80720
cis,cis-Farnesol
≥95.0% (GC)
别名:
(2Z,6Z)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol, 2-cis,6-cis-Farnesol
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选择尺寸
关于此项目
经验公式（希尔记法）:
C15H26O
化学文摘社编号:
分子量:
222.37
UNSPSC Code:
12352200
NACRES:
NA.25
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1723036
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-
SMILES string
C\C(C)=C\CC\C(C)=C/CC\C(C)=C/CO
InChI key
CRDAMVZIKSXKFV-FBXUGWQNSA-N
assay
≥95.0% (GC)
form
liquid
storage temp.
−20°C
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, for example to act as a quorum-sensing molecule to suppress filamentation in the fungus Candida albicans; and to have antibacterial effects against Staphylococcus aureus, including promotion of potassium ion leakage. Its derivatives are involved in the a-factor mating peptide of the dodecapeptide pheromone found in Saccharomyces cerevisiae. The biological activity of farnesol and FPP analogues are investigated in cancer research.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
新产品
此项目有
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
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
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
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
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