(2S)-2-azaniumyl-3-methylbutanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-methylbutanoate
• CAS No.: 72-18-4
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29224995
• Mol file: 72-18-4.mol

Synonyms:(2S)-2-azaniumyl-3-methylbutanoate;L-Val;L-valine zwitterion;L-(+)-valine;(S)-(+)-valine;CHEBI:57762;L-2-Amino-3-methylbutyric acid;(2S)-2-ammonio-3-methylbutanoate;(2S)-2-azaniumyl-3-methyl-butanoate;H-Val-OH;A837443

Chemical Property of (2S)-2-azaniumyl-3-methylbutanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 295-300 °C (subl.)(lit.)
• Refractive Index: 28 ° (C=8, HCl)
• Boiling Point: 213.642 °C at 760 mmHg
• PKA: 2.37±0.10(Predicted)
• Flash Point: 83.008 °C
• PSA: 63.32000
• Density: 1.064 g/cm³
• LogP: 0.75460
• Water Solubility.: 85 g/L (20℃)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 84.9

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC(C)[C@@H](C(=O)[O-])[NH3+]
• Industrial Applications: Description: Valine (L-valine) is one of the three branched-chain amino acids (BCAAs) widely applied in various industrial fields such as pharmaceuticals, cosmetics, food, and feed.; Importance in Animal Feed: Valine is among the four most limiting amino acids in low-crude protein diets for piglets and broiler chicks, and its deficiency negatively impacts animal growth performance.; Increasing Demand: There has been a significant increase in demand for Valine in animal feed additives, driving interest in more efficient and economical production methods.
• Biological Importance: Role in Muscle Tissue Recovery and Repair: Valine aids in muscle tissue recovery and repair, as well as increasing energy and endurance.; Medicinal Qualities: Valine possesses medicinal qualities for lowering elevated blood sugar levels and enhancing growth hormone production.; Chemical Structure: Valine contains an amino group, a carboxyl group, and a sidechain isopropyl group.
• Medical and Nutritional Uses: Inhibition of Tissue Protein Degradation: Valine can inhibit the degradation of tissue proteins, improving the carcass quality of livestock and poultry.; Effects on Immune Function: Valine affects immune function by influencing the development of immune organs and the synthesis of immunoglobulins.; Market Demand: The increasing demand for L-valine in the market highlights the need for cost-effective production methods.
• Production Methods: Microbial Fermentation: Currently, microbial fermentation is the primary method for producing L-valine, with mutagenesis and metabolic engineering strategies employed to enhance production.; Challenges: Despite progress in modification strategies, challenges remain in constructing more efficient industrial strains for L-valine production.; Metabolic Strategies: Various metabolic strategies have been used to increase L-valine titers, including mutagenesis, pathway modification, and enhancing extracellular transport.

Technology Process of (2S)-2-azaniumyl-3-methylbutanoate

There total 390 articles about (2S)-2-azaniumyl-3-methylbutanoate 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%

2C16H16O4*C5H11NO2 → L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (178306-52-0,178306-49-5)

Guidance literature:

In ethyl acetate; at 80 ℃; for 3h; Solvent;

Reference yield: 57.4%

L-Glycin (56-40-6,18875-39-3,25718-94-9) + L-Valin-N-carbonsaeureanhydrid (1676-85-3,2816-12-8,24601-74-9,43089-05-0) → L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + valylglycine (686-43-1,6491-60-7) + Val-Val (3918-94-3) + N-carbamoylglycine (462-60-2)

Guidance literature:

With water; potassium hydroxide; potassium borate buffer; at 3 ℃; Product distribution; effect of use of various amino acid and NCA with various concentrations; effect of use various temp.; extent of hydrolysis;

Reference yield:

C28H41N5O10 → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With hydrogenchloride; water; at 120 ℃; for 14h;

DOI:10.1021/np2008279

upstream raw materials:

trichoderin A₁

trichoderin B

aspereline A

aspereline B

Downstream raw materials:

L-valine methylester hydrochloride

N-phthaloyl L-valine

N-(1-deoxy-D-fructos-1-yl)-L-valine

N-trifluoroacetyl-L-valine

Refernces

• 1、 Sung, Yu-Sheng,Putman, Joshua,Du, Siqi,Armstrong, Daniel W.. "Enhanced carboxypeptidase efficacies and differentiation of peptide epimers". . . Retrieved 2022/01/29.
• 2、 Iwasaki, Arihiro,Ohtomo, Keisuke,Kurisawa, Naoaki,Shiota, Ikuma,Rahmawati, Yulia,Jeelani, Ghulam,Nozaki, Tomoyoshi,Suenaga, Kiyotake. "Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium Caldora penicillata". . p. 126 - 135. Retrieved 2021/01/13.