Page last updated: 2024-12-06

methyl vanillate

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

Description

Methyl vanillate is a naturally occurring organic compound found in various plants, including vanilla beans. It is an ester formed from vanillin and methanol. Its synthesis can be achieved through esterification of vanillin with methanol. Methyl vanillate has been shown to exhibit antioxidant and anti-inflammatory properties, and it is also known to possess analgesic and antipyretic activities. It is a key component of vanilla flavor and is used in various food and beverage products. Its aroma and taste characteristics make it a popular ingredient in perfumes and cosmetics. Research on methyl vanillate is ongoing to explore its potential applications in medicine and other fields. It is of interest due to its promising biological activities and its potential as a natural alternative to synthetic compounds.'

methyl vanillate: isolated from Hovenia dulcis [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methyl vanillate : A benzoate ester that is the methyl ester of vanillic acid. [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 CID19844
CHEMBL ID486214
CHEBI ID46477
SCHEMBL ID275939

Synonyms (61)

Synonym
benzoic acid, 4-hydroxy-3-methoxy-, methyl ester
VXX ,
brn 1369113
ai3-20212
nsc 74385
einecs 223-525-9
methyl 3-methoxy-4-hydroxybenzoate
nsc74385
nsc-74385
methyl 4-hydroxy-3-methoxybenzoate ,
vanillic acid, methyl ester
methyl vanillate
3943-74-6
vanillic acid methyl ester
4-hydroxy-3-methoxybenzoic acid methyl ester
inchi=1/c9h10o4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10h,1-2h
methyl vanillate, >=98%, fg
methyl vanillate, 99%
methyl vanillic acid
CHEBI:46477 ,
M1738
DB08711
4-hydroxy-3-methoxy methyl benzoate
CHEMBL486214
methylvanillate
BMSE010226
methyl (3-methoxy-4-hydroxy)benzoate
AKOS000120673
A824546
S3630
3-10-00-01410 (beilstein handbook reference)
unii-2hxg8qso3d
2hxg8qso3d ,
FT-0600645
SCHEMBL275939
4-hydroxy-3-methoxy benzoic acid methyl ester
methyl 4-hydroxy-3-methoxy-benzoate
4-hydroxy-3-methoxy-benzoic acid methyl ester
4-hydroxy-5-methoxy -benzoic acid methyl ester
3-methoxy-4-(hydroxy)benzoic acid methyl ester
methyl 4-hydroxy-3-methyoxybenzoate
4-hydroxy-5-methoxy-benzoic acid methyl ester
methyl 4-hydroxy-3-(methyloxy)benzoate
methyl ester of 4-hydroxy-3-methoxybenzoic acid
vanillic acid methyl
W-106434
J-650247
mfcd00008438
HY-75342
DTXSID5074345
CS-D0814
AC-9615
SY003406
Q27097897
AS-13512
AMY528
CCG-266450
methyl4-hydroxy-3-methoxybenzoate
PB42723
EN300-21518
Z104500600
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
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 (3)

ClassDescription
benzoate esterEsters of benzoic acid or substituted benzoic acids.
phenolsOrganic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[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 (32)

Assay IDTitleYearJournalArticle
AID354862Antifungal activity against Candida albicans at 60 ug/disk1996Journal of natural products, Aug, Volume: 59, Issue:8
Isoprenyl phenyl ethers from liverworts of the genus Trichocolea: cytotoxic activity, structural corrections, and synthesis.
AID485528Anticancer activity against human U373 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1309206Anti-allergic activity in RBL2H3 cells assessed as inhibition of anti-DNP-IgE-induced degranulation at 1000 uM incubated for 20 mins followed by DNP-labeled human serum albumin addition measured after 1 hr by beta-hexosaminidase release assay2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Structure-activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells.
AID485527Anticancer activity against human T98G cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID338338Antiplatelet activity against rat platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation at 0.1 mg/ml pretreated 2 mins before collagen challenge
AID485529Chemical stability after 7 days by HPLC2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID1309205Anti-allergic activity in RBL2H3 cells assessed as inhibition of anti-DNP-IgE-induced degranulation incubated for 20 mins followed by DNP-labeled human serum albumin addition measured after 1 hr by beta-hexosaminidase release assay2016Bioorganic & medicinal chemistry letters, 08-01, Volume: 26, Issue:15
Structure-activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells.
AID1102544Inhibition of tyrosinase activity in Oryza sativa Indica (rice) bran using L-tyrosine as substrate at 0.5 umol/ml after 60 min by spectrophotometric analysis2003Journal of agricultural and food chemistry, Nov-19, Volume: 51, Issue:24
Tyrosinase inhibitor from black rice bran.
AID1090826Antifeedant activity against Hylobius abietis (pine weevil ) in compound pre-treated Scots pine twig at 50 mM measured after 24 hr by two-choice laboratory bioassay2007Journal of agricultural and food chemistry, Nov-14, Volume: 55, Issue:23
Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach.
AID485521Anticancer activity against human OE21 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID376315Antibacterial activity against Escherichia coli ATCC 35218 after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID485519Anticancer activity against mouse B16F10 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID338335Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 0.25 mg/ml pretreated 2 mins before arachidonic acid challenge
AID376321Antibacterial activity against Staphylococcus aureus ATCC 6538 after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID376320Antibacterial activity against Salmonella enteritidis ATCC 13076 after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID485525Anticancer activity against human LoVo cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID485526Anticancer activity against human Hs683 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID376324Antibacterial activity against Bacillus cereus isolate after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID376319Antibacterial activity against Pseudomonas tolaasii after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID376325Antifungal activity against Candida albicans isolate after 72 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID485522Anticancer activity against human PC3 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID354863Antifungal activity against Trichophyton mentagrophytes at 60 ug/disk1996Journal of natural products, Aug, Volume: 59, Issue:8
Isoprenyl phenyl ethers from liverworts of the genus Trichocolea: cytotoxic activity, structural corrections, and synthesis.
AID376322Antibacterial activity against Micrococcus luteus isolate after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID338336Antiplatelet activity against rat platelet rich plasma assessed as inhibition of collagen-induced platelet aggregation at 0.25 mg/ml pretreated 2 mins before collagen challenge
AID485524Anticancer activity against human A549 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID354860Cytotoxicity against african green monkey BSC1 cells at 60 ug/disk1996Journal of natural products, Aug, Volume: 59, Issue:8
Isoprenyl phenyl ethers from liverworts of the genus Trichocolea: cytotoxic activity, structural corrections, and synthesis.
AID338339Antiplatelet activity against rat platelet rich plasma assessed as inhibition of ADP-induced platelet aggregation at 1 mg/ml pretreated 2 mins before ADP challenge
AID376317Antibacterial activity against Agrobacterium tumefaciens A281 after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID376323Antibacterial activity against Sarcina lutea ATCC 9341 after 48 hrs by serial dilution technique2006Journal of natural products, Apr, Volume: 69, Issue:4
Linear sesquiterpene lactones from Anthemis auriculata and their antibacterial activity.
AID485520Anticancer activity against human OE33 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID485523Anticancer activity against human MCF7 cells after 24 hrs by MTT assay2010Bioorganic & medicinal chemistry, Jun-01, Volume: 18, Issue:11
Simple di- and trivanillates exhibit cytostatic properties toward cancer cells resistant to pro-apoptotic stimuli.
AID338333Antiplatelet activity against rat platelet rich plasma assessed as inhibition of arachidonic acid-induced platelet aggregation at 0.5 mg/ml pretreated 2 mins before arachidonic acid challenge
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (10.00)18.2507
2000's3 (30.00)29.6817
2010's4 (40.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.20

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 Index32.20 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.20)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]