Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 23:08:32 UTC |
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Update Date | 2020-05-11 20:45:39 UTC |
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MCDB ID | BMDB0004215 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3,3',4'5-Tetrahydroxystilbene |
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Description | Piceatannol, also known as RSVL-1 or astringinin, 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. Thus, piceatannol is considered to be an aromatic polyketide lipid molecule. Piceatannol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Piceatannol exists in all living species, ranging from bacteria to humans. |
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Structure | |
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Synonyms | Value | 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 |
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Chemical Formula | C14H12O4 |
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Average Molecular Weight | 244.246 |
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Monoisotopic Molecular Weight | 244.073558866 |
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IUPAC Name | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
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Traditional Name | 4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol |
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CAS Registry Number | 10083-24-6 |
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SMILES | OC1=CC(\C=C\C2=CC(O)=C(O)C=C2)=CC(O)=C1 |
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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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Chemical Taxonomy |
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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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-001i-1642190000-e16674c5bbe3fb0a7cb2 | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-001i-1852290000-a6082a666145e38ac8c1 | 2014-06-16 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-1642190000-e16674c5bbe3fb0a7cb2 | 2017-09-12 | View Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-001i-1852290000-a6082a666145e38ac8c1 | 2017-09-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-006x-0690000000-50e7f72f479a8b6f10a4 | 2016-09-22 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-014i-2000790000-bc4bda52250d1c2c356c | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0006-0490000000-72952d9b2b688fc509a4 | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0190000000-ba683912843d4fe87a70 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0690000000-84fddb6ca6d69b5c7c81 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pbi-4910000000-c3f282dac8a7f5eb07cd | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-328195abcb348d62bbb3 | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0190000000-1eebbf80fc971e14314b | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0m06-1960000000-bef8ef7244293d115d7c | 2016-09-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0090000000-c3ceff739ebba19f299c | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0390000000-3a7ce7071e05030e66db | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0597-2920000000-3df50fc6f200064ed551 | 2021-09-23 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0002-0190000000-9832326339909f022092 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-1950000000-cc84bd0a2d3085415084 | 2021-09-24 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-1900000000-1619a0f3fe3f1ff602a9 | 2021-09-24 | View Spectrum |
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Concentrations |
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Detected but not Quantified | Not Applicable | | | details |
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External Links |
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HMDB ID | HMDB0004215 |
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DrugBank ID | DB08399 |
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Phenol Explorer Compound ID | 582 |
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FoodDB ID | FDB023335 |
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KNApSAcK ID | C00002895 |
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Chemspider ID | 581006 |
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KEGG Compound ID | C05901 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Piceatannol |
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METLIN ID | Not Available |
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PubChem Compound | 667639 |
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PDB ID | PIT |
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ChEBI ID | 28814 |
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References |
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Synthesis Reference | Bajaj, Renu; Gill, Mark T.; McLaughlin, Jerry L. Improved preparative synthesis of piceatannol (3,4,3',5'-tetrahydroxy-trans-stilbene). Revista Latinoamericana de Quimica (1987), 18(2), 79-80. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
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