Английская Википедия:3-Hydroxypropionic acid

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3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.9.[1] It is very soluble in water, soluble in ethanol and diethyl ether. Upon distillation, it dehydrates to form acrylic acid, and is occasionally called hydracrylic acid

3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates.

Synthesis

3-Hydroxypropionic acid can be obtained by base-induced hydration of acrylic acid followed by reacidification. Another synthesis involves cyanation of ethylene chlorohydrin followed by hydrolysis of the resulting nitrile. Hydrolysis of propiolactone is yet another route.[2]

Potential applications

The polyester poly(3-hydroxypropionic acid) is a biodegradable polymer.[3] The method combines the high-molecular weight and control aspects of ring-opening polymerization with the commercial availability of the beta hydroxy acid, 3-hydroxypropionic acid which is abbreviated as 3-HP. Since 3-HPA can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HPA), is biorenewable.

Genetically encoded 3-hydroxypropionic acid inducible system

3-Hydroxypropionic acid can be produced by engineered microbes.[4]

A genetically encoded 3-hydroxypropionic acid inducible system has been characterized in bacteria demonstrating that such system in combination with fluorescent reporter protein can be utilized as a biosensor to measure intracellular and extracellular 3-HP concentrations by fluorescence output.[5]

See also

  • Lactic acid (2-hydroxypropanoic acid)
  • listed as hydracrylic acid in the Merck index, 12th Edition

References

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External links

  1. Ошибка цитирования Неверный тег <ref>; для сносок CRC не указан текст
  2. Шаблон:Ullmann
  3. Шаблон:Cite web
  4. Шаблон:Cite web
  5. Шаблон:Cite journal