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HomeProduct name listL-Citrulline

L-Citrulline

Synonym(s):(S)-2-Amino-5-ureidopentanoic acid;L-2-Amino-5-ureidovaleric acid;L-Citrulline;L-Citrulline

  • CAS NO.:372-75-8
  • Empirical Formula: C6H13N3O3
  • Molecular Weight: 175.19
  • MDL number: MFCD00064397
  • EINECS: 206-759-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:08:57
L-Citrulline Structural

What is L-Citrulline?

Chemical properties

White powder

Originator

StaminO2,ErgoPharm

The Uses of L-Citrulline

An amino acid, L-Citrulline can be used in the treatment of asthenia and as an essential intermediate in the biosynthesis of nitric oxide.

The Uses of L-Citrulline

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.

What are the applications of Application

L-Citrulline is 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.

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.]

Properties of L-Citrulline

Melting point: 214 °C
Boiling point: 306.48°C (rough estimate)
alpha  25.5 º (c=8, 6N HCl)
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
Water Solubility  200 g/L (20 ºC)
Merck  14,2331
BRN  6055157
CAS DataBase Reference 372-75-8(CAS DataBase Reference)
EPA Substance Registry System L-Ornithine, N5-(aminocarbonyl)- (372-75-8)

Safety information for L-Citrulline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for L-Citrulline

InChIKey RHGKLRLOHDJJDR-BYPYZUCNSA-N

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