3-Hydroxypropionic acid

Source: Wikipedia, the free encyclopedia.
3-Hydroxypropionic acid[1]
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
3-Hydroxypropanoic acid
Other names
3-Hydroxypropionic acid
Hydracrylic acid
Ethylene lactic acid
Identifiers
3D model (
JSmol
)
3DMet
773806
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.007.250 Edit this at Wikidata
EC Number
  • 207-974-8
KEGG
UNII
  • InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) checkY
    Key: ALRHLSYJTWAHJZ-UHFFFAOYSA-N checkY
  • InChI=1/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6)
    Key: ALRHLSYJTWAHJZ-UHFFFAOYAU
  • O=C(O)CCO
Properties
C3H6O3
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
2-propanol
propionaldehyde
acrolein
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

pKa of 4.9.[2] 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.[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. ^ a b Handbook of Chemistry and Physics, CRC press, 58th edition page D150-151 (1977)
  3. ISBN 978-3527306732
    .
  4. ^ "3-HP". Retrieved 27 May 2011.
  5. ^ "Scientists Engineer Extreme Microorganisms to Make Fuel from Atmospheric Carbon Dioxide". 27 March 2013.
  6. PMID 28496205
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=3-Hydroxypropionic_acid&oldid=1210160609"