3-Hydroxypropionic acid
- CAS NO.:503-66-2
- Empirical Formula: C3H6O3
- Molecular Weight: 90.08
- MDL number: MFCD00058998
- EINECS: 207-974-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-10-21 14:40:24
What is 3-Hydroxypropionic acid?
Description
3-Hydroxypropionic acid (3-HP) is considered as a potential building block either for organic synthesis or high performance polymers.It is a 3-carbon carboxylic acid, structural isomer of lactic acid, which naturally exists in some thermophilic archaea and bacteria. This organic compound has been pointed out by the US Department of Energy as a promising biomass derivate, which could potentially be used for the production of high added-value chemicals like1,3-propanediol, acrylic acid, acrylamide, and bioplastics.
Being 3-HP a commercially valuable, important platform chemical, researches have been conducted about its production on commercial scale, mainly from renewable sources. The biological production of 3-HP from glycerol and glucose, both based on microbial fermentation, are among the main routes studied. More specifically, research activities have been devoted to goals such as identifying novel biochemical pathways, metabolic engineering of microbial strains for the production of 3-HP, and improvements of cultivation techniques to increase 3-HP production titers.
Despite intense research efforts, there are still important bottlenecks for cost efficient, large scale biological production of 3-Hydroxypropionic Acid.
Description
3-Hydroxypropanoic acid (3-HP) is a β-hydroxy acid that is soluble in water and many oxygenated organic solvents. It can be produced biochemically and used to make a variety of industrial chemicals, especially acrylic acid, its esters, and their polymers.
3-HP can be directly produced from renewable resources or made from another biobased chemical, levulinic acid. When levulinic acid undergoes hydrogen peroxide oxidation in base, 3-HP or, under different conditions, its hydroperoxy cousin is produced. The peroxide can be hydrogenated to 3-HP.
In an unusual example of pH-driven selectivity, if the reaction is run in acid,?the product is succinic acid rather than 3-HP. In both cases, the terminal methyl group of levulinic acid is cleaved.
The Uses of 3-Hydroxypropionic acid
A three carbon non-chiral compound, 3-Hydroxypropionic acid can be used as a building block for industrial chemicals.
The Uses of 3-Hydroxypropionic acid
3-Hydroxypropionic Acid induces gene expressions and also functions as a reagent for industrial application.
What are the applications of Application
3-Hydroxypropionic acid is a three carbon non-chiral compound used as a building block for industrial chemicals
Definition
ChEBI: A 3-hydroxy monocarboxylic acid that is propionic acid in which one of the hydrogens attached to the terminal carbon is replaced by a hydroxy group.
Production Methods
β-Hydroxypropionic acid can be prepared by alkaline hydration of acrylic acid or by treatment of ethylene chlorohydrin with sodium cyanide, followed by hydrolysis of the resulting β-hydroxypropionitrile. It is also readily obtained by hydrolysis of the commercially important and easily accessible compound β-propiolactone.
Properties of 3-Hydroxypropionic acid
Melting point: | 16.8°C (estimate) |
Boiling point: | 212°C (rough estimate) |
Density | 1.066 g/mL at 25 °C |
refractive index | 1.4489 |
storage temp. | 2-8°C |
solubility | Ethanol, Methanol, Water |
form | Colourless Solution |
pka | 4.51(at 25℃) |
color | Colorless to Almost colorless |
Water Solubility | 270.1g/L(25 ºC) |
InChI | InChI=1S/C3H6O3/c4-2-1-3(5)6/h4H,1-2H2,(H,5,6) |
CAS DataBase Reference | 503-66-2(CAS DataBase Reference) |
Safety information for 3-Hydroxypropionic acid
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. |
Computed Descriptors for 3-Hydroxypropionic acid
InChIKey | ALRHLSYJTWAHJZ-UHFFFAOYSA-N |
SMILES | C(O)(=O)CCO |
Related products of tetrahydrofuran
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