3-Hydroxypropionic acid

3-Hydroxypropionic acid^[1]

Names
IUPAC name 3-Hydroxypropanoic acid
Other names 3-hydroxypropionic acid hydracrylic acid ethylene lactic acid
Identifiers
CAS Number	503-66-2 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:33404 Y
ChemSpider	61460 Y
DrugBank	DB03688 Y
ECHA InfoCard	100.007.250
KEGG	C01013 Y
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 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 miscible with diethyl ether. Upon distillation, it dehydrates to form acrylic acid.

3-Hydroxypropionic acid is used in the industrial production of various chemicals such as acrylates. It can be produced by engineered microbes.^[3]

Applications in producing a biodegradable polymer

A method has been developed by the University of Minnesota to produce a biodegradable polymer polyester known as poly(3-hydroxypropionic acid).^[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. 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.

See also

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

References

External links

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