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Merck
CN

46188

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57650730
EC Number:
242-957-9
Beilstein/REAXYS Number:
1723427
MDL number:
MFCD00038089

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Product Name

Farnesal, mixture of isomers, technical

InChI key

YHRUHBBTQZKMEX-YFVJMOTDSA-N

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+

SMILES string

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

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.)

functional group

aldehyde

Quality Level

100

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Application

Farnesal was used in the synthesis of sesquiterpene nanaimoal.

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.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCN7553
BCCM2880
BCCH3313
BCCC9786
BCCB7094

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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
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
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
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
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