(2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 129421
• Molecular Formular: C21H18O12
• Molecular Mass: 462.36042
• Monoisotopic Mass: 462.07982602
• SMILES: O=c1cc(oc2cc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O)c12)c1ccc(O)cc1
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](Oc2cc3oc(cc(=O)c3c(c2O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: DJSISFGPUUYILV-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: scutellarin
• Synonyms: Breviscapine; Breviscapin; Scutellarein-7-glucuronide; Scutellarein-7beta-D-glucuronide; Scutellarein-7beta-D-glucuronoside; Scutellarein-7-O-beta-D-glucuronide; 7-(β-D-glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Scutellarin; 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid hydrate; 7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one hydrate; Scutellarein-7-O-β-D-glucuronide; Scutellarin hydrate; 5,6-Dihydroxy-2-(p-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid; 4',5,6,7-Tetrahydroxyflavone 7-β-D-Glucopyranuronoside; Scutellarein 7-O-β-D-Glucuronide; Scutellarein 7-β-D-Glucuronoside; Scutellarin B; 5,6-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl-β-D-glucopyranosiduronic acid; 7-(β-D-Glucopyranuronosyloxy)-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Scutellarin

Database IDs

• CAS Number: 27740-01-8
• MDL Number: MFCD01861503
• Beilstein Number: 71779
• PubChem SID: 162223715
• PubChem CID: 185617
• CHEMBL: 487805
• Chemspider ID: 161366
• Wikipedia Title: Scutellarin

CALCULATED PROPERTIES

• Acid pKa: 2.6182313
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -2.3393724
• LogD (pH = 7.4): -3.091061
• Log P: 0.45533025
• Molar Refractivity: 106.9066 cm^3
• Polarizability: 41.499382 Å^3
• Polar Surface Area: 203.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥10 mg/mL
• Apperance: yellow powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• LD50: 1314 mg/kg (mouse, intravenous)
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C21H18O12; C21H18O12 · xH2O

DETAILS

Sigma Aldrich - SML0014

Biochem/physiol Actions
Scutellarin is a flavonoid that exhibits a number of cardio- and neuro-protective effects. Scutellarin inhibits p38 activity, ERK phosphorylation, and TGF-β expression and fibrosis in a rat myocardial infarct model. In a cerebral ischemia-reperfusion model, the compound reduced infarct volume and neurological deficits by increasing eNOS expression while inhibiting the induction of iNOS.

Sigma Aldrich - 73577

Biochem/physiol Actions
Scutellarin is a flavonoid that exhibits a number of cardio- and neuro-protective effects. Scutellarin inhibits p38 activity, ERK phosphorylation, and TGF-β expression and fibrosis in a rat myocardial infarct model. In a cerebral ischemia-reperfusion model, the compound reduced infarct volume and neurological deficits by increasing eNOS expression while inhibiting the induction of iNOS.

Toronto Research Chemicals - S201900

Scutellarin is an active flavonoid component from the medical plant Erigeron breviscapus (Vant) Hand-Mazz. Scutellarin is used as a micrpcirculation promoter for the treatment of cardio-cerebrovascular diseases. Studies suggest that Scutellarin has anti-c

REFERENCES

• Gao, C. et al.: Drug Metab. Dispos., 39, 2034 (2011)
• Chan, J.Y. et al.: Anticancer Res., 29, 3043 (2011)
• Wang, C.-Z. et al.: Phytomedicine, 17, 63 (2011)