Threonine

Base Information

• Chemical Name: Threonine
• CAS No.: 72-19-5
• 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
• 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: 72-19-5.mol

Synonyms:L Threonine;L-Threonine;Threonine

Chemical Property of Threonine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 256 °C (dec.)(lit.)
• Refractive Index: -28 ° (C=6, H2O)
• Boiling Point: 345.803 °C at 760 mmHg
• Flash Point: 162.936 °C
• PSA: 83.55000
• Density: 1.307 g/cm³
• LogP: -0.52060
• Water Solubility.: 90 g/L (20℃)
• 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:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

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
• Origin and importance: Threonine (Thr) is an indispensable amino acid for animals and must be obtained from the diet.; Identified as the second limiting amino acid for finishing pigs and the third limiting amino acid for broilers in certain diets.; Plays a crucial role in protein synthesis, energy metabolism, and nutrient absorption.
• Physiological Functions and Metabolism: Adequate dietary levels of Thr promote animal growth, enhance immune function, and maintain intestinal health.; Essential for hepatic lipid metabolism, with Thr deficiency potentially leading to hepatic triglyceride accumulation.; Exerts protective effects on lipid metabolic disorders by regulating lipogenesis signaling pathways and thermogenic gene expression.; Essential for physiological regulation beyond nutrition, including cell growth and proliferation, particularly in embryonic stem cells (ESCs).
• Role in Intestinal Health and Function: About 40鈥?60% of dietary Thr is extracted by the gut during the first pass of metabolism, mostly used for mucosal protein synthesis. Maintains intestinal homeostasis by affecting intestinal morphology, microorganisms, barrier, and immune function.; Regulates immune cell differentiation, cytokine expression, and immune-related signaling cascades to maintain intestinal health, especially during inflammatory states.
• Metabolic Pathways: Serves as a substrate for protein synthesis, particularly mucin, a key component of mucus. Can be catabolized through glycine-independent or glycine-dependent pathways, producing important metabolites like glycine, acetyl CoA, and pyruvate.; Threonine dehydrogenase (TDH) and threonine aldolase are key enzymes in Thr metabolism, with TDH converting Thr to intermediates degraded to produce energy.
• Physiological Variations: Thr metabolism pathways may vary depending on the physiological state, with infants exclusively degrading Thr through the glycine-independent pathway compared to adults. Physiological differences dictate varying proportions of Thr metabolism through different pathways.

Technology Process of Threonine

There total 278 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: 75.0%

(2S,3R)-3-Hydroxy-2-[2-(4-methoxy-phenyl)-2-oxo-ethoxycarbonylamino]-butyric acid (125219-09-2) → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + 1-(4-methoxyphenyl)ethanone (100-06-1)

Guidance literature:

In ethanol; at 0 ℃; for 14h; Irradiation;

DOI:10.1016/S0040-4039(00)99608-4

Reference yield: 5.0%

L-threonine methyl ester hydrochloride (39994-75-7) → L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (2S,3R)-2-amino-3-hydroxybutanamide (49705-99-9)

Guidance literature:

With ammonium hydroxide;

DOI:10.1021/jo00340a048

Reference yield:

pholipeptin → D-Serine (312-84-5,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 20h; Product distribution;

DOI:10.1021/jo9603993

upstream raw materials:

rac-allo-threonine

N-methyl-threonine

2-Dibenzylamino-3-hydroxy-butyric acid

acetaldehyde

Downstream raw materials:

(2S,3R)-threonine ethyl ester

N-(3-amino-2-methoxy-benzoyl)-L_s-threonine

2-Oxobutyric acid

L-2-aminobutyric acid

Refernces

• 1、 Chen, Baosong,Dai, Huanqin,Han, Junjie,Li, Erwei,Liu, Hongwei,Lyu, Zhitang,Song, Fuhang,Sun, Jingzu,Wang, Hanying,Wang, Tao,Wang, Wenzhao,Zhang, Rui. "Cyclic Tetrapeptides with Synergistic Antifungal Activity from the Fungus Aspergillus westerdijkiae Using LC-MS/MS-Based Molecular Networking". . . Retrieved 2022/02/17.
• 2、 De Cesare, Silvia,McKenna, Catherine A.,Mulholland, Nicholas,Murray, Lorna,Bella, Juraj,Campopiano, Dominic J.. "Direct monitoring of biocatalytic deacetylation of amino acid substrates by1H NMR reveals fine details of substrate specificity". supporting information. p. 4904 - 4909. Retrieved 2021/06/16.