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Cynaroside

CAT: 0804-HY-N0540-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No
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CAT#:0804-HY-N0540-02Size:10 mM - 1 mL
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Cynaroside (Luteolin 7-glucoside) is a flavonoid compound that exhibits anti-oxidative capabilities. Cynaroside is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 32 nM. Cynaroside also is a promising inhibitor for H2O2-induced apoptosis, has cytoprotection against oxidative stress-induced cardiovascular diseases. Cynaroside also has antibacterial, antifungal and anticancer activities, antioxidant and anti-inflammatory activities[1][3][4][5].
CAS Number
5373-11-5
Product Name Alternative
Luteolin 7-glucoside; Luteolin 7-O-β-D-glucoside
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Bacterial; DNA/RNA Synthesis; Fungal; Influenza Virus; Parasite
Type
Reference compound
Related Pathways
Anti-infection; Apoptosis; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer; Infection; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/Cynaroside.html
Purity
99.37
Solubility
DMSO : 83.33 mg/mL (ultrasonic)
Smiles
O=C(C=C(C1=CC(O)=C(O)C=C1)OC2=CC(O[C@@H]([C@@H]([C@@H](O)[C@@H]3O)O)O[C@@H]3CO)=C4)C2=C4O
Molecular Formula
C21H20O11
Molecular Weight
448.38
Precautions
H302, H315, H319, H335
References & Citations
[1]Václav Zima, et al. Unraveling the Anti-Influenza Effect of Flavonoids: Experimental Validation of Luteolin and its Congeners as Potent Influenza Endonuclease Inhibitors. Eur J Med Chem. 22 August 2020, 112754.|[2]Liuhua Pei, et al. Cynaroside prevents macrophage polarization into pro-inflammatory phenotype and alleviates cecal ligation and puncture-induced liver injury by targeting PKM2/HIF-1α axis. Fitoterapia. 2021 Jul;152:104922.|[3]Xiao Sun, et al. Protective effects of cynaroside against H₂O₂-induced apoptosis in H9c2 cardiomyoblasts. J Cell Biochem. 2011 Aug;112 (8) :2019-29.|[4]Shams Tabrez, et al. Cynaroside inhibits Leishmania donovani UDP-galactopyranose mutase and induces reactive oxygen species to exert antileishmanial response. Biosci Rep. 2021 Jan 29;41 (1) :BSR20203857.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Luteolin 7-O-glucoside

Luteolin 7-O-beta-D-glucoside is a glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as an antioxidant and a plant metabolite. It is a beta-D-glucoside, a trihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to a luteolin. It is a conjugate acid of a luteolin 7-O-beta-D-glucoside(1-).

CAS Number5373-11-5
PubChem CID5280637
IUPAC Name2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Molecular FormulaC21H20O11
Molecular Weight448.4
XLogP0.5
Topological Polar Surface Area186
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Heavy Atom Count32
Formal Charge0
Complexity714
SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
InChI
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21-/m1/s1
InChIKey
PEFNSGRTCBGNAN-QNDFHXLGSA-N
Chemical Structure
2D Structure
2D structure of Luteolin 7-O-glucoside
CAS: 5373-11-5
CID: 5280637
Formula: C21H20O11
MW: 448.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight448.4
XLogP30.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count4
Exact Mass448.10056145
Monoisotopic Mass448.10056145
Topological Polar Surface Area186 Ų
Heavy Atom Count32
Formal Charge0
Complexity714
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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