基本情報
- 標準SMILES
O=C(O)CCc1c[nH]c2ccccc12- InChIKey
GOLXRNDWAUTYKT-UHFFFAOYSA-N- 分子式
- C11H11NO2
- 平均分子量
- 189.21 g/mol
- 単同位体質量
- 189.07897859
概要
3-(1H-indol-3-yl)propanoic acid is an indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3. It has a role as an auxin, a plant metabolite and a human metabolite. It is functionally related to a propionic acid. It is a conjugate acid of a 3-(1H-indol-3-yl)propanoate.
名称と識別子
- 優先名称
- 1H-Indole-3-propanoic acid
- IUPAC
- 3-(1H-indol-3-yl)propanoic acid
- 現地名
- 3-インドールプロピオン酸
- 英語名
- 3-Indolepropionic acid
- 分子式
- C11H11NO2
- 分子量
- 189.21
名称と別名
名称をさらに表示
データベース識別子
- CAS
830-96-6- PubChem CID
- 3744
- DTXSID
DTXSID7061192- ChEMBL
CHEMBL207225- ChEBI
CHEBI:43580- UNII
- JF49U1Q7KN
- EC Number
- 212-600-1
- Nikkaji
- J7.131E
物性
構造計算による物性
- XLogP
- 1.8
- 極性表面積
- 53.1 Ų
- 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
実験および物理化学的性質
物理化学的性質
- 融点
- 133 °C · ~133 °C
- 沸点
- 82 °C · 82 °C(lit.)
- 比重(密度)
- 0.96 g/mL · 0.960 g/mL at 20 °C
- 蒸気密度
- 2.1 · 2.1 (vs air)
- 蒸気圧
- 33 mm · 33 mm Hg ( 20 °C)
- 屈折率
- 20 · n20/D 1.377(lit.)
- 闪点
- 53 °F · 53 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- 50 mg/mL、透明、黄色から橙色 · エタノール: 可溶50mg/mL、透明、黄色から橙色
- 酸解離定数(Pka)
- 4.77 · 4.77±0.10(Predicted)
- 外見
- 結晶性
- 色
- ライトイエロー
- 水溶解度
- わずかに溶ける
- BRN
- 147733 · 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 · 830-96-6(CAS DataBase Reference)
- NISTの化学物質情報
- -3 · Indole-3-propionic acid(830-96-6)
- EPAの化学物質情報
- 1 H-Indole-3-propanoic · 1H-Indole-3-propanoic acid (830-96-6)
化学的性質
化学的特性pale yellow to yellow crystalline powder
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 18.2% (2 of 11) of reports.
Warning
H302 (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.
危険有害性情報
安全データ
- F
- 8-10-23
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- NM1329000
- 毒性
- LDLo intraperitoneal in mouse: 100mg/kg
- hs_code
- 29339990
- risk_code
- 22-36/37/38
- hazard_code
- Xi
- safety_code
- 26-37/39
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
用途と製造
応用分野
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.
調製方法
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: An indol-3-yl carboxylic acid that is propionic acid substituted by a 1H-indol-3-yl group at position 3.
関連反応
関連ノート
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