Crotonaldehyde

• Trans-2- butenal
• 3- methylacrolein
• (E)- but-2 -enal

• 4170-30-3 (E / Z)- mixture
• 123-73-9 (E)- crotonaldehyde
• 15798-64-8 (Z)- crotonaldehyde

Yellowish liquid with a pungent odor

Liquid

0.85 g · cm -3

-77 ° C

102 ° C

24 hPa ( 20 ° C)

Moderately in water ( 181 g · l-1 at 20 ° C)

1.437 (20 ° C)

Risk

No classification, as evidence of a carcinogenic effect

-138.7 KJ / mol

Template: Infobox chemical / molecular formula search available

Crotonaldehyde (pronounced crotonaldehyde ) is an unsaturated aldehyde and exists in two isomeric forms, of which the trans compound (Synonyms: (E)- crotonaldehyde ) is technically important. In nature, crotonaldehyde occurs in the product obtained from plants of the genus Croton croton oil.

Properties

Crotonaldehyde is a flammable liquid with a pungent odor. The connection is only slightly in water, readily soluble in common organic solvents, however. It tends, in the presence of oxygen to form peroxides and auto-oxidation.

Representation

The industrial synthesis of crotonaldehyde from acetaldehyde occurs. This is reacted at mild temperatures with dilute sodium hydroxide, in an aldol condensation with 3- hydroxybutanal ( acetaldol ) is formed. In a second step, this reacts with acetic acid on dehydration crotonaldehyde.

Biological Significance

In the human body also arises crotonaldehyde from acetaldehyde. Polyamines, usually natural protective substances of the cell, facilitate after alcohol consumption, the conversion of acetaldehyde into crotonaldehyde. This, in turn, is strongly suspected to alter the DNA and to be responsible for the development of cancer.

Use

The oxidation of crotonaldehyde provides crotonic acid. The reduction of crotonaldehyde provides crotyl alcohol.