627-77-0

Basic information

• Product Name: DL-CITRULLINE
• Synonyms: DL-Ornithine, N(5)-(aminocarbonyl)-;Ornithine, N5-carbamoyl-, DL-;LABOTEST-BB LT00244768;DL-CITRULLINE;DL-2-AMINO-5-UREIDOVALERIC ACID;CITRULLINE, DL-;H-DL-Cit-OH;(±)-2-Amino-5-ureidopentanoic acid, DL-2-Amino-5-ureidovaleric acid
• CAS NO: 627-77-0
• Molecular Formula: C₆H₁₃N₃O₃
• Molecular Weight: 175.19
• EINECS: 211-012-2
• Product Categories: Amino Acids;Biochemistry;non-Proteinorganic Amino Acids;Amino Acids;Inhibitors
• Mol File: 627-77-0.mol

Chemical Properties

• Melting Point: 242-244 °C (dec.)
• Boiling Point: 386.7 °C at 760 mmHg
• Flash Point: 187.7 °C
• Appearance: white crystalline powder
• Density: 1.289 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.51±0.24(Predicted)
• CAS DataBase Reference: DL-CITRULLINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-CITRULLINE(627-77-0)
• EPA Substance Registry System: DL-CITRULLINE(627-77-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 627-77-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DL-CITRULLINE is used as a pharmaceutical ingredient for its role in the urea cycle, which helps in the detoxification of ammonia in the body. It is also used for its potential health benefits, such as improving cardiovascular health, supporting immune function, and promoting healthy aging.
Used in Sports Nutrition Industry:
In the sports nutrition industry, DL-CITRULLINE is used as a supplement to enhance athletic performance. It is believed to increase nitric oxide production, which can improve blood flow, reduce muscle fatigue, and support muscle growth.
Used in Cosmetics Industry:
DL-CITRULLINE is used in cosmetics as an ingredient for its potential skin health benefits. It is believed to have antioxidant properties and may help improve skin elasticity and hydration.
Used in Food and Beverage Industry:
In the food and beverage industry, DL-CITRULLINE is used as a natural flavor enhancer and preservative. Its amino acid properties can help improve the taste and texture of various food products.

InChI:InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)

Upstream product

• 74-79-3 L-arginine 
• 556-89-8 nitrourea 
• 3184-13-2 L-ornithine hydrochloride 
• 7664-93-9 sulfuric acid 
• 10334-68-6 N^α-benzoyl-DL-citrulline 

Downstream Products

• 70-26-8 2,5-diaminopentanoic acid 
• 52717-00-7 5-Aminocarbonylamino-2-oxopentansaeure 
• 67736-30-5 1-Aminocarbonyl-2-hydroxy-2-pyrrolidincarbonsaeure 
• 125735-06-0 α-(benzyloxycarbonyl)arginino>succinic acid trimethyl ester 
• 125735-11-7 2-Benzyloxycarbonylamino-5-(2-imino-4-methoxycarbonylmethyl-5-oxo-imidazolidin-1-yl)-pentanoic acid methyl ester 
• 125735-10-6 2-Benzyloxycarbonylamino-5-(5-methoxycarbonylmethyl-4-oxo-4,5-dihydro-1H-imidazol-2-ylamino)-pentanoic acid methyl ester 
• 89499-13-8 N^α-(benzyloxycarbonyl)-L-citrulline methyl ester 
• 125735-05-9 N^α-(benzyloxycarbonyl)-N^δ-cyanoornithine methyl ester 
• 6692-89-3 N^α-(benzyloxycarbonyl)-L-citrulline 
• 166961-73-5 2-oxohexahydro-1,3-diazepinyl-4-carboxylic acid 
• 2139-03-9 Δ¹-pyrroline-2-carboxylic acid 
• 57-13-6 urea 

Relevant articles and documents

ACTIVITY-ENHANCING SUPPLEMENT

An activity-enhancing supplement can include niacin and at least two ingredients selected from citrulline, agmatine, an endurance enhancer, a counteracting agent, a nitrogen-containing compound, a muscle building component, branched chain amino acid, and combinations thereof.

FUNCTIONALIZED FLUORINE CONTAINING PHTHALOCYANINE MOLECULES

Functionalized fluorine containing phthalocyanine molecules, methods of making, and methods of use in diagnostic applications and disease treatment are disclosed herein. In some embodiments, the fluorine containing phthalocyanine molecules are functionalized with a reactive functional group or at least one cancer-targeting ligand (CTL). The CTL can facilitate more efficient binding and/or internalization to a cancer cell than to a healthy cell. The CTL can inhibit expression of oncoprotein in some embodiments. The pthalocyanine moiety can be used in diagnostic applications, such as fluorescence labeling of a cancer cell, and/or treatment applications, such as catalyzing formation of a reactive oxygen species (ROS) which can contribute to cell death of a cancer cell.

Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: A biomimetic model for the H2O2-dependent activity of nitric oxide synthase

A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces N(δ)-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

Urea cycle: Chemical simulation of arginine biosynthesis

We have successfully simulated the salient features of the urea cycle. In this effort an appropriately protected ornithine was transformed to citrulline, via use of a novel amide transfer reagent; the citrulline, in turn, was converted into argininosuccinate which necessitated a new activation procedure to enable acceptance of dimethyl aspartate. Fragmentation of argininosuccinate under carefully controlled conditions afforded arginine. The final step in the cycle, namely, the hydrolysis of arginine to urea and ornithine, has already been accomplished. Amino group transfer from aspartate has also been demonstrated in the conversion of hypoxanthine to adenine.