3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol Acetate (mixture of isomers)

Names

[ Name ]:
3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol Acetate (mixture of isomers)

[Synonym ]:
Farnesy
3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol Acetate
acetic acid-(3,7,11-trimethyl-dodeca-2,6,10-trienyl ester)
EINECS 249-689-1
FARNESYLACETAT
Essigsaeure-(3,7,11-trimethyl-dodeca-2,6,10-trienylester)
1-acetoxy-3,7,11-trimethyl-dodeca-2,6,10-triene
MFCD00036516
farnesol acetate
FARNESYL ACETATE,CIS-TRANS
Farnesyl Acetate
ACETIC ACID FARNESYLACETATE
ACETIC ACID FARNESYL ESTER

Biological Activity

[Description]:

Farnesyl acetate is a sesquiterpene isolated from the leaves of Amomum gagnepainii. Farnesyl acetate has significant toxicity against red palm weevil larvae with a LD50 of 7867 ppm[1][2].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[References]

[1]. Guo D, et al. Biosynthesis of advanced biofuel farnesyl acetate using engineered Escherichia coli. Bioresour Technol. 2018 Dec;269:577-580.

[2]. Hussain A, et al. Lethality of Sesquiterpenes Reprogramming Red Palm Weevil Detoxification Mechanism for Natural Novel Biopesticide Development. Molecules. 2019 Apr 26;24(9).

Chemical & Physical Properties

[ Density]:
0.914 g/mL at 25 °C(lit.)

[ Boiling Point ]:
115-125 °C0.3 mm Hg(lit.)

[ Molecular Formula ]:
C₁₇H₂₈O₂

[ Molecular Weight ]:
264.40300

[ Flash Point ]:
>230 °F

[ Exact Mass ]:
264.20900

[ PSA ]:
26.30000

[ LogP ]:
4.96870

[ Vapour Pressure ]:
5.44E-05mmHg at 25°C

[ Index of Refraction ]:
n20/D 1.477

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Synthetic Route

Click to get detail synthetic route

Articles

The geranyl-modified tryptophan residue is crucial for ComXRO-E-2 pheromone biological activity.

Bioorg. Med. Chem. Lett. 21(13) , 4041-4, (2011)

The ComX pheromone is an isoprenoidal oligopeptide containing a modified tryptophan residue, which stimulates natural genetic competence in gram-positive bacteria, Bacillus. We have reported the struc...

Methyl farnesoate synthesis is necessary for the environmental sex determination in the water flea Daphnia pulex.

J. Insect Physiol. 80 , 22-30, (2015)

Sex-determination systems can be divided into two groups: genotypic sex determination (GSD) and environmental sex determination (ESD). ESD is an adaptive life-history strategy that allows control of s...

Identification of pheromones and optimization of bait composition for click beetle pests (Coleoptera: Elateridae) in Central and Western Europe.

Pest Manag. Sci. 59(4) , 417-25, (2003)

Based on analysis of pheromone gland extracts, highly attractive new baits have been developed for three click beetle pests. That for Agriotes brevis is a mixture of geranyl butanoate and (E,E)-farnes...