Occurrence
Reported found in hydrolyzed soy protein, soybeans and Virginia tobacco.
Application
Benzalacetone(122-57-6) is an endogenous metabolite. It acts as a flavouring agent, a spice, a bacterial metabolite and an inhibitor of EC 3.1.1.4 (phospholipase A2). It is mainly used in food additives, flavours and fragrances, and as an intermediate in chemical synthesis or reaction reagents. In addition, the novel hydrophobic benzazepine acetone can also be used to modify lead dioxide electrodes for electrocatalytic degradation of coal tar wastewater.
Definition
ChEBI: An enone in which a phenyl ring is attached to the beta-carbon atom of but-3-en-2-one. Although both cis- and trans-isomers are possible for the alpha,beta-unsaturated ket
ne, only the trans-isomer is observed.
Preparation
By condensing benzaldehyde and acetone in the presence of an alkaline condensing agent.
Reactions
Benzalacetone can be utilized for catalytic hydrogenation to yield alcohols, employing Raney nickel as the catalyst. Research has demonstrated that in the presence of HCl and H3PO4, Raney nickel experiences a loss of catalytic activity, resulting in a decreased hydrogenation rate; conversely, NaCl does not exert any significant effect. Although the hydrogenation of the ethylene bond in benzalacetone is inhibited, it is primarily the reduction in hydrogen absorption by the carbonyl group that is more significantly impacted, leading to a marked decrease in the quantity of alcohol produced.[1]
Aroma threshold values
Aroma characteristics at 1.0%: sweet, fruity and jamy cherry-like, aldehydic cinnamon spicy, herbal,
anisic, balsamic, toasted almond nutty and woody with slight powdery vanilla nuances.
Taste threshold values
Taste characteristics at 5 to 10 ppm: aldehydic, coumarinic and balsamic, slightly nutty, floral and fruity
with woody nuances.
General Description
trans- 4-Phenyl-3-buten-2-one is substrate for glutathione transferase. It reacts with methyl- and benzylguanidine to yield aromatic N2-substituted 2-pyrimidinamines.
Biochem/physiol Actions
Taste at 5-10 ppm
Purification Methods
Crystallise it from pet ether (b 40-60o), or distil it (b 137-142o /16mm). [Beilstein 7 IV 1003.]
References
[1] Y. ABDOH; M. R D. Selective hydrogenation of benzalacetone[C]//17 9. 1967: 256-257. DOI:10.1002/jctb.5010170904.