Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:26:35 UTC |
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Update date | 2020-09-17 15:41:36 UTC |
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Primary ID | FDB023227 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,4-Dihydroxyphenylacetaldehyde |
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Description | 3,4-Dihydroxyphenylacetaldehyde, also known as protocatechuatealdehyde or 2-(3,4-dihydroxyphenyl)ethanal, 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. 3,4-Dihydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-Dihydroxyphenylacetaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxyphenylacetaldehyde participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylacetaldehyde can be biosynthesized from dopamine through its interaction with the enzyme amine oxidase [flavin-containing] a. In addition, 3,4-dihydroxyphenylacetaldehyde can be converted into 3,4-dihydroxybenzeneacetic acid through the action of the enzyme 3,4-dihydroxyphenylacetaldehyde. In humans, 3,4-dihydroxyphenylacetaldehyde is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as pot marjorams, muscadine grapes, rambutans, summer savories, and cottonseeds. This could make 3,4-dihydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. A phenylacetaldehyde in which the 3 and 4 positions of the phenyl group are substituted by hydroxy groups. |
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CAS Number | 5707-55-1 |
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Structure | |
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Synonyms | Synonym | Source |
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2-(3,4-Dihydroxyphenyl)ethanal | ChEBI | DOPAL | ChEBI | Protocatechuatealdehyde | ChEBI | DHPAA aldehyde | MeSH | 3,4-Dihydroxy-benzeneacetaldehyde | HMDB | 3,4-dihydroxy-Benzeneacetaldehyde | hmdb |
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Predicted Properties | |
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Chemical Formula | C8H8O3 |
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IUPAC name | 2-(3,4-dihydroxyphenyl)acetaldehyde |
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InChI Identifier | InChI=1S/C8H8O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,4-5,10-11H,3H2 |
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InChI Key | IADQVXRMSNIUEL-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=C(O)C=C(CC=O)C=C1 |
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Average Molecular Weight | 152.1473 |
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Monoisotopic Molecular Weight | 152.047344122 |
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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-hydrogen aldehyde
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aldehyde
- 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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Disposition | Route of exposure: Source: |
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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 | 3,4-Dihydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-3900000000-7f82d1d31cd24be9e865 | Spectrum | Predicted GC-MS | 3,4-Dihydroxyphenylacetaldehyde, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00e9-8390000000-bba6c4376314951fb5ee | Spectrum | Predicted GC-MS | 3,4-Dihydroxyphenylacetaldehyde, 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 | splash10-0udi-0900000000-19827d81a06a62c2b70a | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udr-2900000000-479d55c57638faa6d9cd | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udl-9400000000-cadc5e95515b4cecf1f7 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0900000000-b0ef024b4e5895ddea08 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-2900000000-352f5ee2c302c824867e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9500000000-96da2068f1ed3e30ae47 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0pb9-0900000000-588f3b3d236131a4fa7a | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-3900000000-d3765e83b72ff4e9c933 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0zfr-9100000000-63064bac00f3091d89c3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-b75a7231958cf1fc53ec | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-ed865ca228b5007b7ed4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9100000000-7cc4c0962b7233330b8c | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 106504 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C04043 |
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Pubchem Compound ID | 119219 |
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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 | HMDB03791 |
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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 | 43022 |
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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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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 | 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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