Basic information
- CAS
2545-00-8- Standard SMILES
Oc1ccc(C2Oc3cc(O)cc(O)c3CC2O)cc1- InChIKey
RSYUFYQTACJFML-UHFFFAOYSA-N- Molecular formula
- C15H14O5
- Average molar mass
- 274.27 g/mol
- Monoisotopic mass
- 274.08412354
Overview
2-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol is a hydroxyflavan.
Names & identifiers
- Preferred name
- 2-(4-Hydroxyphenyl)-3,4-Dihydro-2H-Chromene-3,5,7-Triol
- IUPAC
- 2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
- English name
- AFZELECHIN
- Molecular formula
- C15H14O5
- Molecular weight
- 274.27
Names & synonyms
2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triolRefChem:10612562-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol(+)-Afzelechin ;NSC 135065Afzelechin, (+)-Flavan-3-ols + 3O(-)-epi-Afzelechin;Epiafzelechin, (-)-; epi-Afzelechin3,4',5,7-tetrahydroxyflavan3,5,7-Flavantetrol (+)-CHEMBL1326092SCHEMBL10405656SCHEMBL30335148
Show more names
(+)-afzelichin(2R)-2α-(4-Hydroxyphenyl)chroman-3β,5,7-triol2H-1-Benzopyran-3,5,7-triol,3,4-dihydro-2-(4-hydroxyphenyl)-, (2R,3S)[2R,3S,(+)]-3,4-Dihydro-2-(4-hydroxyphenyl)-2H-1-benzopyran-3,5,7-triol
3,5,7-Flaventetrol, (+)-CHEBI:181768(+)-3,4',5,7-FlaventetrolDTXSID3011895173,4',5,7-Flavantetrol (+)-NSC135065NCGC00095516-01490-61-9
Database identifiers
- CAS
2545-00-8、490-61-9
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 90.2 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 328
Experimental & physicochemical properties
Melting Point221 - 222 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 252 · 252-254 °C (decomp)
- Boiling point
- 583.4 · 583.4±50.0 °C(Predicted)
- Density
- 1.492 · 1.492±0.06 g/cm3(Predicted)
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 9 · 9+-.0.60(Predicted)
- color
- White to light brown
- InChI
- InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15+/m0/s1
- InChIKey
- RSYUFYQTACJFML-DZGCQCFKSA-N
- SMILES
- [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C[C@@H]1O
- FDA UNII
- 782 YDV47U · W782YDV47U
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Uses(+)-Afzelechin, isolated from rhizomes of Bergenia ligulata, is an alpha-glucosidase activity inhibitor with an ID50 (50% inhibition dose) value of 0.13 mM. (+)-Afzelechin can delay the absorption of carbohydrates in food to suppress postprandial hyperglycemia and hyperinsulinemia[1].
Suppliers41 total
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Related reactions
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Compound notes
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