Page last updated: 2024-12-05

3,4-dihydroxyacetophenone

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

Description

3,4-Dihydroxyacetophenone, also known as 3,4-dihydroxyphenyl methyl ketone, is a naturally occurring phenolic compound found in various plants. It exhibits antioxidant and anti-inflammatory properties, making it a potential therapeutic agent for conditions such as cancer, inflammation, and neurodegenerative diseases. The compound is known to inhibit the activity of enzymes involved in inflammation and oxidative stress. Its synthesis involves the reaction of 3,4-dihydroxybenzaldehyde with methyl magnesium bromide followed by oxidation. 3,4-Dihydroxyacetophenone is also a precursor to other bioactive compounds, such as vanillin and eugenol. Due to its promising pharmacological properties, 3,4-Dihydroxyacetophenone is extensively studied in various research areas, including medicinal chemistry, biochemistry, and pharmacology.'

3,4-dihydroxyacetophenone: shortens action potential duration of cardiac cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3',4'-dihydroxyacetophenone : A dihydroxyacetophenone that is acetophenone carrying hydroxy groups at positions 3' 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 CID14530
CHEMBL ID243161
CHEBI ID19868
CHEBI ID69446
SCHEMBL ID144106
MeSH IDM0102445

Synonyms (51)

Synonym
qingxintong
acetopyrocatechol
4-acetopyrocatechol
4-acetylpyrocatechol
acetophenone-3',4'-dihydroxy
ethanone, 1-(3,4-dihydroxyphenyl)-
3,4-dihydroxyacetophenone
1197-09-7
3',4'-dihydroxyacetophenone
chebi:19868 ,
CHEMBL243161
1-(3,4-dihydroxyphenyl)ethanone
AKOS002231977
FT-0693227
4-acetocatechol
D2345
A804342
1-(3,4-dihydroxyphenyl)ethanone;3',4'-dihydroxyacetophenone
07oq35lvbk ,
unii-07oq35lvbk
FT-0633465
CHEBI:69446
4-acetyl-1,2-benzenediol
acetophenone, 3',4'-dihydroxy-
1-(3,4-dihydroxyphenyl)ethan-1-one
TD1322
SCHEMBL144106
4-acetylcatechol
1-(3,4-dihydroxyphenyl)ethanone #
AE-641/00345018
3-methyl-4-oxo-3,4-dihydro-phthalazine-1-carboxylicacidhydrazide
dihydroxyacetophenone; 98%
DTXSID30152546
J-004179
CS-W008953
mfcd00016439
GS-3459
1-(3,4-dihydroxyphenyl)-ethanone
acetylpyrocatechol
1-(3,4-dihydroxyphenyl)ethanone, 9ci
3 inverted exclamation mark ,4 inverted exclamation mark -dihydroxyacetophenone
SY038279
Q222992
BCP27931
acetopyrocatechol 4-acetocatechol
HY-N1775
HFO ,
1-[3,4-bis(oxidanyl)phenyl]ethanone
EN300-174814
Z234853536
1-(3,4-dihydroxyphenyl)-1-ethanone

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" APDP rapidly transformed into DHAP in vivo and in vitro, indicating that there were no significant differences in the values of mean residence time in vivo [MRT (0‑t)], half‑life [t1/2], oral bioavailability and antiplatelet aggregation activity in vivo and in vitro between the two agents."( Synthesis, oral bioavailability evaluation and antiplatelet aggregation activity of three derivatives of 3,4‑dihydroxyacetophenone.
Duan, Y; Lv, Y; Qu, M; Sun, N; Wang, M; Wei, L, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (3)

ClassDescription
dihydroxyacetophenoneA hydroxyacetophenone carrying two hydroxy substituents.
catecholsAny compound containing an o-diphenol component.
acetophenonesA class or aromatic ketone consisting of acetophenone, PhC(=O)CH3, and its substituted derivatives.
[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]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID360334Antiinflammatory activity in LPS-stimulated mouse RAW264.7 cells assessed as inhibition of TNFalpha formation at 30 uM pretreated 1 hr before LPS challenge measured after 24 hrs by enzyme immunoassay2001Journal of natural products, May, Volume: 64, Issue:5
Bioactive constituents of the roots of Cynanchum atratum.
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.
AID360336Antiinflammatory activity in LPS/IFN-gamma-stimulated mouse N9 cells assessed as inhibition of TNFalpha formation at 30 uM pretreated 1 hr before LPS/IFNgamma challenge measured after 24 hrs by enzyme immunoassay2001Journal of natural products, May, Volume: 64, Issue:5
Bioactive constituents of the roots of Cynanchum atratum.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (36)

TimeframeStudies, This Drug (%)All Drugs %
pre-199011 (30.56)18.7374
1990's10 (27.78)18.2507
2000's8 (22.22)29.6817
2010's5 (13.89)24.3611
2020's2 (5.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.35

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.35 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index29.12 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (5.56%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other34 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]