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
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+
DescriptionCurator'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
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antifungal properties of essential oils and their main components upon Cryptococcus neoformans. | 1994 Dec |
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| Identification of a nuclear receptor that is activated by farnesol metabolites. | 1995 Jun 2 |
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| Lovastatin induces apoptosis by inhibiting mitotic and post-mitotic events in cultured mesangial cells. | 1997 Oct 30 |
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| Antimycobacterial activity of (E)-phytol and derivatives: a preliminary structure-activity study. | 1998 Feb |
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| Farnesol stimulates differentiation in epidermal keratinocytes via PPARalpha. | 2000 Apr 14 |
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| The mevalonate/isoprenoid pathway inhibitor apomine (SR-45023A) is antiproliferative and induces apoptosis similar to farnesol. | 2000 Apr 2 |
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| Xol INXS: role of the liver X and the farnesol X receptors. | 2001 Apr |
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| Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D. | 2001 Mar |
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| Antimycobacterial plant terpenoids. | 2001 Nov |
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| Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB. | 2002 Jan 11 |
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| Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism. | 2002 Mar 25 |
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| Farnesol is glucuronidated in human liver, kidney and intestine in vitro, and is a novel substrate for UGT2B7 and UGT1A1. | 2004 Dec 15 |
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| Lysine beta311 of protein geranylgeranyltransferase type I partially replaces magnesium. | 2004 Jul 16 |
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| Omega-hydroxylation of farnesol by mammalian cytochromes p450. | 2004 Jun 1 |
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| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
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| Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol. | 2005 Apr 15 |
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| Cytochrome P450 expression and activities in human tongue cells and their modulation by green tea extract. | 2005 Jan 15 |
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| Biologically active fluorescent farnesol analogs. | 2005 Jun |
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| In vitro synergistic effect of farnesol and human gingival cells against Candida albicans. | 2006 Jul 15 |
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| Screening of terpenes and derivatives for antimycobacterial activity; identification of geranylgeraniol and geranylgeranyl acetate as potent inhibitors of Mycobacterium tuberculosis in vitro. | 2007 Oct |
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| Farnesol, a mevalonate pathway intermediate, stimulates MCF-7 breast cancer cell growth through farnesoid-X-receptor-mediated estrogen receptor activation. | 2008 Jan |
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| 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 |
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.
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SUBSTANCE RECORD
