Industrial Consultancy & Sponsored Research (IC&SR) , IIT Madras

Synthesis of Amorfrutin and Cajaninstilbense and their Analogues from a common Building Block

Technology Category/Market

Category – Chemistry & Chemical Analysis; Drugs & Pharmaceutical Engineering

Applications – Pharmaceuticals, Chemicals, Food processing, Antimicrobials

Industry –Healthcare, Chemical

Market -Global demand for Stilbene Market is expected to reach a market valuation of US$ 0.5 billion by the end of the year 2023, accelerating at CAGR of 5.5% over the forecast period (2023 to 2033)

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Problem Statement

  • Stilbenoids are biological molecules that are widely  found in plants and other natural sources that are  reported to have exhibited wide range of properties such as antioxidant, antibacterial/antifungalactivity, anticancer, anti-inflammatory and anti-diabetic activity, antiplatelet aggregation , coronovasodilator activity etc.
  • Conventionally existing technologies are unable to cater the  increasing need of stilbenoids viz. Amorfrutin and Cajaninstilbene acid for use of various biological activities

Technology

The present invention discloses process for synthesis of amorfrutin and cajaninistilbenes and their analogues from a common building block that can be adapted for synthesizing the chemical compounds such as amorfrutin (prenylated bibenzyl) and cajaninistilbenes acid (prenylated stilbenoid)

The said process comprising:

  • Alkylating a common building block with various substituted benzyl bromides, (prenylatedbibenzyl), desulfonylation& hydrolysis process for synthesizing the chemical compounds amorfrutin (prenylatedbibenzyl)
  • Substituting aromatic aldehydes in the common building block using Juliaolefination and hydrolysis process for synthesizing chemical compounds, of cajaninistilbenes acid (prenylatedstilbenoids)
  • The process of synthesizing amorfrutin is adapted for synthesizing a series of bi-benzyl derivatives and process of synthesizing cajaninistilbenes acid is adapted for synthesizing a series of stilbene derivatives.

Key Features/Value Proposition

Technical perspective

  • The novel common building block structure is adapted to effectively synthesize multiclass compounds of prenylated bibenzyls and prenylated stilbenoids and analogues of the said compounds 
  • Provides an improved building block molecule structure containing bibenzyl moiety & optimized process for synthesizing both prenylated bibenzyl and stilbenoids

User perspective

  • Provides easily  adaptable process  for medicine/ biotechnology and pharmaceutical applications for producing molecules containing bibenzyl moiety with extensive biological activities
Questions about this Technology?

Contact for Licensing

Research Lab

Prof. Indrapal Singh Aidhen

Department of Chemistry

Intellectual Property

  • IITM IDF Ref. 1132
  • IN328436-Granted

Technology Readiness Level

TRL-3

Experimental proof of concept

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