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Acrolein information


Acrolein
Names
Preferred IUPAC name
Prop-2-enal
Other names
Acraldehyde[1]
Acrylic aldehyde[1]
Allyl aldehyde[1]
Ethylene aldehyde
Acrylaldehyde[1]
Identifiers
CAS Number
  • 107-02-8 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:15368 checkY
ChEMBL
  • ChEMBL721 checkY
ChemSpider
  • 7559 checkY
ECHA InfoCard 100.003.141 Edit this at Wikidata
EC Number
  • 203-453-4
IUPHAR/BPS
  • 2418
KEGG
  • C01471 checkY
PubChem CID
  • 7847
RTECS number
  • AS1050000
UNII
  • 7864XYD3JJ checkY
UN number 1092
CompTox Dashboard (EPA)
  • DTXSID5020023 Edit this at Wikidata
InChI
  • InChI=1S/C3H4O/c1-2-3-4/h2-3H,1H2 checkY
    Key: HGINCPLSRVDWNT-UHFFFAOYSA-N checkY
  • InChI=1/C3H4O/c1-2-3-4/h2-3H,1H2
    Key: HGINCPLSRVDWNT-UHFFFAOYAQ
SMILES
  • O=CC=C
  • C=CC=O
Properties
Chemical formula
C3H4O
Molar mass 56.064 g·mol−1
Appearance Colorless to yellow liquid. Colorless gas in smoke.
Odor Acrid, Foul, Irritating
Density 0.839 g/mL
Melting point −88 °C (−126 °F; 185 K)
Boiling point 53 °C (127 °F; 326 K)
Solubility in water
Appreciable (> 10%)
Vapor pressure 210 mmHg[1]
Hazards[3]
Occupational safety and health (OHS/OSH):
Main hazards
Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor.
GHS labelling:
Pictograms
GHS02: Flammable GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Signal word
Danger
Hazard statements
H225, H300, H311, H314, H330, H410
Precautionary statements
P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P273, P280, P284, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
4
3
3
Flash point −26 °C (−15 °F; 247 K)
Autoignition
temperature
278 °C (532 °F; 551 K)
Explosive limits 2.8-31%[1]
Lethal dose or concentration (LD, LC):
LC50 (median concentration)
875 ppm (mouse, 1 min)
175 ppm (mouse, 10 min)
150 ppm (dog, 30 min)
8 ppm (rat, 4 hr)
375 ppm (rat, 10 min)
25.4 ppm (hamster, 4 hr)
131 ppm (rat, 30 min)[2]
LCLo (lowest published)
674 ppm (cat, 2 hr)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 0.1 ppm (0.25 mg/m3)[1]
REL (Recommended)
TWA 0.1 ppm (0.25 mg/m3) ST 0.3 ppm (0.8 mg/m3)[1]
IDLH (Immediate danger)
2 ppm[1]
Safety data sheet (SDS) Sigma-Aldrich SDS
Related compounds
Related alkenals
Crotonaldehyde

cis-3-Hexenal
(E,E)-2,4-Decadienal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.

  1. ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0011". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b "Acrolein". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ^ "Archived copy". Archived from the original on 2015-04-02. Retrieved 2015-03-26.{{cite web}}: CS1 maint: archived copy as title (link)

and 24 Related for: Acrolein information

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Acrolein

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Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat...

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Malolactic fermentation

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to the wine such as the bitter-tasting "acrolein taint" that comes from degradation of glycerol into acrolein which then reacts with phenolic compounds...

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Crotonaldehyde

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Other names Crotonaldehyde Crotoinic aldehyde β-Methacrolein β-Methyl acrolein 2-butenal Propylene aldehyde Identifiers CAS Number 4170-30-3 (E/Z) Y 123-73-9...

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Glycerol

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efforts are being made to convert glycerol to synthetic precursors, such as acrolein and epichlorohydrin. Although usually not cost-effective because so much...

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Mesna

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anticancer agents, in vivo, may be converted to urotoxic metabolites, such as acrolein. Mesna assists to detoxify these metabolites by reaction of its sulfhydryl...

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Dehydration reaction

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water. Double dehydration is illustrated by the conversion of glycerol to acrolein: The formation of the pyrophosphate bond is an important dehydration relevant...

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Knoevenagel condensation

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modification the base is pyridine. For example, the reaction product of acrolein and malonic acid in pyridine is trans-2,4-Pentadienoic acid with one carboxylic...

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Reuterin

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acrolein. In fact, the term reuterin is the name given to the dynamic system formed by 3-hydroxypropionaldehyde, its hydrate, the dimer, and acrolein...

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Cyclophosphamide

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and detoxifies acrolein. Intermittent dosing of cyclophosphamide decreases cumulative drug dose, reduces bladder exposure to acrolein and has equal efficacy...

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Hydrohalogenation

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nucleophilic conjugate addition for example in the reaction of HCl with acrolein. Recent research has found that adding silica gel or alumina to H-Cl (or...

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Oxiranol

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glycolaldehyde (a constitutional isomer of oxiranol) and the oxidation of acrolein in the environment. Wang, Tianfang; Bowie, John H. (2010). "Radical routes...

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Allyl alcohol

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gives allyl alcohol. In alternative fashion, propylene can be oxidized to acrolein, which upon hydrogenation gives the alcohol. In principle, allyl alcohol...

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Cinnamaldehyde

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viewed as a derivative of acrolein. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards...

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Tetrahydrobenzaldehyde

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derivative of benzaldehyde. It is produced by the Diels-Alder reaction of acrolein to butadiene. It is of interest as a precursor to 3,4-epoxycyclohexylmethyl-3′...

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Acrylonitrile

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dehydration and ammoxidation. The glycerol route begins with its dehydration to acrolein, which undergoes ammoxidation to give acrylonitrile. The glutamic acid...

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Acroleinide

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a functional group which is composed of a cyclic ketal of a diol with acrolein. In pharmaceutical chemistry, it is present in acrocinonide (triamcinolone...

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Acrylic acid

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annually. The word "acrylic" was coined in 1843, for a chemical derivative of acrolein, an acrid-smelling oil derived from glycerol. Acrylic acid is produced...

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Scutellaria baicalensis

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"Protective effects of the aqueous extract of Scutellaria baicalensis against acrolein-induced oxidative stress in cultured human umbilical vein endothelial cells"...

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Turmeric

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi)...

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Propiolaldehyde

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the exothermicity of its polymerization. Its acetal can be prepared from acrolein. Propynal has been observed in the interstellar medium. It is hypothesized...

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Ginger

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi)...

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Clotrimazole

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14-prostaglandin J2 α-Sanshool (ginger, Sichuan and melegueta peppers) Acrolein Allicin (garlic) Allyl isothiocyanate (mustard, radish, horseradish, wasabi)...

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Lactic acid

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Hydroxybutyric acid Related compounds 1-Propanol 2-Propanol Propionaldehyde Acrolein Sodium lactate Ethyl lactate Pharmacology ATC code G01AD01 (WHO) QP53AG02...

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Propionaldehyde

Last Update:

three-carbon building block used in organic synthesis. Propionaldehyde along with acrolein has been detected in the molecular cloud Sagittarius B2 near the center...

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