| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:35:50 UTC |
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| Update date | 2020-04-21 18:02:34 UTC |
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| Primary ID | FDB023855 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | 3,4-Dihydroxymandelaldehyde |
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| Description | 3,4-Dihydroxymandelaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of both norepinephrine and epinephrine. 3,4- dihydroxymandelaldehyde generates a free radical and activates mitochondrial permeability transition, a mechanism implicated in neuron death. There is an increasing body of evidence suggesting that these compounds are neurotoxic, and it has been recently hypothesized that neurodegenerative disorders may be associated with increased levels of this biogenic aldehyde. It is possible to speculate that reduced detoxification of 3,4- dihydroxymandelaldehyde from impaired or deficient aldehyde dehydrogenase function may be a contributing factor in the suggested neurotoxicity of these compounds. Aldehyde dehydrogenases are a group of NAD(P)+ -dependent enzymes that catalyze the oxidation of aldehydes, such as those derived from catecholamines, to their corresponding carboxylic acids. To date, 19 aldehyde dehydrogenase genes have been identified in the human genome. Mutations in these genes and subsequent inborn errors in aldehyde metabolism are the molecular basis of several diseases. Several pharmaceutical agents and environmental toxins are also known to disrupt or inhibit aldehyde dehydrogenase function. (PMID: 17379813, 14697885, 11164826) [HMDB]. 3,4-Dihydroxymandelaldehyde is found in many foods, some of which are jute, lettuce, citrus, and pasta. |
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| CAS Number | 13023-73-9 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C8H8O4 |
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| IUPAC name | 2-(3,4-dihydroxyphenyl)-2-hydroxyacetaldehyde |
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| InChI Identifier | InChI=1S/C8H8O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-4,8,10-12H |
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| InChI Key | YUGMCLJIWGEKCK-UHFFFAOYSA-N |
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| Isomeric SMILES | OC(C=O)C1=CC(O)=C(O)C=C1 |
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| Average Molecular Weight | 168.1467 |
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| Monoisotopic Molecular Weight | 168.042258744 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as phenylacetaldehydes. Phenylacetaldehydes are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Phenylacetaldehydes |
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| Direct Parent | Phenylacetaldehydes |
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| Alternative Parents | |
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| Substituents | - Phenylacetaldehyde
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alpha-hydroxyaldehyde
- Secondary alcohol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Aldehyde
- Aromatic alcohol
- 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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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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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 | 3,4-Dihydroxymandelaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-06ri-1900000000-d14339278a251a7d9df1 | Spectrum | | Predicted GC-MS | 3,4-Dihydroxymandelaldehyde, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01b9-7079000000-441c5f66bee2b8f14be7 | Spectrum | | Predicted GC-MS | 3,4-Dihydroxymandelaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | 3,4-Dihydroxymandelaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-01c8f9ca75c86beb7118 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gb9-0900000000-30165da526b8042721a9 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kn9-9800000000-24ef8505a6b8f892128d | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0900000000-2ce2cd9a3f1a5d4737b3 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aor-0900000000-a9b6cf257bb2c852ffd9 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6900000000-1f2d65b1c1a32c4ea1fd | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014j-0900000000-876434025a3e5951556f | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-667ec91845715350734f | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9200000000-1663e47bc16a5fa465e4 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fki-0900000000-d67f635e503103dc887e | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0r7i-4900000000-0f535b7035498a1a6303 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ue9-9200000000-344fc9120de4f34191d3 | 2021-09-22 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 133725 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | C05577 |
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| Pubchem Compound ID | 151725 |
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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 | HMDB06242 |
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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 | 46056 |
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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 | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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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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| 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 | Not Available |
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| Files |
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| MSDS | Not Available |
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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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