Page last updated: 2024-12-07

3,5-dihydroxy-4-methoxybenzoic acid

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

Description

3,5-dihydroxy-4-methoxybenzoic acid, also known as syringic acid, is a phenolic compound found in various plants, particularly in the lignin of hardwoods. It exhibits antioxidant and anti-inflammatory properties. It is studied for its potential therapeutic applications in treating conditions such as diabetes, cancer, and cardiovascular diseases. The synthesis of syringic acid typically involves the oxidation of syringaldehyde, a compound derived from lignin. It is also synthesized through microbial fermentation using microorganisms like fungi and bacteria. Syringic acid's importance lies in its potential to modulate metabolic pathways, inhibit enzyme activity, and protect cells from oxidative stress. Researchers explore its interactions with various biological systems to elucidate its mechanisms of action and develop new therapeutic strategies.'

3,5-dihydroxy-4-methoxybenzoic acid: catechol methyltransferase inhibitor; N1 same as NM [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID78016
CHEMBL ID118992
CHEBI ID88738
SCHEMBL ID793706
MeSH IDM0082314

Synonyms (29)

Synonym
unii-0xw32qvu6j
benzoic acid, 3,5-dihydroxy-4-methoxy-
3,5-dihydroxy-p-anisic acid
0xw32qvu6j ,
einecs 224-346-9
4-o-methylgallic acid
4-methoxy-3,5-dihydroxybenzoic acid
4319-02-2
5-hydroxyisovanillic acid
4-methoxygallic acid
chebi:88738 ,
CHEMBL118992 ,
3,5-dihydroxy-4-methoxybenzoic acid
AKOS006280824
3,5-dihydroxy-4-methoxy-benzoic acid
bdbm50405317
.alpha.-resorcylic acid, 4-methoxy-
gallic acid 4-methyl ether
DTXSID8063412
SCHEMBL793706
3,5-dihydroxy-4-methoxybenzoicacid
4-methoxy-3,5-dihydroxybenzoate
3,5-dihydroxy-4-methoxy-benzoate
3,5-dihydroxy-4-methoxybenzoate
Q27160668
CS-0181941
AS-0234
E82260
PD128849

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Concentrations of GA and its metabolite, 4-O-methylgallic acid (4OMGA), were determined, and the pharmacokinetic parameters were calculated."( Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans.
Aoyagi, K; Bitsch, I; Koyama, A; Shahrzad, S; Winter, A, 2001
)
0.31

Bioavailability

ExcerptReferenceRelevance
" We conducted a study using acidum gallicum tablets that contained 10% GA and 90% glucose and a black tea brew that contained 93% of its GA in free form to determine the pharmacokinetics and relative bioavailability of GA in healthy humans."( Pharmacokinetics of gallic acid and its relative bioavailability from tea in healthy humans.
Aoyagi, K; Bitsch, I; Koyama, A; Shahrzad, S; Winter, A, 2001
)
0.31
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
trihydroxybenzoic acid
[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]

Pathways (1)

PathwayProteinsCompounds
Flavan-3-ol metabolic pathway070

Protein Targets (1)

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]

Biological Processes (4)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThiopurine S-methyltransferaseHomo sapiens (human)
xenobiotic metabolic processThiopurine S-methyltransferaseHomo sapiens (human)
methylationThiopurine S-methyltransferaseHomo sapiens (human)
xenobiotic catabolic processThiopurine S-methyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
protein bindingThiopurine S-methyltransferaseHomo sapiens (human)
thiopurine S-methyltransferase activityThiopurine S-methyltransferaseHomo sapiens (human)
S-adenosyl-L-methionine bindingThiopurine S-methyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
cytosolThiopurine S-methyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID1674378Antifungal activity against Cryptococcus neoformans H99 by CLSI protocol-based broth serial dilution method
AID377909Antioxidant activity assessed as DPPH free radical scavenging activity2000Journal of natural products, Oct, Volume: 63, Issue:10
Urinary metabolites of gallic acid in rats and their radical-scavenging effects on 1,1-diphenyl-2-picrylhydrazyl radical.
AID1674379Antifungal activity against Cryptococcus neoformans JEC21 by CLSI protocol-based broth serial dilution method
AID213093Inhibition of purified human kidney thiopurine methyltransferase (TPMT)1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Thiopurine methyltransferase: structure-activity relationships for benzoic acid inhibitors and thiophenol substrates.
AID1674380Antifungal activity against Candida albicans SC5314 by CLSI protocol-based broth serial dilution method
AID515791Inhibition of telomerase in human A549 cells at 25 uM after 24 hrs by TRAP assay2010Bioorganic & medicinal chemistry, Oct-01, Volume: 18, Issue:19
Identification of small molecule inhibitors of telomerase activity through transcriptional regulation of hTERT and calcium induction pathway in human lung adenocarcinoma A549 cells.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (32)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (6.25)18.7374
1990's3 (9.38)18.2507
2000's20 (62.50)29.6817
2010's5 (15.63)24.3611
2020's2 (6.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.25

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

MetricThis Compound (vs All)
Research Demand Index11.25 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.25)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (21.88%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other25 (78.13%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]