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46188

Sigma-Aldrich

Farnesal, mixture of isomers

technical

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C15H24O
CAS Number:
19317-11-4
Molecular Weight:
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

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Tomoyo Sakata et al.
Experimental & applied acarology, 29(3-4), 279-291 (2003-11-26)
The composition of oil gland exudates from two oribatid mites, Trhypochthoniellus sp. and Trhypochthonius japonicus, was studied with reference to the related species Trhypochthoniellus crassus. Trhypochthoniellus sp. contained a mixture of seven compounds; (Z,Z)-6,9-heptadecadiene, geranial, 3-hydroxybenzene-1,2-dicarbaldehyde (gamma-acaridial), neryl formate, neral
Kenji Shimomura et al.
Journal of chemical ecology, 34(4), 467-477 (2008-03-21)
The southern cowpea weevil, Callosobruchus chinensis (Coleoptera: Bruchidae), is a major pest of stored legumes in warm temperate and tropical climates. The female sex attractant pheromone was extracted from filter-paper shelters taken from containers that housed virgin females. The extracts
Satoshi Endo et al.
Bioorganic & medicinal chemistry, 18(7), 2485-2490 (2010-03-23)
A human aldose reductase-like protein, AKR1B10 in the aldo-keto reductase (AKR) superfamily, was recently identified as a therapeutic target in the treatment of several types of cancer. In order to identify potential leads for new inhibitors of AKR1B10, we adopted
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
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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