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331929

Sigma-Aldrich

trans,trans-Farnesyl bromide

95%

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Synonym(s):
trans,trans-1-Bromo-3,7,11-trimethyl-2,6,10-dodecatriene
Linear Formula:
(CH3)2C=CH[CH2CH2C(CH3)=CH]2CH2Br
CAS Number:
28290-41-7
Molecular Weight:
285.26
MDL number:
MFCD00054465
PubChem Substance ID:
24860010
NACRES:
NA.22

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

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

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H315 - H318 - H335

Precautionary Statements

P261 - P280 - P305 + P351 + P338

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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