94967
2-cis,6-trans-Farnesol
≥95.0% (GC)
Synonym(s):
(2Z,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol, cis,trans-Farnesol
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About This Item
Empirical Formula (Hill Notation):
C15H26O
CAS Number:
Molecular Weight:
222.37
Beilstein:
1723038
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.25
Pricing and availability is not currently available.
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Assay
≥95.0% (GC)
form
liquid
storage temp.
−20°C
SMILES string
C\C(C)=C\CC\C(C)=C\CC\C(C)=C/CO
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-PVMFERMNSA-N
Biochem/physiol Actions
Farnesol is an acyclic sesquiterpene alcohol, with four possible isomers, the E/E-isomer being the most common in nature. It was found to have different biological functions[1], for example to act as a quorum-sensing molecule to suppress filamentation in the fungus Candida albicans[2]; and to have antibacterial effects against Staphylococcus aureus, including promotion of potassium ion leakage[3]. Its derivatives are involved in the a-factor mating peptide of the dodecapeptide pheromone found in Saccharomyces cerevisiae[4]. The biological activity of farnesol and FPP analogues are investigated in cancer research[5][6]. 2-cis,6-trans-Farnesol is a metabolite in the sesquiterpenoid and triterpenoid biosynthesis, a reactant of farnesol 2-isomerase (EC: 5.2.1.9)
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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José S Yu et al.
Organic letters, 7(22), 4803-4806 (2005-10-21)
[structure: see text] The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of beta-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons
Roman Shchepin et al.
Chemistry & biology, 10(8), 743-750 (2003-09-05)
The dimorphic fungus Candida albicans produces extracellular farnesol (3,7,11-trimethyl-2,6,10-dodecatriene-1-ol) which acts as a quorum-sensing molecule (QSM) to suppress filamentation. Of four possible geometric isomers of farnesol, only the E,E isomer possesses QSM activity. We tested 40 natural and synthetic analogs
Yoshihiro Inoue et al.
FEMS microbiology letters, 237(2), 325-331 (2004-08-24)
The study was made of the antibacterial effects of three terpene alcohols on Staphylococcus aureus, focusing on the leakage of K+ ions and toxicity over time. The leakage of K+ ions was monitored continuously with a K+-electrode. Our results suggested
R J Hohl et al.
Lipids, 33(1), 39-46 (1998-02-21)
This investigation compares the effects of three farnesyl pyrophosphate analogs on selected aspects of isoprenoid metabolism. E,E-alpha-Hydroxyfarnesylphosphonate was prepared by an improved variation on a literature synthesis, which also gave access to the new Z,E-alpha-hydroxyfarnesyl- and alpha-hydroxygeranylphosphonates. A striking find
H Xie et al.
The Journal of organic chemistry, 65(25), 8552-8563 (2000-12-12)
The a-factor of Saccharomyces cerevisiae is a dodecapeptide pheromone (YIIKGVFWDPAC(Farnesyl)-OCH(3), 1), in which post-translational modification with a farnesyl isoprenoid and carboxymethyl group is required for full biological activity. This peptide has been used as a model system to explore the
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