Compounds > 2-hydroxy-5-methoxybenzaldehyde
Page last updated: 2024-11-07

2-hydroxy-5-methoxybenzaldehyde

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

Description

2-hydroxy-5-methoxybenzaldehyde, also known as vanillin, is a naturally occurring organic compound with a characteristic sweet and aromatic odor. It is the primary component of vanilla extract, which is derived from the vanilla bean.

Vanillin is a colorless, crystalline solid that is soluble in ethanol and ether. It is a weak acid and can be synthesized from various sources, including lignin, eugenol, and guaiacol.

Vanillin has a wide range of applications in the food, beverage, and pharmaceutical industries. It is commonly used as a flavoring agent, a fragrance component, and a pharmaceutical intermediate.

The compound is studied extensively due to its various pharmacological effects, including antioxidant, anti-inflammatory, and antimicrobial activities. It has been shown to protect against oxidative stress and inflammation in various biological systems.

Vanillin is a valuable compound due to its versatility and wide range of applications. It is also an important component of the vanilla bean, which is a valuable agricultural commodity.'
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2-hydroxy-5-methoxybenzaldehyde: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5-methoxysalicylaldehyde : A member of the class of benzaldehydes carrying hydroxy and methoxy substituents at positions 2 and 5 respectively. [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 CID95695
CHEMBL ID3660371
CHEBI ID137359
SCHEMBL ID120412
MeSH IDM0561621

Synonyms (51)

Synonym
einecs 211-589-0
brn 1100532
nsc 30116
ai3-19305
2-hydroxy-5-methoxy-benzaldehyde
5-methoxysalicylaldehyde
salicylaldehyde, 5-methoxy-
m-anisaldehyde, 6-hydroxy-
672-13-9
benzaldehyde, 2-hydroxy-5-methoxy-
nsc-30116
wln: vhr bq eo1
2-hydroxy-5-methoxybenzaldehyde
nsc30116
inchi=1/c8h8o3/c1-11-7-2-3-8(10)6(4-7)5-9/h2-5,10h,1h
2-hydroxy-5-methoxybenzaldehyde, 98%
CHEBI:137359
4-methoxy-2-formylphenol
2-formyl-4-methoxyphenol
AKOS000112554
6-hydroxy-m-anisaldehyde
H0881
gyt2q9ur3w ,
unii-gyt2q9ur3w
5-methoxy-2-hydroxybenzaldehyde
FT-0600619
STL374089
AM20040993
2-formyl-4-methoxyphenol;2-hydroxy-5-methoxy-benzaldehyd;6-hydroxy-m-anisaldehyd
CL8287
SCHEMBL120412
BBL027434
bdbm111039
us8614253, .3-70
2-hydroxy-5-methoxybenzal dehyde
5-methoxy-salicylaldehyde
5-methoxy-2-hydroxy-benzaldehyde
2-hydroxy-5-methoxy benzaldehyde
W-104727
CHEMBL3660371
mfcd00003332
DTXSID40217478
F2113-0146
CS-W001206
GS-6684
3-biphenyl-(3-methoxy)aceticacid
Z56899054
Q15634035
EN300-17188
3-methoxy-6-hydroxybenzaldehyde
PD193523
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
benzaldehydesAny arenecarbaldehyde that consists of a formyl substituted benzene ring and its substituted derivatives thereof.
monomethoxybenzeneCompounds containing a benzene skeleton substituted with one methoxy group.
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]

Bioassays (13)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's3 (60.00)24.3611
2020's2 (40.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.51

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 Index28.51 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
3-hydroxybenzaldehyde
[no description available]		2.1310hydroxybenzaldehyde
4-hydroxybenzaldehyde
[no description available]		2.1310hydroxybenzaldehydeEC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor;
mouse metabolite;
plant metabolite
benzaldehyde
[no description available]		2.1310benzaldehydesEC 3.1.1.3 (triacylglycerol lipase) inhibitor;
EC 3.5.5.1 (nitrilase) inhibitor;
flavouring agent;
fragrance;
odorant receptor agonist;
plant metabolite
catechol
[no description available]		2.1310catecholsallelochemical;
genotoxin;
plant metabolite
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.2510trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
hydroquinone
[no description available]		2.1310benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
phenol
[no description available]		2.1310phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
vanillin
Vanilla: A plant genus of the family ORCHIDACEAE that is the source of the familiar flavoring used in foods and medicines (FLAVORING AGENTS).		2.1310benzaldehydes;
monomethoxybenzene;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
flavouring agent;
plant metabolite
aspirin
Aspirin: The prototypical analgesic used in the treatment of mild to moderate pain. It has anti-inflammatory and antipyretic properties and acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Aspirin also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. (From Martindale, The Extra Pharmacopoeia, 30th ed, p5). acetylsalicylate : A benzoate that is the conjugate base of acetylsalicylic acid, arising from deprotonation of the carboxy group.. acetylsalicylic acid : A member of the class of benzoic acids that is salicylic acid in which the hydrogen that is attached to the phenolic hydroxy group has been replaced by an acetoxy group. A non-steroidal anti-inflammatory drug with cyclooxygenase inhibitor activity.		2.1310benzoic acids;
phenyl acetates;
salicylates		anticoagulant;
antipyretic;
cyclooxygenase 1 inhibitor;
cyclooxygenase 2 inhibitor;
drug allergen;
EC 1.1.1.188 (prostaglandin-F synthase) inhibitor;
geroprotector;
non-narcotic analgesic;
non-steroidal anti-inflammatory drug;
plant activator;
platelet aggregation inhibitor;
prostaglandin antagonist;
teratogenic agent
2,5-dihydroxybenzoic acid
2,5-dihydroxybenzoic acid: RN given refers to parent cpd; a oxidative product of saligenin. 2,5-dihydroxybenzoic acid : A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions.		2.2510dihydroxybenzoic acidEC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
fungal metabolite;
human metabolite;
MALDI matrix material;
mouse metabolite
resorcinol
resorcinol: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7951. resorcinol : A benzenediol that is benzene dihydroxylated at positions 1 and 3.		2.1310benzenediol;
phenolic donor;
resorcinols		erythropoietin inhibitor;
sensitiser
1,2-diaminopropane
1,2-diaminopropane: RN given for parent cpd without isomeric designation. propylenediamine : A diamine that is propane substituted by amino groups at positions 1 and 2. Propylenediamine is commonly used as a bidentate ligand in the formation of coordination complexes.		2.0610diamineligand
salicylaldehyde
o-hydroxybenzaldehyde: structure in first source		2.1310hydroxybenzaldehydenematicide;
plant metabolite
veratrole
veratrole: structure. dimethoxybenzene : Any methoxybenzene that consists of a benzene skeleton substituted with two methoxy groups and its derivatives.. veratrole : A dimethoxybenzene with the methoxy groups at ortho-positions.		2.1310dimethoxybenzeneplant metabolite
2,4-dihydroxybenzaldehyde
2,4-dihydroxybenzaldehyde : A dihydroxybenzaldehyde that is resorcinol which has been substituted by a formyl group para to one of the hydroxy groups.		2.1310dihydroxybenzaldehyde
anisole
anisole : A monomethoxybenzene that is benzene substituted by a methoxy group.		2.1310monomethoxybenzeneplant metabolite
acrolein
[no description available]		2.5520enalherbicide;
human xenobiotic metabolite;
toxin
ethyl vanillin
ethyl vanillin : A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.		2.1310aromatic ether;
benzaldehydes;
phenols		antioxidant;
flavouring agent
2-Methoxybenzaldehyde
[no description available]		2.1310carbonyl compound
protocatechualdehyde
protocatechualdehyde: found in wheat grains, wheat seedlings, & other plants; RN given refers to parent cpd; see also rancinamycins; structure		2.1310dihydroxybenzaldehyde
2-vanillin
ortho-vanillin : A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.		2.4920benzaldehydes;
guaiacols		antimutagen;
plant metabolite
1,4-dimethoxybenzene
1,4-dimethoxybenzene: structure given in first source		2.1310dimethoxybenzene
1,3-dimethoxybenzene
1,3-dimethoxybenzene: structure given in first source		2.1310methoxybenzenes
carvacrol
carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).		2.110botanical anti-fungal agent;
p-menthane monoterpenoid;
phenols		agrochemical;
antimicrobial agent;
flavouring agent;
TRPA1 channel agonist;
volatile oil component
3-methoxybenzaldehyde
3-methoxybenzaldehyde : A member of the class of benzaldehydes in which the hydrogen at position 3 of benzaldehyde has been replaced by a methoxy group.		2.1310benzaldehydes;
monomethoxybenzene		Brassica napus metabolite
isovanillin
isovanillin: inhibits aldehyde oxidase. isovanillin : A member of the class of benzaldehydes that is 4-methoxybenzaldehyde substituted by a hydroxy group at position 3. It is an inhibitor of aldehyde oxidase.		2.1310benzaldehydes;
monomethoxybenzene;
phenols		animal metabolite;
antidiarrhoeal drug;
antifungal agent;
EC 1.2.3.1 (aldehyde oxidase) inhibitor;
HIV protease inhibitor;
plant metabolite
zinc oxide
Zinc Oxide: A mild astringent and topical protectant with some antiseptic action. It is also used in bandages, pastes, ointments, dental cements, and as a sunblock.		2.0610zinc molecular entity
manganese
Manganese: A trace element with atomic symbol Mn, atomic number 25, and atomic weight 54.94. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver. (From AMA Drug Evaluations Annual 1992, p2035). manganese(4+) : A manganese cation that is monoatomic and has a formal charge of +4.		2.0610elemental manganese;
manganese group element atom		Escherichia coli metabolite;
micronutrient
4-anisaldehyde
4-anisaldehyde: RN given refers to cpd with specified locants for methoxy moieties; structure in Merck, 9th ed, #696. p-methoxybenzaldehyde : A member of the class of benzaldehydes consisting of benzaldehyde itself carrying a methoxy substituent at position 4.		2.1310benzaldehydesbacterial metabolite;
human urinary metabolite;
insect repellent;
plant metabolite
octyl gallate
[no description available]		2.2510gallate esterfood antioxidant;
hypoglycemic agent;
plant metabolite
2,4-dimethoxybenzaldehyde
[no description available]		2.1310
2-hydroxy-4-methoxybenzaldehyde
2-hydroxy-4-methoxybenzaldehyde: from African medicinal plants: Mondia whitei (Apocynaceae), Rhus vulagaris (Anacardiaceae), Sclerocarya caffra (Anacardiaceae)		2.1310methoxybenzenes;
phenols
2,5-dihydroxybenzaldehyde
2,5-dihydroxybenzaldehyde: structure in first source. 2,5-dihydroxybenzaldehyde : A dihydroxybenzaldehyde carrying hydroxy groups at positions 2 and 5.		2.5220dihydroxybenzaldehydehuman metabolite;
mouse metabolite;
Penicillium metabolite
2-hydroxy-4-methoxy benzoic acid
[no description available]		2.1310methoxybenzoic acid
2,3-dihydroxybenzaldehyde
dihydroxybenzaldehyde : Any member of the class of benzaldehydes in which the phenyl ring is substituted by two hydroxy groups.		2.1310dihydroxybenzaldehyde
cinnamaldehyde
3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.		2.55203-phenylprop-2-enal;
cinnamaldehydes		antifungal agent;
EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor;
flavouring agent;
hypoglycemic agent;
plant metabolite;
sensitiser;
vasodilator agent
geraniol
[no description available]		2.1103,7-dimethylocta-2,6-dien-1-ol;
monoterpenoid;
primary alcohol		allergen;
fragrance;
plant metabolite;
volatile oil component
ConditionIndicatedRelationship StrengthStudiesTrials