Threonine

Base Information

• Chemical Name: Threonine
• CAS No.: 80-68-2
• Deprecated CAS: 13095-55-1,36676-50-3,25275-17-6,1043597-96-1,1370710-06-7,154605-64-8,154605-68-2,1644578-86-8,31138-27-9,5090-44-8,1187422-62-3,1043597-96-1,1370710-06-7,154605-64-8,154605-68-2,1644578-86-8,25275-17-6,7004-04-8
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• Hs Code.: 29225000
• European Community (EC) Number: 200-774-1
• NSC Number: 760118
• UNII: TFM6DU5S6A,2ZD004190S
• DSSTox Substance ID: DTXSID2046412,DTXSID70893087
• Nikkaji Number: J21.883I
• Wikipedia: Threonine
• Wikidata: Q186521
• NCI Thesaurus Code: C29602
• RXCUI: 10524
• Metabolomics Workbench ID: 37113
• ChEMBL ID: CHEMBL291747
• Mol file: 80-68-2.mol

Synonyms:L Threonine;L-Threonine;Threonine

Chemical Property of Threonine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Melting Point: 244 °C
• Refractive Index: 1.507
• Boiling Point: 345.8 °C at 760 mmHg
• PKA: 2.09(at 25℃)
• Flash Point: 162.9 °C
• PSA: 83.55000
• Density: 1.307 g/cm³
• LogP: -0.52060
• Storage Temp.: Store at RT.
• Water Solubility.: 200 g/L (25 ºC)
• XLogP3: -2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 119.058243149
• Heavy Atom Count: 8
• Complexity: 93.3

Purity/Quality:

99% up ^*data from raw suppliers

DL-Threonine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: CC(C(C(=O)O)N)O
• Isomeric SMILES: C[C@H]([C@@H](C(=O)O)N)O
• Uses: DL-Threonine is as an additive to animal feed. They are also used to chelate metal cations in order to improve the absorption of minerals from supplements, which may be required to improve the health or production of animals. This chelating ability is also used in fertilizers for agriculture.DL-Threonine is an essential, non-protein amino acid naturally occurring in the human body and it is involved in many biological processes. DL-threonine takes part in the conversion of glycogen into the glucose pathway, supports muscle tissue maintenance and growth, and plays a key role in regulating levels of other amino acids.L-threonine? is essential amino acids with the physiological effect of DL-threonine being half of that of the L-threonine. Upon its lack, people is easily susceptible to loss of appetite and fatty liver embolism. Threonine can not be de novo synthesized inside the higher animals body and must be supplied externally. The cereal protein, in addition to should being provided of L-lysine, should also be supplied with L-threonine. This is due to that although there is a high content of L-threonine, but the combination of threonine and peptide in the protein is difficult to be hydrolyzed and is not easily digested and absorbed. As a nutritional supplement, in order to play the best use of fruit, it can be co-used with glycine in the rice, co-used with glycine and valine in wheat flour, and co-used with glycine and methionine in the barley, oats as well as co-used with glycine and tryptophan in corn. Co-heating with hot grapes can easily produce empyreumatique and chocolate flavor with aromatherapy role. It can also be used for separation to obtain L-threonine and further for the preparation of amino acid infusion and integrated amino acid preparations. DL-Threonine is used as a polar essential amino acid. It serves as a precursor of glycine as well as used in the biosynthesis of proteins. Further, it is used for biochemical research. In addition to this, it is used as a nutrition enhancer.
• Description: Threonine (abbreviated as Thr or T) is an α-amino acid with the chemical formula HO2CCH(NH2)CH(OH)CH3. Its codons are ACU, ACA, ACC, and ACG. This essential amino acid is classified as polar. Together with serine, threonine is one of two proteinogenic amino acids bearing an alcohol group (tyrosine is not an alcohol but a phenol, since its hydroxyl group is bonded directly to an aromatic ring, giving it different acid/base and oxidative properties). It is also one of two common amino acids that bear a chiral side chain, along with isoleucine.The threonine residue is susceptible to numerous posttr anslational modifications. The hydroxy side-chain can undergo Olinked glycosylation. In addition, threonine residues undergo phospho rylation through the action of a threonine kinase. In its phosphorylated form, it can be referred to as phospho threonine.

Technology Process of Threonine

There total 103 articles about Threonine 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: 92.0%

2-amino-3-hydroxybutyronitrile (344328-90-1) → DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; ammonium hydroxide; In water; at 150 ℃; for 5h; under 22502.3 Torr; Autoclave; Inert atmosphere;

Reference yield: 89.4%

DL-5-(2-hydroxyethyl)hydantoin (64420-00-4) → DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6)

Guidance literature:

DL-5-(2-hydroxyethyl)hydantoin; With calcium hydroxide; ammonia; In water; butan-1-ol; at 160 - 170 ℃; for 4h; under 11251.1 - 15001.5 Torr;

With carbon dioxide; In water; butan-1-ol; at 20 ℃; pH=8;

Reference yield: 87.0%

→ DL-threonine (72-19-5,80-68-2,144-98-9,632-20-2,2676-21-3,7004-04-8,24830-94-2,28954-12-3,36676-50-3,134357-96-3,7013-32-3,82822-12-6) + thr-NCA

Guidance literature:

upstream raw materials:

rac-allo-threonine

N-methyl-threonine

2-Dibenzylamino-3-hydroxy-butyric acid

acetaldehyde

Downstream raw materials:

(+/-) threonine methyl ester hydrochloride

allo-Thr-OMe

H-DL-aThr-OMe*HCl

N-carbamoyl-threonine

Refernces

• 1、 -. "Preparation and purification method of amino acid compound". Paragraph 0066; 0067. . Retrieved 2018/06/21.
• 2、 -. "New polypeptides inducing apoptosis and uses thereof". . . Retrieved 2009/02/10.