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Sigma-Aldrich

trans,trans-Farnesyl chloride

97%

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Synonym(s):
trans,trans-1-Chloro-3,7,11-trimethyl-2,6,10-dodecatriene
Linear Formula:
(CH3)2C=CH[CH2CH2C(CH3)=CH]2CH2Cl
CAS Number:
67023-84-1
Molecular Weight:
240.81
MDL number:
MFCD00192172
UNSPSC Code:
12352100
PubChem Substance ID:
24864794
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.493 (lit.)

bp

59-60 °C/2.4 mmHg (lit.)

density

0.916 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]\C(CCl)=C(\C)CC\C([H])=C(/C)CC\C([H])=C(/C)C

InChI

1S/C15H25Cl/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

BJVUJIDTICYHLL-YFVJMOTDSA-N

Related Categories

General description

Physical properties (density, refractive index and boiling point) of trans,trans-farnesyl chloride have been reported.

Application

trans,trans-Farnesyl chloride (all-trans-farnesyl chloride) is suitable for use in the preparation of (S)-farnesyl thiopyrophosphate.
Farnesyl chloride may be used in the synthesis of isoprenoid conjugates of nucleoside 5′-diphosphates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Certificates of Analysis (COA)

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Youngha Ryu et al.
Organic letters, 5(24), 4713-4715 (2003-11-25)
[reaction: see text] Isoprenoid conjugates of nucleoside 5'-diphosphates were efficiently synthesized by one-step nucleophilic displacement reactions of either isoprenyl chlorides or isopentenyl tosylate with nucleoside 5'-diphosphates.
Yaws CL.
The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals, 487-487 (2015)
Yi-Hung Chen et al.
The Journal of biological chemistry, 277(9), 7369-7376 (2001-12-18)
Undecaprenyl pyrophosphate synthase (UPPS) catalyzes the consecutive condensation reactions of eight isopentenyl pyrophosphate (IPP) with farnesyl pyrophosphate (FPP) to generate C(55) undecaprenyl pyrophosphate (UPP). In the present study, site-directed mutagenesis, fluorescence quenching, and stopped-flow methods were utilized to examine the

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