331929
trans,trans-Farnesyl bromide
95%
Synonym(s):
trans,trans-1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene
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About This Item
Linear Formula:
(CH3)2C=CH[CH2CH2C(CH3)=CH]2CH2Br
CAS Number:
Molecular Weight:
285.26
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
95%
form
liquid
refractive index
n20/D 1.509 (lit.)
bp
100-110 °C/15 mmHg (lit.)
density
1.052 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
[H]\C(CBr)=C(\C)CC\C([H])=C(/C)CC\C=C(\C)C
InChI
1S/C15H25Br/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+
InChI key
FOFMBFMTJFSEEY-YFVJMOTDSA-N
Related Categories
Application
Farnesyl bromide was used in the preparation of:
- S-trans, trans-farnesyl-L-cysteine methylester, a post translational modified amino acid
- umbelliprenin, starting reagent for the synthesis of (±)-farnesiferol A and (±)-farnesiferol C
- prenylated peptides
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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M Liakopoulou-Kyriakides et al.
Amino acids, 2(3), 285-288 (1992-10-01)
S-trans, trans-farnesyl-L-cysteine methylester, a post translational modified amino acid, was synthesized from farnesyl bromide and L-cysteine methylester hydrochloride salt in the presence of triethylamine. Its purification as well as separation from the other isomers by HPLC on RP Vydac C4
Biogentic-type synthesis of (?)-farnesiferol A and (?)-farnesiferol C.
van Tamelen EE and Coates RM.
Chemical Communications (Cambridge, England), 13, 413-415 (1996)
O Kisselev et al.
The Journal of biological chemistry, 270(43), 25356-25358 (1995-10-27)
Post-translational prenylation of the carboxyl-terminal cysteine is a characteristic feature of the guanine nucleotide-binding protein (G protein) gamma subunits. Recent findings show that the farnesylated COOH-terminal tail of the gamma 1 subunit is a specific determinant of rhodopsin-transducin coupling. We
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