,11-Trimethyl-2,6,10-dodecatrienol	biospider
3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	biospider
FEMA 2478	db_source
trans,trans-α-farnesol	Generator

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	28.7 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

(2E,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-YFVJMOTDSA-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:16619 )
Other Prenol lipids (C06081 )
Acyclic farnesane sesquiterpenoids (LMPR0103010001 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 81.02%; H 11.78%; O 7.19%	DFC
Melting Point	< 25 oC
Boiling Point	Not Available
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-014l-9200000000-8e5fae6943a545e4bc0b	2014-09-20	View Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, 1 TMS, GC-MS Spectrum	splash10-000x-9800000000-0366097ae9a2af6bafce	Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, 1 TMS, GC-MS Spectrum	splash10-001l-9800000000-eec57a93bb5862e554f1	Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, 1 TMS, GC-MS Spectrum	splash10-000x-8900000000-9c20df8f2d1959c137d7	Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, GC-MS Spectrum	splash10-000x-9800000000-0366097ae9a2af6bafce	Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, GC-MS Spectrum	splash10-001l-9800000000-eec57a93bb5862e554f1	Spectrum
GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, GC-MS Spectrum	splash10-000x-8900000000-9c20df8f2d1959c137d7	Spectrum
Predicted GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4u-9830000000-5e08d59a4cc2e87c9984	Spectrum
Predicted GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05xr-9860000000-2eeca721058a47519afd	Spectrum
Predicted GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3,7,11-Trimethyl-1,2,6,10-dodecatrienol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-003u-0790000000-578343425424f42c9d58	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-1590000000-88a1356fe7cab3171954	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0avi-7930000000-81c18181dbd66735216a	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gi0-9400000000-e44ecbea8a96f84abd43	2016-06-03	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, Negative	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0690000000-8a43271c10743cad1e3e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00l2-4900000000-7dcaa3b1e66cfbe960c9	2021-09-22	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

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28600

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04305

CRC / DFC (Dictionary of Food Compounds) ID

JXF41-J:JXF41-J

EAFUS ID

1334

Dr. Duke ID

FARNESOL

BIGG ID

Not Available

KNApSAcK ID

C00003132

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1005091

SuperScent ID

Not Available

Wikipedia ID

Farnesol

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	DUKE
Anti adenomic	35610	An agent that inhibits adenoma growth, reducing tumor formation. It plays a biological role in regulating cell proliferation and differentiation. Therapeutically, it is used to prevent or treat adenoma-related disorders, with key medical applications in managing conditions such as colon polyps, pituitary adenomas, and other glandular tumors.	DUKE
Anti-cancer	35610	An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.	DUKE
Anti carcinomic	35610	An agent that inhibits the growth and proliferation of cancer cells, playing a crucial role in cancer prevention and treatment. Therapeutically, it is used to manage and treat various types of cancer, reducing tumor size and slowing disease progression, with key medical uses in oncology and chemotherapy.	DUKE
Anti leukemic	35610	An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.	DUKE
Anti-melanomic	35610	An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
Apoptotic		An agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.	DUKE
Name	48318	flavor	DUKE
Juvabional		A regulator of insect development, reproduction, and growth, juvenile hormone inhibitor, used in pest control and insecticide development, with potential applications in agriculture and entomology.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Pheromonal	26013	A chemical signal that induces a biological response, playing a key role in social and reproductive behaviors. Therapeutically, pheromones have applications in mood regulation, social anxiety, and reproductive health. Medical uses include treating reproductive disorders, anxiety, and mood-related conditions, with potential in autism and Alzheimer's therapy.	DUKE
Sedative	35717	An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures.	DUKE
Trichomonicide		An agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.	DUKE
Anti microbial	33281	An agent that inhibits the growth of microorganisms, such as bacteria, viruses, and fungi, playing a crucial role in preventing infections. Therapeutically, it is used to treat various infectious diseases, with key medical applications including wound care, respiratory infections, and gastrointestinal infections, ultimately reducing the risk of infection and promoting healing.	CHEBI

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mild	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
linden	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
angelica	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.