C7629

Sigma-Aldrich

L-Citrulline

≥98% (TLC)

Synonym(s):
(S)-2-Amino-5-ureidopentanoic acid, L-2-Amino-5-ureidovaleric acid
Empirical Formula (Hill Notation):
C6H13N3O3
CAS Number:
Molecular Weight:
175.19
Beilstein/REAXYS Number:
1725416
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98% (TLC)

form

powder

application(s)

detection: suitable

color

white to off-white

SMILES string

N[C@@H](CCCNC(N)=O)C(O)=O

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

InChI key

RHGKLRLOHDJJDR-BYPYZUCNSA-N

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Application

L-Citrulline has been used in ultra-performance liquid chromatography to validate, metabolites involved in the coordination of metamorphic processes.

Packaging

10 mg in autosample vial
5, 25 g in poly bottle

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.
Intermediate in the production of nitric oxide from L-arginine by NO synthetase.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C7629.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

l-Citrulline and l-arginine supplementation retards the progression of high-cholesterol-diet-induced atherosclerosis in rabbits.
Hayashi T
Proceedings of the National Academy of Sciences of the USA null
Nu-Hydroxy-L-arginine Is an Intermediate in the Biosynthesis of Nitric Oxide from L-Arginin
Dennis J. Stuehr
The Journal of Biological Chemistry, 266, 6259-6263 (1991)
Pharmacokinetic and pharmacodynamic properties of oral L-citrulline and L-arginine: impact on nitric oxide metabolism.
Schwedhelm E
British Journal of Clinical Pharmacology, 65(1), 51-59 (2008)
Metabolomic insights into system-wide coordination of vertebrate metamorphosis.
Ichu TA
BMC Developmental Biology, 14:5, 1-24 (2014)
C C Reparon-Schuijt et al.
Arthritis and rheumatism, 44(1), 41-47 (2001-02-24)
To understand the regulation of anti-citrulline-containing peptide antibody (anti-CCP) production in rheumatoid arthritis (RA), production of anti-CCP by B cells derived from peripheral blood (PB), bone marrow (BM), and synovial fluid (SF) was examined. Purified PB and SF B cells...
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