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

• ChemBase ID: 155969
• Molecular Formular: C21H20O12
• Molecular Mass: 464.3763
• Monoisotopic Mass: 464.09547608
• SMILES: c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1
• InChIKey: OVSQVDMCBVZWGM-QSOFNFLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: isoquercitin
• Synonyms: 3,3′,4′,5,7-Pentahydroxyflavone 3-β-glucoside; Isoquercitrin; Quercetin 3-β-D-glucoside; Quercetin 3-β-D-glucoside; Isoquercitrin; Quercetin 3-O-glucoside; Hirsutrin; Quercetin 3-glucoside; 3,3′,4′,5,7-五羟基黄酮 3-β-葡萄糖甙; 异栎素; 槲皮素 3-β-D-葡萄糖甙; 槲皮素 3-β-D-葡萄糖甙; 异栎素

Database IDs

• CAS Number: 482-35-9
• MDL Number: MFCD00017746
• Beilstein Number: 100989
• PubChem SID: 24850700; 162250107
• PubChem CID: 5280804

CALCULATED PROPERTIES

• Acid pKa: 6.3724055
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -0.19928613
• LogD (pH = 7.4): -1.3000474
• Log P: -0.1448353
• Molar Refractivity: 109.2755 cm^3
• Polarizability: 42.19499 Å^3
• Polar Surface Area: 206.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Safety Information

• RTECS: DJ2982500
• 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

Pharmacology Properties

• Gene Information: mouse ... Hexa(15211)

Product Information

• Purity: ≥90% (HPLC); ≥98% (HPLC)
• Grade: analytical standard; primary reference standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H20O12

DETAILS

Sigma Aldrich - 17793

Application
Quercetin 3-β-D-glucoside can be used to study cell biology, bioactive small molecules, biochemicals found in plants and nutrition. Quercetin-3-β-d-glucoside, a glucoside form of quercetin, significantly reduced the replication of influenza viruses in vitro and in vivo. Quercetin-3-β-d-glucoside has been used in a study to compare the anti-proliferative activities of quercetin derivatives using six different cancer cell lines (colon, breast, hepatocellular and lung cancer).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 17793.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references

Sigma Aldrich - 00140585

Application
Reference standard in the analysis of herbal medicinal products.
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate