10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 3 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Product Application:
Grape seed extract is a natural product, with anti-inflammatory and anti-proliferative effects. Grape seed extract shows inhibitory activity on the fat-metabolizing enzymes pancreatic lipase and lipoprotein lipase. Grape seed extract induces apoptotic in human colorectal cancer cells
| Canonical Smiles | CC1=CC(=C(C2=C1CC(C(O2)C3=CC(=C(C=C3)O)O)(C)O)C4C(C(OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O |
|---|---|
| IUPAC Name | (2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,5-dimethyl-2,4-dihydrochromen-8-yl]-3,4-dihydro-2H-chromene-3,5,7-triol |
| InChIKey | VWKAFYWVDIOMSL-PMFFMQSYSA-N |
| INCHI | 1S/C32H30O11/c1-13-7-22(38)26(30-17(13)12-32(2,41)31(43-30)15-4-6-19(35)21(37)9-15)27-25-23(39)10-16(33)11-24(25)42-29(28(27)40)14-3-5-18(34)20(36)8-14/h3-11,27-29,31,33-41H,12H2,1-2H3/t27-,28-,29+,31+,32+/m0/s1 |
| Isomeric SMILES | CC1=CC(=C(C2=C1C[C@@]([C@H](O2)C3=CC(=C(C=C3)O)O)(C)O)[C@H]4[C@@H]([C@H](OC5=CC(=CC(=C45)O)O)C6=CC(=C(C=C6)O)O)O)O |
| PubChem CID | 78577443 |
| Molecular Weight | 590.581 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Biflavonoids and polyflavonoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Biflavonoids and polyflavonoids |
| Alternative Parents | B-type proanthocyanidins Catechins 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids 1-benzopyrans Catechols Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Benzene and substituted derivatives Tertiary alcohols Secondary alcohols Oxacyclic compounds Polyols Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | B-type proanthocyanidin - Bi- and polyflavonoid skeleton - Proanthocyanidin - Catechin - 3'-hydroxyflavonoid - 3-hydroxyflavonoid - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavan-3-ol - Hydroxyflavonoid - Flavan - Chromane - Benzopyran - 1-benzopyran - Catechol - Phenol - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Monocyclic benzene moiety - Tertiary alcohol - Secondary alcohol - Organoheterocyclic compound - Polyol - Oxacycle - Ether - Hydrocarbon derivative - Organooxygen compound - Alcohol - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. |
| External Descriptors | Not available |
| Molecular Weight | 590.600 g/mol |
|---|---|
| XLogP3 | 3.300 |
| Hydrogen Bond Donor Count | 9 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 3 |
| Exact Mass | 590.179 Da |
| Monoisotopic Mass | 590.179 Da |
| Topological Polar Surface Area | 201.000 Ų |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Complexity | 970.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 5 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Wenhui Li, Lidan Ran, Fei Liu, Ran Hou, Wei Zhao, Yingbiao Li, Chunyan Wang, Juan Dong. (2019) Preparation and Characterisation of Polyphenol-HP-β-Cyclodextrin Inclusion Complex that Protects Lamb Tripe Protein against Oxidation. MOLECULES, 24 (24): (4487). [PMID:31817887] [10.3390/molecules24244487] |
| 2. Yun-Lu Song, Jia-Lin Xing, Charles Ampomah-Dwamena, Shuai-Hui Ma, Mao-Song Pei, Han-Li Liu, Rui-Ping Feng, Yong-Ke Wu, Tong-Lu Wei, Hai-Nan Liu, Da-Long Guo. (2025) CHI–GSE–Nano-ZnO coating delays grape postharvest deterioration by inhibiting excess ROS via MYB714-pSTS484-mediated resveratrol biosynthesis. Food Bioscience, [PMID:] [10.1016/j.fbio.2025.107889] |
| 3. Dina Chang, Lixia Ma, Yan Yan, Anxu Zheng, Xuehang Wang, Yue Leng, Bin Jiang, Dayong Ren, Lixin You, Ji Wang. (2026) Covalently cross-linked walnut protein-proanthocyanidin composite nanoparticles: Preparation, characterization, and Pickering emulsifying properties. FOOD CHEMISTRY, [PMID:] [10.1016/j.foodchem.2026.148775] |
