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00071

Sigma-Aldrich

Acetaldehyde

ReagentPlus®, ≥99.0% (GC)

Synonym(s):

Ethanal

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About This Item

Linear Formula:
CH3CHO
CAS Number:
Molecular Weight:
44.05
Beilstein/REAXYS Number:
505984
EC Number:
MDL number:
UNSPSC Code:
12352114
eCl@ss:
39021102
PubChem Substance ID:
NACRES:
NA.21

biological source

synthetic

Quality Level

vapor density

1.52 (vs air)

vapor pressure

14.63 psi ( 20 °C)

product line

ReagentPlus®

assay

≥99.0% (GC)

form

liquid

autoignition temp.

365 °F

expl. lim.

60 %

refractive index

n20/D 1.332 (lit.)

bp

21 °C (lit.)

mp

−125 °C (lit.)

density

0.785 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC=O

InChI

1S/C2H4O/c1-2-3/h2H,1H3

InChI key

IKHGUXGNUITLKF-UHFFFAOYSA-N

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General description

Acetaldehyde is an organic colorless flammable liquid. It can be produced by hydration of acetylene and by catalytic oxidation of ethyl alcohol. It is mainly used in manufacturing acetic acid.
Mechanism of the thermal decomposition of acetaldehyde has been reported. It is a product of ethanol metabolism in the liver, binds covalently to various proteins, thereby alters the liver function and structure. The aldol condensation of acetaldehyde and heptanal in the presence of hydrotalcite-type catalysts has been described.

Application

Acetaldehyde may be used for the enzymatic synthesis of fatty acids.
It was used in the plasma polymerization for deposition of reactive aldehyde groups onto substrate, in a study to produce fibrous biomaterials with cell adhesive and also repulsive capability in biomedical applications. It was also used as calibration standard during determination of acetone, acetaldehyde, ethanol, and methanol in different human matrices, such as whole blood, vitreous humour, and urine using gas chromatography with flame ionization detection method (GC–FID).

Caution

forms easily paraldehyde

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Carc. 1B - Eye Irrit. 2 - Flam. Liq. 1 - Muta. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-38.0 °F - closed cup

flash_point_c

-38.89 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves


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THE ENZYMATIC SYNTHESIS OF FATTY ACIDS BY ALDOL CONDENSATION.
R O Brady
Proceedings of the National Academy of Sciences of the United States of America, 44(10), 993-998 (1958-10-15)
C S Lieber
Biochemical Society transactions, 16(3), 241-247 (1988-06-01)
Acetaldehyde, the toxic product of ethanol metabolism in the liver, covalently binds to a variety of proteins, thereby altering liver function and structure. Through its binding to tubulin, acetaldehyde decreases the polymerization of microtubules thereby impairing protein secretion and favouring
GC determination of acetone, acetaldehyde, ethanol, and methanol in biological matrices and cell culture.
Pontes, Helena, et al.
Journal of Chromatographic Science, 47.4, 272-278 (2009)
The aldol condensation of acetaldehyde and heptanal on hydrotalcite-type catalysts.
Tichit D, et al.
J. Catal., 219(1), 167-175 (2003)
Acetaldehyde plasma polymer-coated PET fibers for endothelial cell patterning: Chemical, topographical, and biological analysis.
Hadjizadeh, Afra.
Journal of Biomedical Materials Research. Part B, Applied Biomaterials, 94.1, 11-21 (2010)

Articles

The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.

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