FARNESOL, (2E,6E)-

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 Search

SMILES

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

InChI

InChIKey=CRDAMVZIKSXKFV-YFVJMOTDSA-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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17333335
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20014777	Inhibitor 8297	81.4 µM [IC50]
UDP-glucuronosyltransferase 1-1 15 Target ID: CHEMBL1287617 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21030469	Inhibitor 8297	47.0 µM [IC50]
Bile acid receptor FXR 31 Target ID: CHEMBL2047 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21893226	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17333335	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification of a nuclear receptor that is activated by farnesol metabolites.	1995 Jun 2	7774010
Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study.	1998 Feb	9491760
Xol INXS: role of the liver X and the farnesol X receptors.	2001 Apr	11264982
Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D.	2001 Mar	11254751
Antimycobacterial plant terpenoids.	2001 Nov	11731906
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.	2002 Jan 11	11779144
Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism.	2002 Mar 25	11958988
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.	2004 Oct	15491415
Cytochrome P450 expression and activities in human tongue cells and their modulation by green tea extract.	2005 Jan 15	15629189
Farnesol, a mevalonate pathway intermediate, stimulates MCF-7 breast cancer cell growth through farnesoid-X-receptor-mediated estrogen receptor activation.	2008 Jan	17333335

Patents

Sample Use Guides

In Vivo Use Guide

mice were maintained for 5 wk on adiet containing 0.25%, 0.5% farnesol

Route of Administration: Oral

In Vitro Use Guide

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 15:34:44 UTC 2023` Edited by `admin` on `Fri Dec 15 15:34:44 UTC 2023`
Record UNII	X23PI60R17
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FARNESOL, (2E,6E)-

Systematic Name

English

2,6,10-DODECATRIEN-1-OL, 3,7,11-TRIMETHYL-, (2E,6E)-

Systematic Name

English

3,7,11-TRIMETHYLDODECA-2-TRANS,6-TRANS,10-TRIEN-1-OL

Common Name

English

(E,E)-FARNESOL

Systematic Name

English

FEMA NO. 2478, (2E,6E)-

Code

English

FARNESOL TRANS,TRANS-FARNESOL [MI]

Common Name

English

ALL-E-FARNESOL

Common Name

English

2,6-DI-TRANS-FARNESOL

Common Name

English

(E,E)-3,7,11-TRIMETHYL-2,6,10-DODECATNEN-1-OL

Common Name

English

(2E,6E)-FARNESOL

Systematic Name

English

(E)-.BETA.-FARNESOL

Common Name

English

INHIBITOR A2

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C860