3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.5. 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
ethylene lactic acid
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||90.08 g/mol|
|Melting point||<25 °C|
143 °C (sodium salt)
Related carboxylic acids
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Applications in producing a biodegradable polymerEdit
A method has been developed by the University of Minnesota to produce a biodegradable polymer polyester known as poly(3-hydroxypropionic acid). 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-HP can be derived from biological sources, the resulting material, poly(3-hydroxypropionic acid) or P(3-HP), is biorenewable. The new method allows direct synthesis of the bio-based polymer P(3-HP) from 3-HP, a commercial monomer that is derived from corn. The method uses a single vessel reactor for simple synthesis and rapid scale up. The method results in a higher molecular weight which makes the polymer more structurally sound using a process with lower toxicity than competing technologies.
The market for a bio-based and biodegradable replacement for polyester is expected to grow rapidly during the next five years. The bio-based polyester, P(3-HP), has attractive mechanical properties, such as rigidity, ductility, and exceptional tensile strength in drawn films and can be created using the new lower toxicity method. On account of these properties, P(3-HP) has applications in packaging or biodegradable plastics.
Genetically encoded 3-hydroxypropionic acid inducible systemEdit
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.
- Lactic acid (2-hydroxypropanoic acid)
- listed as hydracrylic acid in the Merck index, 12th Edition
- Merck Index, 11th Edition, 4681.
- Handbook of Chemistry and Physics, CRC press, 58th edition page D150-151 (1977)
- "3-HP". Retrieved 27 May 2011.
- Hanko, E.K.R.; Minton, N.P.; Malys, N. (2017). "Characterisation of a 3-hydroxypropionic acid-inducible system from Pseudomonas putida for orthogonal gene expression control in Escherichia coli and Cupriavidus necator". Scientific Reports. 7 (1724). doi:10.1038/s41598-017-01850-w. PMC 5431877.
- Chisholm, Hugh, ed. (1911). Encyclopædia Britannica. 14 (11th ed.). Cambridge University Press. p. 34. .