L-Citrulline

• CAT Number: R011952
• CAS Number: 372-75-8
• Molecular Formula: C6H13N3O3
• Molecular Weight: 175.188
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (2S)-2-amino-5-(carbamoylamino)pentanoic acid
• 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)/t4-/m0/s1
• InChIKey: RHGKLRLOHDJJDR-BYPYZUCNSA-N
• SMILES: C(CC(C(=O)O)N)CNC(=O)N

Citrulline(CAT: R011952), also known as L-Citrulline, is an α-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1914 by Koga & Odake. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia. In the body, citrulline is produced as a byproduct of the enzymatic production of nitric oxide from the amino acid arginine, catalyzed by nitric oxide synthase. This is an essential reaction in the body because nitric oxide is an important vasodilator required for regulating blood pressure.

Reference

1:Consumption of watermelon juice enriched in L-citrulline and pomegranate ellagitannins enhanced metabolism during physical exercise. Martinez-Sanchez A, Alacid F, Rubio-Arias JA, Fernandez-Lobato B, Ramos-Campo DJ, Aguayo E.J Agric Food Chem. 2017 May 17. doi: 10.1021/acs.jafc.7b00586. [Epub ahead of print] PMID: 28513179 2:Characteristics of L-citrulline transport through blood-brain barrier in the brain capillary endothelial cell line (TR-BBB cells). Lee KE, Kang YS.J Biomed Sci. 2017 May 10;24(1):28. doi: 10.1186/s12929-017-0336-x. PMID: 28490336 Free PMC Article3:A novel mass spectrometry-based method for simultaneous determination of asymmetric and symmetric dimethylarginine, L-arginine, and L-citrulline optimized for LC-MS-TOF and LC-MS/MS. Wiśniewski J, Fleszar MG, Piechowicz J, Krzystek-Korpacka M, Chachaj A, Szuba A, Lorenc-Kukula K, Masłowski L, Witkiewicz W, Gamian A.Biomed Chromatogr. 2017 Apr 24. doi: 10.1002/bmc.3994. [Epub ahead of print] PMID: 28436051 4:Evaluation of the Effects and Mechanism of L-Citrulline on Anti-obesity by Appetite Suppression in Obese/Diabetic KK-Ay Mice and High-Fat Diet Fed SD Rats. Kudo M, Yoshitomi H, Momoo M, Suguro S, Yamagishi Y, Gao M.Biol Pharm Bull. 2017;40(4):524-530. doi: 10.1248/bpb.b16-01002. PMID: 28381807 Free Article5:l-Citrulline ameliorates cerebral blood flow during cortical spreading depression in rats: Involvement of nitric oxide- and prostanoids-mediated pathway. Kurauchi Y, Mokudai K, Mori A, Sakamoto K, Nakahara T, Morita M, Kamimura A, Ishii K.J Pharmacol Sci. 2017 Mar;133(3):146-155. doi: 10.1016/j.jphs.2017.02.004. Epub 2017 Feb 17. PMID: 28325558 Free Article6:Combined l-citrulline and glutathione administration prevents neuronal cell death following transient brain ischemia. Matsuo K, Yabuki Y, Fukunaga K.Brain Res. 2017 May 15;1663:123-131. doi: 10.1016/j.brainres.2017.03.014. Epub 2017 Mar 14. PMID: 28315310 7:Treatment with L-citrulline in patients with post-polio syndrome: study protocol for a single-center, randomised, placebo-controlled, double-blind trial. Schmidt S, Gocheva V, Zumbrunn T, Rubino-Nacht D, Bonati U, Fischer D, Hafner P.Trials. 2017 Mar 9;18(1):116. doi: 10.1186/s13063-017-1829-3. PMID: 28274276 Free PMC Article8:Levels of l-arginine and l-citrulline in patients with erectile dysfunction of different etiology. Barassi A, Corsi Romanelli MM, Pezzilli R, Damele CA, Vaccalluzzo L, Goi G, Papini N, Colpi GM, Massaccesi L, Melzi d/’Eril GV.Andrology. 2017 Mar;5(2):256-261. doi: 10.1111/andr.12293. Epub 2017 Feb 8. PMID: 28178400 9:The Importance of Quality Specifications in Safety Assessments of Amino Acids: The Cases of l-Tryptophan and l-Citrulline. Oketch-Rabah HA, Roe AL, Gurley BJ, Griffiths JC, Giancaspro GI.J Nutr. 2016 Dec;146(12):2643S-2651S. Epub 2016 Nov 9. Review. PMID: 27934657 10:Influence of L-citrulline and watermelon supplementation on vascular function and exercise performance. Figueroa A, Wong A, Jaime SJ, Gonzales JU.Curr Opin Clin Nutr Metab Care. 2017 Jan;20(1):92-98. PMID: 27749691