Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:26:33 UTC |
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Update date | 2020-09-17 15:40:43 UTC |
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Primary ID | FDB023224 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 4-Hydroxyphenylacetaldehyde |
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Description | 4-Hydroxyphenylacetaldehyde, also known as POH-PH-CH2CHO, 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. 4-Hydroxyphenylacetaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Hydroxyphenylacetaldehyde has been detected, but not quantified in, several different foods, such as purple mangosteens, cottonseeds, garden cress, borages, and colorado pinyons. This could make 4-hydroxyphenylacetaldehyde a potential biomarker for the consumption of these foods. The condensation of 4-hydroxyphenylacetaldehyde and dopamine is a key step in the biosynthesis of benzylisoquinoline alkaloids. In both species, it is subsequently metabolized into 4-hydroxyphenylacetate by aldehyde dehydrogenase (ALDH) enzymes in humans and the phenylacetaldehyde dehydrogenase (feaB) enzyme in E. coli. These natural products include berberine and morphine. |
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CAS Number | 7339-87-9 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C8H8O2 |
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IUPAC name | 2-(4-hydroxyphenyl)acetaldehyde |
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InChI Identifier | InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2 |
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InChI Key | IPRPPFIAVHPVJH-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=C(CC=O)C=C1 |
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Average Molecular Weight | 136.1479 |
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Monoisotopic Molecular Weight | 136.0524295 |
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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
- 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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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 | 4-Hydroxyphenylacetaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a4r-5900000000-dee6bd2327885b9b9c35 | Spectrum | Predicted GC-MS | 4-Hydroxyphenylacetaldehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05g0-5900000000-052b7c5a508b36e0512f | Spectrum | Predicted GC-MS | 4-Hydroxyphenylacetaldehyde, 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 | splash10-000i-0900000000-c592acce12d2ba134040 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kr-2900000000-90058ffcbfd58f5dff5b | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0690-9500000000-a8abea2510950f337295 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-3f4ed034f10b0d6a25b4 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-99115e80b538ba6b2306 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-6c9913d203a267c92186 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-4900000000-e2bf91e8ab2ae47d9096 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4l-9600000000-ff10a0510f947f476688 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004l-9100000000-b447fa4b15009b677f8f | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-2900000000-59dcda3398a30862c88d | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1900000000-7a7b9a9d95399c23529b | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-b2c6c4e6f393a7458822 | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 389113 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C03765 |
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Pubchem Compound ID | 440113 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15666 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03767 |
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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 | 42489 |
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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 | 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 | 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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