DL-Citrulline

Base Information

• Chemical Name: DL-Citrulline
• CAS No.: 627-77-0
• Molecular Formula: C6H13N3O3
• Molecular Weight: 175.188
• Hs Code.: 2924199090
• European Community (EC) Number: 211-012-2
• NSC Number: 206276,46711,27425
• UNII: 1OYO2NV4NM
• DSSTox Substance ID: DTXSID40861910
• Nikkaji Number: J3.054.119G
• Wikidata: Q27102910
• ChEMBL ID: CHEMBL187855
• Mol file: 627-77-0.mol

Synonyms:DL-Citrulline;627-77-0;2-Amino-5-ureidopentanoic acid;Citrullin;2-amino-5-(carbamoylamino)pentanoic acid;DL-2-Amino-5-ureidovaleric acid;citrulina;CITRULLINE, (DL);CHEBI:18211;Ornithine, N5-carbamoyl-, DL-;DL-Ornithine, N5-(aminocarbonyl)-;H-D-Orn(carbamoyl)-OH;Citrulline, (+/-)-;1OYO2NV4NM;DL-Ornithine, N(5)-(aminocarbonyl)-;N(5)-carbamoyl-DL-ornithine;N(5)-(aminocarbonyl)ornithine;NSC27425;NSC46711;EINECS 211-012-2;N(5)-(aminocarbonyl)-DL-ornithine;NSC-46711;N~5~-carbamoylornithine;L-citrullin;L-Citruline;N(5)-carbamoylornithine;cit;H-Orn(carbamoyl)-OH;L-Citrulline;MFCD00216469;Citrulline,(l);citrulline (DL-form);Spectrum_000037;.delta.-Ureidonorvaline;CITRULLINE, DL-;SpecPlus_000523;L(+)CITRULLINE;Spectrum2_001371;Spectrum3_001045;Spectrum4_001185;Spectrum5_001792;UNII-1OYO2NV4NM;N.delta.-Carbamylornithine;bmse000209;Epitope ID:141797;N~5~-carbamoyl-L-ornithine;SCHEMBL20587;BSPBio_002570;KBioGR_001849;KBioSS_000397;N(.delta.)-Carbamylornithine;DivK1c_006619;SPBio_001322;CHEMBL187855;SGCUT00061;DL-2-amino-5-ureidovalericacid;SCHEMBL13282334;KBio1_001563;KBio2_000397;KBio2_002965;KBio2_005533;KBio3_001790;DTXSID40861910;to_000034;BBL027668;CCG-38847;MFCD00007955;NSC 46711;NSC206276;s5124;STK802460;STL455121;AKOS005622468;L-(+)-2-Amino-5-ureidovaleric acid;L-CITRULLINE (1.12117);N~5~-[hydroxy(imino)methyl]ornithine;2-Amino-5-carbamoylaminopentanoic acid;CS-W017450;HY-W016734;PB48354;SDCCGMLS-0066976.P001;NCGC00178596-01;.alpha.-Amino-.delta.-ureidovaleric acid;AS-60168;SY023288;SY032853;FT-0625451;FT-0627745;FT-0659369;NORVALINE, 5-((AMINOCARBONYL)AMINO)-;C-6150;D89239;EN300-1168657;A833990;L000975;SR-05000002410;1,2,2,6,6-PENTAMETHYLPIPERIDINED-TARTRATE;SR-05000002410-1;Q27102910

Chemical Property of DL-Citrulline

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 242-244 °C (dec.)
• Boiling Point: 386.7 °C at 760 mmHg
• PKA: 2.51±0.24(Predicted)
• Flash Point: 187.7 °C
• PSA: 118.44000
• Density: 1.289 g/cm³
• LogP: 0.63830
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 175.09569129
• Heavy Atom Count: 12
• Complexity: 171

Purity/Quality:

98% ^*data from raw suppliers

2-Amino-5-ureidopentanoicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CNC(=O)N
• Recent ClinicalTrials: Arginine + Citrulline as a Supplement for Weight Gain in Fetus With a Decrease in Their Growth Curve

Technology Process of DL-Citrulline

There total 8 articles about DL-Citrulline 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:

→ citrulline (627-77-0)

Guidance literature:

With copper (II) carbonate hydroxide; water; at 100 ℃; Durch Umsetzung des erhaeltlichen Kupfer(II)-Komplexsalzes mit Harnstoff in Wasser bei 100grad und Zerlegung der gebildeten Kupfer(II)-Verbindung des DL-Citrullins mit H₂S in wss. Loesung;

DOI:10.1021/jo01203a005

Reference yield:

N-hydroxyarginine → citrulline (627-77-0) + Nδ-cyanoornithine

Guidance literature:

With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride; dihydrogen peroxide; In methanol; 1,2-dichloro-ethane; at 20 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1016/S0960-894X(00)00345-0

Reference yield:

L-arginine (74-79-3,25212-18-4) → citrulline (627-77-0)

Guidance literature:

With sodium hydroxide;

upstream raw materials:

L-arginine

sulfuric acid

N^α-benzoyl-DL-citrulline

nitrourea

Downstream raw materials:

2,5-diaminopentanoic acid

N^α-(benzyloxycarbonyl)-L-citrulline

5-Aminocarbonylamino-2-oxopentansaeure

1-Aminocarbonyl-2-hydroxy-2-pyrrolidincarbonsaeure

Refernces

• 1、 -. "FUNCTIONALIZED FLUORINE CONTAINING PHTHALOCYANINE MOLECULES". . . Retrieved 2015/03/16.
• 2、 Ranganathan,Rathi. "Urea cycle: Chemical simulation of arginine biosynthesis". . p. 2351 - 2354. Retrieved 2007/10/02.