Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:05:25 UTC |
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Update date | 2015-10-09 22:29:32 UTC |
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Primary ID | FDB021931 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Vanillylmandelic acid |
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Description | Vanillylmandelic acid, also known as vanillylmandelate or VMA, 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. Vanillylmandelic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanillylmandelic acid exists in all living organisms, ranging from bacteria to humans. Vanillylmandelic acid is a sweet and vanilla tasting compound. Vanillylmandelic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, and brunner syndrome; vanillylmandelic acid has also been linked to several inborn metabolic disorders including aromatic l-amino acid decarboxylase deficiency and phenylketonuria. |
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CAS Number | 55-10-7 |
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Structure | |
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Synonyms | Synonym | Source |
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Vanillylmandelate | Generator | (4-Hydroxy-3-methoxyphenyl)glycolate | HMDB | (4-Hydroxy-3-methoxyphenyl)glycolic acid | HMDB | 3-Methoxy-4-hydroxy-mandelic acid | HMDB | 3-Methoxy-4-hydroxymandelate | HMDB | 3-Methoxy-4-hydroxymandelic acid | HMDB | 3-Methoxy-4-hydroxyphenylhydroxyacetate | HMDB | 3-Methoxy-4-hydroxyphenylhydroxyacetic acid | HMDB | 4'-Hydroxy-3'-methoxymandelate | HMDB | 4'-Hydroxy-3'-methoxymandelic acid | HMDB | 4-Hydroxy 3-methoxymandelic acid | HMDB | 4-Hydroxy-3-methoxy-DL-mandelate | HMDB | 4-Hydroxy-3-methoxy-DL-mandelic acid | HMDB | 4-Hydroxy-3-methoxy-mandelate | HMDB | 4-Hydroxy-3-methoxy-mandelic acid | HMDB | 4-Hydroxy-3-methoxymandelate | HMDB | 4-Hydroxy-3-methoxymandelic acid | HMDB | DL-3-Methoxy-4-hydroxymandelate | HMDB | DL-3-Methoxy-4-hydroxymandelic acid | HMDB | DL-4-Hydroxy-3-methoxymandelate | HMDB | DL-4-Hydroxy-3-methoxymandelic acid | HMDB | DL-Vanillomandelate | HMDB | DL-Vanillomandelic acid | HMDB | DL-Vanillylmandelate | HMDB | DL-Vanillylmandelic acid | HMDB | HMMA | HMDB | Hydroxymethoxymandelic acid | HMDB | Lopac-H-0131 | HMDB | Vainillylmandelic acid | HMDB | Vanillinmandelate | HMDB | Vanillinmandelic acid | HMDB | Vanillomandelate | HMDB | Vanillomandelic acid | HMDB | Vanillyl-mandelic acid | HMDB | Vanillylmandellic acid | HMDB | Vanillymandelic acid | HMDB | Vanilmandelate | HMDB | Vanilmandelic acid | HMDB | Vanilylmandelic acid | HMDB | Vanyl-mandelic acid | HMDB | Vanylmandelic acid | HMDB | VMA | HMDB | 2-Phenyllactic acid | HMDB | VMA CPD | HMDB | Atrolactic acid | HMDB | Atrolactic acid monosodium salt, (S)-isomer | HMDB | Atrolactic acid, (+-)-isomer | HMDB | Hydroxymethylmandelic acid | HMDB | (+)-4-Hydroxy-3-methoxymandelic acid | HMDB | (+)-Vanilmandelic acid | HMDB | (2S)-2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid | HMDB | (S)-4-Hydroxy-3-methoxymandelic acid | HMDB | (alphaS)-alpha,4-Dihydroxy-3-methoxybenzeneacetic acid | HMDB | (αS)-α,4-Dihydroxy-3-methoxybenzeneacetic acid | HMDB | 2-(4'-Hydroxy-3'-methoxyphenyl)-2-hydroxyethanoic acid | HMDB | 2-(4’-Hydroxy-3’-methoxyphenyl)-2-hydroxyethanoic acid | HMDB | 2-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid | HMDB | 4’-Hydroxy-3’-methoxymandelic acid | HMDB | L-(+)-3-Methoxy-4-hydroxymandelic acid | HMDB | Vanillylmandelic acid | HMDB | alpha,4-Dihydroxy-3-methoxybenzeneacetic acid | HMDB | α,4-Dihydroxy-3-methoxybenzeneacetic acid | HMDB | 3-methoxy-4-hydroxy-mandelic acid | hmdb | 3-methoxy-4-hydroxymandelic acid | hmdb | 4-hydroxy 3-methoxymandelic acid | hmdb | 4-hydroxy-3-methoxy-Mandelate | hmdb | 4-hydroxy-3-methoxy-Mandelic acid | hmdb | DL-vanillomandelate | hmdb | DL-vanillomandelic acid | hmdb | DL-vanillylmandelate | hmdb | DL-vanillylmandelic acid | hmdb | vainillylmandelic acid | hmdb | vanillyl-mandelic acid | hmdb | vanillylmandellic acid | hmdb | vanillymandelic acid | hmdb | vanilylmandelic acid | hmdb | vanyl-mandelic acid | hmdb | vanylmandelic acid | hmdb |
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Predicted Properties | |
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Chemical Formula | C9H10O5 |
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IUPAC name | (2S)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid |
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InChI Identifier | InChI=1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)/t8-/m0/s1 |
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InChI Key | CGQCWMIAEPEHNQ-QMMMGPOBSA-N |
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Isomeric SMILES | COC1=C(O)C=CC(=C1)[C@H](O)C(O)=O |
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Average Molecular Weight | 198.1727 |
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Monoisotopic Molecular Weight | 198.05282343 |
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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
- Alpha-hydroxy acid
- Monocyclic benzene moiety
- Hydroxy acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Organooxygen compound
- Aromatic alcohol
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Biological location: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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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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Predicted GC-MS | Vanillylmandelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-3900000000-97b85fd5a9736a5d5eb0 | Spectrum | Predicted GC-MS | Vanillylmandelic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-009t-7396100000-b5450c24921a68f5f6b3 | Spectrum | Predicted GC-MS | Vanillylmandelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Vanillylmandelic acid, TBDMS_3_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) | splash10-000b-0900000000-1e2dedd8e81249787b29 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-000i-0900000000-3d2cd918dc6b76dfba3f | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-000i-2900000000-b543807e43e5091abb53 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1900000000-1c88ce4d32680e3379de | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-30e1c8cb4fa5443c687e | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-c4c762f850d22fee6281 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6t-0900000000-1308d37a2313f5479365 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fmj-0900000000-bcdff30bcec2389ffef6 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0ab9-3900000000-cd2db271b5a0926adfeb | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00dj-9700000000-2c212037a037fcd229d0 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0kg9-1900000000-81b2ab77bf3382c9f5de | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-4900000000-e3b77a4d29235649ecce | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f8a-0900000000-04d80bfab4984d07e479 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-23d4830296b7ea07f0d5 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fki-5900000000-9b9364530caece4b6c12 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f7t-0900000000-ac32d971a0581e8b6cb6 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-bce2f2854f319781df10 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0umi-9700000000-311af8dc825e2dd02614 | 2021-09-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, 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, 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 | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | 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 | 643307 |
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ChEMBL ID | CHEMBL1603851 |
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KEGG Compound ID | C05584 |
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Pubchem Compound ID | 736172 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00291 |
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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 | Not Available |
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BIGG ID | 46071 |
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KNApSAcK ID | Not Available |
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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 | rw1486281 |
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SuperScent ID | Not Available |
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Wikipedia ID | Vanillylmandelic acid |
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Phenol-Explorer Metabolite ID | Not Available |
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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 | |
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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 | Flavor | Citations |
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sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| vanilla |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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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 | |
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