3-Hydroxypropionic acid

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3-Hydroxypropionic acid[1]
Skeletal formula
Ball-and-stick model
Preferred IUPAC name
3-Hydroxypropanoic acid
Other names
3-Hydroxypropionic acid
Hydracrylic acid
Ethylene lactic acid
3D model (JSmol)
ECHA InfoCard 100.007.250 Edit this at Wikidata
EC Number
  • 207-974-8
  • InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) checkY
  • InChI=1/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
  • O=C(O)CCO
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Very soluble
Acidity (pKa) 4.87[2]
Related compounds
acetic acid
glycolic acid
propionic acid
lactic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

3-Hydroxypropionic acid is a carboxylic acid, specifically a beta hydroxy acid. It is an acidic viscous liquid with a pKa of 4.5.[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


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..[3]

Potential applications[edit]

The polyester poly(3-hydroxypropionic acid) is a biodegradable polymer.[4] 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.

Genetically encoded 3-hydroxypropionic acid inducible system[edit]

3-Hydroxypropionic acid can be produced by engineered microbes.[5]

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.[6]

See also[edit]

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


  1. ^ a b Merck Index, 11th Edition, 4681.
  2. ^ Handbook of Chemistry and Physics, CRC press, 58th edition page D150-151 (1977)
  3. ^ Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507.
  4. ^ "3-HP". Retrieved 27 May 2011.
  5. ^ "Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide". 27 March 2013.
  6. ^ 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): 1724. Bibcode:2017NatSR...7.1724H. doi:10.1038/s41598-017-01850-w. PMC 5431877. PMID 28496205.

External links[edit]