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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2018-04-09 19:42:34 UTC
Update Date2023-02-21 17:33:48 UTC
HMDB IDHMDB0240266
Secondary Accession NumbersNone
Metabolite Identification
Common NameMethyl vanillate
DescriptionMethyl vanillate is a member of the class of compounds known as m-methoxybenzoic acids and derivatives. These compounds are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. Methyl vanillate is considered to be a slightly soluble in water acidic compound. Methyl vanillate can be synthesized from vanillic acid. Vanillic acid is a phenolic acid or chlorogenic acid that is an oxidized form of vanillin. Vanillic acid is also an intermediate in the production of vanillin from ferulic acid. It is found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. Vanillic acid is also found in wine and vinegar. Vanillic acid is a metabolic by-product of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5'-nucleotidase activity (PMID:16899266 ). Vanillic acid is also a microbial metabolite found in several bacterial genera including Amycolatopsis, Delftia, and Pseudomonas (PMID:11152072 , 10543794 , 11728709 , 9579070 ). Methyl vanillate has been identified in foods such as cow's milk (PMID:4682334 ) and beer (PMID:20800742 ).
Structure
Data?1677000828
Synonyms
ValueSource
4-Hydroxy-3-methoxybenzoic acid methyl esterChEBI
Methyl 3-methoxy-4-hydroxybenzoateChEBI
Methyl vanillic acidChEBI
VANILLATEChEBI
Vanillic acid, methyl esterChEBI
4-Hydroxy-3-methoxybenzoate methyl esterGenerator
Methyl 3-methoxy-4-hydroxybenzoic acidGenerator
VANILLic acidGenerator
Vanillate, methyl esterGenerator
MethylvanillateHMDB
Methylvanillic acidHMDB
Methyl 4-hydroxy-3-methoxybenzoic acidHMDB
4-Hydroxy-3-methoxy methyl benzoateHMDB
Methyl 4-hydroxy-3-methoxybenzoateHMDB
4-Hydroxy-3-methoxy methyl benzoic acidHMDB
Chemical FormulaC9H10O4
Average Molecular Weight182.1733
Monoisotopic Molecular Weight182.057908808
IUPAC Namemethyl 4-hydroxy-3-methoxybenzoate
Traditional Namevanillate
CAS Registry Number3943-74-6
SMILES
COC(=O)C1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
InChI KeyBVWTXUYLKBHMOX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentM-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
  • P-hydroxybenzoic acid ester
  • M-methoxybenzoic acid or derivatives
  • Methoxyphenol
  • Benzoate ester
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.12ALOGPS
logP1.52ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.53 m³·mol⁻¹ChemAxon
Polarizability18.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M-H]-137.40531661259
AllCCS[M+H]+139.12231661259
DeepCCS[M+H]+140.19730932474
DeepCCS[M-H]-137.38230932474
DeepCCS[M-2H]-173.63930932474
DeepCCS[M+Na]+149.17730932474
AllCCS[M+H]+139.132859911
AllCCS[M+H-H2O]+134.932859911
AllCCS[M+NH4]+143.132859911
AllCCS[M+Na]+144.232859911
AllCCS[M-H]-137.432859911
AllCCS[M+Na-2H]-138.332859911
AllCCS[M+HCOO]-139.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methyl vanillateCOC(=O)C1=CC(OC)=C(O)C=C12527.4Standard polar33892256
Methyl vanillateCOC(=O)C1=CC(OC)=C(O)C=C11499.1Standard non polar33892256
Methyl vanillateCOC(=O)C1=CC(OC)=C(O)C=C11475.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methyl vanillate,1TMS,isomer #1COC(=O)C1=CC=C(O[Si](C)(C)C)C(OC)=C11653.4Semi standard non polar33892256
Methyl vanillate,1TBDMS,isomer #1COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C11899.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)splash10-0udi-3900000000-baea5cfe4e199a5ff3bc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)splash10-0ue9-0900000000-c2808da990a74bab50382017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)splash10-0udi-3900000000-baea5cfe4e199a5ff3bc2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)splash10-0ue9-0900000000-c2808da990a74bab50382018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uk9-0900000000-8058aca97e516d13c2872016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOFsplash10-0zor-5900000000-a4ed8f03061acdf96ef72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOFsplash10-0a6r-9400000000-bc72ccdad3422a05a9842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 35V, Negative-QTOFsplash10-1000-0900000000-ebaae574a4f0209032d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOFsplash10-002f-9100000000-ae59e1a1723666bf192b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOFsplash10-0udi-9200000000-5f071ead2181ac329e6a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOFsplash10-0pvi-0900000000-18ac4d71743edfc16d7a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOFsplash10-014i-0900000000-4ec70507ab24e73fa6292021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOFsplash10-001i-0900000000-6b73fb15e83c912383652016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOFsplash10-0f89-0900000000-d82161f65e3b085bdacb2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOFsplash10-0uk9-2900000000-65592de2b7ae3ee7aa942016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOFsplash10-001i-0900000000-0252284dd0d745a2e0ae2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOFsplash10-001i-0900000000-0da26709ef2caf03994a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOFsplash10-00ks-4900000000-6ec4c48ab5df172a962b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOFsplash10-001i-0900000000-f31118255833f0bedd5a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOFsplash10-0aca-0900000000-6c702260f9d096ceb11d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOFsplash10-052f-9200000000-548a6adb75eeb4caefdd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOFsplash10-0udi-0900000000-98a5dc0bd0bee77718862021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOFsplash10-0kji-1900000000-708fba6151de4d11d60e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOFsplash10-0uk9-9500000000-ccb31762970f385033702021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08711
Phenol Explorer Compound IDNot Available
FooDB IDFDB029771
KNApSAcK IDC00030768
Chemspider ID18693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethyl group
METLIN IDNot Available
PubChem Compound19844
PDB IDNot Available
ChEBI ID46477
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1047511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dhananjaya BL, Nataraju A, Rajesh R, Raghavendra Gowda CD, Sharath BK, Vishwanath BS, D'Souza CJ: Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006 Sep 15;48(4):411-21. Epub 2006 Jul 7. [PubMed:16899266 ]
  2. Brewington CR, Parks OW, Schwartz DP: Conjugated compounds in cow's milk. J Agric Food Chem. 1973 Jan-Feb;21(1):38-9. [PubMed:4682334 ]
  3. Sterckx FL, Saison D, Delvaux FR: Determination of volatile monophenols in beer using acetylation and headspace solid-phase microextraction in combination with gas chromatography and mass spectrometry. Anal Chim Acta. 2010 Aug 31;676(1-2):53-9. doi: 10.1016/j.aca.2010.07.043. Epub 2010 Aug 5. [PubMed:20800742 ]
  4. Achterholt S, Priefert H, Steinbuchel A: Identification of Amycolatopsis sp. strain HR167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol. 2000 Dec;54(6):799-807. [PubMed:11152072 ]
  5. Overhage J, Priefert H, Steinbuchel A: Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp. Strain HR199. Appl Environ Microbiol. 1999 Nov;65(11):4837-47. [PubMed:10543794 ]
  6. Plaggenborg R, Steinbuchel A, Priefert H: The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett. 2001 Nov 27;205(1):9-16. doi: 10.1111/j.1574-6968.2001.tb10918.x. [PubMed:11728709 ]
  7. Venturi V, Zennaro F, Degrassi G, Okeke BC, Bruschi CV: Genetics of ferulic acid bioconversion to protocatechuic acid in plant-growth-promoting Pseudomonas putida WCS358. Microbiology. 1998 Apr;144 ( Pt 4):965-73. doi: 10.1099/00221287-144-4-965. [PubMed:9579070 ]