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Details

Stereochemistry ACHIRAL
Molecular Formula C15H26O
Molecular Weight 222.3669
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

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

SMILES

CC(=CCC/C(=C(/[H])\CC/C(=C(/[H])\CO)/C)/C)C

InChI

InChIKey=CRDAMVZIKSXKFV-FBXUGWQNSA-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 222.3669
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
Antifungal properties of essential oils and their main components upon Cryptococcus neoformans.
1994 Dec
Identification of a nuclear receptor that is activated by farnesol metabolites.
1995 Jun 2
Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells.
1997 Oct 30
Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.
1998 Feb
Farnesol stimulates differentiation in epidermal keratinocytes via PPARalpha.
2000 Apr 14
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
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.
2002 Jan 11
Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.
2002 Mar 25
Farnesol is glucuronidated in human liver, kidney and intestine in vitro, and is a novel substrate for UGT2B7 and UGT1A1.
2004 Dec 15
Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium.
2004 Jul 16
Omega-hydroxylation of farnesol by mammalian cytochromes p450.
2004 Jun 1
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol.
2005 Apr 15
Cytochrome P450 expression and activities in human tongue cells and their modulation by green tea extract.
2005 Jan 15
Biologically active fluorescent farnesol analogs.
2005 Jun
In vitro synergistic effect of farnesol and human gingival cells against Candida albicans.
2006 Jul 15
Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro.
2007 Oct
Farnesol, a mevalonate pathway intermediate, stimulates MCF-7 breast cancer cell growth through farnesoid-X-receptor-mediated estrogen receptor activation.
2008 Jan
Farnesol ameliorates massive inflammation, oxidative stress and lung injury induced by intratracheal instillation of cigarette smoke extract in rats: an initial step in lung chemoprevention.
2008 Nov 25
The evolution of farnesoid X, vitamin D, and pregnane X receptors: insights from the green-spotted pufferfish (Tetraodon nigriviridis) and other non-mammalian species.
2011 Feb 3
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 Sat Jun 26 14:47:52 UTC 2021
Edited
by admin
on Sat Jun 26 14:47:52 UTC 2021
Record UNII
J03523NK03
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FARNESOL, (2Z,6Z)-
Systematic Name English
3,7,11-TRIMETHYLDODECA-2-CIS,6-CIS,10-TRIEN-1-OL
Common Name English
2,6,10-DODECATRIEN-1-OL, 3,7,11-TRIMETHYL-, (2Z,6Z)-
Systematic Name English
FEMA NO. 2478, (2Z,6Z)-
Code English
(Z,Z)-FARNESOL
Systematic Name English
CIS,CIS-FARNESOL
Common Name English
CIS-FARNESOL
Common Name English
Code System Code Type Description
FDA UNII
J03523NK03
Created by admin on Sat Jun 26 14:47:52 UTC 2021 , Edited by admin on Sat Jun 26 14:47:52 UTC 2021
PRIMARY
PUBCHEM
1549107
Created by admin on Sat Jun 26 14:47:52 UTC 2021 , Edited by admin on Sat Jun 26 14:47:52 UTC 2021
PRIMARY
CAS
16106-95-9
Created by admin on Sat Jun 26 14:47:52 UTC 2021 , Edited by admin on Sat Jun 26 14:47:52 UTC 2021
PRIMARY