Methyl vanillate (YMDB01747)

Identification

YMDB ID

YMDB01747

Name

Methyl vanillate

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Methyl vanillate, also known as vanillATE or vanillic acid, 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. Based on a literature review a significant number of articles have been published on Methyl vanillate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

4-HYDROXY-3-METHOXYBENZOATE
4-Hydroxy-3-methoxybenzoic acid methyl ester
Benzoic acid, 4-hydroxy-3-methoxy-, methyl ester
Methyl 3-methoxy-4-hydroxybenzoate
Methyl 4-hydroxy-3-methoxybenzoate
Methyl ester of 4-hydroxy-3-methoxybenzoic acid
Methyl vanillate
VANILLATE
Vanillic acid methyl
Vanillic acid methyl ester
Vanillic acid, methyl ester
Methyl vanillic acid
4-Hydroxy-3-methoxybenzoate methyl ester
Methyl 3-methoxy-4-hydroxybenzoic acid
VANILLic acid
Vanillate, methyl ester
Methylvanillate
Methylvanillic acid
Methyl 4-hydroxy-3-methoxybenzoic acid
4-Hydroxy-3-methoxy methyl benzoate
4-Hydroxy-3-methoxy methyl benzoic acid

CAS number

3943-74-6

Weight

Average: 182.1733
Monoisotopic: 182.057908808

InChI Key

BVWTXUYLKBHMOX-UHFFFAOYSA-N

InChI

InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3

IUPAC Name

methyl 4-hydroxy-3-methoxybenzoate

Traditional IUPAC Name

vanillate

Chemical Formula

C₉H₁₀O₄

SMILES

COC(=O)C1=CC(OC)=C(O)C=C1

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 )

Physical Properties

State

Solid

Charge

Melting point

64 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-3900000000-baea5cfe4e199a5ff3bc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ue9-0900000000-c2808da990a74bab5038	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-3900000000-baea5cfe4e199a5ff3bc	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ue9-0900000000-c2808da990a74bab5038	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0900000000-8058aca97e516d13c287	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0zor-5900000000-a4ed8f03061acdf96ef7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9400000000-bc72ccdad3422a05a984	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-1000-0900000000-ebaae574a4f0209032d0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-002f-9100000000-ae59e1a1723666bf192b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-9200000000-5f071ead2181ac329e6a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0pvi-0900000000-18ac4d71743edfc16d7a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0900000000-4ec70507ab24e73fa629	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-6b73fb15e83c91238365	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-0900000000-d82161f65e3b085bdacb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-2900000000-65592de2b7ae3ee7aa94	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-0252284dd0d745a2e0ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-0da26709ef2caf03994a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ks-4900000000-6ec4c48ab5df172a962b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-f31118255833f0bedd5a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aca-0900000000-6c702260f9d096ceb11d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9200000000-548a6adb75eeb4caefdd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-98a5dc0bd0bee7771886	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kji-1900000000-708fba6151de4d11d60e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uk9-9500000000-ccb31762970f38503370	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	46477
HMDB ID	HMDB0240266
Pubchem Compound ID	19844
Kegg ID	Not Available
ChemSpider ID	18693
FOODB ID	FDB029771
Wikipedia ID	Methyl group
BioCyc ID	Not Available

Structure for #<Compound:0xb3cb56c0>