3-インドールプロピオン酸
3-インドールプロピオン酸 · 3-(1H-インドール-3-イル)プロピオン酸 · インドールプロピオン酸 · 3-(1H-インドール-3-イル)プロパン酸 · 1H-インドール-3-プロピオン酸 · 3-インドリルプロピオン酸 · IPA【オーキシン】 · 1H-インドール-3-プロパン酸
識別子と物理属性
| CAS No. | 830-96-6 |
|---|---|
| 分子式 | C11H11NO2 |
| 平均分子量 | 189.21 g/mol |
| 単同位体質量 | 189.07897859 g/mol |
| SMILES | O=C(O)CCc1c[nH]c2ccccc12 |
| InChIKey | GOLXRNDWAUTYKT-UHFFFAOYSA-N |
| PubChem CID | 3744 |
| ChEMBL | CHEMBL207225 |
| ChEBI | CHEBI:43580 |
| EC No. | 212-600-1 |
| DTXSID | DTXSID7061192 |
| 現地名 | 3-インドールプロピオン酸 |
化学・物理的性質
| XLogP | 1.8 |
|---|---|
| 極性表面積 | 53.1 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 3 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 217 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 1.75 |
| 融点 | 134 - 135 °C~133 °C |
| Physical Description | Solid |
| 沸点 | 82 °C(lit.) |
| 密度 | 0.960 g/mL at 20 °C |
| 蒸気密度 | 2.1 (vs air) |
| 蒸気圧 | 33 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.377(lit.) |
| 引火点 | 53 °F |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 溶解度 | エタノール: 可溶50mg/mL、透明、黄色から橙色わずかに溶ける |
| pKa（酸解離定数） | 4.77±0.10(Predicted) |
| 外観・状態 | 結晶性 |
| 色 | ライトイエロー |
| BRN | 147733 |
| InChI | 1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14) |
| InChIKey | GOLXRNDWAUTYKT-UHFFFAOYSA-N |
| SMILES | OC(=O)CCc1c[nH]c2ccccc12 |
| CAS データベース | 830-96-6(CAS DataBase Reference) |
| NISTの化学物質情報 | Indole-3-propionic acid(830-96-6) |
| EPAの化学物質情報 | 1H-Indole-3-propanoic acid (830-96-6) |
化学的特性
pale yellow to yellow crystalline powder
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 18.2% (2 of 11) of reports.WarningH302 (18.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 11 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | 1H-Indole-3-propanoic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (18.2%) |
| F | 8-10-23 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | NM1329000 |
| 毒性 | LDLo intraperitoneal in mouse: 100mg/kg |
| 税関コード | 29339990 |
| 危険文句（R） | 22-36/37/38 |
| 危険表示 | Xi |
| 安全措置（S） | 26-37/39 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
説明
3-Indolepropionic acid is a bacterial metabolite that has antioxidant and neuroprotective activities. It scavenges ABTS radicals in a cell-free assay when used at concentrations ranging from 50 to 150 μM and decreases hydrogen peroxide-induced malondialdehyde (MDA) levels in rat striatal membranes (IC50 = 180 μM). Indole-3-propionic acid also decreases increases in MDA levels induced by amyloid β (1-42) in PC12 cells. It decreases ischemia-induced increases in cell death of pyramidal neurons and levels of 4-hydroxy nonenal (HNE; ) and glial fibrillary acidic protein (GFAP) in the hippocampal CA1 region in gerbils when administered at a dose of 10 mg/kg per day.
使用
3-Indolepropionic acid is a deamination product of Tryptophan (T947200) that protects the hippocampus (studied in gerbils) from ischemic damage and oxidative stress. It’s ability to protect the neurons in this way is attributed to its potent antioxidative effects. 3-Indolepropionic acid is also hypothesized to have protective effects on the thyroid gland.
一般的な説明
3-Indolepropionic acid is an effective inhibitor of aggregation of misfolded β-amyloid protein (Abeta). Three-component one-pot procedure has been reported to assemble 3-indolepropionic acids.
製法・合成法
純化方法
Recrystallise it from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. The picrate has m 143-144o, and the methyl ester crystallises from *C6H6 or MeOH with m 81-83o. [Beilstein 22 III/IV 1113, 22/3 V 114.]