Homovanillic acid (YMDB01711)

Identification

YMDB ID

YMDB01711

Name

Homovanillic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Homovanillic acid, also known as vanillacetate or homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Homovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Homovanillic acid exists in all living species, ranging from bacteria to humans. Homovanillic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(4-Hydroxy-3-methoxyphenyl)acetate
(4-Hydroxy-3-methoxyphenyl)acetic acid
3-methoxy-4-hydroxy-phenylacetic acid
3-Methoxy-4-hydroxyphenylacetate
3-Methoxy-4-hydroxyphenylacetic acid
4-Hydroxy-3-methoxybenzeneacetate
4-Hydroxy-3-methoxybenzeneacetic acid
4-Hydroxy-3-methoxyphenylacetic acid
Acetic acid, (4-hydroxy-3-methoxyphenyl)-
Benzeneacetic acid, 4-hydroxy-3-methoxy-
HMPA
Homovanilate
Homovanilic acid
Homovanillate
Homovanillic acid
Homovanillinic acid
HVA
Vanilacetate
Vanilacetic acid
Vanillacetic Acid
Vanillacetate
4-Hydroxy 3-methoxyphenylacetic acid
3 Methoxy 4 hydroxyphenylacetic acid
Acid, 3-methoxy-4-hydroxyphenylacetic
Acid, 4-hydroxy-3-methoxyphenylacetic
4 Hydroxy 3 methoxyphenylacetic acid
Acid, homovanillic
3'-Methoxy-4'-hydroxyphenylacetic acid
3’-methoxy-4’-hydroxyphenylacetic acid
4'-Hydroxy-3'-methoxy-phenylacetic acid
2-(4-Hydroxy-3-methoxyphenyl)acetic acid
4'-Hydroxy-3'-methoxyphenylacetic acid

CAS number

Not Available

Weight

Average: 182.1733
Monoisotopic: 182.057908808

InChI Key

QRMZSPFSDQBLIX-UHFFFAOYSA-N

InChI

InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)

IUPAC Name

2-(4-hydroxy-3-methoxyphenyl)acetic acid

Traditional IUPAC Name

homovanillic acid

Chemical Formula

C₉H₁₀O₄

SMILES

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

Chemical Taxonomy

Description

belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:545959 )
phenols (CHEBI:545959 )
monomethoxybenzene (CHEBI:545959 )

Physical Properties

State

Solid

Charge

Melting point

138-140 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	0.33 [LAHANN,TR ET AL. (1989)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.72 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.15	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.74	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	3	ChemAxon
Refractivity	45.81 m³·mol⁻¹	ChemAxon
Polarizability	17.74 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 - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-056r-1962000000-4f8e427392aa8e136095	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-056r-2972000000-f53a7b3ac40c099e3c99	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9800000000-def178a40b9d8cc16724	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06vi-0596000000-729a4b24107b98261cb2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056r-1962000000-4f8e427392aa8e136095	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-056r-2972000000-f53a7b3ac40c099e3c99	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-056r-1962000000-24557ef3db49c59cd5dd	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1900000000-cb0e3eb7a6d9e785a2f8	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-01w0-9352000000-0e2f11bc503dd5ce6345	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 (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0900000000-994a78c607c1b6a724d2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-00fr-4900000000-ca5ef14a72dcdf3cf9fe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-00dl-9700000000-44f2784ec5407e93ea57	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0019-0900000000-aafe8aee1cf8c42b941a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-1900000000-313fe6eb451badd5c052	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0609-6900000000-11aa4fb169e782205ea3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-014i-9200000000-637a59b417fe2b2e7f58	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-014i-9000000000-7b87b58730add4511c8a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0019-0900000000-aafe8aee1cf8c42b941a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-1900000000-313fe6eb451badd5c052	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0609-6900000000-11aa4fb169e782205ea3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9200000000-1bc951858c2e658a79af	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-9000000000-7b87b58730add4511c8a	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0900000000-0c3c4c703b4b9743a521	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0900000000-a5e048e5e58ed8e57ecd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-0079-0900000000-35fbf40336719c96dd3d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-b408942abbf2cafac06e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-39dd2b8775ad5c5ec2f0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4900000000-c9fd7643f48c0e43dc87	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-57e5685e37a2d70f9ab4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-0900000000-b8470b9851db4df96b61	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-3900000000-2690d7c586d4f7c3dccf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-0900000000-713f0600845faa67fec3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01qi-0900000000-30a79a8a4d5cf0ffc864	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-2900000000-6f967f9e7f7117a9d1e4	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-000i-3900000000-b8c848b70c066282b36f	JSpectraViewer \| MoNA
1D NMR	1H 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	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
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D 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	545959
HMDB ID	HMDB00118
Pubchem Compound ID	1738
Kegg ID	C05582
ChemSpider ID	1675
FOODB ID	FDB001783
Wikipedia ID	Homovanillic_acid
BioCyc ID	Not Available

Structure for #<Compound:0xa8706504>