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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Vicenin 1 is a C-glycosylflavone that has an inhibitory effect on angiotensin-converting enzyme ( ACE )( IC 50 =52.50 μM)
In Vitro
The target-isolated C-glycosylflavone (Vicenin 1) is evaluated for inhibitory activities. Vicenin 1 embodies effective ACE inhibitory activities with an IC 50 value of 52.50 μM. The tested compound 3 (Vicenin 1) shows activity via the generation of chelate complexes within the active center of ACE. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:IC50: 52.50 μM (ACE)
| Canonical Smiles | C1C(C(C(C(O1)C2=C(C(=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)C5C(C(C(C(O5)CO)O)O)O)O)O)O)O |
|---|---|
| IUPAC Name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]chromen-4-one |
| InChIKey | OVMFOVNOXASTPA-MCIQUCDDSA-N |
| INCHI | 1S/C26H28O14/c27-6-13-18(32)21(35)23(37)26(40-13)16-20(34)15(25-22(36)17(31)11(30)7-38-25)19(33)14-10(29)5-12(39-24(14)16)8-1-3-9(28)4-2-8/h1-5,11,13,17-18,21-23,25-28,30-37H,6-7H2/t11-,13-,17+,18-,21+,22-,23-,25+,26+/m1/s1 |
| Isomeric SMILES | C1[C@H]([C@@H]([C@H]([C@@H](O1)C2=C(C(=C3C(=C2O)C(=O)C=C(O3)C4=CC=C(C=C4)O)[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O |
| Alternate CAS | 35927-38-9 |
| PubChem CID | 13644663 |
| MeSH Entry Terms | 6-C-beta-D-xylopyranosyl-8-C-beta-D-glucopyranosyl apigenin;vicenin;vicenin-1 |
| Molecular Weight | 564.49 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Phenylpropanoids and polyketides |
| Class | Flavonoids |
| Subclass | Flavonoid glycosides |
| Intermediate Tree Nodes | Flavonoid C-glycosides |
| Direct Parent | Flavonoid 8-C-glycosides |
| Alternative Parents | 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids Flavones Phenolic glycosides C-glycosyl compounds Chromones 1-hydroxy-2-unsubstituted benzenoids Pyranones and derivatives Monosaccharides Benzene and substituted derivatives Oxanes Heteroaromatic compounds Vinylogous acids Secondary alcohols Oxacyclic compounds Dialkyl ethers Polyols Organic oxides Hydrocarbon derivatives Primary alcohols |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Flavonoid-8-c-glycoside - 4'-hydroxyflavonoid - 5-hydroxyflavonoid - 7-hydroxyflavonoid - Flavone - Hydroxyflavonoid - Phenolic glycoside - C-glycosyl compound - Chromone - Glycosyl compound - Benzopyran - 1-benzopyran - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Pyranone - Pyran - Monocyclic benzene moiety - Oxane - Monosaccharide - Benzenoid - Heteroaromatic compound - Vinylogous acid - Secondary alcohol - Polyol - Oxacycle - Dialkyl ether - Ether - Organoheterocyclic compound - Hydrocarbon derivative - Organic oxygen compound - Organooxygen compound - Primary alcohol - Organic oxide - Alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as flavonoid 8-c-glycosides. These are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. |
| External Descriptors | Not available |
| Solubility | DMSO : 100 mg/mL (177.15 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 564.500 g/mol |
| XLogP3 | -2.200 |
| Hydrogen Bond Donor Count | 10 |
| Hydrogen Bond Acceptor Count | 14 |
| Rotatable Bond Count | 4 |
| Exact Mass | 564.148 Da |
| Monoisotopic Mass | 564.148 Da |
| Topological Polar Surface Area | 247.000 Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 938.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 9 |
| 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 |