L-Citrulline CAS 372-75-8
Introduction：Basic information about L-Citrulline CAS 372-75-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 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) |
| pka | 2.43(at 25℃) |
| form | Crystals or Crystalline Powder |
| color | White |
| Odor | Odorless |
| Optical Rotation | +4.025 (H2O) +24.225 (1 mol dm-3 HCl) |
| Water Solubility | 200 g/L (20 ºC) |
| Merck | 14,2331 |
| BRN | 6055157 |
| Major Application | detection |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| 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 | N[C@@H](CCCNC(N)=O)C(O)=O |
| LogP | -3.190 |
| CAS DataBase Reference | 372-75-8(CAS DataBase Reference) |
| EPA Substance Registry System | L-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 | TSCA listed |
| HS Code | 29241900 |
| Storage Class | 11 - Combustible Solids |
| Chemical Properties | White powder |
| Originator | StaminO2,ErgoPharm |
| Uses | An amino acid, L-Citrulline can be used in the treatment of asthenia and as an essential intermediate in the biosynthesis of nitric oxide. |
| Uses | L-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. |
| Definition | ChEBI: 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 Process | Citrulline is obtained as a result of a reaction of L-arginine hydrochloride withsodium hydroxide, copper oxide and hydrogen sulfide. In practice it is usually used as malate salt |
| Therapeutic Function | Stimulant, Detoxicant |
| benefits | L-citrulline is used for Alzheimer's disease, dementia, fatigue, muscle weakness, sickle cell disease, erectile dysfunction, high blood pressure, and diabetes. It is used for heart disease, body building, increasing energy, and for improving athletic performance. |
| Biochem/physiol Actions | L-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. |
| target | NO | IL Receptor |
| Drug interactions | There are no reported side effects of L-citrulline. However, the supplement may affect the way certain drugs work in your body. Do not take this supplement if you are taking: Nitrates for heart disease ED drugs such as sildenafil (Revatio, Viagra), tadalafil (Cialis), or vardenafil (Levitra, Staxyn) Combining L-citrulline with those drugs may cause a dangerous drop in blood pressure. You should also be careful when taking L-citrulline if you take any type of blood pressure medicine. Do not use L-citrulline if you are pregnant or breastfeeding. |
| Purification Methods | Likely 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.] |
| References | [1] Patent: WO2009/25829, 2009, A1. Location in patent: Page/Page column 14-15 [2] Chemical communications (Cambridge, England), 2001, # 18, p. 1870 - 1871 [3] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1931, vol. 203, p. 66 [4] Tohoku Journal of Experimental Medicine, 1941, vol. 41, p. 317 [5] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1933, vol. 216, p. 244 |
L-Citrulline Preparation Products And Raw materials
| Raw materials | Hydroxide-->L(+)-Arginine |
| Preparation Products | H-LYS(ALLOC)-OH-->MC-Val-Cit-PAB-->FMoc-Val-Cit-PAB-->FMoc-Val-Cit-PAB-PNP-->Mc-Val-Cit-PABC-PNP |
