ChemicalBook--->CAS DataBase List--->5373-11-5

5373-11-5

5373-11-5 Structure

5373-11-5 Structure
IdentificationMore
[Name]

Cynaroside
[CAS]

5373-11-5
[Synonyms]

CYNAROSIDE
LUTEOLIN-7-GLUCOSIDE
LUTEOLIN-7-O-GLUCOSIDE
PETUNIDIN
2-(3,4-dihydroxyphenyl)-7-(beta-d-glucopyranosyloxy)-5-hydroxy-4h-1-benzopyr
4h-1-benzopyran-4-one,2-(3,4-dihydroxyphenyl)-7-(beta-d-glucopyranosyloxy)-5-h
7-glucoluteolin
7-glucosylluteolin
cinaroside
glucoluteolin
luteolin7-monoglucoside
luteolin7-o-glucopyranoside
luteoloside
LUTEOLIN-7-O-GLUCOSIDE 98+%
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-
Galuteolin
LUTEOLIN-7-GLUCOSIDE hplc
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Luteolin 7-O-D-glucoside
LUTEOLIN-7-O-GLUCOSIDE WITH HPLC
[EINECS(EC#)]

226-365-8
[Molecular Formula]

C21H20O11
[MDL Number]

MFCD06799436
[Molecular Weight]

448.38
[MOL File]

5373-11-5.mol
Chemical PropertiesBack Directory
[Melting point ]

256~258℃
[storage temp. ]

Sealed in dry,2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[Boiling point ]

838.1±65.0 °C(Predicted)
[density ]

1.713±0.06 g/cm3(Predicted)
[form ]

neat
[pka]

6.10±0.40(Predicted)
[color ]

Yellow to Very Dark Yellow
[Stability:]

Hygroscopic
[Major Application]

metabolomics
vitamins, nutraceuticals, and natural products
[InChIKey]

PEFNSGRTCBGNAN-QNDFHXLGSA-N
[SMILES]

C1(C2=CC=C(O)C(O)=C2)OC2=C(C(O)=CC(O[C@H]3[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O3)=C2)C(=O)C=1 |&1:17,18,20,22,24,r|
[LogP]

-0.090 (est)
[CAS DataBase Reference]

5373-11-5(CAS DataBase Reference)
Questions And AnswerBack Directory
[Effects]

Luteolin has a strong bactericidal effect on the respiratory tract, and it is the main active ingredient in the treatment of bronchitis in Qinglan, a unique medicinal material in Xinjiang. Lowers the role of cholesterol in atherosclerosis and enhances capillary relaxation.
Safety DataBack Directory
[Hazard Codes ]

Xi
[Safety Statements ]

24/25
[WGK Germany ]

3
[RTECS ]

DJ3009400
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Description]

Luteoloside is a flavonoid that has been found in many Chinese herbs with diverse biological activities. It reduces lactate dehydrogenase (LDH) and caspase-3 activities and production of reactive oxygen species (ROS) and increases cell viability and 14-3-3η protein levels in H9C2 cardiomyocytes after anoxia/reoxygenation injury. Luteoloside blocks 3C protease activity (IC50 = 0.36 mM) and reduces the cytopathic effect of enterovirus 71 in rhabdomyosarcoma cells (EC50 = 0.43 mM). It inhibits the growth of hepatocellular carcinoma (HCC) cells in vitro via reduction in ROS accumulation, caspase-1 activity, and expression of the NLRP3 inflammasome and reduces the number of lung metastases in an SMMC-7721 HCC mouse xenograft model when administered at a dose of 2 mg/kg. Luteoloside also reduces acanthosis and expression of epidermal differentiation markers in a mouse model of psoriasis induced by imiquimod (Item No. 14956).
[Chemical Properties]

Off-white powder
[Uses]

Luteolin 7-Glucoside is a strong antioxidant ant radical scavenger. Used in cancer prevention.
[Definition]

ChEBI: A glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.
[in vivo]

Cynaroside (i.p.; 5mg/kg) reduces binding of PKM2 to hypoxia-inducible factor-1α (HIF-1α) by abolishing translocation of PKM2 to the nucleus and promoting PKM2 tetramer formation, as well as suppressing phosphorylation of PKM2 at Y105[2].

Animal Model:Mice model of sepsis[2]
Dosage:5mg/kg
Administration:Cynaroside (i.p.; 5mg/kg)
Result:Inhibited PKM2 dimer formation in liver of septic mice.
[References]

[1] ZHANTU LIU. Luteoloside attenuates anoxia/reoxygenation-induced cardiomyocytes injury via mitochondrial pathway mediated by 14-3-3η protein.[J]. Phytotherapy Research, 2018, 32 6: 1126-1134. DOI: 10.1002/ptr.6053
[2] ZEYU CAO. Luteoloside Acts as 3C Protease Inhibitor of Enterovirus 71 In Vitro.[J]. PLoS ONE, 2016, 11 1: e0148693. DOI: 10.1371/journal.pone.0148693
[3] SHAO-HUA FAN. Luteoloside suppresses proliferation and metastasis of hepatocellular carcinoma cells by inhibition of NLRP3 inflammasome.[J]. PLoS ONE, 2014: e89961. DOI: 10.1371/journal.pone.0089961
[4] R PALOMBO. Luteolin-7-glucoside inhibits IL-22/STAT3 pathway, reducing proliferation, acanthosis, and inflammation in keratinocytes and in mouse psoriatic model[J]. Cell Death & Disease, 2016, 7 8: e2344-e2344. DOI: 10.1038/cddis.2016.201
Spectrum DetailBack Directory
[Spectrum Detail]

Cynaroside(5373-11-5)1HNMR
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