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46188

Sigma-Aldrich

Farnesal, mixture of isomers

technical

Sinónimos:

3,7,11-Trimethyl-2,6,10-dodecatrienal

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About This Item

Fórmula empírica (notación de Hill):
C15H24O
Número de CAS:
19317-11-4
Peso molecular:
220.35
Beilstein/REAXYS Number:
1723427
EC Number:
242-957-9
MDL number:
MFCD00038089
UNSPSC Code:
12352100
PubChem Substance ID:
57650730
NACRES:
NA.22

grade

technical

impurities

≤3% water

refractive index

n20/D >1.4920 (lit.)
n20/D 1.497

bp

126-129 °C/3.5 mmHg (lit.)

density

0.909 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C15H24O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11-12H,5-6,8,10H2,1-4H3/b14-9+,15-11+

InChI key

YHRUHBBTQZKMEX-YFVJMOTDSA-N

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General description

Farnesal has been reported as specific lipid substrate for aldo-keto reductase 1B10 (AKR1B10). The incubation of farnesol with the protoplast of Botryococcus braunii B race strain leads to the formation of farnesal and 3-hydroxy-2,3-dihydrofarnesal.

Application

Farnesal was used in the synthesis of sesquiterpene nanaimoal.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

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H Inoue et al.
Biochemical and biophysical research communications, 196(3), 1401-1405 (1993-11-15)
Farnesal and 3-hydroxy-2,3-dihydrofarnesal (3-hydroxy-3,7,11-trimethyl-6,10-dodecadiene-1-al) were formed from farnesol when the alcohol was incubated with the protoplast of Botryococcus braunii B race strain. This fact suggests the existence of farnesal hydratase in the alga. Feeding experiments showed that both farnesal and
Grace Jones et al.
The FEBS journal, 273(21), 4983-4996 (2006-10-27)
The in vivo ligand-binding function and ligand-binding activity of the Drosophila melanogaster retinoid-X receptor (RXR) ortholog, ultraspiracle, toward natural farnesoid products of the ring gland were assessed. Using an equilibrium fluorescence-binding assay, farnesoid products in the juvenile hormone (JH) biosynthesis
Constantinos Tsangarakis et al.
The Journal of organic chemistry, 73(7), 2905-2908 (2008-03-07)
The sesquiterpene nanaimoal was synthesized in 21% overall yield and in a biomimetic manner. As a key step, the acid-catalyzed cyclization of farnesal under zeolite NaY confinement conditions was used. The intrazeolite cyclization of farnesal affords as major product a
W R Tschantz et al.
The Journal of biological chemistry, 276(4), 2321-2324 (2000-11-18)
Prenylated proteins contain either a 15-carbon farnesyl or a 20-carbon geranylgeranyl isoprenoid covalently attached via a thioether bond to a cysteine residue at or near their C terminus. As prenylated proteins comprise up to 2% of the total protein in
Kenji Shimomura et al.
Journal of chemical ecology, 36(8), 824-833 (2010-07-08)
Callosobruchus rhodesianus (Pic) (Coleoptera: Chrysomelidae: Bruchinae) is a pest of stored legumes through the Afro-tropical region. In laboratory bioassays, males of C. rhodesianus were attracted to volatiles collected from virgin females. Collections were purified by various chromatographic techniques, and the
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