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L(+)-Citrulline
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Name

L(+)-Citrulline

 EINECS 206-759-6
CAS No. 372-75-8 Density 1.289 g/cm3
PSA 118.44000 LogP 0.63830
Solubility 200 g/L (20 °C) in water Melting Point 214 °C
Formula C6H13N3O3 Boiling Point 386.7 °C at 760 mmHg
Molecular Weight 175.188 Flash Point 187.7 °C
Transport Information N/A Appearance white powder
Safety 24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 372-75-8 (L(+)-Citrulline) Hazard Symbols IrritantXi
Synonyms

L-Citrullin;L-Cit-OH;L-Citrulline;N5-(Aminocarbonyl)ornithine;L-Citrulline (Fermentation);H-Cit-OH;.delta.-Ureidonorvaline;2-Amino-5-uredovaleric acid;Ngamma-carbamylornithine;delta-Ureidonorvaline;N~5~-(aminocarbonyl)ornithine;2-amino-5-(carbamoylamino)pentanoic acid;L-Citrulline;(2S)-2-amino-5-(carbamoylamino)pentanoic acid;Ornithine, N5-carbamoyl-, L- (8CI);L-Ornithine, N5-(aminocarbonyl)-;Ornithine, N5-(aminocarbonyl)-;Citrulline, L-;Ornithine, N5-carbamoyl-, L-;Citrulline;L-Ornithine,N5-(aminocarbonyl)-;.alpha.-Amino-.delta.-ureidovaleric acid;N5-(Aminocarbonyl)-L-ornithine;alpha-Amino-delta-ureidovaleric acid;N(.delta.)-Carbamylornithine;

Article Data 48

L(+)-Citrulline Synthetic route

74-79-3

L-arginine

372-75-8

Citrulline

Conditions
ConditionsYield
for 46 - 120h; Product distribution / selectivity; Enzymatic reaction;91%
With dihydrogen peroxide; K[Ru(Hedta)Cl]*2H2O71%
durch Einwirkung von Faeulnisbakterien;
70-26-8

L-ornithine

372-75-8

Citrulline

Conditions
ConditionsYield
With carbamoyl phosphate
1188-38-1

L-carglumic acid

372-75-8

Citrulline

Conditions
ConditionsYield
Biosynthese;
1119-34-2

L-arginine hydrochloride

372-75-8

Citrulline

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; phosphoric acid; water at 25 - 37℃; Thermodynamic data; ΔH; aginine deiminase (EC 3.5.3.6) from Pseudomonas putida; var. pH and ionic strength;
L-ornithine-monohydrochloride

L-ornithine-monohydrochloride

372-75-8

Citrulline

Conditions
ConditionsYield
With copper (II) carbonate hydroxide; water at 100℃; Durch Erhitzen des erhaeltlichen Komplexsalzes mit Harnstoff in wss. Loesung auf 100grad und Zerlegung des gebildeten Kupfer(II)-Komplexsalzes des L-Citrullins mit H2S in Wasser;
139461-37-3

Nω-allyl-L-arginine

A

372-75-8

Citrulline

B

107-02-8

acrolein

Conditions
ConditionsYield
With NADPH; calcium chloride; calmodulin; neuronal nitric oxide synthase at 20℃; pH=7.5; Enzyme kinetics; Oxidation; Enzymatic reaction;

Nω-allyl-Nω-hydroxy-L-arginine

A

372-75-8

Citrulline

B

107-02-8

acrolein

Conditions
ConditionsYield
With NADPH; calcium chloride; calmodulin; neuronal nitric oxide synthase at 20℃; pH=7.5; Enzyme kinetics; Oxidation; Enzymatic reaction;
53054-07-2

L-NOHA

372-75-8

Citrulline

Conditions
ConditionsYield
With mammalian nitric oxide synthase; oxygen Enzyme kinetics;

Nω-tert-butoxy-L-arginine

372-75-8

Citrulline

Conditions
ConditionsYield
With mammalian nitric oxide synthase; NADPH; diothiothreitol; tetrahydrobiopterin In various solvent(s) at 30℃; for 0.0333333h; Enzyme kinetics;

Nω-O-(3-methyl-2-butenyl)hydroxy-L-arginine

372-75-8

Citrulline

Conditions
ConditionsYield
With mammalian nitric oxide synthase; NADPH; diothiothreitol; tetrahydrobiopterin In various solvent(s) at 30℃; for 0.0333333h; Enzyme kinetics;

L(+)-Citrulline Specification

1. Introduction of L(+)-Citrulline

L(+)-Citrulline (372-75-8), with its IUPAC name of (2S)-2-amino-5-(carbamoylamino)pentanoic acid, is one kind of white powder. The product's categories are Citruline [Cit]; Amino Acids; Unusual Amino Acids; Biochemistry; non-Proteinorganic Amino Acids; Nutritional Supplements; L-Amino Acids; Amino Acids. Besides, it should be sealed in a cool and dry place at 0-5 °C.

2. Properties of L(+)-Citrulline

The other characteristics of L(+)-Citrulline can be summarized as: (1)EINECS: 206-759-6; (2)ACD/LogP: -1.53; (3)# of Rule of 5 Violations: 1; (4)ACD/LogD (pH 5.5): -4.03; (5)ACD/LogD (pH 7.4): -4.03; (6)ACD/BCF (pH 5.5): 1; (7)ACD/BCF (pH 7.4): 1; (8)ACD/KOC (pH 5.5): 1; (9)ACD/KOC (pH 7.4): 1; (10)#H bond acceptors: 6; (11)#H bond donors: 6; (12)#Freely Rotating Bonds: 6; (13)Index of Refraction: 1.531; (14)Molar Refractivity: 42.06 cm3; (15)Molar Volume: 135.8 cm3; (16)Surface Tension: 61.9 dyne/cm; (17)Density: 1.289 g/cm3; (18)Flash Point: 187.7 °C; (19)Melting Point: 214-216 °C; (20)alpha: 25.5 °(c=8, 6N HCl); (21)Water solubility: 200 g/L (20 °C); (22)Enthalpy of Vaporization: 69.78 kJ/mol; (23)Boiling Point: 386.7 °C at 760 mmHg; (24)Vapour Pressure: 4.7E-07 mmHg at 25 °C.

3. Structure Descriptors of L(+)-Citrulline

You could convert the following datas into the molecular structure:
(1)SMILES: O=C(O)[C@@H](N)CCCNC(=O)N
(2)InChI: InChI=1/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
(3)InChIKey: RHGKLRLOHDJJDR-BYPYZUCNBX

4. Uses of L-Citrulline

L-Citrulline is amino acids drug used for the treatment of hyperammonemia. Moreover, it can react with trifluoroacetic acid anhydride to get 2-oxo-3-(2,2,2-trifluoro-acetylamino)-piperidine-1-carboxylic acid amide and 1-[3-(5-oxo-2-trifluoromethyl-2,5-dihydro-oxazol-4-yl)-propyl]-3-trifluoroacetyl-urea.



This reaction will occur by heating for 24 hours. The yield is 48 %.

5. Safety information of L(+)-Citrulline

Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36-26
WGK Germany 3
HS Code 29241900

When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing to avoid contact with skin and eyes.

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