3-Hydroxypropionic acid

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[1]
Names
Preferred IUPAC name
3-Hydroxypropanoic acid
Other names
3-Hydroxypropionic acid
Hydracrylic acid
Ethylene lactic acid
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 773806
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.007.250
EC Number
  • 207-974-8
KEGG
PubChem CID
UNII
InChI
  • InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) Y
    Key: ALRHLSYJTWAHJZ-UHFFFAOYSA-N Y
  • InChI=1/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
    Key: ALRHLSYJTWAHJZ-UHFFFAOYAU
SMILES
  • O=C(O)CCO
Properties
Chemical formula
 C3H6O3
Molar mass 90.08 g/mol
Melting point <25 °C
143 °C (sodium salt)
Boiling point Decomposes
Solubility in water
 Very soluble
Acidity (pKa) 4.87[2]
Related compounds
Related carboxylic acids
 acetic acid
glycolic acid
propionic acid
lactic acid
malonic acid
butyric acid
hydroxybutyric acid
Related compounds
 1-propanol
2-propanol
propionaldehyde
acrolein
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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..[3]

Potential applications

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

References
  1. 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.
  • Chisholm, Hugh, ed. (1911). "Hydracrylic Acid" . Encyclopædia Britannica. Vol. 14 (11th ed.). Cambridge University Press. p. 34.
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