L-Citrulline Chemical Properties

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. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Aqueous Acid (Sparingly). Water (Slightly)

form 

Crystals or Crystalline Powder

pka

2.43(at 25℃)

color 

White

Odor

Odorless

optical activity

+4.025 (H2O) +24.225 (1 mol dm-3 HCl)

Water Solubility 

200 g/L (20 ºC)

Merck 

14,2331

BRN 

6055157

InChIKey

RHGKLRLOHDJJDR-BYPYZUCNSA-N

LogP

-3.190

CAS DataBase Reference

372-75-8(CAS DataBase Reference)

EPA Substance Registry System

L-Ornithine, N5-(aminocarbonyl)- (372-75-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29241900

MSDS

• Language:English Provider:L(+)-2-Amino-5-ureidovaleric acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

L-Citrulline Usage And Synthesis

Chemical Properties

White powder

Originator

StaminO2,ErgoPharm

Uses

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.

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.

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.]

L-Citrulline(372-75-8)Related Product Information

• Pivalic acid
• ALTRENOGEST
• 5-AMINOVALERIC ACID
• L-Tryptophan
• L(+)-Arginine
• Glycine
• Semicarbazide
• Estradiol valerate
• MAGNESIUM DIPROPYLACETATE HYDRATE
• 2-Propylpentanoic acid
• L-Serine
• L-Glutamine
• L-Prolinamide
• L-Proline
• L-Methionine
• N-[(tert-Butoxy)carbonyl]-D-tryptophan
• BOC-CIT-OH
• DL-CITRULLINE