Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:28:16 UTC |
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Update date | 2019-11-26 03:21:08 UTC |
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Primary ID | FDB023335 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 3,3',4'5-Tetrahydroxystilbene |
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Description | 3,3',4'5-Tetrahydroxystilbene (or Piceatannol) is a phenolic stilbenoid. It is a metabolite of resveratrol found in red wine. A viral protein-tyrosine kinase (LMP2A) implicated in leukemia, non-Hodgkin's lymphoma and other diseases associated with Epstein-Barr virus, was recently found to be blocked by picetannol in vitro (PMID 2590224). Therefore there is research interest in piceatannol as an anti-cancer and anti-EBV drug. Piceatannol can also act as an agonist for estrogen receptor alpha in human breast cancer cells (PMID: 16216908). [HMDB] |
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CAS Number | 10083-24-6 |
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Structure | |
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Synonyms | Synonym | Source |
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3,5,3',4'-Tetrahydroxystilbene | ChEBI | 3-Hydroxyresveratol | ChEBI | 4-[(e)-2-(3,5-Dihydroxyphenyl)vinyl]benzene-1,2-diol | ChEBI | 3,4,3',5'-Tetrahydroxy-trans-stilbene | HMDB | 3,3',4',5-Tetrahydroxystilbene | HMDB | 3,3',4,5'-Tetrahydroxy stilbene | HMDB | RSVL-1 | HMDB | 3'-Hydroxyresveratol | HMDB | 3,3',4,5'-Tetrahydroxystilbene | HMDB | 3,5,3',4'-Tetrahydroxy-trans-stilbene | HMDB | Astringinin | HMDB | Demethyl isorhapontigenin | HMDB | Piceatanol | HMDB | 3,5,3',4'-Tetrahydroxy-stilbene | HMDB | Piceatannol | HMDB | 3,3',4'5-Tetrahydroxystilbene | ChEBI | (E)-3,3',4,5'-Stilbenetetrol | PhytoBank | (E)-3,3’,4,5’-Stilbenetetrol | PhytoBank | 4-[(1E)-2-(3,5-Dihydroxyphenyl)ethenyl]-1,2-benzenediol | PhytoBank | (E)-Piceatannol | PhytoBank | Astringenin | PhytoBank | trans-3,3',4,5'-Tetrahydroxystilbene | PhytoBank | trans-3,3’,4,5’-Tetrahydroxystilbene | PhytoBank | trans-Piceatannol | PhytoBank | 3,4,3',5'-tetrahydroxy-trans-stilbene | hmdb |
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Predicted Properties | |
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Chemical Formula | C14H12O4 |
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IUPAC name | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
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InChI Identifier | InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H/b2-1+ |
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InChI Key | CDRPUGZCRXZLFL-OWOJBTEDSA-N |
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Isomeric SMILES | OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 |
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Average Molecular Weight | 244.246 |
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Monoisotopic Molecular Weight | 244.073558866 |
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Classification |
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Description | Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Stilbenes |
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Sub Class | Not Available |
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Direct Parent | Stilbenes |
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Alternative Parents | |
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Substituents | - Stilbene
- Styrene
- Resorcinol
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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 | Source: Biological location: |
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Role | Industrial application: |
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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 | 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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GC-MS | 3,3',4'5-Tetrahydroxystilbene, 4 TMS, GC-MS Spectrum | splash10-001i-1642190000-e16674c5bbe3fb0a7cb2 | Spectrum | GC-MS | 3,3',4'5-Tetrahydroxystilbene, 4 TMS, GC-MS Spectrum | splash10-001i-1852290000-a6082a666145e38ac8c1 | Spectrum | GC-MS | 3,3',4'5-Tetrahydroxystilbene, non-derivatized, GC-MS Spectrum | splash10-001i-1642190000-e16674c5bbe3fb0a7cb2 | Spectrum | GC-MS | 3,3',4'5-Tetrahydroxystilbene, non-derivatized, GC-MS Spectrum | splash10-001i-1852290000-a6082a666145e38ac8c1 | Spectrum | Predicted GC-MS | 3,3',4'5-Tetrahydroxystilbene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-0690000000-50e7f72f479a8b6f10a4 | Spectrum | Predicted GC-MS | 3,3',4'5-Tetrahydroxystilbene, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-2000790000-bc4bda52250d1c2c356c | Spectrum | Predicted GC-MS | 3,3',4'5-Tetrahydroxystilbene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 3,3',4'5-Tetrahydroxystilbene, 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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MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0006-0490000000-72952d9b2b688fc509a4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0190000000-ba683912843d4fe87a70 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0690000000-84fddb6ca6d69b5c7c81 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbi-4910000000-c3f282dac8a7f5eb07cd | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-328195abcb348d62bbb3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0190000000-1eebbf80fc971e14314b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0m06-1960000000-bef8ef7244293d115d7c | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-c3ceff739ebba19f299c | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0390000000-3a7ce7071e05030e66db | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0597-2920000000-3df50fc6f200064ed551 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0190000000-9832326339909f022092 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-1950000000-cc84bd0a2d3085415084 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-1900000000-1619a0f3fe3f1ff602a9 | Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 581006 |
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ChEMBL ID | CHEMBL69863 |
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KEGG Compound ID | C05901 |
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Pubchem Compound ID | 667639 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 28814 |
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Phenol-Explorer ID | 582 |
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DrugBank ID | DB08399 |
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HMDB ID | HMDB04215 |
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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 | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | PIT |
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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 | Piceatannol |
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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 | 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 | |
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