Luteolin 7-galactoside

Base Information

• Chemical Name: Luteolin 7-galactoside
• CAS No.: 5373-11-5
• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.383
• Hs Code.: 29389090
• NSC Number: 724451,700145
• Wikidata: Q105207085
• Mol file: 5373-11-5.mol

Synonyms:NSC700145;Luteolin 7-galactoside;2-(3,4-Dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl hexopyranoside;Luteolin 7-glucoside;Luteolin 7-O-beta-D-glucoside;Luteolin-7-glucosid;SCHEMBL149119;MEGxp0_000562;SCHEMBL19523005;NSC724451;STK763169;AKOS001483348;PENTA-L-PHENYLALANINEACETATESALT;Luteolin-7-O-.beta.-D-glucopyranoside;NSC-700145;NCGC00017208-02;NCGC00142376-01;2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4 ,5,6-tetrahydropyran-2-yloxy)]chromen-4-one;2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one;NCI60_035927;FT-0778096;2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-(4,5,6-trihydroxy-3-(hydroxymethyl)(2-oxanyloxy))-4H-chromen-4-one;2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one

Chemical Property of Luteolin 7-galactoside

Chemical Property:

• Vapor Pressure: 8.25E-30mmHg at 25°C
• Melting Point: 256～258℃
• Refractive Index: 1.74
• Boiling Point: 838.089 °C at 760 mmHg
• PKA: 6.10±0.40(Predicted)
• Flash Point: 296.779 °C
• PSA: 190.28000
• Density: 1.714 g/cm³
• LogP: -0.24450
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 448.10056145
• Heavy Atom Count: 32
• Complexity: 714

Purity/Quality:

Luteoloside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• Description: Luteolin-7-O-glucoside 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 .
• Uses: Luteolin 7-Glucoside is a strong antioxidant ant radical scavenger. Used in cancer prevention.

Technology Process of Luteolin 7-galactoside

There total 11 articles about Luteolin 7-galactoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxo-4H-chromen-7-yl]oxy}tetrahydro-2H-pyran-3,4,5-triyl triacetate → luteolin 7-O-glucoside (5373-11-5,68321-11-9)

Guidance literature:

With sodium methylate; In methanol; chloroform; at 20 ℃; for 4h; Reagent/catalyst; Solvent;

DOI:10.1055/a-1531-2385

Reference yield:

luteolin-7-O-[2-(β-D-apiosyl)-6-malonyl-β-D-glucoside] → luteolin 7-O-glucoside (5373-11-5,68321-11-9)

Guidance literature:

luteolin-7-O-[2-(β-D-apiosyl)-6-malonyl-β-D-glucoside]; With sodium hydroxide; at 20 ℃; for 0.166667h;

With hydrogenchloride; In water; at 80 ℃; for 1h;

DOI:10.1021/acs.jafc.8b03273

Reference yield:

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3) → luteolin 7-O-glucoside (5373-11-5,68321-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1,4-dioxane / 2 h / 185 °C

2: potassium carbonate; tetrabutylammomium bromide / water; chloroform / 5 h / 45 °C

3: palladium 10% on activated carbon; hydrogen / 1,4-dioxane; ethanol / 24 h / 20 °C / 1520.1 Torr

4: sodium methylate / chloroform; methanol / 4 h / 20 °C

With palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; sodium methylate; potassium carbonate; In 1,4-dioxane; methanol; ethanol; chloroform; water;

DOI:10.1055/a-1531-2385

upstream raw materials:

luteolin 4'-O-β-D-glucopyranoside 7-O-β-D-glucopyranoside

luteolin-7-O-(6′′-O-malonyl)-β-D-glucopyranoside

luteolin 7-O-β-glucuronopyranosyl-(1->6)-O-β-glucopyranoside

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Downstream raw materials:

D-glucose

luteolin tetraacetate

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

β-D-glucose

Refernces

• 1、 Teslov. "". . . Retrieved 1977.
• 2、 Hayasaka, Natsumi,Shimizu, Naoki,Komoda, Toshikazu,Mohri, Satoshi,Tsushida, Tojiro,Eitsuka, Takahiro,Miyazawa, Teruo,Nakagawa, Kiyotaka. "Absorption and Metabolism of Luteolin in Rats and Humans in Relation to in Vitro Anti-inflammatory Effects". . p. 11320 - 11329. Retrieved 2018/11/20.
• 3、 Schwinn,Markham,Given. "Floral flavonoids and the potential for pelargonidin biosynthesis in commercial chrysanthemum cultivars". . p. 145 - 150. Retrieved 2007/10/02.