5373-11-5

Basic information

• Product Name: Cynaroside
• Synonyms: 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
• CAS NO: 5373-11-5
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.38
• EINECS: 226-365-8
• Product Categories: Tetra-substituted Flavones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Cofactor
• Mol File: 5373-11-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 256～258℃
• Boiling Point: 838.089 °C at 760 mmHg
• Flash Point: 296.779 °C
• Appearance: /
• Density: 1.714 g/cm³
• Vapor Pressure: 8.25E-30mmHg at 25°C
• Refractive Index: 1.74
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.10±0.40(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Cynaroside(CAS DataBase Reference)
• NIST Chemistry Reference: Cynaroside(5373-11-5)
• EPA Substance Registry System: Cynaroside(5373-11-5)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: DJ3009400
• Hazardous Substances Data: 5373-11-5(Hazardous Substances Data)

Usage

Description

Cynaroside, also known as Luteolin-7-O-glucoside, is a glycosyloxyflavone that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It is an off-white powder and has been found in many Chinese herbs with diverse biological activities.

Uses

Used in Antioxidant and Radical Scavenging Applications:
Cynaroside is used as a strong antioxidant and radical scavenger for cancer prevention. It reduces lactate dehydrogenase (LDH) and caspase-3 activities, production of reactive oxygen species (ROS), and increases cell viability and 14-3-3η protein levels in H9C2 cardiomyocytes after anoxia/reoxygenation injury.
Used in Antiviral Applications:
Cynaroside is used as an antiviral agent, specifically for blocking 3C protease activity (IC50 = 0.36 mM) and reducing the cytopathic effect of enterovirus 71 in rhabdomyosarcoma cells (EC50 = 0.43 mM).
Used in Cancer Treatment:
Cynaroside is used as an anticancer agent, particularly for inhibiting the growth of hepatocellular carcinoma (HCC) cells in vitro via reduction in ROS accumulation, caspase-1 activity, and expression of the NLRP3 inflammasome. It also reduces the number of lung metastases in an SMMC-7721 HCC mouse xenograft model when administered at a dose of 2 mg/kg.
Used in Dermatological Applications:
Cynaroside is used as a treatment for reducing acanthosis and expression of epidermal differentiation markers in a mouse model of psoriasis induced by imiquimod.

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.

InChI:InChI=1/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

Upstream product

• 70404-47-6 luteolin 4'-O-β-D-glucopyranoside 7-O-β-D-glucopyranoside 
• 98767-38-5 luteolin-7-O-(6′′-O-malonyl)-β-D-glucopyranoside 
• 1002295-90-0 luteolin 7-O-β-glucuronopyranosyl-(1->6)-O-β-glucopyranoside 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 1201808-21-0 2-(2,2-diphenyl-1,3-benzodioxol-5-yl)-5,7-dihydroxy-4H-1-benzopyran-4-one 

Downstream Products

• 4712-12-3 5,7-dihydroxy-3',4'-dimethoxy flavone 
• 22030-05-3 5-acetoxy-2-(3,4-diacetoxy-phenyl)-7-(tetra-O-acetyl-β-D-glucopyranosyloxy)-chromen-4-one 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 2280-44-6 D-Glucose 
• 492-61-5 β-D-glucose 
• 50-99-7 D-glucose 
• 1061-93-4 luteolin tetraacetate 

Relevant articles and documents

FLAVONOIDS OF Campanula persicifolia. I.

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A Practical and Efficient Conversion of Luteolin into Luteoloside

A new practical and efficient preparation of the flavonoid luteoloside is reported in an excellent overall yield of 40% via a four-step synthetic approach.

Flavonoids and phenolic acids of Nepeta cataria L. var. citriodora (Becker) Balb. (Lamiaceae)

Luteolin 7-O-glucuronide, luteolin 7-O-glucurono-(1→6)-glucoside, apigenin 7-O-glucuronide as well as free aglycones luteolin and apigenin have been isolated from lemon catnip herb (Nepeta cataria L. var. citriodora). Luteolin 7-O-glucurono-(1→6)-glucoside is probably a new compound, for the first time described. Two minor constituents of flavonoid fraction have been identified as apigenin 7-O-glucoside and luteolin 7-O-glucoside by means of HPLC method. The percentage of total flavonoids determined by use of spectrophotometric method was in the range from 0.30 to 0.46% of dry mass. In phenolic acid fraction, caffeic, rosmarinic and p-coumaric acids have been identified. Total amount of phenolic acids determined by spectrophotometric method was in the range of 0.75% to 1.4 % and the content of rosmarinic acid quantified by HPLC method fluctuated in the wide range from 0.06% to 0.15% depending on the sample. The results of the investigations showed that the composition of flavonoid compounds and phenolic acids in lemon catnip are similar to those in lemon balm (Melissa officinalis L.). The amount of flavonoids are similar in both plants, and the percentage of rosmarinic acid is about ten times lower in lemon catnip than in lemon balm. The presence of luteolin, apigenin and their glycosides, caffeic acid as well as the previously described terpenoids (ursolic acid, citral, nerol, geraniol) suggests the possibility of the use of lemon catnip herb as a constituent of phytopharmaceutical preparations with mild sedative, antispasmodic, antioxidative and antiinflammatory action.