Page last updated: 2024-11-06

2-hydroxy-4-methoxybenzaldehyde

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Description

2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Sclerocaryagenus[no description available]AnacardiaceaeThe sumac plant family in the order Sapindales, subclass Rosidae, class Magnoliopsida. They are tropical and subtropical trees, shrubs, and woody vines that have resin ducts in the bark. The sap of many of the species is irritating to the skin.[MeSH]
RhusgenusA plant genus of the family Anacardiaceae, order Sapindales, subclass Rosidae. It is a source of gallotannin (TANNIC ACID) and of somewhat edible fruit. Do not confuse with TOXICODENDRON which used to be part of this genus.[MeSH]AnacardiaceaeThe sumac plant family in the order Sapindales, subclass Rosidae, class Magnoliopsida. They are tropical and subtropical trees, shrubs, and woody vines that have resin ducts in the bark. The sap of many of the species is irritating to the skin.[MeSH]
Mondiagenus[no description available]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]
Mondia whiteispecies[no description available]ApocynaceaeThe dogbane family of the order Gentianales. Members of the family have milky, often poisonous juice, smooth-margined leaves, and flowers in clusters.[MeSH]

Cross-References

ID SourceID
PubMed CID69600
CHEMBL ID350966
CHEBI ID183274
SCHEMBL ID133876
MeSH IDM0303244

Synonyms (62)

Synonym
nsc 155334
brn 1072443
ai3-38507
einecs 211-604-0
EN300-24375
CHEBI:183274
4-methoxysalicyaldehyde
nsc155334
benzaldehyde, 2-hydroxy-4-methoxy-
o-hydroxy-p-methoxybenzaldehyde
salicylaldehyde, 4-methoxy-
2-hydroxy-4-methoxybenzaldehyde
p-anisaldehyde, 2-hydroxy-
nsc-155334
673-22-3
4-methoxysalicylaldehyde
inchi=1/c8h8o3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10h,1h
GHL.PD_MITSCHER_LEG0.298
2-hydroxy-4-methoxybenzaldehyde, 98%
bdbm50139368
2-hydroxy-4-methoxy-benzaldehyde
AKOS000112553
CHEMBL350966 ,
2-hydroxy-p-anisaldehyde
H0699
A835710
4-08-00-01754 (beilstein handbook reference)
unii-2n395p88lw
2n395p88lw ,
2-formyl-5-methoxyphenol
BP-11480
FT-0602352
PS-3237
AM20060850
fema no. 4435
S5156
CL8285
SCHEMBL133876
mfcd00003327
SY012932
4-methoxy-2-hydroxybenzaldehyde
2-hydroxy-4-methoxy benzaldehyde
2-hydroxy4methoxybenzaldehyde
2-hydroxy-4methoxybenzaldehyde
4-methoxy-2-hydroxy-benzaldehyde
2-hydroxyl-4-methoxybenzaldehyde
2-hydroxyanisaldehyde
4-methoxy salicylaidehyde
DTXSID1060970
4-o-methylresorcylaldehyde
W-104720
AC-24065
2-hydroxy-4-methoxybenazldehyde
4-methoxy-6-hydroxybenzaldehyde
CS-D1182
HY-N0445
4-methoxysalicylaldehyde,(s)
Q15634116
STL195538
CCG-266224
PD088138
Z188964138
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
methoxybenzenesAny aromatic ether that consists of a benzene skeleton substituted with one or more methoxy groups.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Transcription intermediary factor 1-alphaHomo sapiens (human)IC50 (µMol)0.21970.13581.837910.0000AID1619194
TyrosinaseHomo sapiens (human)IC50 (µMol)30.00000.02304.459310.0000AID213388
E3 ubiquitin-protein ligase TRIM33Homo sapiens (human)IC50 (µMol)0.30060.23351.01654.6900AID1619193
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (29)

Processvia Protein(s)Taxonomy
transcription by RNA polymerase IITranscription intermediary factor 1-alphaHomo sapiens (human)
positive regulation of gene expressionTranscription intermediary factor 1-alphaHomo sapiens (human)
protein ubiquitinationTranscription intermediary factor 1-alphaHomo sapiens (human)
protein catabolic processTranscription intermediary factor 1-alphaHomo sapiens (human)
regulation of protein stabilityTranscription intermediary factor 1-alphaHomo sapiens (human)
regulation of apoptotic processTranscription intermediary factor 1-alphaHomo sapiens (human)
response to peptide hormoneTranscription intermediary factor 1-alphaHomo sapiens (human)
negative regulation of DNA-templated transcriptionTranscription intermediary factor 1-alphaHomo sapiens (human)
positive regulation of DNA-templated transcriptionTranscription intermediary factor 1-alphaHomo sapiens (human)
epithelial cell proliferationTranscription intermediary factor 1-alphaHomo sapiens (human)
negative regulation of epithelial cell proliferationTranscription intermediary factor 1-alphaHomo sapiens (human)
calcium ion homeostasisTranscription intermediary factor 1-alphaHomo sapiens (human)
regulation of vitamin D receptor signaling pathwayTranscription intermediary factor 1-alphaHomo sapiens (human)
cellular response to estrogen stimulusTranscription intermediary factor 1-alphaHomo sapiens (human)
regulation of signal transduction by p53 class mediatorTranscription intermediary factor 1-alphaHomo sapiens (human)
melanin biosynthetic process from tyrosineTyrosinaseHomo sapiens (human)
eye pigment biosynthetic processTyrosinaseHomo sapiens (human)
visual perceptionTyrosinaseHomo sapiens (human)
cell population proliferationTyrosinaseHomo sapiens (human)
response to UVTyrosinaseHomo sapiens (human)
response to blue lightTyrosinaseHomo sapiens (human)
response to vitamin DTyrosinaseHomo sapiens (human)
melanin biosynthetic processTyrosinaseHomo sapiens (human)
thymus developmentTyrosinaseHomo sapiens (human)
response to cAMPTyrosinaseHomo sapiens (human)
pigmentationTyrosinaseHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
protein ubiquitinationE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
regulation of transforming growth factor beta receptor signaling pathwayE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
negative regulation of BMP signaling pathwayE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
negative regulation of DNA-templated transcriptionE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
methylated histone bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
p53 bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
chromatin bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
transcription coactivator activityTranscription intermediary factor 1-alphaHomo sapiens (human)
protein kinase activityTranscription intermediary factor 1-alphaHomo sapiens (human)
signaling receptor bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
protein bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
zinc ion bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
nuclear receptor bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
estrogen response element bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
ubiquitin protein ligase activityTranscription intermediary factor 1-alphaHomo sapiens (human)
lysine-acetylated histone bindingTranscription intermediary factor 1-alphaHomo sapiens (human)
tyrosinase activityTyrosinaseHomo sapiens (human)
copper ion bindingTyrosinaseHomo sapiens (human)
protein bindingTyrosinaseHomo sapiens (human)
identical protein bindingTyrosinaseHomo sapiens (human)
protein homodimerization activityTyrosinaseHomo sapiens (human)
DNA bindingE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
ubiquitin-protein transferase activityE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
protein bindingE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
zinc ion bindingE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
co-SMAD bindingE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
R-SMAD bindingE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
male germ cell nucleusTranscription intermediary factor 1-alphaHomo sapiens (human)
nucleusTranscription intermediary factor 1-alphaHomo sapiens (human)
nucleoplasmTranscription intermediary factor 1-alphaHomo sapiens (human)
perichromatin fibrilsTranscription intermediary factor 1-alphaHomo sapiens (human)
mitochondrionTranscription intermediary factor 1-alphaHomo sapiens (human)
cytosolTranscription intermediary factor 1-alphaHomo sapiens (human)
euchromatinTranscription intermediary factor 1-alphaHomo sapiens (human)
chromatinTranscription intermediary factor 1-alphaHomo sapiens (human)
cytoplasmTyrosinaseHomo sapiens (human)
lysosomeTyrosinaseHomo sapiens (human)
Golgi-associated vesicleTyrosinaseHomo sapiens (human)
melanosome membraneTyrosinaseHomo sapiens (human)
melanosomeTyrosinaseHomo sapiens (human)
intracellular membrane-bounded organelleTyrosinaseHomo sapiens (human)
perinuclear region of cytoplasmTyrosinaseHomo sapiens (human)
nucleusE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
nucleoplasmE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
chromatinE3 ubiquitin-protein ligase TRIM33Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1291718Protective activity against Daboia russellii venom-induced mortality in Swiss albino mouse at 100 mmol, iv administered immediately after venom injection measured after 24 hrs relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291715Protective activity against Daboia russellii venom-induced hemorrhage in intradermally dosed Swiss albino mouse at 100 mmol assessed as hemorhagic lesion preincubated with venom for 1 hr followed by administration to mouse measured after 24 hrs relative t2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291716Lipophilicity, log P of compound2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID213388Inhibitory activity was evaluated against the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by mushroom tyrosinase2004Bioorganic & medicinal chemistry letters, Feb-09, Volume: 14, Issue:3
2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor.
AID1291729Protective activity against Daboia russellii venom-induced coagulation in goat plasma assessed as increase in plasma recalcification time at 20 mmol preincubated with venom for 1 hr followed by plasma addition2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID293934Inhibition of pieris rapae Phenoloxidase2007Bioorganic & medicinal chemistry, Mar-01, Volume: 15, Issue:5
3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors.
AID1291710Protective activity against Daboia russellii venom-induced mortality by measuring venom LD50 in Swiss albino mouse at 100 mmol, iv preincubated with venom for 1 hr followed by administration to mouse measured after 24 hrs (Rvb = 2.28 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291731Protective activity against Daboia russellii venom-induced defibrinogenation in iv dosed Swiss albino mouse assessed as venom level causing blood coagulation at 100 mmol preincubated with venom for 1 hr followed by administration to mouse (Rvb = 2.5 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291724Protective activity against Daboia russellii venom-induced mortality in iv dosed Swiss albino mouse administered 30 mins after venom injection relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291727Protective activity against Daboia russellii venom-induced defibrinogenation in iv dosed Swiss albino mouse assessed as venom level causing blood coagulation at 100 mmol preincubated with venom for 1 hr followed by administration to mouse relative to untr2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291712Protective activity against Naja kaouthia venom-induced mortality in Swiss albino mouse at 100 mmol, iv by measuring venom LD50 preincubated with venom for 1 hr followed by administration to mouse measured after 24 hrs (Rvb = 2.82 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291719Protective activity against Naja kaouthia venom-induced mortality in Swiss albino mouse at 100 mmol, iv by measuring venom LD50 administered immediately after venom injection measured after 24 hrs (Rvb = 2.82 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291713Protective activity against Naja kaouthia venom-induced mortality in Swiss albino mouse at 100 mmol, iv preincubated with venom for 1 hr followed by administration to mouse measured after 24 hrs relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291725Protective activity against Daboia russellii venom-induced mortality in iv dosed Swiss albino mouse administered 60 mins after venom injection relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291726Protective activity against Naja kaouthia venom-induced mortality in iv dosed Swiss albino mouse assessed as administered 30 to 60 mins after venom injection2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291717Protective activity against Daboia russellii venom-induced mortality in Swiss albino mouse at 100 mmol, iv by measuring venom LD50 administered immediately after venom injection measured after 24 hrs (Rvb = 2.28ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291721Protective activity against Daboia russellii venom-induced hemorrhage in Swiss albino mouse at 100 mmol, iv assessed as hemorhagic lesion by measuring minimal hemolytic dose administered immediately after venom injection measured after 24 hrs (Rvb =5 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291720Protective activity against Naja kaouthia venom-induced mortality in Swiss albino mouse at 100 mmol, iv administered immediately after venom injection measured after 24 hrs relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291732Protective activity against Daboia russellii venom-induced defibrinogenation in iv dosed Swiss albino mouse assessed as venom level causing blood coagulation at 100 mmol administered immediately after venom injection (Rvb = 2.5 ug)2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID288818Cytotoxicity against BAEC after 2 days by MTT assay2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1.
AID1291714Protective activity against Daboia russellii venom-induced hemorrhage in intradermally dosed Swiss albino mouse at 100 mmol assessed as hemorhagic lesion by measuring minimal hemolytic dose preincubated with venom for 1 hr followed by administration to mo2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291711Protective activity against Daboia russellii venom-induced mortality in Swiss albino mouse at 100 mmol, iv preincubated with venom for 1 hr followed by administration to mouse measured after 24 hrs relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291722Protective activity against Daboia russellii venom-induced hemorrhage in Swiss albino mouse at 100 mmol, iv assessed as hemorhagic lesion administered immediately after venom injection measured after 24 hrs relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291728Protective activity against Daboia russellii venom-induced defibrinogenation in iv dosed Swiss albino mouse assessed as blood coagulation at 100 mmol administered immediately after venom injection relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID1291723Protective activity against Daboia russellii venom-induced mortality in iv dosed Swiss albino mouse administered immediately after venom injection relative to untreated control2016European journal of medicinal chemistry, May-23, Volume: 114Molecular modeling and snake venom phospholipase A2 inhibition by phenolic compounds: Structure-activity relationship.
AID288819Effect on tube formation of BAEC assessed as sprouting inhibition after 48 hrs2007Bioorganic & medicinal chemistry, Aug-01, Volume: 15, Issue:15
Antiangiogenic versus cytotoxic activity in analogues of aeroplysinin-1.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (26)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (3.85)18.2507
2000's6 (23.08)29.6817
2010's14 (53.85)24.3611
2020's5 (19.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.02

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 Index34.02 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.37 (4.65)
Search Engine Demand Index41.22 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (34.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (96.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]