122-57-6 | 4-Phenylbut-3-en-2-one

Packsize	Purity	Availability	Price	Discounted Price
1g	90%	in stock	$15.00	$10.00
5g	90%	in stock	$16.00	$11.00
25g	90%	in stock	$18.00	$12.00
100g	90%	in stock	$19.00	$13.00

Description

• Catalog Number: AA54918
• Chemical Name: 4-Phenylbut-3-en-2-one
• CAS Number: 122-57-6
• Molecular Formula: C10H10O
• Molecular Weight: 146.1858
• MDL Number: MFCD00008779
• SMILES: CC(=O)/C=C/c1ccccc1
• NSC Number: 5605

Computed Properties

• Complexity: 152
• Covalently-Bonded Unit Count: 1
• Defined Bond Stereocenter Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 2.1

Upstream Synthesis Route

4-Phenylbut-3-en-2-one, also known as benzalacetone, serves as a versatile building block in chemical synthesis due to its unique structure and reactivity. This compound is commonly used as a key intermediate in the preparation of various valuable organic compounds. One prominent application of 4-Phenylbut-3-en-2-one is its utilization in the synthesis of pharmaceuticals, flavors, fragrances, and other fine chemicals. Its conjugated structure allows for diverse functional group transformations, making it a valuable starting material for complex molecule synthesis. Additionally, the α,β-unsaturated ketone moiety in 4-Phenylbut-3-en-2-one enables it to participate in Michael additions, Knoevenagel condensations, and other important organic reactions, further expanding its utility in chemical synthesis.

Literature

• Design, synthesis and exploring the quantitative structure-activity relationship of some antioxidant flavonoid analogues.

  Bioorganic & medicinal chemistry letters 20141101

• Gas phase retro-Michael reaction resulting from dissociative protonation: fragmentation of protonated warfarin in mass spectrometry.

  Journal of mass spectrometry : JMS 20120801

• Toxicology and carcinogenesis studies of methyl trans-styryl ketone (CAS NO 1896-62-4) in F344/N rats and B6C3F1 mice (feed and dermal studies).

  National Toxicology Program technical report series 20120501

• Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen-Schmidt condensation, displaying diverse biological activities as curcumin analogues.

  Organic & biomolecular chemistry 20120214

• Relating skin sensitizing potency to chemical reactivity: reactive Michael acceptors inhibit NF-κB signaling and are less sensitizing than S(N)Ar- and S(N)2- reactive chemicals.

  Chemical research in toxicology 20111121

• Bacterial metabolites of an entomopathogenic bacterium, Xenorhabdus nematophila, inhibit a catalytic activity of phenoloxidase of the diamondback moth, Plutella xylostella.

  Journal of microbiology and biotechnology 20110301

• Benzylideneacetone, an eicosanoid biosynthesis inhibitor enhances baculovirus pathogenicity in the diamondback moth, Plutella xylostella.

  Journal of invertebrate pathology 20110201

• The enzymatic asymmetric conjugate umpolung reaction.

  Angewandte Chemie (International ed. in English) 20100903

• Synthesis and anti-inflammatory activity of novel (substituted)benzylidene acetone oxime ether derivatives: molecular modeling study.

  European journal of medicinal chemistry 20100401

• Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives.

  European journal of medicinal chemistry 20091201

• DNA-targeting pyrroloquinoline-linked butenone and chalcones: synthesis and biological evaluation.

  European journal of medicinal chemistry 20090701

• Quantitative structure-activity relationship modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors.

  Chemical biology & drug design 20090501

• Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones.

  Chirality 20081101

• Crystallization and preliminary crystallographic analysis of a plant type III polyketide synthase that produces benzalacetone.

  Acta crystallographica. Section F, Structural biology and crystallization communications 20080401

• Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensis against beet armyworm (Lepidoptera: Noctuidae).

  Journal of economic entomology 20080201

• Microbial production of 4-hydroxybenzylidene acetone, the direct precursor of raspberry ketone.

  Letters in applied microbiology 20070701

• Structure function analysis of benzalacetone synthase from Rheum palmatum.

  Bioorganic & medicinal chemistry letters 20070601

• Highly asymmetric Michael addition to alpha,beta-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine.

  Angewandte Chemie (International ed. in English) 20070101

• Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.

  Journal of natural products 20061001

• Microsphere-based protease assays and screening application for lethal factor and factor Xa.

  Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

• Concise asymmetric total synthesis of obolactone.

  The Journal of organic chemistry 20060331

• Metabolism of the alpha,beta-unsaturated ketones, chalcone and trans-4-phenyl-3-buten-2-one, by rat liver microsomes and estrogenic activity of the metabolites.

  Drug metabolism and disposition: the biological fate of chemicals 20050801

• Antioxidant effects of hydroxybenzalacetones on peroxynitrite-induced lipid peroxidation in red blood cell membrane ghost and SOS response in Salmonella typhimurium TA4107/pSK1002.

  Chemical & pharmaceutical bulletin 20050801

• Quantitative structure-activity relationship analyses of antioxidant and free radical scavenging activities for hydroxybenzalacetones.

  Bioorganic & medicinal chemistry letters 20041115

• Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plant-pathogenic bacteria.

  FEMS microbiology letters 20041015

• Site-directed mutagenesis of benzalacetone synthase. The role of the Phe215 in plant type III polyketide synthases.

  The Journal of biological chemistry 20030704

• Enzymatic formation of an unnatural C(6)-C(5) aromatic polyketide by plant type III polyketide synthases.

  Organic letters 20021017

• Quantum chemical- and 3-D-QSAR (CoMFA) studies of benzalacetones and 1,1,1-trifluoro-4-phenyl-3-buten-2-ones.

  Bioorganic & medicinal chemistry letters 20020902

• Reductive metabolism of an alpha,beta-ketoalkyne, 4-phenyl-3-butyn-2-one, by rat liver preparations.

  Drug metabolism and disposition: the biological fate of chemicals 20020401

• Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase.

  The Journal of biological chemistry 20011102

• Role of 4-phenyl-3-buten-2-one in boar taint: identification of new compounds related to sensorial descriptors in pig fat.

  Journal of agricultural and food chemistry 20011101

• Structure-antimutagenic activity relationships of benzalacetone derivatives against UV-induced mutagenesis in E. coli WP2uvrA and gamma-induced mutagenesis in Salmonella typhimurium TA2638.

  Mutation research 20010301

• Parallel induction of heme oxygenase-1 and chemoprotective phase 2 enzymes by electrophiles and antioxidants: regulation by upstream antioxidant-responsive elements (ARE).

  Molecular medicine (Cambridge, Mass.) 19951101

• Electrophile and antioxidant regulation of enzymes that detoxify carcinogens.

  Proceedings of the National Academy of Sciences of the United States of America 19950912

• Hepatic glutathione S-transferases in mice fed on a diet containing the anticarcinogenic antioxidant butylated hydroxyanisole. Isolation of mouse glutathione S-transferase heterodimers by gradient elution of the glutathione-Sepharose affinity matrix.

  The Biochemical journal 19910715

• Antigenic competition in the induction of contact sensitivity in the guinea pig.

  International archives of allergy and applied immunology 19850101