benzylidene acetone

4-phenyl-3-buten-2-one

CAS: 122-57-6 C10 H10 O MW: 146.18890000 spicy spicy

Identification

Namebenzylidene acetone
IUPAC4-phenylbut-3-en-2-one
CAS Number122-57-6
EINECS204-555-1
FDA UNIISearch
Molecular FormulaC10 H10 O
Molecular Weight146.18890000
MDL NumberMFCD00008779
Beilstein0742047
CoE Number158
XlogP32.10 (est)

Regulatory

JECFA Food Flavoring820 4-phenyl-3-buten-2-one
DG SANTE Food Flavourings07.024 4-phenylbut-3-en-2-one
FEMA Number2881
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)122-57-6 ; 4-PHENYL-3-BUTEN-2-ONE
FDA RegulationFDA PART 172 -- FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION

Physical Properties

Appearance white to yellow crystalline solid (est)
Assay 97.00 to 100.00 sum of isomers
Food Chemicals Codex Listed No
Melting Point 39.00 to 42.00 °C. @ 760.00 mm Hg
Boiling Point 260.00 to 261.00 °C. @ 760.00 mm Hg, 147.00 to 149.00 °C. @ 20.00 mm Hg
Congealing Point 39.00 °C.
Vapor Pressure 0.012000 mmHg @ 25.00 °C. (est)
Flash Point 253.00 °F. TCC ( 122.78 °C. )
logP (o/w) 2.070
Soluble in alcohol
Stability bath foam

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesnot used anymore

Organoleptic Properties

Odor Strength medium ,
Substantivity 400 hour(s) at 20.00 %
Odor Description
at 1.00 % in dipropylene glycol.
Sweet, spicy, cinnamon, balsamic, anisyl, powdery and phenolic with jammy, fruity notes
almond; anise; balsam; butter; cherry; cinnamon; creamy; jam; floral; herbaceous; sweet; vanilla; woody
Odor sample from Fritzsche Dodge & Olcott, Inc.
Taste Description at 30.00 ppm.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Human Experience2 % solution: no irritation or sensitization.
Oral/Parenteral Toxicityoral-rat LD50 2031 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
IFRA Critical EffectDermal sensitization
Recommendation for benzylidene acetone usage levels up toPROHIBITED: Should not be used as a fragrance ingredient.
Maximised Survey-derived Daily Intakes (MSDI-EU)1.20 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)7.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)1100 (μg/person/day)
Threshold of Concern1800 (μg/person/day)
Structure ClassI
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-
Dairy products, excluding products of category 02.0 (01.0)1.59000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)0.02000
Edible ices, including sherbet and sorbet (03.0)-
Processed fruit (04.1)-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)4.44000
Chewing gum (05.3)1.59000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)5.25000
Bakery wares (07.0)-
Meat and meat products, including poultry and game (08.0)-
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)0.89000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)1.28000
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)-

Alfrebro LLC/ Archer Daniels Midland Company

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Berje Inc.

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Where the world comes to its senses - Berjé is a global distributor of Essential Oils and Aromatic Chemicals.

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Charkit Chemical Corporation

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CJ Latta & Associates, LLC

Extensive Line

Aromatic Chemicals and Organic Acids.

View All Website (630) 240-8079 chiplatta@msn.com

Lluch Essence S.L.

A family company dedicated to sales and distribution

Flexibility, availability, price and quality.

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Moellhausen S.P.A.

THE CHEMISTRY OF EMOTIONS

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Penta International Corporation

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Sigma-Aldrich

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SRS Aromatics Ltd

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Bringing flavour and fragrance into your world.

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TCI AMERICA

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We continuously strive to advance our technology.

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The John D. Walsh Company, Inc

Suppliers Since 1942

Supplying the fragrance and flavor industry with high quality products.

View All Website 973-962-1400 info@johndwalsh.com

R C Treatt and Co Ltd

Innovative ingredient solutions

World-leading innovative ingredient solutions provider for the flavour, fragrance and FMCG industries.

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Ernesto Ventós S.A.

Leaders in essence

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Potential Uses

FL almond FR apple blossom FL blackberry FR castoreum FL cherry FL chocolate cocoa FR currant FR fern fixer FR fruit FL grape FR hawthorn FR hay new mown hay FR heliotrope FR jonquil FR lavender FL lemon FR lilac FR musk FR neroli FL nut FR pine FL raspberry FR rhubarb FL strawberry FR sweet pea FL vanilla FL violet

Natural Occurrence

coffee roasted coffee PMC soybean tobacco virginia tobacco

Synonyms

acetocinnamone benzal acetone benzalacetone benzylideneacetone 3- buten-2-one, 4-phenyl- methyl 2-phenyl vinyl ketone methyl beta-styryl ketone methyl styryl ketone 4- phenyl but-3-en-2-one 4- phenyl butenone 2- phenyl vinyl methyl ketone 4- phenyl-3-buten-2-one 4- phenylbut-3-en-2-one 4- phenylbutenone styryl methyl ketone PubMed: Digallane with redox-active diimine ligand: dualism of electron-transfer reactions. PubMed: Ferrous Carbonyl Dithiolates as Precursors to FeFe, FeCo, and FeMn Carbonyl Dithiolates. PubMed: Additive-assisted regioselective 1,3-dipolar cycloaddition of azomethine ylides with benzylideneacetone. PubMed: Protein preparation, crystallization and preliminary X-ray analysis of Polygonum cuspidatum bifunctional chalcone synthase/benzalacetone synthase. PubMed: An entomopathogenic bacterium, Xenorhabdus nematophila, suppresses expression of antimicrobial peptides controlled by Toll and Imd pathways by blocking eicosanoid biosynthesis. PubMed: (99m)Tc-labeled dibenzylideneacetone derivatives as potential SPECT probes for in vivo imaging of β-amyloid plaque. PubMed: Metabolism of BYZX in human liver microsomes and cytosol: identification of the metabolites and metabolic pathways of BYZX. PubMed: Engineering of plant type III polyketide synthases. PubMed: Gas phase retro-Michael reaction resulting from dissociative protonation: fragmentation of protonated warfarin in mass spectrometry. PubMed: Gas chromatography with flame ionization detection for determination of additives in an electrolytic Zn bath. PubMed: 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). PubMed: Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata. PubMed: A facile solvent free Claisen-Schmidt reaction: synthesis of α,α'-bis-(substituted-benzylidene)cycloalkanones and α,α'-bis-(substituted-alkylidene)cycloalkanones. PubMed: On the accuracy of DFT methods in reproducing ligand substitution energies for transition metal complexes in solution: the role of dispersive interactions. PubMed: Synthesis of the pyridinyl analogues of dibenzylideneacetone (pyr-dba) via an improved Claisen-Schmidt condensation, displaying diverse biological activities as curcumin analogues. PubMed: Evaluation of hepatic glutathione transferase Mu 1 and Theta 1 activities in humans and mice using genotype information. PubMed: Ni(II) and Pd(II) pyridinyloxazolidine-compounds: synthesis, X-ray characterisation and catalytic activities in the aza-Michael reaction. PubMed: Bacterial metabolites of an entomopathogenic bacterium, Xenorhabdus nematophila, inhibit a catalytic activity of phenoloxidase of the diamondback moth, Plutella xylostella. PubMed: A New Route to Azadithiolato Complexes. PubMed: Pd-NHC catalyzed conjugate addition versus the Mizoroki-Heck reaction. PubMed: Benzylideneacetone, an eicosanoid biosynthesis inhibitor enhances baculovirus pathogenicity in the diamondback moth, Plutella xylostella. PubMed: A structure-based mechanism for benzalacetone synthase from Rheum palmatum. PubMed: Synthesis and anti-inflammatory activity of novel (substituted)benzylidene acetone oxime ether derivatives: molecular modeling study. PubMed: Quantitative structure-activity relationship modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors. PubMed: Highly enantioselective organocatalytic conjugate addition of nitromethane to benzylidene acetones. PubMed: Crystallization and preliminary crystallographic analysis of a plant type III polyketide synthase that produces benzalacetone. PubMed: Benzylideneacetone, an immunosuppressant, enhances virulence of Bacillus thuringiensis against beet armyworm (Lepidoptera: Noctuidae). PubMed: New "green" approaches to the synthesis of pyrazole derivatives. PubMed: Microbial production of 4-hydroxybenzylidene acetone, the direct precursor of raspberry ketone. PubMed: Novel hydrido-ruthenium(II) complexes with histidine derivatives and their application in the hydrogenation of ketones. PubMed: Phenolic Michael reaction acceptors: combined direct and indirect antioxidant defenses against electrophiles and oxidants. PubMed: An entomopathogenic bacterium, Xenorhabdus nematophila, inhibits hemocyte phagocytosis of Spodoptera exigua by inhibiting phospholipase A(2). PubMed: Structure function analysis of benzalacetone synthase from Rheum palmatum. PubMed: Highly asymmetric Michael addition to alpha,beta-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine. PubMed: Concise asymmetric total synthesis of obolactone. PubMed: Antioxidant effects of hydroxybenzalacetones on peroxynitrite-induced lipid peroxidation in red blood cell membrane ghost and SOS response in Salmonella typhimurium TA4107/pSK1002. PubMed: 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. PubMed: Reaction of metalated nitriles with enones. PubMed: Solution and solid state structure and tautomerism of azo coupled enaminone derivatives of benzoylacetone. PubMed: Highly enantioselective conjugate additions of potassium organotrifluoroborates to enones by use of monodentate phosphoramidite ligands. PubMed: Quantitative structure-activity relationship analyses of antioxidant and free radical scavenging activities for hydroxybenzalacetones. PubMed: Identification of an antibacterial compound, benzylideneacetone, from Xenorhabdus nematophila against major plant-pathogenic bacteria. PubMed: Site-directed mutagenesis of benzalacetone synthase. The role of the Phe215 in plant type III polyketide synthases. PubMed: Organocatalytic asymmetric conjugate addition of nitroalkanes to alpha,beta-unsaturated enones using novel imidazoline catalysts. PubMed: Enzymatic formation of an unnatural C(6)-C(5) aromatic polyketide by plant type III polyketide synthases. PubMed: Quantum chemical- and 3-D-QSAR (CoMFA) studies of benzalacetones and 1,1,1-trifluoro-4-phenyl-3-buten-2-ones. PubMed: Reductive metabolism of an alpha,beta-ketoalkyne, 4-phenyl-3-butyn-2-one, by rat liver preparations. PubMed: Role of 4-phenyl-3-buten-2-one in boar taint: identification of new compounds related to sensorial descriptors in pig fat. PubMed: Potency of Michael reaction acceptors as inducers of enzymes that protect against carcinogenesis depends on their reactivity with sulfhydryl groups. PubMed: Structure-antimutagenic activity relationships of benzalacetone derivatives against UV-induced mutagenesis in E. coli WP2uvrA and gamma-induced mutagenesis in Salmonella typhimurium TA2638. PubMed: Production and elicitation of benzalacetone and the raspberry ketone in cell suspension cultures of Rubus idaeus. PubMed: Structure-activity relationship in potentially anti-tumor promoting benzalacetone derivatives, as assayed by the epstein-barr virus early antigen activation. PubMed: Microsomal carbonyl reductase responsible for reduction of 4-phenyl-3-buten-2-one in rats. PubMed: Reductive metabolism In vivo of trans-4-phenyl-3-buten-2-one in rats and dogs. PubMed: Anticandidial effect of phenylbutene derivatives and their interaction with ergosterol. PubMed: The three-dimensional structure of an avian class-mu glutathione S-transferase, cGSTM1-1 at 1.94 A resolution. PubMed: The inhibition by flavonoids of 2-amino-3-methylimidazo[4,5-f]quinoline metabolic activation to a mutagen: a structure-activity relationship study. PubMed: Absorption, disposition, and metabolism of trans-methyl styryl ketone in female B6C3F1 mice. PubMed: Antimutagenic effects of dehydrozingerone and its analogs on UV-induced mutagenesis in Escherichia coli. PubMed: Oral and topical absorption, disposition kinetics, and the metabolic fate of trans-methyl styryl ketone in the male Fischer 344 rat. PubMed: Glutathione transferase mimics: micellar catalysis of an enzymic reaction. PubMed: Distribution of glutathione S-transferase isoforms in rat liver after induction by beta-naphthoflavone or 3-methylcholanthrene. PubMed: Multiplicity of rat liver 15-ketoprostaglandin delta 13-reductases. PubMed: Glutathione S-transferases in the Japanese quail: tissue distribution and purification of the liver isozymes. PubMed: Stereoselective catalysis of a retro-Michael reaction by class mu glutathione transferases. Consequences for the internal distribution of products in the active site. PubMed: The high non-enzymatic conjugation rates of some glutathione S-transferase (GST) substrates at high glutathione concentrations. PubMed: Biochemical analysis of recombinant glutathione S-transferase of Fasciola hepatica. PubMed: Rational reconstruction of the active site of a class mu glutathione S-transferase. PubMed: Influences of dietary deoxycholic acid on progression of hepatocellular neoplasms and expression of glutathione S-transferases in rats. PubMed: Reduced expression of glutathione S-transferase Yb2 during progression of chemically induced hepatocellular carcinomas in Fischer 344 rats. PubMed: Effects of age and dietary restriction on liver glutathione transferase activities in Lobund-Wistar rats. PubMed: Purification and kinetic mechanism of the glutathione S-transferase from C6/36, an Aedes albopictus cell line. PubMed: Inter-individual variability of human hepatic glutathione S-transferase isozymes assessed by inhibitory capacity. PubMed: Structure and function of the xenobiotic substrate binding site of a glutathione S-transferase as revealed by X-ray crystallographic analysis of product complexes with the diastereomers of 9-(S-glutathionyl)-10-hydroxy-9,10-dihydrophenanthrene. PubMed: Human Mu-class glutathione S-transferases present in liver, skeletal muscle and testicular tissue. PubMed: Purification and characterization of class mu glutathione S-transferase isozymes from rabbit hepatic tissue. PubMed: Characterization of a novel microsomal glutathione S-transferase produced by Aspergillus ochraceus TS. PubMed: Schistosoma mansoni: single-step purification and characterization of glutathione S-transferase isoenzyme 4. PubMed: Contribution of tyrosine 6 to the catalytic mechanism of isoenzyme 3-3 of glutathione S-transferase. PubMed: Are the histidine residues of glutathione S-transferase important in catalysis? An assessment by 13C NMR spectroscopy and site-specific mutagenesis. PubMed: A novel glutathione transferase (13-13) isolated from the matrix of rat liver mitochondria having structural similarity to class theta enzymes. PubMed: 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. PubMed: Variation in the expression of Mu-class glutathione S-transferase isoenzymes from human skeletal muscle. Evidence for the existence of heterodimers. PubMed: The isolation and characterization of the major glutathione S-transferase from the squid Loligo vulgaris. PubMed: Xenobiotic-inducible expression of murine glutathione S-transferase Ya subunit gene is controlled by an electrophile-responsive element. PubMed: S-(1,2-dicarboxyethyl)glutathione and activity for its synthesis in rat tissues. PubMed: Effect of aflatoxin B1 treatment in vivo on the in vitro activity of hepatic and extrahepatic glutathione S-transferase. PubMed: Sex differences in the subunits of glutathione-S-transferase isoenzyme from rat and human kidney. PubMed: Changes in hepatic cytosolic glutathione S-transferase enzymes induced by clotrimazole treatment in rats. PubMed: Purification and properties of glutathione transferase from Issatchenkia orientalis. PubMed: Differences in the influence of diet on hepatic glutathione S-transferase activity and glutathione content between young and old C57 black female mice. PubMed: Xenobiotic metabolizing enzyme systems in test fish. III. Comparative studies of liver cytosolic glutathione S-transferases. PubMed: Fluorometric determination of benzylideneacetone in fragrance products by liquid chromatography with post-column derivatization. PubMed: Purification of three cytosolic glutathione S-transferases from adult Schistosoma mansoni. PubMed: Halothane: inhibition and activation of rat hepatic glutathione S-transferases. PubMed: Paradoxical inhibition of rat glutathione transferase 4-4 by indomethacin explained by substrate-inhibitor-enzyme complexes in a random-order sequential mechanism. PubMed: Differential induction of rat hepatic glutathione S-transferase isoenzymes by hexachlorobenzene and benzyl isothiocyanate. Comparison with induction by phenobarbital and 3-methylcholanthrene. PubMed: Sex- and substrate-dependent changes in hepatic cytosolic glutathione S-transferase enzymes produced by dietary choline-deficiency. PubMed: The purification and characterization of glutathione S-transferase from the hepatopancreas of the blue crab, Callinectes sapidus. PubMed: Synthesis and antiarrhythmic activity of new 3-[2-(omega-aminoalkoxy)phenoxy]-4-phenyl-3-buten-2-ones and related compounds. PubMed: The major isozyme of rat cardiac glutathione transferases. Its correspondence to hepatic transferase X. PubMed: Kinetic independence of the subunits of cytosolic glutathione transferase from the rat. PubMed: Synthesis of 3-(4,4-dimethyl-2-piperidon-6-yl)methyl-2-pyrazoline derivatives. PubMed: Effects of pH on weak and positive control mutagens in the Ames Salmonella plate assay. PubMed: Antigenic competition in the induction of contact sensitivity in the guinea pig. PubMed: Age-development and inducibility of hepatic glutathione S-transferase activities in mice, rats, rabbits and guinea-pigs. PubMed: Purification and characterization of glutathione S-transferases P, S and N. Isolation from rat liver of Yb1 Yn protein, the existence of which was predicted by subunit hybridization in vitro. PubMed: Mannich bases of 4-phenyl-3-buten-2-one: a new class of antiherpes agent. PubMed: Regulation of epididymal glutathione S-transferases: effects of orchidectomy and androgen replacement. PubMed: Purification of a new glutathione S-transferase (transferase mu) from human liver having high activity with benzo(alpha)pyrene-4,5-oxide. PubMed: The presence and longitudinal distribution of the glutathione S-transferases in rat epididymis and vas deferens. PubMed: Stoichiometric model of alpha-cyclodextrin complex formation. PubMed: Glutathione S-transferases in earthworms (Lumbricidae). PubMed: Isoelectric focusing of glutathione S-transferases from rat liver and kidney. PubMed: [Halogenated 4-phenyl-3-buten-2-one Oximes (author's transl)]. PubMed: Distribution of enzymes that catalyse reactions of glutathione with alpha beta-unsaturated compounds. PubMed: Enzymes catalysing conjugations of glutathione with alpha-beta-unsaturated carbonyl compounds.