ChemicalBook Product Catalog Biochemical Engineering Amino Acids and proteins L-Citrulline

L-Citrulline

L-Citrulline Basic information
Product Name:L-Citrulline
Synonyms:Ibuprofen Impurity 78;Arginine Impurity 2（Arginine EP Impurity B）（Citrulline）;L-CTRULLINE;L-Citrullne;Arginine EP Impurity B;n5-(aminocarbonyl)-l-ornithin;N5-(aminocarbonyl)-L-Ornithine;ALPHA-AMINO-DELTA-UREIDO-N-VALERIC ACID
CAS:372-75-8
MF:C6H13N3O3
MW:175.19
EINECS:206-759-6
Product Categories:Amino Acids;Citruline [Cit];Amino Acids;Unusual Amino Acids;Biochemistry;non-Proteinorganic Amino Acids;Nutritional Supplements;L-Amino Acids;Aliphatics;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;API;372-75-8
Mol File:372-75-8.mol
L-Citrulline Structure
L-Citrulline Chemical Properties
Melting point 214 °C
alpha 25.5 º (c=8, 6N HCl)
Boiling point 306.48°C (rough estimate)
density 1.2919 (rough estimate)
refractive index 26 ° (C=8, 6mol/L HCl)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility Aqueous Acid (Sparingly). Water (Slightly)
form Crystals or Crystalline Powder
pka2.43(at 25℃)
color White
OdorOdorless
Water Solubility 200 g/L (20 ºC)
Merck 14,2331
BRN 6055157
InChIKeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
LogP-3.190
CAS DataBase Reference372-75-8(CAS DataBase Reference)
EPA Substance Registry SystemL-Ornithine, N5-(aminocarbonyl)- (372-75-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
TSCA Yes
HS Code 29241900
MSDS Information
ProviderLanguage
L(+)-2-Amino-5-ureidovaleric acid English
ACROS English
SigmaAldrich English
ALFA English
L-Citrulline Usage And Synthesis
Chemical PropertiesWhite powder
OriginatorStaminO2,ErgoPharm
UsesAn amino acid, L-Citrulline can be used in the treatment of asthenia and as an essential intermediate in the biosynthesis of nitric oxide.
UsesL-Citrulline, is used as an essential intermediate in the biosynthesis of nitric oxide from L-arginine . It is also used as a nutritional drink and biochemical reagent.
DefinitionChEBI: L-citrulline is the L-enantiomer of citrulline. It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor, a protective agent, a nutraceutical, a micronutrient, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is an enantiomer of a D-citrulline. It is a tautomer of a L-citrulline zwitterion.
Manufacturing ProcessCitrulline is obtained as a result of a reaction of L-arginine hydrochloride with sodium hydroxide, copper oxide and hydrogen sulfide.
In practice it is usually used as malate salt
Therapeutic FunctionStimulant, Detoxicant
Biochem/physiol ActionsL-Citrulline, when orally administered is found to ameliorate the condition of sickle cell disease in humans. L-citrulline can be a replacement for L-arginine administration in case of defective NO synthetase. L-Citrulline supplementation is found to fulfill the purpose of NO-dependent signaling.
targetNO | IL Receptor
Purification MethodsLikely impurities are arginine and ornithine. Crystallise S-citrulline from water by adding 5 volumes of EtOH. Also crystallise it from water by addition of MeOH. [Ellenbogen J Am Chem Soc 74 5198 1952, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2491-2494 1961, Beilstein 4 IV 2647.]
Estradiol valerate H-SER-PHE-LEU-LEU-CIT-OH DANSYL-L-CITRULLINE MAGNESIUM DIPROPYLACETATE HYDRATE BOC-CIT-OH CITRULLIN [3H(G)] N-[(tert-Butoxy)carbonyl]-D-tryptophan L-Citrulline-4,4,5,5-d4 L-Tryptophan ALTRENOGEST Pivalic acid Glycine Semicarbazide L-Citrulline 2-Propylpentanoic acid Fmoc-L-citrulline L(+)-Arginine 5-AMINOVALERIC ACID
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