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110221

Sigma-Aldrich

Acrolein

contains hydroquinone as stabilizer, 90%

Synonym(s):

2-Propenal

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About This Item

Linear Formula:
CH2=CHCHO
CAS Number:
107-02-8
Molecular Weight:
56.06
Beilstein:
741856
MDL number:
MFCD00006998
UNSPSC Code:
12352100
PubChem Substance ID:
24846970

vapor density

1.94 (vs air)

Quality Level

100

vapor pressure

4.05 psi ( 20 °C)

Assay

90%

form

liquid

autoignition temp.

428 °F

contains

hydroquinone as stabilizer

expl. lim.

31 %

impurities

<10% water and cyclic dimer

refractive index

n20/D 1.403 (lit.)

bp

53 °C (lit.)

mp

−87 °C (lit.)

solubility

H2O: soluble 2
alcohol: soluble
benzene: miscible
diethyl ether: miscible

density

0.839 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]C(=O)C=C

InChI

1S/C3H4O/c1-2-3-4/h2-3H,1H2

InChI key

HGINCPLSRVDWNT-UHFFFAOYSA-N

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General description

Acrolein causes transient urothelial loss and exposes local afferent terminals to a toxic environment.
Acrolein is a metabolite that is generated by catabolic pathaways via many oxidases.

Application

Acrolein has been used in the preparation of monomeric and dimeric β-hydroxypropionaldehyde in a hydration reaction.

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-20.2 °F - closed cup

Flash Point(C)

-29 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBG3751V
SHBF8661V
SHBF0540V
STBC4612V
14721KEV

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T L Talarico et al.
Antimicrobial agents and chemotherapy, 33(5), 674-679 (1989-05-01)
Lactobacillus reuteri converts glycerol into a potent cell growth inhibitor. This substance, termed reuterin, inhibits the growth of gram-positive and gram-negative bacteria as well as yeasts, fungi, and protozoa. Semipreparative chromatography was used to purify reuterin, and Fourier transform infrared
Anthony E Pegg
Chemical research in toxicology, 26(12), 1782-1800 (2013-11-15)
Polyamines are ubiquitous and essential components of mammalian cells. They have multiple functions including critical roles in nucleic acid and protein synthesis, gene expression, protein function, protection from oxidative damage, the regulation of ion channels, and maintenance of the structure
Kiflai Bein et al.
Molecular nutrition & food research, 55(9), 1342-1360 (2011-10-14)
Acrolein is a respiratory irritant that can be generated during cooking and is in environmental tobacco smoke. More plentiful in cigarette smoke than polycyclic aromatic hydrocarbons (PAH), acrolein can adduct tumor suppressor p53 (TP53) DNA and may contribute to TP53-mutations
Richard M LoPachin et al.
Chemical research in toxicology, 22(9), 1499-1508 (2009-07-21)
Acrolein and 4-hydroxy-2-nonenal (HNE) are byproducts of lipid peroxidation and are thought to play central roles in various traumatic injuries and disease states that involve cellular oxidative stress, for example, spinal cord trauma, diabetes, and Alzheimer's disease. In this review
Moon-shong Tang et al.
Molecular nutrition & food research, 55(9), 1291-1300 (2011-06-30)
Acrolein (Acr) is a ubiquitous environmental contaminant; it also can be generated endogenously by lipid peroxidation. Acr contains a carbonyl group and an olefinic double bond; it can react with many cellular molecules including amino acids, proteins and nucleic acids.
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