| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-10 18:36:53 UTC |
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| Updated at | 2024-09-03 04:22:56 UTC |
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| NP-MRD ID | NP0044867 |
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| Natural Product DOI | https://doi.org/10.57994/3036 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common 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 is a non-cannabinoid estrogenic compound found in cannabis (PMID: 6991645 ). 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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| Structure | OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 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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| Synonyms | | Value | Source |
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| 3,4',5-Trihydroxybibenzyl | ChEBI | | Dihydro-resveratrol | MeSH |
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| Chemical Formula | C14H14O3 |
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| Average Mass | 230.2592 Da |
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| Monoisotopic Mass | 230.09429 Da |
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| IUPAC Name | 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol |
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| Traditional Name | dihydroresveratrol |
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| CAS Registry Number | Not Available |
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| SMILES | OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1 |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | bernd.schmidt@uni-potsdam.de | University of Potsdam | Bernd Schmidt | 2024-07-05 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | bernd.schmidt@uni-potsdam.de | University of Potsdam | Bernd Schmidt | 2024-07-05 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | bernd.schmidt@uni-potsdam.de | University of Potsdam | Bernd Schmidt | 2024-07-05 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | bernd.schmidt@uni-potsdam.de | University of Potsdam | Bernd Schmidt | 2024-07-05 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental) | bernd.schmidt@uni-potsdam.de | University of Potsdam | Bernd Schmidt | 2024-07-05 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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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
- 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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| Physical Properties |
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| State | Not Available |
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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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| General References | - Montes R, Garcia-Lopez M, Rodriguez I, Cela R: Mixed-mode solid-phase extraction followed by acetylation and gas chromatography mass spectrometry for the reliable determination of trans-resveratrol in wine samples. Anal Chim Acta. 2010 Jul 12;673(1):47-53. doi: 10.1016/j.aca.2010.05.021. Epub 2010 Jun 4. [PubMed:20630177 ]
- Juan ME, Alfaras I, Planas JM: Determination of dihydroresveratrol in rat plasma by HPLC. J Agric Food Chem. 2010 Jun 23;58(12):7472-5. doi: 10.1021/jf100836j. [PubMed:20509689 ]
- Gakh AA, Anisimova NY, Kiselevsky MV, Sadovnikov SV, Stankov IN, Yudin MV, Rufanov KA, Krasavin MY, Sosnov AV: Dihydro-resveratrol--a potent dietary polyphenol. Bioorg Med Chem Lett. 2010 Oct 15;20(20):6149-51. doi: 10.1016/j.bmcl.2010.08.002. Epub 2010 Aug 5. [PubMed:20813524 ]
- van der Made SM, Plat J, Mensink RP: Resveratrol does not influence metabolic risk markers related to cardiovascular health in overweight and slightly obese subjects: a randomized, placebo-controlled crossover trial. PLoS One. 2015 Mar 19;10(3):e0118393. doi: 10.1371/journal.pone.0118393. eCollection 2015. [PubMed:25790328 ]
- Aiyedun PO, Sonibare MA, Ajiboye CO, Gueye B, Paliwal R, Albach DC, Nchiozem-Ngnitedem VA, Schmidt B: Phytoecdysteroids from Dioscorea dumetorum (Kunth) Pax. and their antioxidant and antidiabetic activities. Fitoterapia. 2024 Jun 28;177:106103. doi: 10.1016/j.fitote.2024.106103. [PubMed:38945493 ]
- DOI: 10.1016/j.fitote.2024.106103
- PII: s0367326x24002867
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