Record Information |
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Version | 1.0 |
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Creation date | 2012-01-20 01:16:41 UTC |
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Update date | 2020-09-17 15:30:07 UTC |
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Primary ID | FDB029989 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Dihydroresveratrol |
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Description | Dihydroresveratrol or 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol is a stilbenol where hydroxy groups at positions 1, 3 and 4' are added to 1,1'-ethane-1,2-diyldibenzene. Dihydroresveratrol is an aromatic polyketide, which contains alternating carbonyl groups and methylene groups. Dihydroresveratrol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Dihydroresveratrol, a prominent polyphenol component of red wine (PMID: 20630177), has a profound proliferative effect on hormone-sensitive tumor cell lines at picomolar concentrations. Dihydroresveratol is a derivative of resveratol and one of the main metabolites of two stereoisomers of resveratol, trans resveratrol and cis resveratrol. Dihydroresveratrol is formed in the intestine by microbial hydrogenation of trans-resveratrol (PMID: 20509689). Trans-resveratrol is a common component of fruits and berries, particularly grapes (Vitis vinifera), where it is formed as a response to the stress of weather conditions, microbe infections, or direct sunlight. Cis resveratrol is as a minor component in some berries, grapes, and wines along with trans-resveratrol (PMID: 20813524). Resveratrol has received special attention due to its diverse and potentially beneficial biological properties. The compound is currently on the market as a popular dietary supplement and is under clinical trials for treatment of some types of cancers (PMID: 25446990), metabolic syndrome, Alzheimer’s disease, type 2 diabetes, obesity (PMID: 25790328), neurologic syndrome, and some symptoms of aging. |
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CAS Number | 58436-28-5 |
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Structure | |
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Synonyms | Synonym | Source |
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3,4',5-Trihydroxybibenzyl | ChEBI | Dihydro-resveratrol | MeSH | 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol | biospider |
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Predicted Properties | |
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Chemical Formula | C14H14O3 |
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IUPAC name | 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol |
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InChI Identifier | InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2 |
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InChI Key | HITJFUSPLYBJPE-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 |
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Average Molecular Weight | 230.2592 |
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Monoisotopic Molecular Weight | 230.094294314 |
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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
- Resorcinol
- 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 | - stilbenol (CHEBI:4582 )
- Diphenyl ethers, biphenyls, dibenzyls and stilbenes (C10255 )
- Bibenzyls (C10255 )
- Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090035 )
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Ontology |
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Foods | Beverages: Fruits and vegetables: |
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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 | Not Available | |
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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 | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0adi-3920000000-719fe242334d208b9ba6 | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-0019-0930000000-98789a2bfadb2e5294f9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive | splash10-0a4i-3900000000-8401a4b05cec11937e91 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 50V, positive | splash10-0a4i-1900000000-63077beabbd74f9667da | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 6V, positive | splash10-0019-0930000000-d89311ce59a12d10e350 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative | splash10-00fr-0940000000-e764d7f7fec0ad95522d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative | splash10-004i-0590000000-c0d04f560a51a3bb619d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative | splash10-001i-9500000000-361c896f8255aa9a4a1d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative | splash10-00di-3900000000-71299800417044263bbb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 50V, negative | splash10-001i-9000000000-35af2f10fc300befdb21 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 50V, negative | splash10-003r-9100000000-ac6d40eae4eba92c915d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 6V, negative | splash10-004i-0590000000-c0d04f560a51a3bb619d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 6V, negative | splash10-00fr-0940000000-ef1a37528e823253c1b3 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0190000000-dbff90b6a63d99897a08 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-053r-0950000000-1f3064cc04762cbfb39f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-5900000000-e5b4f11464b84f6190ef | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0090000000-3f1af4fc1138d28d1e8f | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0190000000-b3b2e29cac9a8f7c4f14 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0553-1920000000-bc1898e08955e5b6385a | JSpectraViewer |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 185914 |
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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 | DB08466 |
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HMDB ID | Not Available |
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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 | 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 | 1008 |
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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 | 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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