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Citrulline

Citrulline structure

CAS No:
372-75-8
Formula:
C6H13N3O3
Chemical Name:
Citrulline
Synonyms:
L-Ornithine,N5-(aminocarbonyl)-;Ornithine,N5-carbamoyl-,L-;N5-(Aminocarbonyl)-L-ornithine;α-Amino-δ-ureidovaleric acid;Nδ-Carbamylornithine;δ-Ureidonorvaline;Citrulline;N5-Carbamoyl-L-ornithine;Cit;L-Citrulline;NSC 27425;L-(+)-Citrulline
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

L-Citrulline is an amino acid derived from ornithine in the catabolism of proline or glutamine and glutamate, or from l-arginine via arginine-citrulline pathway.

Solid

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.|Citrulline is an amino acid. It is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.|Citrulline is a non-essential amino acid. In hepatocytes, L-citrulline is synthesized in the urea cycle by the addition of carbon dioxide and ammonia to ornithine. L-citrulline is converted into L-arginine by the enzymes argininosuccinate synthetase and argininosuccinate lyase in the presence of L-aspartate and ATP. Subsequently, L-arginine is converted to nitric oxide by nitric oxide synthase and L-citrulline is regenerated as a by-product.

Citrulline Basic Attributes

Molecular Weight：

175.19

Exact Mass：

175.19

BRN：

6055157

EC Number：

206-759-6

UNII：

29VT07BGDA

NCI Thesaurus Code：

C53406

HScode：

29241900

Characteristics

PSA：

118

XLogP3：

-3.19

Appearance：

White Crystals or Crystalline Powder

Density：

1.3±0.1 g/cm3

Melting Point：

235.5 °C

Boiling Point：

306.48°C (rough estimate)

Flash Point：

187.7±27.9 °C

Refractive Index：

1.531

Water Solubility：

H2O: 200 g/L (20 ºC)

Storage Conditions：

Store at 0-5°C

Specific rotation：

25.5 º (c=8, 6N HCl)

PKA：

2.43(at 25 °C)

Dissociation Constants：

2.43 (at 25 °C)

Collision Cross Section：

138 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|139.51 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|132 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine]|137.7 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|139.4 Å² [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|135.4 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|135.5 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

24/25-36-26

Marks：

Precautionary statement(s)：

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

Hazard Statements：

H315

Drug Information

Drug Indication：

Used for nutritional supplementation, also for treating dietary shortage or imbalance.

Pharmacology：

A non-essential amino acid and a precursor of arginine. Citrulline supplements have been claimed to promote energy levels, stimulate the immune system and help detoxify ammonia (a cell toxin). L-citrulline is made from L-ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from L-arginine as a by-product of the reaction catalyzed by the enzyme NO synthase. L-citrulline, while being an amino acid, is not involved in protein synthesis and is not one of the amino acids coded for by DNA. Although citrulline cannot be incorporated in proteins during protein synthesis, several proteins are known to contain citrulline as an amino acid. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert the amino acid arginine into citrulline. Proteins that contain citrulline residues include myelin basic protein (MBP), fillagrin and several histone proteins.

Mechanism of Action：

L-citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic affects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3',5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase.

NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium.

All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O₂) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, L-arginine could enhance endothelial-dependent vasodilation and NO production.

MeSH Entry Terms：

Citrulline

Citrulline Use and Manufacturing

Uses

An essential intermediate in the biosynthesis of nitric oxide.

Manufacturing Info：

L-Ornithine, N5-(aminocarbonyl)-: ACTIVE

Use Classification：

Cosmetics -> Skin conditioning

Computed Properties

Molecular Weight:175.19
XLogP3:-4.3
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:5
Exact Mass:175.09569129
Monoisotopic Mass:175.09569129
Topological Polar Surface Area:118
Heavy Atom Count:12
Complexity:171
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Urea

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