化工社化工社 化学情報印刷レポート · 研究参考用
L-シトルリン
L-シトルリン · N5-(アミノカルボニル)-L-オルニチン · N5-アミノカルボニル-L-オルニチン · L-2-アミノ-5-ウレイド吉草酸 · N5-カルバモイル-L-オルニチン · (S)-2-アミノ-5-ウレイド吉草酸 · シトルリン · L‐シトルリン
識別子と物理属性
| CAS No. | 372-75-8 |
|---|---|
| 分子式 | C6H13N3O3 |
| 平均分子量 | 175.19 g/mol |
| 単同位体質量 | 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 |
| 現地名 | L-シトルリン |
化学・物理的性質
| XLogP | -4.3 |
|---|---|
| 極性表面積 | 118 |
| 水素結合供与体数 | 4 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 5 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 171 |
| LogP（分配係数） | -3.19 |
| 溶解度 | 200212 mg/mL水性酸（控えめに）。水（少々）200g/L(20℃) |
| 融点 | 235.5235.5 °C214 °C |
| Physical Description | Solid |
| Dissociation Constants | 2.43 (at 25 °C) |
| Collision Cross Section | 138 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]132 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]135.4 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]137.7 Ų [M+H]+ [CCS Type: DT139.4 Ų [M+Na]+ [CCS Type: DT139.51 Ų [M-H]- [CCS Type: DTMethod: stepped-field]135.5 Ų [M-H]-139.2 Ų [M+Na]+ |
| 比旋光度 | 25.5 º (c=8, 6N HCl) |
| 沸点 | 306.48°C (rough estimate) |
| 密度 | 1.2919 (rough estimate) |
| 屈折率 | 26 ° (C=8, 6mol/L HCl) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 外観・状態 | 結晶または結晶性粉末 |
| pKa（酸解離定数） | 2.43(at 25℃) |
| 色 | 白い |
| 臭い | 無臭 |
| Merck | 14,2331 |
| BRN | 6055157 |
| 主な用途 | 検査 |
| 化粧品成分の機能 | スキンコンディショニング |
| 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（分配係数） | -3.190 |
| CAS データベース | 372-75-8(CAS DataBase Reference) |
| EPAの化学物質情報 | L-Ornithine, N5-(aminocarbonyl)- (372-75-8) |
化学的特性
White powder
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | Chemical: L-Ornithine, N5-(aminocarbonyl)-L-Ornithine, N5-(aminocarbonyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | 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%) |
| 毒性の概要 | 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). |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29241900 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (9)-503 |
| 危険表示 | Xi |
| 安全措置（S） | 24/25-36-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
解説
プリズム状(水，メタノール)．融点222 ℃(分解)．[α]20D＋3.2°(水)．p-ジメチルアミノベンズアルデヒド塩酸塩で黄色を呈する．生体内では，オルニチンサイクル中で尿素の生成に重要な役割を果たしている．森北出版「化学辞典（第2版）
使用
An amino acid, L-Citrulline can be used in the treatment of asthenia and as an essential intermediate in the biosynthesis of nitric oxide.
製法・合成法
純化方法
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.]