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27740-01-8 molecular structure
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(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 and InChIs

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

Cite this record

CBID:129421 http://www.chembase.cn/molecule-129421.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 2.6182313  H Acceptors 12 
H Donor LogD (pH = 5.5) -2.3393724 
LogD (pH = 7.4) -3.091061  Log P 0.45533025 
Molar Refractivity 106.9066 cm3 Polarizability 41.499382 Å3
Polar Surface Area 203.44 Å2 Rotatable Bonds
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: ≥10 mg/mL expand Show data source
Apperance
yellow powder expand Show data source
Storage Condition
desiccated expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
LD50
1314 mg/kg (mouse, intravenous) expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥98.0% (HPLC) expand Show data source
Grade
analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source
Shelf Life
(limited shelf life, expiry date on the label) expand Show data source
Empirical Formula (Hill Notation)
C21H18O12 expand Show data source
C21H18O12 · xH2O expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - SML0014 external link
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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