Product Name

  • Name

    L(+)-Citrulline

  • EINECS 206-759-6
  • CAS No. 372-75-8
  • Article Data48
  • CAS DataBase
  • Density 1.289 g/cm3
  • 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
  • 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;
  • PSA 118.44000
  • LogP 0.63830

Synthetic route

L-arginine
74-79-3

L-arginine

Citrulline
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;
L-ornithine
70-26-8

L-ornithine

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With carbamoyl phosphate
L-carglumic acid
1188-38-1

L-carglumic acid

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
Biosynthese;
L-arginine hydrochloride
1119-34-2

L-arginine hydrochloride

Citrulline
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

Citrulline
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;
Nω-allyl-L-arginine
139461-37-3

Nω-allyl-L-arginine

A

Citrulline
372-75-8

Citrulline

B

acrolein
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

Nω-allyl-Nω-hydroxy-L-arginine

A

Citrulline
372-75-8

Citrulline

B

acrolein
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;
L-NOHA
53054-07-2

L-NOHA

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With mammalian nitric oxide synthase; oxygen Enzyme kinetics;
Nω-tert-butoxy-L-arginine

Nω-tert-butoxy-L-arginine

Citrulline
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

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

Citrulline
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;
N-hydroxy-L-arginine

N-hydroxy-L-arginine

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With dihydrogen peroxide; Cl8TPPFe(III)Cl In various solvent(s) at 20℃;
Nω-hydroxy-L-arginine

Nω-hydroxy-L-arginine

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With full-length inducible nitric oxide synthase; (6R)-5,6,7,8-tetrahydro-L-biopterin; oxygen at 37℃; pH=7.4; Kinetics; aq. buffer;
With 1,4-dithio-D,L-threitol; neuronal NO synthase; NADPH; FAD; 4-(2-hydroxyethyl)-1-piperazinepropanesulfonic acid; (6-R,S)-5,6,7,8-tetrahydro-L-biopterin dihydrochloride; Flavin mononucleotide; superoxide dismutase; catalase; calmodulin at 25℃; Enzymatic reaction;
With recombinant murine inducible nitric oxide synthase-oxy substituted with mesohaem; (1'R,2'S,6R)-2-amino-6-(1',2'-dihydroxypropyl)-5,6,7,8-tetrahydropterin-4(3H)-one-dihydrochloride In aq. phosphate buffer Kinetics; Reagent/catalyst;
L-N-gamma-Aminoarginine

L-N-gamma-Aminoarginine

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With α-ketoglutaric acid; recombinant Giardia lamblia arginine deiminase; water; NADH at 25℃; Kinetics; Reagent/catalyst; Time; pH-value; aq. buffer;
L-ornithine hydrochloride
3184-13-2

L-ornithine hydrochloride

urea
57-13-6

urea

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
Stage #1: L-ornithine hydrochloride With sodium hydrogencarbonate In water at 20℃;
Stage #2: With copper(ll) sulfate pentahydrate In water at 100℃;
Stage #3: urea Further stages;
Nω-hydroxy-L-arginine

Nω-hydroxy-L-arginine

A

Citrulline
372-75-8

Citrulline

B

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

Conditions
ConditionsYield
With nitric oxide synthase; NADH at 25℃; Catalytic behavior; Kinetics; Enzymatic reaction;
L-arginine
74-79-3

L-arginine

A

Citrulline
372-75-8

Citrulline

B

nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

Conditions
ConditionsYield
With inducible NO synthase at 20℃; Enzymatic reaction;
With dihydrogen peroxide; C48H28ClFeN4O8 In aq. phosphate buffer for 0.416667h; pH=7.4; Kinetics; Green chemistry;
L-citrulline copper complex

L-citrulline copper complex

Citrulline
372-75-8

Citrulline

Conditions
ConditionsYield
With sodium sulfide In water Reagent/catalyst; Large scale;

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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