3-Hydroxyphthalic anhydride

Description

3-Hydroxyphthalic anhydride: a valuable raw material for chemical industry and pharmaceutical research.
Phthalic anhydride derivatives have been applied as plasticizers and heat-resistant polymers in the chemical industry. One of its derivatives is the 3-hydroxyphthalic anhydride (3-HPA), which exhibits a hydroxyl group substituent in position 3. 3-Hydroxyphthalic anhydride can be used as raw material for heat-resistant resins such as epoxy resins, polyesters, polyimides, etc., or as raw material for physiologically active substances such as medicines and pesticides. It has been shown that 3-HPA can serve as a raw material to obtain drugs with potential applications, such as anticancer, antimicrobial and in treating diabetes, herpes, and HIV[1].

Chemical Properties

Beige powder

Uses

3-Hydroxyphthalic Anhydride is used to synthesize 3-Hydroxyphthalic Anhydride-modified human serum albumin whichhas high potency as a microbicide for prevention of the sexual transmission of HIV. It is also used as a reagent in organicsynthesis of other compounds including that of inhibitors of NF-κB derived from thalidomide.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 5092, 1955 DOI: 10.1021/ja01624a042
Synthesis, p. 788, 1985 DOI: 10.1055/s-1985-31350

Synthesis

In the presence of triethylamine, the 2-oxo-2, 5-dihydrofuran, and pivaloyl chloride reactions generate 2-valeryl oxo furans. The affixture with 2-valeryl oxo furans and maleic anhydride uses vitriolization, which thereby generates the method of 3-hydroxyl phthalic anhydride.

References

[1] M. López-Ortega. “Standard enthalpies of formation of 3-hydroxyphthalic anhydride.” Revista Mexicana De Fisica (2022).