Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Citrulline, (+-)-
D-CITRULLINE · (R)-2-AMINO-5-UREIDOPENTANOIC ACID · C6H13N3O3 · H-D-Cit-OH · D-CITRULLIN · H-D-CITRULLINE · H-D-ORN(CONH2)-OH · D-Citrulline ,99%
식별자 및 물리적 특성
| CAS No. | 13594-51-9 |
|---|---|
| 분자식 | C6H13N3O3 |
| 평균 분자량 | 175.19 g/mol |
| 단동위원소 질량 | 175.09569128 g/mol |
| SMILES | NC(=O)NCCCC(N)C(=O)O |
| InChIKey | RHGKLRLOHDJJDR-UHFFFAOYSA-N |
| PubChem CID | 833 |
| ChEBI | CHEBI:18211 |
| EC No. | 211-012-2 |
| DTXSID | DTXSID40861910 |
화학 및 물리적 성질
| XLogP | -4.3 |
|---|---|
| 극성 표면적 | 118 |
| 수소 결합 공여자 수 | 4 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 5 |
| 무거운 원자 수 | 12 |
| 형식 전하 | 0 |
| 복잡도 | 171 |
| 녹는점 | 220-221°C |
| 끓는 점 | 386.7±42.0 °C(Predicted) |
| 밀도 | 1.289±0.06 g/cm3(Predicted) |
| 저장 조건 | -20°C |
| pKa(산도 계수) | 2.51±0.24(Predicted) |
| 물리적 상태 | powder |
| BRN | 1725415 |
| 주요 응용 | 펩타이드 합성 |
| InChI | 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-/m1/s1 |
| InChIKey | RHGKLRLOHDJJDR-SCSAIBSYSA-N |
| SMILES | C(O)(=O)[C@@H](CCCNC(N)=O)N |
화학적 성질
White powder
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.Not ClassifiedAggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | Chemical: DL-Ornithine, N5-(aminocarbonyl)- |
| 기타 안전 정보 | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| Hazard Classes and Categories | Not Classified |
| 독성 요약 | 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. <br/><br/>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. <br/><br/>All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O<sub>2</sub>) 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. <i>In vitro</i> 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, <i>in vivo</i> studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, L-arginine could enhance endothelial-dependent vasodilation and NO production. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| 수질 위해 등급(WGK) | 3 |
| 저장 분류 | 11 - Combustible Solids |