3-Hydroxypropionic acid

Base Information

• Chemical Name: 3-Hydroxypropionic acid
• CAS No.: 503-66-2
• Molecular Formula: C3H6O3
• Molecular Weight: 90.0788
• Hs Code.: 29181990
• European Community (EC) Number: 207-974-8
• UNII: C4ZF6XLD2X
• DSSTox Substance ID: DTXSID50198305
• Nikkaji Number: J6.213H
• Wikipedia: 3-Hydroxypropionic_acid
• Wikidata: Q2823220
• Metabolomics Workbench ID: 37373
• ChEMBL ID: CHEMBL1205969
• Mol file: 503-66-2.mol

Synonyms:3-hydroxypropanoic acid;3-hydroxypropionate;3-hydroxypropionic acid;beta-lactic acid;hydracrylic acid

Chemical Property of 3-Hydroxypropionic acid

Chemical Property:

• Vapor Pressure: 0.000476mmHg at 25°C
• Melting Point: 16.8°C (estimate)
• Refractive Index: 1.455
• Boiling Point: 279.7 °C at 760 mmHg
• PKA: 4.51(at 25℃)
• Flash Point: 137.2 °C
• PSA: 57.53000
• Density: 1.283 g/cm³
• LogP: -0.54660
• Storage Temp.: 2-8°C
• Solubility.: Ethanol, Methanol, Water
• Water Solubility.: 270.1g/L(25 oC)
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 90.031694049
• Heavy Atom Count: 6
• Complexity: 50

Purity/Quality:

99% ^*data from raw suppliers

3-HydroxypropionicAcid,Approx30%inWater(withvaryingamountsof3,3''-OxydipropanoicAcid) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CO)C(=O)O
• 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.
• Uses: 3-Hydroxypropionic Acid induces gene expressions and also functions as a reagent for industrial application. A three carbon non-chiral compound, 3-Hydroxypropionic acid can be used as a building block for industrial chemicals.

Technology Process of 3-Hydroxypropionic acid

There total 88 articles about 3-Hydroxypropionic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3-(hydroperoxy)propanoic acid → 3-hydroxypropionic acid (503-66-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 0.666667h; under 2888.19 Torr;

DOI:10.1002/cssc.201500025

Reference yield: 100.0%

2-acetoxypropionic acid (535-17-1) + 3-acetoxypropionic acid (4272-12-2) → LACTIC ACID (849585-22-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + 3-hydroxypropionic acid (503-66-2)

Guidance literature:

With water; Amberlite IR 120; at 80 ℃; for 16h; Product distribution / selectivity;

Reference yield: 99.0%

3-iodopropanoic acid (141-76-4) → 3-hydroxypropionic acid (503-66-2)

Guidance literature:

With sodium hydroxide; In water; hexan-1-ol; at 80 ℃; for 2h; Solvent; Temperature; Reagent/catalyst;

upstream raw materials:

oxirane

hydrogen cyanide

3-Bromopropionic acid

propan-1-ol

Downstream raw materials:

3-(4-Methylphenyl)propanoic acid

6,6-dimethyltetrahydro-2H-pyran-2-one

acrylic acid methyl ester

formaldehyd

Refernces

• 1、 Yu, Shanshan,Yao, Peiyuan,Li, Jianjiong,Ren, Jie,Yuan, Jing,Feng, Jinhui,Wang, Min,Wu, Qiaqing,Zhu, Dunming. "Enzymatic synthesis of 3-hydroxypropionic acid at high productivity by using free or immobilized cells of recombinant Escherichia coli". . p. 37 - 42. Retrieved 2016.
• 2、 Reiff, Emily A.,Nair, Sajiv K.,Narayan Reddy,Inagaki, Jun,Henri, John T.,Greiner, Jack F.,Georg, Gunda I.. "Practical syntheses of the C12-C21 epothilone subunit via catalytic asymmetric reductions: Itsuno-Corey oxazaborolidine reduction and asymmetric Noyori hydrogenation". . p. 5845 - 5847. Retrieved 2004.
• 3、 Liang, Bo,Sun, Guannan,Wang, Zhaobao,Xiao, Jian,Yang, Jianming. "Production of 3-hydroxypropionate using a novel malonyl-CoA-mediated biosynthetic pathway in genetically engineered: E. coli strain". . p. 6103 - 6115. Retrieved 2019.
• 4、 Rayavarapu, Pratima,Shah, Shikha,Sunder, Avinash Vellore,Wangikar, Pramod P.. "Expanding the repertoire of nitrilases with broad substrate specificity and high substrate tolerance for biocatalytic applications". . p. 289 - 296. Retrieved 2020/05/18.
• 5、 -. "Environment-friendly and efficient synthesis method of 3-hydracrylic acid". Paragraph 0030-0060. . Retrieved 2020/07/27.