U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H26O
Molecular Weight 222.3663
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of FARNESOL, (2E,6Z)-

SMILES

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

InChI

InChIKey=CRDAMVZIKSXKFV-GNESMGCMSA-N
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+

HIDE SMILES / InChI

Molecular Formula C15H26O
Molecular Weight 222.3663
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21893226 | https://www.ncbi.nlm.nih.gov/pubmed/20014777 | https://www.ncbi.nlm.nih.gov/pubmed/21862726 | https://www.ncbi.nlm.nih.gov/pubmed/21030469

Farnesol, (2E,6E)- is an isoprenoid found in many aromatic plants and is also produced in humans, where it acts on numerous nuclear receptors and has received considerable attention due to its apparent anticancer properties. 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. Farnesol has been suggested to function as a chemopreventative and anti-tumor agent. Farnesol is subject to restrictions on its use in perfumery as some people may become sensitized to it, however, the evidence that farnesol can cause an allergic reaction in humans is disputed.

Originator

Sources: Chemistry & Industry (London, United Kingdom) (1961), 1907-8

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
81.4 µM [IC50]
47.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The mevalonate/isoprenoid pathway inhibitor apomine (SR-45023A) is antiproliferative and induces apoptosis similar to farnesol.
2000 Apr 2
Xol INXS: role of the liver X and the farnesol X receptors.
2001 Apr
Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D.
2001 Mar
Antimycobacterial plant terpenoids.
2001 Nov
Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.
2002 Mar 25
Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium.
2004 Jul 16
Cytochrome P450 expression and activities in human tongue cells and their modulation by green tea extract.
2005 Jan 15
Farnesol attenuates 1,2-dimethylhydrazine induced oxidative stress, inflammation and apoptotic responses in the colon of Wistar rats.
2011 Jul 15
Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol.
2011 May 30
Patents

Sample Use Guides

mice were maintained for 5 wk on adiet containing 0.25%, 0.5% farnesol
Route of Administration: Oral
The ER-positive MCF-7 breast cancer cell line and MDAMB-231 breast carcinoma cells (ATCC HTB-26) lacking ER expression were used for activity evaluation. Cells were cultured at 37C in a humidified 95% air and 5% CO2 atmosphere. One day after seeding, the culture medium was replaced by fresh SFM containing farnesol (10-200mkM, MP Biomedicals, Aurora, OH), 17b-estradiol (Sigma, St Louis, MO), 4-hydroxytamoxifen (Sigma, St Louis, MO), the raloxifen analog LY 117,018 (a gift from Eli Lilly & Co., Indianapolis, IN), fulvestrant (ICI 182,780, Tocris, Bristol, UK), ibandronate (a gift from Hoffmann-LaRoche, Basel, Switzerland), mevastatin (Sigma, St Louis, MO), or vehicle. Cells were treated for 1–3 days, with drugs alone or in combinations. The FXR activator farnesol, a mevalonate pathway intermediate, exerts a mitogenic effect on MCF-7 cells.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:29:41 GMT 2023
Edited
by admin
on Fri Dec 15 19:29:41 GMT 2023
Record UNII
413TVZ4919
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FARNESOL, (2E,6Z)-
Systematic Name English
(E,Z)-FARNESOL
Systematic Name English
3,7,11-TRIMETHYLDODECA-2-TRANS,6-CIS,10-TRIEN-1-OL
Common Name English
TRANS,CIS-FARNESOL
Common Name English
FEMA NO. 2478, (2E,6Z)-
Code English
2,6,10-DODECATRIEN-1-OL, 3,7,11-TRIMETHYL-, (2E,6Z)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID501034821
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
PUBCHEM
1549109
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
RXCUI
2200390
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
CAS
3879-60-5
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
FDA UNII
413TVZ4919
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
CHEBI
35966
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY
DAILYMED
413TVZ4919
Created by admin on Fri Dec 15 19:29:41 GMT 2023 , Edited by admin on Fri Dec 15 19:29:41 GMT 2023
PRIMARY