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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
Anna Luxová et al.
Chirality, 16(4), 228-233 (2004-03-23)
The absolute configurations of citronellol, 2,3-dihydrofarnesol, and 2,3-dihydrofarnesal in male marking pheromones of seven species of bumblebees and cuckoo bumblebees were determined by enantioselective gas chromatography on a capillary column coated with 60% heptakis(2,3-di-O-acetyl-6-O-TBDMS)-beta-cyclodextrin in polysiloxane PS 268. Pure (-)-S-enantiomers
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
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