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

• ChemBase ID: 155916
• 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-DTGCRPNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: hyperoside
• Synonyms: 3,3′,4′,5,7-Pentahydroxyflavone 3-D-galactoside; Hyperin; Hyperoside; Quercetin 3-D-galactoside; Quercetin 3-D-galactoside; Hyperoside; Quercetin 3-O-galactoside; Hyperin; 海棠因; 金丝桃苷; 槲皮素 3-D-半乳糖苷; 槲皮素 3-D-半乳糖苷; 金丝桃甙

Database IDs

• CAS Number: 482-36-0
• EC Number: 207-580-6
• MDL Number: MFCD00016933
• Beilstein Number: 5784795
• PubChem SID: 162250054; 24888115
• PubChem CID: 5281643

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: DJ3009200
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

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

Product Information

• Purity: ≥97.0% (HPLC)
• Grade: primary reference standard
• Empirical Formula (Hill Notation): C21H20O12

DETAILS

Sigma Aldrich - 83388

Other Notes
A flavonol glycoside widely distribute in plants, including mimosa and St. John′s wort.
Biochem/physiol Actions
Protects against peroxide-induced oxidative damage to cells by scavenging reactive oxygen species and enhancing activity of anti-oxidant enzymes, in particular, catalase and glutathione peroxidase.

Sigma Aldrich - 00180585

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
Other Notes
A flavonol glycoside widely distribute in plants, including mimosa and St. John′s wort.
Biochem/physiol Actions
Protects against peroxide-induced oxidative damage to cells by scavenging reactive oxygen species and enhancing activity of anti-oxidant enzymes, in particular, catalase and glutathione peroxidase.