L-(-)-キシロース
L-(-)-キシロース · (-)-L-キシロース · (2S,3R,4S)-2,3,4,5-テトラヒドロキシペンタナール · L-キシロース · L(-)-キシロース · L(-)‐キシロース · キシロース, L- · L-キシロ-ス
識別子と物理属性
| CAS No. | 609-06-3 |
|---|---|
| 分子式 | C5H10O5 |
| 平均分子量 | 150.13 g/mol |
| 単同位体質量 | 150.05282342 g/mol |
| SMILES | O=C[C@@H](O)[C@H](O)[C@@H](O)CO |
| InChIKey | PYMYPHUHKUWMLA-WISUUJSJSA-N |
| PubChem CID | 95259 |
| ChEBI | CHEBI:17979 |
| EC No. | 210-174-1 |
| DTXSID | DTXSID50883340 |
| 現地名 | L-(-)-キシロース |
化学・物理的性質
| XLogP | -2.3 |
|---|---|
| 極性表面積 | 98 |
| 水素結合供与体数 | 4 |
| 水素結合受容体数 | 5 |
| 回転可能結合数 | 4 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 104 |
| 融点 | 150-152 °C(lit.) |
| 沸点 | 191.65°C (rough estimate) |
| 密度 | 1.525 |
| 屈折率 | -20 ° (C=10, H2O) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 溶解度 | H2O: 0.1 g/mL 無色透明ほぼ透明度内 |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 12.46±0.20(Predicted) |
| 色 | ホワイトからオフホワイト |
| BRN | 1723080 |
| InChI | 1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4+,5+/m1/s1 |
| InChIKey | SRBFZHDQGSBBOR-VVZXFQNISA-N |
| SMILES | O[C@H]1COC(O)[C@@H](O)[C@@H]1O |
| LogP（分配係数） | -2.390 (est) |
| CAS データベース | 609-06-3(CAS DataBase Reference) |
| EPAの化学物質情報 | L-Xylose (609-06-3) |
化学的特性
L-Xylose is a white fine crystalline powder. It is an aldopentose that has a molecular formula C5H10O5 and a molar mass of 150.13 g/mol. The structure of L-xylose is presented in Figure 1. The optical rotations of D- and L-xylose are α20D = -18.6° and α20D = +18.6°, respectively (Fischer and Ruff, 1900). L-Xylose can exist in open chain form, as a pyranose or as a furanose. The relative concentrations of different stereoisomers have not been specified for L-xylose. However, for D-xylose the distribution of different forms in water are: 36.5% α-pyranose, 6% β-pyranose and less than 1 % in open chain and furanose form (Pastinen, 2000). Most likely L-xylose acts similarly to its enantiomer, and thus pyranose rings are predominant.Figure 1. Structure of L-xylose A) as a Fischer projection, B) as a ball and stick model in acyclic form and C) as a ball and stick model in pyranose ring form.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 71.4% (5 of 7) of all reports.WarningH315 (28.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | L-Xylose: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (28.6%) |
| F | 3-10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 29400000 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (9)-318 届出不要化学物質 |
| 危険表示 | Xi |
| 安全措置（S） | 24/25-36-26 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
使用
L-Xylose is used in the synthesis of L-Xylose derivatives as selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
製法・合成法
製造方法
L-Xylose can be produced from L-xylulose by isomerization. This can be achieved either enzymatically or chemically under alkaline conditions. The equilibrium of the reaction between D-xylose and D-xylulose in an aqueous solution has been determined at pH 6.8-7.4 and at 25 °C to be 85:15 in favor of D-xylose (Tewari et al., 1985).