Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:06 UTC |
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Update date | 2019-11-26 02:56:40 UTC |
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Primary ID | FDB001783 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3-Methoxy-4-hydroxyphenylacetic acid |
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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 found, on average, in the highest concentration within olives and beers. Homovanillic acid has also been detected, but not quantified in, avocado and milk (cow). This could make homovanillic acid a potential biomarker for the consumption of these foods. Homovanillic acid is a potentially toxic compound. |
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CAS Number | 306-08-1 |
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Structure | |
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Synonyms | Synonym | Source |
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(4-Hydroxy-3-methoxyphenyl)acetic acid | ChEBI | 3-Methoxy-4-hydroxyphenylacetate | ChEBI | 3-Methoxy-4-hydroxyphenylacetic acid | ChEBI | 4-Hydroxy-3-methoxybenzeneacetic acid | ChEBI | HVA | ChEBI | Vanillacetic acid | ChEBI | (4-Hydroxy-3-methoxyphenyl)acetate | Generator | 4-Hydroxy-3-methoxybenzeneacetate | Generator | Vanillacetate | Generator | Homovanillate | Generator | 3-Methoxy-4-hydroxy-phenylacetic acid | HMDB | 4-Hydroxy 3-methoxyphenylacetic acid | HMDB | 4-Hydroxy-3-methoxyphenylacetic acid | HMDB | Homovanilate | HMDB | Homovanilic acid | HMDB | Homovanillinic acid | HMDB | Vanilacetate | HMDB | Vanilacetic acid | HMDB | 3 Methoxy 4 hydroxyphenylacetic acid | HMDB | Acid, 3-methoxy-4-hydroxyphenylacetic | HMDB | Acid, 4-hydroxy-3-methoxyphenylacetic | HMDB | 4 Hydroxy 3 methoxyphenylacetic acid | HMDB | Acid, homovanillic | HMDB | 3'-Methoxy-4'-hydroxyphenylacetic acid | HMDB | 3’-methoxy-4’-hydroxyphenylacetic acid | HMDB | 4'-Hydroxy-3'-methoxy-phenylacetic acid | HMDB | 2-(4-Hydroxy-3-methoxyphenyl)acetic acid | HMDB | 4'-Hydroxy-3'-methoxyphenylacetic acid | HMDB | HMPA | biospider | Homovanillic acid | biospider |
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Predicted Properties | |
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Chemical Formula | C9H10O4 |
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IUPAC name | 2-(4-hydroxy-3-methoxyphenyl)acetic acid |
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InChI Identifier | 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) |
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InChI Key | QRMZSPFSDQBLIX-UHFFFAOYSA-N |
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Isomeric SMILES | COC1=CC(CC(O)=O)=CC=C1O |
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Average Molecular Weight | 182.1733 |
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Monoisotopic Molecular Weight | 182.057908808 |
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Classification |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Methoxyphenols |
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Direct Parent | Methoxyphenols |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | 138-140 oC | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | 0.33 | LAHANN,TR ET AL. (1989) |
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Experimental pKa | 4.41 | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-000i-3900000000-b8c848b70c066282b36f | 2014-09-20 | View Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-056r-1962000000-4f8e427392aa8e136095 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, 2 TMS, GC-MS Spectrum | splash10-056r-2972000000-f53a7b3ac40c099e3c99 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-0006-9800000000-def178a40b9d8cc16724 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-06vi-0596000000-729a4b24107b98261cb2 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-056r-1962000000-4f8e427392aa8e136095 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-056r-2972000000-f53a7b3ac40c099e3c99 | Spectrum | GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, GC-MS Spectrum | splash10-056r-1962000000-24557ef3db49c59cd5dd | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-1900000000-cb0e3eb7a6d9e785a2f8 | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01w0-9352000000-0e2f11bc503dd5ce6345 | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3-Methoxy-4-hydroxyphenylacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-0900000000-994a78c607c1b6a724d2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00fr-4900000000-ca5ef14a72dcdf3cf9fe | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00dl-9700000000-44f2784ec5407e93ea57 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0019-0900000000-aafe8aee1cf8c42b941a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-1900000000-313fe6eb451badd5c052 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0609-6900000000-11aa4fb169e782205ea3 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-014i-9200000000-637a59b417fe2b2e7f58 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-014i-9000000000-7b87b58730add4511c8a | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0019-0900000000-aafe8aee1cf8c42b941a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-1900000000-313fe6eb451badd5c052 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0609-6900000000-11aa4fb169e782205ea3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-9200000000-1bc951858c2e658a79af | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-9000000000-7b87b58730add4511c8a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-000i-0900000000-0c3c4c703b4b9743a521 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-000i-0900000000-a5e048e5e58ed8e57ecd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0079-0900000000-35fbf40336719c96dd3d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9100000000-b408942abbf2cafac06e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00di-4900000000-39dd2b8775ad5c5ec2f0 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-000i-4900000000-c9fd7643f48c0e43dc87 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-57e5685e37a2d70f9ab4 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-0900000000-b8470b9851db4df96b61 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-052r-3900000000-2690d7c586d4f7c3dccf | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001r-0900000000-713f0600845faa67fec3 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01qi-0900000000-30a79a8a4d5cf0ffc864 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05fr-2900000000-6f967f9e7f7117a9d1e4 | 2015-04-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C05582 |
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Pubchem Compound ID | 1738 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 574 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00118 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | 4-HYDROXY-3-METHOXYPHENYLACETIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00029504 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Homovanillic acid |
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Phenol-Explorer Metabolite ID | 574 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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