Page last updated: 2024-11-05

resacetophenone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Resacetophenone, also known as 2,4-dihydroxy acetophenone, is a naturally occurring phenolic compound found in various plants. It has garnered interest for its diverse pharmacological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. Resacetophenone has been synthesized through various methods, including the Claisen condensation of resorcinol with ethyl acetate. Its antioxidant properties have been attributed to its ability to scavenge free radicals, while its anti-inflammatory effects may be related to its inhibition of inflammatory mediators. Resacetophenone's potential as an antimicrobial agent against a range of bacteria and fungi has also been investigated. Ongoing research aims to explore its therapeutic applications in areas like skin diseases, wound healing, and cancer treatment. The multifaceted nature of resacetophenone's biological activities has made it a promising candidate for the development of novel therapeutic agents.'

resacetophenone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2',4'-dihydroxyacetophenone : A dihydroxyacetophenone that is acetophenone carrying hydroxy substituents at positions 2' and 4'. [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 CID6990
CHEMBL ID243374
CHEBI ID18414
SCHEMBL ID26357
MeSH IDM0369276

Synonyms (75)

Synonym
BIDD:ER0659
nsc 10883
einecs 201-945-3
brn 1282505
ai3-00866
1-(2,4-dihydroxy-phenyl)-ethanone
CHEBI:18414 ,
ethanone, 1-(2,4-dihydroxyphenyl)-
acetophenone, 2',4'-dihydroxy-
nsc-37559
nsc37559
.beta.-resacetophenone
nsc-10883
nsc10883
4-acetylresorcinol
resoacetophenone
wln: qr cq dv1
resorcinol, 4-acetyl-
1-(2,4-dihydroxyphenyl)ethanone
STK084318
resacetophenone
2',4'-dihydroxyacetophenone
C03663
89-84-9
2,4-dihydroxyacetophenone
inchi=1/c8h8o3/c1-5(9)7-3-2-6(10)4-8(7)11/h2-4,10-11h,1h
2',4'-dihydroxyacetophenone, 99%
AC-1105
bdbm50241221
2'',4''-dihydroxyacetophenone
D0561
2,4-dihydroxy acetophenone
CHEMBL243374 ,
1-acetyl-2,4-dihydroxybenzene
AKOS000119522
1-(2,4-dihydroxyphenyl)ethan-1-one
A843341
BBL012128
S4762
uc3v356vzc ,
4-08-00-01792 (beilstein handbook reference)
unii-uc3v356vzc
FT-0610122
FS-3456
AM20041337
S12324
resacetophenone [inci]
resacetophenone [mi]
SCHEMBL26357
2,4-dihydroxy actophenone
1,3-dihydroxy-4-acetylbenzene
2,4-dihyroxyacetophenone
2,4,-dihydroxyacetophenone
2'4'-dihydroxyacetophenone
2',4'-dihydroxy-acetophenone
DTXSID4058998
4-acetyl-1,3-benzenediol
1-acetylbenzene-2,4-diol
beta-resacetophenone
W-100356
STR03384
mfcd00002279
CS-W008599
F1995-0239
Z57101026
1-(2,4-dihydroxyphenyl)-ethanone
4-acetyl-resorcinol
1-(2,4-dihydroxyphenyl)ethanone, 9ci
2 inverted exclamation mark ,4 inverted exclamation mark -dihydroxyacetophenone
SY004020
HY-Y0694
Q27103063
CCG-259076
1-?(2,?4-?dihydroxyphenyl)?ethanone
EN300-18418
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
dihydroxyacetophenoneA hydroxyacetophenone carrying two hydroxy substituents.
resorcinolsAny benzenediol in which the two hydroxy groups are meta to one another.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier family 28 member 3Homo sapiens (human)Ki100.00002.10002.75003.4000AID370698
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processSolute carrier family 28 member 3Homo sapiens (human)
xenobiotic transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
pyrimidine nucleobase transportSolute carrier family 28 member 3Homo sapiens (human)
uridine transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
sodium ion transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
pyrimidine-containing compound transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
nucleoside transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
purine nucleobase transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
pyrimidine nucleoside transportSolute carrier family 28 member 3Homo sapiens (human)
purine nucleoside transmembrane transportSolute carrier family 28 member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
purine nucleobase transmembrane transporter activitySolute carrier family 28 member 3Homo sapiens (human)
nucleoside:sodium symporter activitySolute carrier family 28 member 3Homo sapiens (human)
protein bindingSolute carrier family 28 member 3Homo sapiens (human)
uridine transmembrane transporter activitySolute carrier family 28 member 3Homo sapiens (human)
purine-specific nucleoside:sodium symporter activitySolute carrier family 28 member 3Homo sapiens (human)
pyrimidine- and adenosine-specific:sodium symporter activitySolute carrier family 28 member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneSolute carrier family 28 member 3Homo sapiens (human)
plasma membraneSolute carrier family 28 member 3Homo sapiens (human)
brush border membraneSolute carrier family 28 member 3Homo sapiens (human)
plasma membraneSolute carrier family 28 member 3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1465300Inhibition of equine serum BuChE at 50 uM incubated for 15 mins by Ellman's method relative to control2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease.
AID370698Binding affinity to human recombinant CNT3 expressed in pig PK15NTD cells assessed as [3H]uridine uptake by beta-scintillation counter2009Bioorganic & medicinal chemistry letters, Feb-01, Volume: 19, Issue:3
Synthesis and biological evaluation of phloridzin analogs as human concentrative nucleoside transporter 3 (hCNT3) inhibitors.
AID395642Activity of Crotalus adamanteus venom PLA2 assessed as 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol hydrolysis at 0.15 uM2009European journal of medicinal chemistry, Jan, Volume: 44, Issue:1
Molecular modeling and inhibition of phospholipase A2 by polyhydroxy phenolic compounds.
AID607596Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID607598Cytotoxicity against human LoVo cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID395643Activity of Crotalus adamanteus venom PLA2 assessed as 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol hydrolysis at 0.30 uM2009European journal of medicinal chemistry, Jan, Volume: 44, Issue:1
Molecular modeling and inhibition of phospholipase A2 by polyhydroxy phenolic compounds.
AID1150150In vivo inhibition of mixed function oxidase system in rat assessed as increase in zoxazolamine-induced paralysis time at 100 mg/kg, ip pretreated for 10 mins followed by zoxazolamine-challenge relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
AID1465297Inhibition of electric eel AChE at 50 uM using acetylthiocholine as substrate incubated for 15 mins by Ellman's method relative to control2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease.
AID1465303Inhibition of recombinant human MAO-B using kynuramine as substrate after 30 mins by fluorescence method2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease.
AID1150149In vivo inhibition of mixed function oxidase system in rat assessed as prolongation of hexobarbital-induced sleeping time at 100 mg/kg, ip pretreated for 10 mins followed by hexobarbital-challenge relative to control1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
AID395645Inhibition of Crotalus adamanteus venom PLA2 assessed as effect on 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol hydrolysis at 0.30 uM2009European journal of medicinal chemistry, Jan, Volume: 44, Issue:1
Molecular modeling and inhibition of phospholipase A2 by polyhydroxy phenolic compounds.
AID295603Inhibition of Helicobacter pylori ATCC 43504 urease at 400 ug/mL after 3 hrs pre-incubation2007Bioorganic & medicinal chemistry, Jun-01, Volume: 15, Issue:11
Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease.
AID1557174Inhibition of human recombinant MAO-B using kynuramine as substrate measured after 30 mins by fluorimetric assay2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
The development of 2-acetylphenol-donepezil hybrids as multifunctional agents for the treatment of Alzheimer's disease.
AID607594Cytotoxicity against human OE21 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID607597Cytotoxicity against human SK-MEL-28 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1465304Antioxidant activity assessed as trolox equivalent of APPH-induced radical scavenging activity measured every minute for 90 mins by ORAC fluorescein assay2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease.
AID395644Inhibition of Crotalus adamanteus venom PLA2 assessed as effect on 1-hexadecanoyl-2-(1-pyrenedecanoyl)-sn-glycero-3-phosphoglycerol hydrolysis at 0.15 uM2009European journal of medicinal chemistry, Jan, Volume: 44, Issue:1
Molecular modeling and inhibition of phospholipase A2 by polyhydroxy phenolic compounds.
AID607593Cytotoxicity against human U373 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1150146Inhibition of aniline hydroxylase activity of mixed function oxidase system in Wistar rat liver microsomes assessed as conversion of aniline to p-aminophenol after 10 mins1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
AID1557171Inhibition of electric eel AChE using acetylthiocholine iodide as substrate at 50 uM incubated for 15 mins by Ellman's method relative to control2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
The development of 2-acetylphenol-donepezil hybrids as multifunctional agents for the treatment of Alzheimer's disease.
AID607595Cytotoxicity against human A549 cells after 72 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1465302Inhibition of recombinant human MAO-A using kynuramine as substrate after 30 mins by fluorescence method2017Bioorganic & medicinal chemistry letters, 11-15, Volume: 27, Issue:22
Design, synthesis and biological evaluation of 2-acetyl-5-O-(amino-alkyl)phenol derivatives as multifunctional agents for the treatment of Alzheimer's disease.
AID607601Cytotoxicity against human U373 cells assessed as growth inhibition at MTT assay-related IC50 by quantitative video microscopy relative to control2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1557172Inhibition of equine serum BuChE using S-butyrylthiocholine chloride as substrate at 50 uM incubated for 15 mins by Ellman's method relative to control2019Bioorganic & medicinal chemistry letters, 10-01, Volume: 29, Issue:19
The development of 2-acetylphenol-donepezil hybrids as multifunctional agents for the treatment of Alzheimer's disease.
AID607600Induction of human U373 cell death assessed as morphological changes at MTT assay-related IC50 after 72 hrs by quantitative video microscopy2011Bioorganic & medicinal chemistry letters, Jul-15, Volume: 21, Issue:14
Growth inhibitory activities of oxyprenylated and non-prenylated naturally occurring phenylpropanoids in cancer cell lines.
AID1150147Inhibition of aminopyrine demethylase activity of mixed function oxidase system in Wistar rat liver microsomes assessed as conversion of aminopyrine to 4-aminoantipyrine after 20 mins1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Inhibitors of hepatic mixed function oxidase. 3. Inhibition of hepatic microsomal aniline hydroxylase and aminopyrine demethylase by 2,6- and 2,4-dihydroxyphenyl alkyl ketones and related compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (17.86)18.7374
1990's2 (7.14)18.2507
2000's10 (35.71)29.6817
2010's9 (32.14)24.3611
2020's2 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.70

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index37.70 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index49.01 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (37.70)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies2 (7.14%)4.05%
Observational0 (0.00%)0.25%
Other26 (92.86%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]