시트룰린

L-(+)-시트룰린 · L-시트룰린 · 시트룰린 · CITRULLINE · (S)-2-AMINO-5-UREIDOPENTANOIC ACID · H-CIT-OH · L-CITRULINE · L-CIT

식별자 및 물리적 특성

CAS No.	372-75-8
분자식	C6H13N3O3
평균 분자량	175.19 g/mol
단동위원소 질량	175.09569129 g/mol
SMILES	NC(=O)NCCC[C@H](N)C(=O)O
InChIKey	RHGKLRLOHDJJDR-BYPYZUCNSA-N
PubChem CID	9750
ChEMBL	CHEMBL444814
ChEBI	CHEBI:16349
EC No.	206-759-6
DTXSID	DTXSID80883373
현지명	시트룰린

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
LogP(분배 계수)	-3.19
용해도	200212 mg/mL수성 산(드물게). 물(약간 용해됨)
녹는점	235.5235.5 °C214 °C
Physical Description	Solid
Dissociation Constants	2.43 (at 25 °C)
Collision Cross Section	138 Å² [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]132 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]135.4 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]137.7 Å² [M+H]+ [CCS Type: DT139.4 Å² [M+Na]+ [CCS Type: DT139.51 Å² [M-H]- [CCS Type: DTMethod: stepped-field]135.5 Å² [M-H]-139.2 Å² [M+Na]+
끓는 점	306.48°C (rough estimate)
밀도	1.2919 (rough estimate)
굴절률	26 ° (C=8, 6mol/L HCl)
저장 조건	Keep in dark place,Sealed in dry,Room Temperature
물리적 상태	결정 또는 결정성 분말
pKa(산도 계수)	2.43(at 25℃)
색상	하얀색
냄새	냄새 없는
용해도	200g/L(20℃)
Merck	14,2331
BRN	6055157
주요 응용	발각
화장품 원료 기능	피부 컨디셔닝
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
InChIKey	RHGKLRLOHDJJDR-BYPYZUCNSA-N
SMILES	N[C@@H](CCCNC(N)=O)C(O)=O
LogP(분배 계수)	-3.190
EPA	L-Ornithine, N5-(aminocarbonyl)- (372-75-8)

화학적 성질

White powder

안전 및 규제

GHS 분류	This chemical does not meet GHS hazard criteria for 14.5% (10 of 69) of reports.WarningH315 (85.5%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (85.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 10 of 69 reports by companies.There are 2 notifications provided by 59 of 69 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
규제 정보	Chemical: L-Ornithine, N5-(aminocarbonyl)-L-Ornithine, N5-(aminocarbonyl)-: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보	Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazard Classes and Categories	Skin Irrit. 2 (85.5%)Eye Irrit. 2A (85.5%)
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
Carcinogen Classification	No indication of carcinogenicity to humans (not listed by IARC).
수질 위해 등급(WGK)	3
TSCA 등재 상태	TSCA listed
관세 코드	29241900
위험 문구(R)	36/37/38
위험 표시	Xi
안전 문구(S)	24/25-36-26
저장 분류	11 - Combustible Solids

용도

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