Milk Composition Database: Showing metabocard for Vanillic acid (BMDB0062211)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2018-07-17 17:17:57 UTC

Update Date

2020-04-22 15:51:34 UTC

MCDB ID

BMDB0062211

Secondary Accession Numbers

BMDB62211

Metabolite Identification

Common Name

Vanillic acid

Description

Vanillic acid, also known as vanillate or acid, vanillic, 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. Vanillic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Vanillic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-Hydroxy-3-methoxybenzoic acid	ChEBI
4-Hydroxy-3-methoxybenzoate	Kegg
Vanillate	Generator
3-Methoxy-4-hydroxybenzoate	HMDB
3-Methoxy-4-hydroxybenzoic acid	HMDB
4-Hydroxy-3-methoxy-benzoate	HMDB
4-Hydroxy-3-methoxy-benzoic acid	HMDB
4-Hydroxy-m-anisate	HMDB
4-Hydroxy-m-anisic acid	HMDB
Acide vanillique	HMDB
p-Vanillate	HMDB
p-Vanillic acid	HMDB
Protocatechuic acid 3-methyl ester	HMDB
Acid, 4-hydroxy-3-methoxybenzoic	HMDB
p Hydroxy m methoxy benzoic acid	HMDB
4 Hydroxy 3 methoxybenzoic acid	HMDB
Acid, vanillic	HMDB
Acid, p-hydroxy-m-methoxy-benzoic	HMDB
p-Hydroxy-m-methoxy-benzoic acid	HMDB
2-Methoxy-4-carboxyphenol	HMDB
Methylprotocatechuic acid	HMDB
VA	HMDB
m-Methoxy-p-hydroxy-benzoic acid	HMDB
Vanillic acid	KEGG

Chemical Formula

C₈H₈O₄

Average Molecular Weight

168.148

Monoisotopic Molecular Weight

168.042258738

IUPAC Name

4-hydroxy-3-methoxybenzoic acid

Traditional Name

vanillic acid

CAS Registry Number

121-34-6

SMILES

COC1=C(O)C=CC(=C1)C(O)=O

InChI Identifier

InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)

InChI Key

WKOLLVMJNQIZCI-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

M-methoxybenzoic acid or derivatives
Hydroxybenzoic acid
Methoxyphenol
Benzoic acid
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:30816 )
methoxybenzoic acid (CHEBI:30816 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	211.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.5 mg/mL at 14 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP	1.43	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.7	ALOGPS
logP	1.17	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	41.76 m³·mol⁻¹	ChemAxon
Polarizability	15.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-0hp2-2691000000-8409d9c758b023c6576b	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0gb9-2900000000-ccd8d4a214bc1a7f08c5	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0hp2-2691000000-8409d9c758b023c6576b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0g0b-2981000000-a58243e35d1e3a64d2aa	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g4i-1900000000-851f4a1738be8dd91d47	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dj-7390000000-18c5f822b380ea00aa26	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0gb9-0900000000-0aa6709c16899e222086	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-0900000000-9aa2b9d4aa89e6ac12ab	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-0900000000-6d98ebfa89f4b8ee1e6b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0gb9-2900000000-babed327a6e49c6f7d51	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-105f33777cee542cf6df	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-05fr-1900000000-a502792703fa2f211035	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4l-5900000000-037ef32f4c68a5252b92	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9800000000-ecd60ac022f5fee1d5ef	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-066u-9300000000-c63f7f792794f3c748a0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-014i-0923211100-7e9f357f7429cff05524	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0a4i-0900000000-8e112ffa4dcc7c08b0fd	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0a4i-0429110000-57f8760ce65d48cdc01f	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0uxr-0900000000-29a2674dccd1fa478bd5	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-105f33777cee542cf6df	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-05fr-1900000000-c4ce596998934098267b	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-342964fa3647815dd1d2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uxr-0900000000-f16c365899f9d95733d3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zfs-5900000000-e5593db0a935e1534bc6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-6a1a2db582acd95348ea	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0600-0900000000-eda6cfe601d63ed00f8d	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-6900000000-b2c1e3f6b255e94a10af	2016-09-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0gb9-6900000000-c13506201c3612fc7ca5	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, DMSO, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, DMSO, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0000484

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vanillic acid

METLIN ID

5471

PubChem Compound

8468

PDB ID

Not Available

ChEBI ID

30816

References

Synthesis Reference

Pearl, Irwin A. Reactions of vanillin and its derived compounds. I. The reaction of vanillin with silver oxide. Journal of the American Chemical Society (1946), 68 429-32.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]

Showing metabocard for Vanillic acid (BMDB0062211)

Structure for BMDB0062211 (Vanillic acid)