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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-04-09 19:42:34 UTC

Update Date

2023-02-21 17:33:48 UTC

HMDB ID

HMDB0240266

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl vanillate

Description

Methyl 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0    8668.6388667.437   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8669.9718666.666   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8671.3048667.437   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8668.6388668.979   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.2978667.437   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8661.9548666.665   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8663.2978664.355   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8667.3008666.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.9668667.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.6338666.666   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.6328665.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9668664.356   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.3008665.127   0.000  0.00  0.00           C+0
CONECT    1    2    4    8                                                  
CONECT    2    1    3                                                       
CONECT    3    2                                                            
CONECT    4    1                                                            
CONECT    5    6   10                                                       
CONECT    6    5                                                            
CONECT    7   11                                                            
CONECT    8    9   13    1                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    5                                                  
CONECT   11   10   12    7                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3-methoxybenzoic acid methyl ester	ChEBI
Methyl 3-methoxy-4-hydroxybenzoate	ChEBI
Methyl vanillic acid	ChEBI
VANILLATE	ChEBI
Vanillic acid, methyl ester	ChEBI
4-Hydroxy-3-methoxybenzoate methyl ester	Generator
Methyl 3-methoxy-4-hydroxybenzoic acid	Generator
VANILLic acid	Generator
Vanillate, methyl ester	Generator
Methylvanillate	HMDB
Methylvanillic acid	HMDB
Methyl 4-hydroxy-3-methoxybenzoic acid	HMDB
4-Hydroxy-3-methoxy methyl benzoate	HMDB
Methyl 4-hydroxy-3-methoxybenzoate	HMDB
4-Hydroxy-3-methoxy methyl benzoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

vanillate

CAS Registry Number

3943-74-6

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 Key

BVWTXUYLKBHMOX-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:46477 )
phenols (CHEBI:46477 )
benzoate ester (CHEBI:46477 )

Ontology

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.12	ALOGPS
logP	1.52	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.53 m³·mol⁻¹	ChemAxon
Polarizability	18.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	137.405	31661259
AllCCS	[M+H]+	139.122	31661259
DeepCCS	[M+H]+	140.197	30932474
DeepCCS	[M-H]-	137.382	30932474
DeepCCS	[M-2H]-	173.639	30932474
DeepCCS	[M+Na]+	149.177	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.1	32859911
AllCCS	[M+Na]+	144.2	32859911
AllCCS	[M-H]-	137.4	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl vanillate	COC(=O)C1=CC(OC)=C(O)C=C1	2527.4	Standard polar	33892256
Methyl vanillate	COC(=O)C1=CC(OC)=C(O)C=C1	1499.1	Standard non polar	33892256
Methyl vanillate	COC(=O)C1=CC(OC)=C(O)C=C1	1475.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl vanillate,1TMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C)C(OC)=C1	1653.4	Semi standard non polar	33892256
Methyl vanillate,1TBDMS,isomer #1	COC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	1899.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)	splash10-0udi-3900000000-baea5cfe4e199a5ff3bc	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)	splash10-0ue9-0900000000-c2808da990a74bab5038	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)	splash10-0udi-3900000000-baea5cfe4e199a5ff3bc	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl vanillate EI-B (Non-derivatized)	splash10-0ue9-0900000000-c2808da990a74bab5038	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0900000000-8058aca97e516d13c287	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl vanillate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOF	splash10-0zor-5900000000-a4ed8f03061acdf96ef7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOF	splash10-0a6r-9400000000-bc72ccdad3422a05a984	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 35V, Negative-QTOF	splash10-1000-0900000000-ebaae574a4f0209032d0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOF	splash10-002f-9100000000-ae59e1a1723666bf192b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOF	splash10-0udi-9200000000-5f071ead2181ac329e6a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOF	splash10-0pvi-0900000000-18ac4d71743edfc16d7a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOF	splash10-014i-0900000000-4ec70507ab24e73fa629	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOF	splash10-001i-0900000000-6b73fb15e83c91238365	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOF	splash10-0f89-0900000000-d82161f65e3b085bdacb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOF	splash10-0uk9-2900000000-65592de2b7ae3ee7aa94	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOF	splash10-001i-0900000000-0252284dd0d745a2e0ae	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOF	splash10-001i-0900000000-0da26709ef2caf03994a	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOF	splash10-00ks-4900000000-6ec4c48ab5df172a962b	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 10V, Negative-QTOF	splash10-001i-0900000000-f31118255833f0bedd5a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 20V, Negative-QTOF	splash10-0aca-0900000000-6c702260f9d096ceb11d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 40V, Negative-QTOF	splash10-052f-9200000000-548a6adb75eeb4caefdd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 10V, Positive-QTOF	splash10-0udi-0900000000-98a5dc0bd0bee7771886	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 20V, Positive-QTOF	splash10-0kji-1900000000-708fba6151de4d11d60e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl vanillate 40V, Positive-QTOF	splash10-0uk9-9500000000-ccb31762970f38503370	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08711

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029771

KNApSAcK ID

C00030768

Chemspider ID

18693

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl group

METLIN ID

Not Available

PubChem Compound

19844

PDB ID

Not Available

ChEBI ID

46477

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1047511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Methyl vanillate (HMDB0240266)

MOL for HMDB0240266 (Methyl vanillate)

3D MOL for HMDB0240266 (Methyl vanillate)

3D SDF for HMDB0240266 (Methyl vanillate)

3D-SDF for HMDB0240266 (Methyl vanillate)

PDB for HMDB0240266 (Methyl vanillate)

3D PDB for HMDB0240266 (Methyl vanillate)

SMILES for HMDB0240266 (Methyl vanillate)

INCHI for HMDB0240266 (Methyl vanillate)

Structure for HMDB0240266 (Methyl vanillate)

3D Structure for HMDB0240266 (Methyl vanillate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra