Page last updated: 2024-09-22

benzylideneacetone

Description

benzylideneacetone: RN given refers to cpd without isomeric; structure in Merck Index, 9th ed, #1153 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trans-benzylideneacetone : The trans-isomer of benzylideneacetone. It acts as an inhibitor of the enzyme phospholipase A2 (EC 3.1.1.4) of insects like diamond back moth. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

benzylideneacetone : 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 ketone, only the trans-isomer is observed. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID637759
CHEMBL ID73639
CHEBI ID78399
CHEBI ID217301
SCHEMBL ID76632
SCHEMBL ID312972
MeSH IDM0084647

Synonyms (134)

Synonym
CHEMBL73639
chebi:78399 ,
4-07-00-01003 (beilstein handbook reference)
b03x40bmt5 ,
unii-b03x40bmt5
LS-13761
3-buten-2-one, 4-phenyl-
nsc5605
4-phenylbutenone
4-phenyl-3-buten-2-one
acetocinnamone
methyl styryl ketone
wln: 1v1u1r
styryl methyl ketone
benzalacetone
2-phenylvinyl methyl ketone
methyl .beta.-styryl ketone
benzylidene acetone
benzalaceton
122-57-6
benzylideneacetone
nsc-5605
trans-benzalacetone
3-buten-2-one, 4-phenyl-, (e)-
NCGC00091356-01
trans-benzylidenacetone
trans-4-phenyl-3-butene-2-one
einecs 204-555-1
ketone, methyl styryl
methyl beta-styryl ketone
benzilidene acetone
trans-4-phenylbut-3-en-2-one
ai3-00944
brn 0742046
brn 0742047
benzalaceton [german]
benzylidene acetone (natural)
fema no. 2881
einecs 217-587-6
tpbo
trans-benzylideneacetone
methyl 2-phenylvinyl ketone
nsc 5605
benzilideneacetone
ccris 5319
ai3-52291
4-phenyl-3-butene-2-one
inchi=1/c10h10o/c1-9(11)7-8-10-5-3-2-4-6-10/h2-8h,1h3/b8-7
3-buten,2-one,4-phenyl (trans) benzalacetone
GHL.PD_MITSCHER_LEG0.147 ,
benzylideneacetone, >=98%, fg
trans-4-phenyl-3-buten-2-one, >=99%
4-phenyl-3-buten-2-one, 99%
(3e)-4-phenylbut-3-en-2-one
1896-62-4
methyl styryl acetone
methyl trans-styryl ketone
benzylideneacetone, (z)-isomer
trans-4-phenyl-3-buten-2-one
t-pbo
benzylideneacetone, (e)-isomer
smr001252234
MLS002454416
P0163
STK803195
benz
CHEBI:217301 ,
4-phenylbut-3-en-2-one
(e)-4-phenylbut-3-en-2-one
AKOS000119902
A804921
NCGC00091356-02
ec 204-555-1
2-07-00-00287 (beilstein handbook reference)
NCGC00257166-01
dtxsid1031626 ,
cas-1896-62-4
cas-122-57-6
dtxcid305662
tox21_303222
dtxcid9011626
NCGC00255323-01
tox21_301598
dtxsid4025662 ,
NCGC00259053-01
tox21_201502
A813340
(e)-4-phenyl-3-buten-2-one
(e)-4-phenyl-but-3-en-2-one
HMS2268K18
S9478
(3e)-4-phenyl-3-buten-2-one
EPITOPE ID:120383
benzylideneacetone [mi]
(3e)-4-phenylbut-3-en-2-one (benzalacetone)
4-phenyl-3-buten-2-one [fhfi]
warfarin sodium impurity c [ep impurity]
4-phenyl-3-buten-2-one, trans
benzylideneacetone, (e)-
benzalacetone [usp impurity]
cinnamyl methyl ketone
3-buten-2-one, 4-phenyl-, (3e)-
benzalacetone-d4
SCHEMBL76632
SCHEMBL312972
e-4-phenyl-3-buten-2-one
4-phenyl-but-3-en-2-one
(e)-1-buten-3-one, 1-phenyl
W-107746
1-buten-3-one-1-phenyl
1-phenyl-1-buten-3-one
W-109036
benzalacetone, analytical standard
F0001-0357
mfcd00008779
fema 2881
trans-4-phenyl-but-3-en-2-one
(3e)-4-phenylbut-3-en-2-one; warfarin sodium imp. c (ep); benzalacetone; warfarin sodium impurity c; warfarin impurity c
benzalaceton (german)
4-phenyl-(e)-3-buten-2-one
3-buten,2-one,4-phenyl (trans) benzalacetone
methyl beta -styryl ketone
CS-W013311
DS-4780
Q4380955
EN300-18891
AMY6963
benzylidenacetone
trans-benzylideneacetone;benzalacetone
D70186
D70528
HY-W012595
EN300-366968
Z2582847786

Roles (4)

RoleDescription
flavouring agentA food additive that is used to added improve the taste or odour of a food.
fragranceA substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.1.1.4 (phospholipase A2) inhibitorAn EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
benzylideneacetoneAn 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 ketone, only the trans-isomer is observed.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (19)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency19.95260.004023.8416100.0000AID485290
RAR-related orphan receptor gammaMus musculus (house mouse)Potency68.58960.006038.004119,952.5996AID1159521
ATAD5 protein, partialHomo sapiens (human)Potency11.57740.004110.890331.5287AID504467
AR proteinHomo sapiens (human)Potency75.55220.000221.22318,912.5098AID1259243
glucocorticoid receptor [Homo sapiens]Homo sapiens (human)Potency0.22390.000214.376460.0339AID588532
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency75.55220.003041.611522,387.1992AID1159552
retinoid X nuclear receptor alphaHomo sapiens (human)Potency42.87110.000817.505159.3239AID1159527; AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency95.11460.001530.607315,848.9004AID1224841
pregnane X nuclear receptorHomo sapiens (human)Potency76.95880.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency15.40340.000229.305416,493.5996AID743075; AID743079
alpha-galactosidaseHomo sapiens (human)Potency7.07954.466818.391635.4813AID2107
thyroid stimulating hormone receptorHomo sapiens (human)Potency67.33600.001628.015177.1139AID1259385
chromobox protein homolog 1Homo sapiens (human)Potency100.00000.006026.168889.1251AID540317
heat shock protein beta-1Homo sapiens (human)Potency55.30550.042027.378961.6448AID743210
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency55.93330.000627.21521,122.0200AID743202
Guanine nucleotide-binding protein GHomo sapiens (human)Potency28.18381.995325.532750.1187AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Substance-P receptorCavia porcellus (domestic guinea pig)CD15.00000.90004.50009.8000AID144377
Quinone oxidoreductaseMus musculus (house mouse)CD15.00000.20002.74219.8000AID144377
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID440586Acute toxicity in rat2009European journal of medicinal chemistry, Dec, Volume: 44, Issue:12
Analgesic, anticonvulsant and anti-inflammatory activities of some synthesized benzodiazipine, triazolopyrimidine and bis-imide derivatives.
AID1810347Glutathione reactivity at pH 7.4 assessed as glutathione-conjugated products measured after 4 hrs by LC-MS/MS method2021Journal of medicinal chemistry, 05-27, Volume: 64, Issue:10
Synthesis and Evaluation of PPARĪ“ Agonists That Promote Osteogenesis in a Human Mesenchymal Stem Cell Culture and in a Mouse Model of Human Osteoporosis.
AID144377Ability to induce NAD(P)H quinone reductase activity in cultured Hepa 1c1c7 murine hepatoma cells.1998Journal of medicinal chemistry, Dec-17, Volume: 41, Issue:26
Chemoprotective properties of phenylpropenoids, bis(benzylidene)cycloalkanones, and related Michael reaction acceptors: correlation of potencies as phase 2 enzyme inducers and radical scavengers.
AID426106Antiproliferative activity against human HeLa cells after 72 hrs by trypan blue assay2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
DNA-targeting pyrroloquinoline-linked butenone and chalcones: synthesis and biological evaluation.
AID1092125Inhibition of phenoloxidase activity in hemolymph of Spodoptera exigua fifth-instar larvae using DOPA substrate2012Applied and environmental microbiology, Jun, Volume: 78, Issue:11
Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID379150Cytotoxicity against human KB cells after 2 days by sulforhodamine B assay2006Journal of natural products, Oct, Volume: 69, Issue:10
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.
AID1092126Inhibition of PLA2 in hemocytes of Spodoptera exigua fifth-instar larvae using pyrene-labeled phospholipid substrate by spectrofluorometry2012Applied and environmental microbiology, Jun, Volume: 78, Issue:11
Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID379151Cytotoxicity against multidrug-resistant human KB-VCR cells after 2 days by sulforhodamine B assay2006Journal of natural products, Oct, Volume: 69, Issue:10
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.
AID426108Binding affinity to salmon testes DNA assessed as occurrence of intercalative molecular complex by linear flow dichroism2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
DNA-targeting pyrroloquinoline-linked butenone and chalcones: synthesis and biological evaluation.
AID1092122Potentiation of 1000 ppm Bacillus thuringiensis-induced pathogenicity against Plutella xylostella (diamondback moth) fourth-instar larvae at 10000 ppm measured 48 hr post compound treatment2012Applied and environmental microbiology, Jun, Volume: 78, Issue:11
Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID426105Antiproliferative activity against human HL60 cells after 72 hrs by trypan blue assay2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
DNA-targeting pyrroloquinoline-linked butenone and chalcones: synthesis and biological evaluation.
AID1092123Insecticidal activity against Plutella xylostella (diamondback moth) fourth-instar larvae fed on cabbage leaves soaked in compound solutions measured 48 hr post compound treatment by leaf-dipping method2012Applied and environmental microbiology, Jun, Volume: 78, Issue:11
Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID1092124Inhibition of immune responses in Spodoptera exigua fifth-instar larvae assessed as inhibition of hemocytic nodulation in response to Escherichia coli challenge by stereomicroscopy2012Applied and environmental microbiology, Jun, Volume: 78, Issue:11
Phospholipase A2 inhibitors synthesized by two entomopathogenic bacteria, Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata.
AID379152Cytotoxicity against human A549 cells after 2 days by sulforhodamine B assay2006Journal of natural products, Oct, Volume: 69, Issue:10
Dehydrozingerone, chalcone, and isoeugenol analogues as in vitro anticancer agents.
AID70871Inhibition of UV-induced mutagenesis in Escherichia coli WP2uvrA2002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
Quantum chemical- and 3-D-QSAR (CoMFA) studies of benzalacetones and 1,1,1-trifluoro-4-phenyl-3-buten-2-ones.
AID1269940Cytotoxicity against human Raji cells expressing EBV-EA assessed as inhibition of TPA-induced EBV-EA activation after 48 hrs by trypan blue staining based immunofluorescence method relative to TPA2016Bioorganic & medicinal chemistry, Feb-15, Volume: 24, Issue:4
An appraisal on recent medicinal perspective of curcumin degradant: Dehydrozingerone (DZG).
AID426107Antiproliferative activity against human JR8 cells after 72 hrs by trypan blue assay2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
DNA-targeting pyrroloquinoline-linked butenone and chalcones: synthesis and biological evaluation.
AID1167300Antioxidant activity assessed as DPPH radical scavenging activity incubated at room temperature for 20 mins by UV-visible spectrophotometry2014Bioorganic & medicinal chemistry letters, Nov-01, Volume: 24, Issue:21
Design, synthesis and exploring the quantitative structure-activity relationship of some antioxidant flavonoid analogues.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (71)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (9.86)18.7374
1990's12 (16.90)18.2507
2000's24 (33.80)29.6817
2010's22 (30.99)24.3611
2020's6 (8.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.35%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other73 (98.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Bioavailability (2)

ArticleYear
An appraisal on recent medicinal perspective of curcumin degradant: Dehydrozingerone (DZG).
Bioorganic & medicinal chemistry, Feb-15, Volume: 24, Issue: 4
2016
Absorption, disposition, and metabolism of trans-methyl styryl ketone in female B6C3F1 mice.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 25, Issue: 10
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (3)

ArticleYear
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, Issue: 572
2012
Absorption, disposition, and metabolism of trans-methyl styryl ketone in female B6C3F1 mice.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 25, Issue: 10
1997
Oral and topical absorption, disposition kinetics, and the metabolic fate of trans-methyl styryl ketone in the male Fischer 344 rat.
Drug metabolism and disposition: the biological fate of chemicals, Volume: 25, Issue: 6
1997
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]