| Identification | More | [Name]
L(+)-Citrulline | [CAS]
372-75-8 | [Synonyms]
ALPHA-AMINO-DELTA-UREIDO-N-VALERIC ACID
CITRULLINE
CITRULLINE, L-
H-CIT-OH
H-L-CIT-OH
H-ORN(CARBAMOYL)-OH
H-ORN(CONH2)-OH
L-2-AMINE-5-UREIDOVAIERIC ACID
L-2-AMINE-5-UREIDOVALERIC ACID
L-2-AMINO-5-UREIDO-N-VALERIC ACID
L(+)-2-AMINO-5-UREIDOVALERIC ACID
L-2-AMINO-5-UREIDOVALERIC ACID
L-CIT
L-CITRULINE
L-(+)-CITRULLINE
L-CITRULLINE
N-DELTA-CARBAMOYL-L-ORNITHINE
N-ORN(CARBAMOYL)-OH
(S)-2-AMINO-5-UREIDOPENTANOIC ACID
2-Amino-5-ureidovalericacid | [EINECS(EC#)]
206-759-6 | [Molecular Formula]
C6H13N3O3 | [MDL Number]
MFCD00064397 | [Molecular Weight]
175.19 | [MOL File]
372-75-8.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [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. ]
Store at 0-5°C | [solubility ]
Aqueous Acid (Sparingly). Water (Slightly) | [form ]
Crystals or Crystalline Powder | [pka]
2.43(at 25℃) | [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]
372-75-8(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302-H315-H319-H335 | [Precautionary statements ]
P280-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [TSCA ]
Yes | [HS Code ]
29241900 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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]
An essential intermediate in the biosynthesis of nitric oxide. | [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 with
sodium 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 |
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Alfa Aesar
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Energy Chemical
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www.energy-chemical.com |
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