L-ornithine

Base Information

• Chemical Name: L-ornithine
• CAS No.: 3184-13-2
• Deprecated CAS: 7006-33-9,410523-46-5,204201-13-8
• Molecular Formula: C5H13ClN2O2
• Molecular Weight: 168.623
• Hs Code.: 29224995
• European Community (EC) Number: 200-731-7
• NSC Number: 758894
• UNII: E524N2IXA3
• DSSTox Substance ID: DTXSID00883219
• Nikkaji Number: J9.177D
• Wikipedia: Ornithine
• Wikidata: Q410198
• NCI Thesaurus Code: C29611
• Pharos Ligand ID: X77237H6KSUJ
• Metabolomics Workbench ID: 37139
• ChEMBL ID: CHEMBL446143
• Mol file: 3184-13-2.mol

Synonyms:2,5 Diaminopentanoic Acid;2,5-Diaminopentanoic Acid;Ornithine;Ornithine Dihydrochloride, (L)-Isomer;Ornithine Hydrochloride, (D)-Isomer;Ornithine Hydrochloride, (DL)-Isomer;Ornithine Hydrochloride, (L)-Isomer;Ornithine Monoacetate, (L)-Isomer;Ornithine Monohydrobromide, (L)-Isomer;Ornithine Monohydrochloride, (D)-Isomer;Ornithine Monohydrochloride, (DL)-Isomer;Ornithine Phosphate (1:1), (L)-Isomer;Ornithine Sulfate (1:1), (L)-Isomer;Ornithine, (D)-Isomer;Ornithine, (DL)-Isomer;Ornithine, (L)-Isomer

Chemical Property of L-ornithine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.00015mmHg at 25°C
• Melting Point: 245 °C
• Refractive Index: 24 ° (C=4, 6mol/L HCl)
• Boiling Point: 308.7oC at 760 mmHg
• Flash Point: 140.5oC
• PSA: 89.34000
• Density: 1.57 g/cm³
• LogP: 1.33980
• Storage Temp.: Store at RT.
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: Soluble in water (543 mg/ml at 20°C), and alcohol.
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 132.089877630
• Heavy Atom Count: 9
• Complexity: 95

Purity/Quality:

99% ^*data from raw suppliers

L-Ornithine Hydrochloride ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CC(C(=O)O)N)CN
• Isomeric SMILES: C(C[C@@H](C(=O)O)N)CN
• Recent NIPH Clinical Trials: Effect of intake of supplements containing ornithine on human health.
• Description: L-Ornithine hydrochloride, formed from L-ornithine and hydrochloric acid, is highly soluble in water and organic solvents like methanol, ethanol, and DMSO. Functioning as a non-protein derived amino acid, it holds significance in the urea cycle, aiding in the elimination of ammonia from the body and regulating excess nitrogen disposal. Moreover, L-ornithine hydrochloride serves as a precursor to methionine and arginine, crucial compounds derived from L-glutamine..
• Used in Pharmaceutical Industries: In the pharmaceutical sector, L-Ornithine hydrochloride serves as a nutritional supplement, supplying the body with ornithine and potentially offering health benefits, especially in sports nutrition and performance products. L-ornithine hydrochloride is employed in medical treatments, aiding in amino acid metabolism regulation and urea cycle management, particularly in liver and kidney disease therapies.^[2]
• Used in Sports Nutrition Industries: Recent research indicates its potential in enhancing human growth hormone secretion post-strength training and improving performance during exhaustive ergometer bicycle exercises, showcasing its versatility in sports nutrition and performance enhancement.
• Used in Cosmetic Industries: L-Ornithine hydrochloride is utilized in cosmetics for its purported moisturizing and antioxidant properties, contributing to skin health and care.
• References: [1] Redetermination, invariom-model and multipole refinement of L-ornithine hydrochloride; DOI 10.1107/S0108768107014838; [2] Kinetics and Mechanism of Oxidation of L-Isoleucine and L-Ornithine Hydrochloride by Sodium N-Bromobenzenesulphonamide in Perchloric Acid Medium; [3] The effect of L-ornithine hydrochloride ingestion on performance during incremental exhaustive ergometer bicycle exercise and ammonia metabolism during and after exercise; DOI 10.1038/ejcn.2010.149

Technology Process of L-ornithine

There total 8 articles about L-ornithine 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: 85.0%

(R)-methyl 2-acetamido-7-chloroheptanoate → (R)-2,5-diaminopentanoic acid dihydrochloride (1069-31-4,3184-13-2,6211-16-1,15160-12-0,16682-12-5,20724-48-5,22834-83-9,26982-21-8,66837-02-3,99815-05-1,36630-89-4)

Guidance literature:

With hydrogenchloride; In water; for 10h; Reflux;

DOI:10.1039/c5ob01111f

Reference yield: 78.0%

2,5-Bis(methoxycarbonylamino)valeriansaeure-methylester (77300-45-9) → Ornithin-dihydrochlorid (1069-31-4,3184-13-2,6211-16-1,15160-12-0,16682-12-5,20724-48-5,22834-83-9,26982-21-8,66837-02-3,99815-05-1,36630-89-4)

Guidance literature:

With hydrogenchloride; formic acid; In water; at 125 ℃; for 24h;

Reference yield:

L-arginine hydrochloride (1119-34-2) → L-ornithine hydrochloride (3184-13-2,36630-89-4) + urea (57-13-6)

Guidance literature:

With dipotassium hydrogenphosphate; phosphoric acid; water; at 25 - 37.1 ℃; Thermodynamic data; ΔH; arginase (EC 3.5.3.1); var. pH and ionic strength;

DOI:10.1006/jcht.1993.1028

upstream raw materials:

L-arginine hydrochloride

L-ornithine tert-butyl ester

1,1-dimethylethyl 4-cyano-(2S)-[(diphenylmethylene)amino]butanoate

tert-butyl 2-amino-4-cyanobutanoate

Downstream raw materials:

N^δ-(tert-butoxycarbonyl)-L-ornithine

N-carboxybenzyl-L-ornithine

NMMA

3-aminopiperidin-2-one

Refernces

• 1、 Ji, Jianjian,Chen, Caiyou,Cai, Jiayu,Wang, Xinrui,Zhang, Kai,Shi, Liyang,Lv, Hui,Zhang, Xumu. "Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation". supporting information. p. 7624 - 7627. Retrieved 2015/07/15.
• 2、 -. "Polyunsaturated fatty acid derivatives, pharmaceutical compositions containing the same, method for the preparation thereof, and their use as medicament". . . Retrieved 2008/06/13.