6468-55-9

Basic information

• Product Name: demethylwedelolactone
• Synonyms: demethylwedelolactone;1,3,8,9-TetrahydroxycouMestan;DesMethylwedelolactone;Norwedelolactone;IsodeMethyl-wedelolactone;1,3,8,9-Tetrahydroxy-6H-benzofuro-[3,2-c]chromen-6-one;Demethylwedelolactone, 98%, from Eclipta prostrata (L. ) L.
• CAS NO: 6468-55-9
• Molecular Formula: C₁₅H₈O₇
• Molecular Weight: 300.221
• Mol File: 6468-55-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: >360 °C
• Boiling Point: 531.4 °C at 760 mmHg
• Flash Point: 275.2 °C
• Appearance: /
• Density: 1.827 g/cm³
• Vapor Pressure: 6.6E-12mmHg at 25°C
• Refractive Index: 1.847
• Storage Temp.: 2-8°C
• PKA: 7.07±0.20(Predicted)
• CAS DataBase Reference: demethylwedelolactone(CAS DataBase Reference)
• NIST Chemistry Reference: demethylwedelolactone(6468-55-9)
• EPA Substance Registry System: demethylwedelolactone(6468-55-9)

Safety Data

• Hazardous Substances Data: 6468-55-9(Hazardous Substances Data)

Usage

Description

Demethylwedelolactone, also known as 1,3,8,9-tetrahydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, is a natural compound with anti-cancer properties. It is characterized by its unique chemical structure and has the ability to inhibit the anchorage-independent growth and suppress cell motility and cell invasion of MDA-MB-231.

Uses

Used in Anticancer Applications:
Demethylwedelolactone is used as an anti-cancer agent for its ability to inhibit the anchorage-independent growth and suppress cell motility and cell invasion of MDA-MB-231, a type of cancer cell. This makes it a promising candidate for the development of new cancer therapies.
Used in Drug Development:
Demethylwedelolactone can be used as a lead compound in the development of new drugs targeting cancer cells. Its unique chemical structure and anti-cancer properties make it a valuable starting point for further research and development.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, demethylwedelolactone can be used as an active ingredient in the formulation of new cancer treatments. Its ability to inhibit the growth and spread of cancer cells makes it a potentially effective component in anti-cancer drugs.
Used in Research:
Demethylwedelolactone can also be used in research settings to study the mechanisms of cancer growth and invasion. Understanding how this compound interacts with cancer cells can provide valuable insights into the development of new cancer therapies and treatment strategies.

InChI:InChI=1/C15H8O7/c16-5-1-9(19)13-11(2-5)22-15(20)12-6-3-7(17)8(18)4-10(6)21-14(12)13/h1-4,16-19H

Upstream product

• 1023744-96-8 1,3-diacetoxy-8,9-diisopropyloxy-benzo[4,5]furo[3,2-c]chromen-6-one 
• 162888-73-5 4-amino-5,7-dihydroxycoumarin 
• 108-73-6 3,5-dihydroxyphenol 
• 113138-94-6 4,5,7-trihydroxy-3-(2',4',5'-trihydroxyphenyl)coumarin 
• 17575-26-7 4,5,7-trihydroxycoumarin 
• 120-80-9 benzene-1,2-diol 

Downstream Products

• 6468-56-0 1,3,8,9-tetraacetoxycoumestan 

Relevant articles and documents

Total synthesis of demethylwedelolactone and wedelolactone by Cu-mediated/Pd(0)-catalysis and oxidative-cyclization

Hedysarimcoumestan B, which can be isolated from Chinese herbal medicine, is achieved, in which the longest linear sequence is only eight steps, in 50% overall yield from commercially available phloroglucinol. The key transformations in the synthesis are Cu-mediated/Pd(0)-catalysis and I2/pyridine oxidative-cyclization reactions. This synthetic strategy can be applied to give access to the demethylwedelolactone (4) and wedelolactone (5), which were afforded from commercially available phloroglucinol in high 38 and 33% yields, respectively.

Wedelolactone and coumestan derivatives as new antihepatotoxic and antiphlogistic principles

For the study of structure-activity relationships, the antihepatotoxic wedelolactone (7-methoxy-5,11,12-trihydroxy-coumestan) and 6 coumestan derivatives were synthesized by the application of a modified method of Wanzlich. An evaluation of the biological characteristics of the synthetic compounds and acuminatin from Musa acuminata showed that most of the wedelolactone derivatives significantly protected primary cultured liver cells from the toxicity of CCl4, galactosamine (Galc), and phalloidin, and strongly inhibited the activity of 5-lipoxygenase in porcine leukocytes. The hepatocyte protective activity was dependent on the C-7 substitution with pharmacological efficacy decreasing in the following order: EtO > MeO > OH > CH3(CH2)9. In addition, a free OH at C-5 of the wedelolactone molecule was shown to be important in protecting hepatocytes from CCl4 and Galc damage. Similar observation regarding the effect of C-7 substitution in wedelolactone was obtained in the 5-lipoxygenase test. In general, an increase in the lipophilicity in ring A increased the inhibition of 5-lipoxygenase activity. The synthetic wedelolactone was also found to have stimulatory effect on the RNA synthesis in isolated nuclei from hepatocytes.

Electrochemical Synthesis of Heterocyclic Compounds. XII. Anodic Oxidation of Catechol in the Presence of Nucleophiles

The electrochemical synthesis of coumestan derivatives and some related heterocyclic system (2a-11a) by anodic oxidation of catechol (1) in the presence of various nucleophiles 2-11 is described.Products were obtained in good yields and purity.The mechanism of oxidation was deduced from voltammetric data and by coulometry at controlled potential.