5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 125966
• Molecular Formular: C21H20O11
• Molecular Mass: 448.3769
• Monoisotopic Mass: 448.10056146
• SMILES: O=c1c(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)c(oc2cc(O)cc(O)c12)c1ccc(O)cc1
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1
• InChIKey: JPUKWEQWGBDDQB-QSOFNFLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: astragalin
• Synonyms: Astragaline; asragalin; kaempferol-3-glucoside; Kaempferol 3-glucoside; Kaempferol 3-O-glucoside; Kaempferol-3-O-glucoside; Kaempferol-3-D-glucoside; Kaempferol-3-beta-monoglucoside; Kaempferol 3-O-β-D-glucopyranoside; Astragalin; Astragalin; Kaempferol 3-β-D-glucopyranoside; Kaempferol 3-glucoside; 3-(β-D-Glucopyranosyloxy)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 3-Glucosylkaempferol; Astragalin; Kaempferol 3-β-D-glucopyranoside

Database IDs

• CAS Number: 480-10-4
• MDL Number: MFCD00075932
• Beilstein Number: 100568
• PubChem SID: 162220309
• PubChem CID: 5282102
• CHEBI ID: 30200
• CHEMBL: 453290
• Chemspider ID: 4445311
• Wikipedia Title: Astragalin

CALCULATED PROPERTIES

• Acid pKa: 6.3723483
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): 0.10427076
• LogD (pH = 7.4): -0.99738866
• Log P: 0.15873003
• Molar Refractivity: 107.2946 cm^3
• Polarizability: 41.517902 Å^3
• Polar Surface Area: 186.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder
• Density: 1.791 g/mL

Safety Information

• RTECS: DJ3080000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); ≥97.0% (HPLC); 98.0
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H20O11

DETAILS

Sigma Aldrich - 43951

Biochem/physiol Actions
Similar kaempferol glycosides reduce food intake and corresponding weight gain in Wistar rats.1The glucoside was not tested.

Sigma Aldrich - 79851

Biochem/physiol Actions
Similar kaempferol glycosides reduce food intake and corresponding weight gain in Wistar rats.1The glucoside was not tested.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 79851.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 68437

Biochem/physiol Actions
Similar kaempferol glycosides reduce food intake and corresponding weight gain in Wistar rats.1The glucoside was not tested.