Arginine

Base Information

• Chemical Name: Arginine
• CAS No.: 74-79-3
• Deprecated CAS: 142-49-4,7004-12-8,667422-95-9,1332377-47-5,154605-63-7,154605-67-1,1332377-47-5,154605-63-7,154605-67-1,667422-95-9,7004-12-8
• Molecular Formula: C6H14N4O2
• Molecular Weight: 174.203
• Hs Code.: 29252000
• European Community (EC) Number: 200-811-1
• UNII: 94ZLA3W45F
• DSSTox Substance ID: DTXSID6041056
• Nikkaji Number: J9.182K
• Wikipedia: Arginine
• Wikidata: Q173670
• NCI Thesaurus Code: C62008
• RXCUI: 1091
• Pharos Ligand ID: Q4C8CG2XA8B3
• Metabolomics Workbench ID: 37289
• ChEMBL ID: CHEMBL1485
• Mol file: 74-79-3.mol

Synonyms:Arginine;Arginine Hydrochloride;Arginine, L Isomer;Arginine, L-Isomer;DL Arginine Acetate, Monohydrate;DL-Arginine Acetate, Monohydrate;Hydrochloride, Arginine;L Arginine;L-Arginine;L-Isomer Arginine;Monohydrate DL-Arginine Acetate

Chemical Property of Arginine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.7E-08mmHg at 25°C
• Melting Point: 222 °C (dec.)(lit.)
• Refractive Index: 27 ° (C=8, 6mol/L HCl)
• Boiling Point: 409.14 °C at 760 mmHg
• PKA: 1.82, 8.99, 12.5(at 25℃)
• Flash Point: 201.241 °C
• PSA: 125.22000
• Density: 1.467 g/cm³
• LogP: 0.55280
• Storage Temp.: Store at 0-5
• Sensitive.: Air Sensitive
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: 148.7 g/L (20 ºC)
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.11167570
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

99.0-101.0% ^*data from raw suppliers

L-Arginine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 36-36/37/38-20/21/22-61
• Safety Statements: 24/25-36-26-45-53-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CC(C(=O)O)N)CN=C(N)N
• Isomeric SMILES: C(C[C@@H](C(=O)O)N)CN=C(N)N
• Recent ClinicalTrials: An Exploratory Study of Arginine Supplementation and the Postoperative Immune REsponse
• Recent EU Clinical Trials: A multicenter, open-label post authorization safety study to evaluate the effect of LysaKare? infusion on serum potassium levels in GEP-NET patients eligible for Lutathera? treatment
• Recent NIPH Clinical Trials: HMB study
• Biological Functions: Arginine is an amino acid involved in various biological functions, including cell proliferation, cell signaling, muscle contraction, immunity, neurotransmission, vasodilation, synthesis of growth factors, and other amino acids.
• Sources of Arginine: Three major sources of arginine include dietary intake (found in foods such as chicken, pork loin, pumpkin seeds, peanuts, soybeans, etc.), endogenous synthesis from citrulline, and protein catabolism.
• Metabolism: Arginine serves as a direct resource for nitric oxide (NO), ornithine, and agmatine through enzyme reactions involving nitric oxide synthase (NOS), arginase, and arginine decarboxylase (ADC).
• Role as a Nutraceutical: L-arginine, the L-isomer of arginine, functions as a nutraceutical and is involved in various metabolic processes in mammals, including humans.
• Synthesis of Nitric Oxide (NO): Arginine is an essential substrate for the synthesis of nitric oxide (NO), a major vasodilator that increases blood flow to tissues, regulates nutrient metabolism, and exhibits antimicrobial properties.
• Physiological Roles: Arginine activates cellular signaling pathways, including mechanistic target of rapamycin (MTOR) and focal adhesion kinase, stimulating protein synthesis, inhibiting autophagy and proteolysis, enhancing wound healing, promoting spermatogenesis and fertility, and augmenting milk protein production.
• Health Benefits: Oral supplementation of arginine within the physiological range can confer various health benefits, including enhanced immunity, anti-infectious, and anti-oxidative responses, improved fertility, wound healing, ammonia detoxification, nutrient digestion and absorption, lean tissue mass, and brown adipose tissue development.
• Medical Uses: Arginine supplementation has been used to treat conditions such as erectile dysfunction, sickle cell disease, muscular dystrophy, and pre-eclampsia. It also shows potential in ameliorating metabolic syndromes such as dyslipidemia, obesity, diabetes, and hypertension.

Technology Process of Arginine

There total 212 articles about Arginine 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:

H-Arg-pNA (6154-84-3) → L-arginine (74-79-3,25212-18-4) + 4-nitro-aniline (100-01-6,104810-17-5)

Guidance literature:

With Tris-HCl buffer; an aminopeptidase from the seeds of Cannabis sativa; water; at 37 ℃; pH=7.5; Enzyme kinetics; Enzymatic reaction;

DOI:10.1271/bbb.64.1055

Reference yield:

L-Arg-D-Asp (275354-61-5) → (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-arginine (74-79-3,25212-18-4)

Guidance literature:

With recombinant Streptomyces coelicolor Sco₃₀₅₈ dipeptidase; water; at 30 ℃; pH=8; Concentration; Kinetics; aq. buffer; Enzymatic reaction;

DOI:10.1021/bi901935y

Reference yield:

2-Benzyloxycarbonylamino-5-guanidino-pentanoic acid (1234-35-1,5619-02-3,6382-93-0) → L-arginine (74-79-3,157-06-2,7004-12-8,7200-25-1,25212-18-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With N^α-benzyloxycarbonyl amino acid urethane hydrolase II; cobalt(II); at 33 ℃; for 0.5h; Rate constant; pH=6.5;

upstream raw materials:

D-ornithine

CYANAMID

Arg

Citrulline

Downstream raw materials:

L-arginine methyl ester

Nα-acetylarginine

N^α-(N-benzyloxycarbonyl-glycyl)-L-arginine

D-ornithine

Refernces

• 1、 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.
• 2、 Bayer, Peter,Hof, Fraser,Isaacs, Lyle,Kamba, Bianca E.,Le, My-Hue,Schrader, Thomas,Warmerdam, Zoey. "Binding Methylarginines and Methyllysines as Free Amino Acids: A Comparative Study of Multiple Host Classes**". . . Retrieved 2021/11/30.