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27980

Crotonaldehyde, mixture of cis and trans

ratio of cis- and trans-isomers (~1:20), ≥99.5% (GC)

Synonym(s):

2-Butenal, mixture of cis and trans

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About This Item

Linear Formula:
CH3CH=CHCHO
CAS Number:
4170-30-3
Molecular Weight:
70.09
Beilstein/REAXYS Number:
1209254
MDL number:
MFCD00007003
UNSPSC Code:
12352100
PubChem Substance ID:
57648285
NACRES:
NA.22

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Quality Level

200

assay

≥99.5% (GC)

form

liquid

contains

~0.1% 2,6-di-tert-butyl-4-methylphenol as stabilizer
~1% H2O as stabilizer

refractive index

n20/D 1.437

bp

101-102 °C (lit.)

density

0.853 g/mL at 20 °C (lit.)

functional group

aldehyde

storage temp.

2-8°C

SMILES string

C\C=C\C=O

InChI

1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+

InChI key

MLUCVPSAIODCQM-NSCUHMNNSA-N

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1 of 4

This Item
2525228.02667C86006
Crotonaldehyde, mixture of cis and trans ratio of cis- and trans-isomers (~1:20), ≥99.5% (GC)

Sigma-Aldrich

27980

Crotonaldehyde, mixture of cis and trans

Crotononitrile, mixture of cis and trans 99%

Sigma-Aldrich

252522

Crotononitrile, mixture of cis and trans

Crotonaldehyde (mixture of isomers) for synthesis

Sigma-Aldrich

8.02667

Crotonaldehyde

Crotyl alcohol, mixture of cis and trans 96%

Sigma-Aldrich

C86006

Crotyl alcohol, mixture of cis and trans

assay

≥99.5% (GC)

assay

99%

assay

≥99.0% (GC)

assay

96%

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

form

liquid

form

liquid

form

liquid

form

liquid

refractive index

n20/D 1.437

refractive index

n20/D 1.419 (lit.)

refractive index

-

refractive index

n20/D 1.427 (lit.)

bp

101-102 °C (lit.)

bp

120-121 °C (lit.)

bp

104 °C/1013 hPa

bp

121-122 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

General description

Crotonaldehyde(2-Butenal) is an α, β-unsaturated aldehyde and extremely reactive compound. It serves as a chemical building block in the production of solvents, sorbates, and, to a lower extent, pharmaceuticals and aroma compounds. Additionally, it can be used as an alcohol denaturant, in leather tanning and in the manufacturing of rubber accelerators.

Application

Crotonaldehyde is used:

  • In the manufacturing of sorbic acid that are widely employed as food preservatives to avoid the food spoilage by microorganisms.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Aquatic Acute 1 - Eye Dam. 1 - Flam. Liq. 2 - Muta. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

55.4 °F - closed cup

flash_point_c

13 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9019
BCCN3954
BCCN3953
BCCM9018
BCCM6770

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F L Chung et al.
Cancer research, 44(3), 990-995 (1984-03-01)
Acrolein reacted with deoxyguanosine at pH 7 and 37 degrees to give three major products, Adducts 1 to 3, which were separated by high-performance liquid chromatography. They were identified by their ultraviolet, mass, and nuclear magnetic resonance spectra, by the
Reactions of acrolein, crotonaldehyde and pivalaldehyde with Cl atoms: structure-activity relationship and comparison with OH and NO3 reactions.
Ullerstam M, et al.
Physical Chemistry Chemical Physics, 3(6), 986-992 (2001)
Organocatalytic asymmetric inverse-electron-demand Diels-Alder reaction of electron-deficient dienes and crotonaldehyde.
Jun-Long Li et al.
Angewandte Chemie (International ed. in English), 49(36), 6418-6420 (2010-07-31)
Seung Eun Lee et al.
Toxicology letters, 201(3), 240-248 (2011-01-18)
Crotonaldehyde, a highly reactive α, β-unsaturated aldehyde, is a ubiquitous environmental pollutant and a product of endogenous lipid peroxidation. It is also a major component of cigarette smoke and is present in many foods and beverages, and has also been
Thomas W Kensler et al.
Carcinogenesis, 33(1), 101-107 (2011-11-03)
Epidemiological evidence has suggested that consumption of a diet rich in cruciferous vegetables reduces the risk of several types of cancers and chronic degenerative diseases. In particular, broccoli sprouts are a convenient and rich source of the glucosinolate, glucoraphanin, which
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