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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)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
S Vamsee Raju et al.
American journal of respiratory and critical care medicine, 188(11), 1321-1330 (2013-09-18)
Several extrapulmonary disorders have been linked to cigarette smoking. Smoking is reported to cause cystic fibrosis transmembrane conductance regulator (CFTR) dysfunction in the airway, and is also associated with pancreatitis, male infertility, and cachexia, features characteristic of cystic fibrosis and
Riyi Shi et al.
Molecular nutrition & food research, 55(9), 1320-1331 (2011-08-09)
Acrolein, an α,β-unsaturated aldehyde, is a ubiquitous pollutant that is also produced endogenously through lipid peroxidation. This compound is hundreds of times more reactive than other aldehydes such as 4-hydroxynonenal, is produced at much higher concentrations, and persists in solution
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