3-インドールプロピオン酸

1H-Indole-3-propanoic acid

HCID 3744CAS 830-96-6

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

3-Indolepropionic acid830-96-6Indole-3-propionic acid1H-Indole-3-propanoic acidIndolepropionic acid3-(3-Indolyl)propionic acid3-(3-Indolyl)propanoic acidOxigon3-(Indol-3-yl)propionic acid1H-INDOLE-3-PROPIONIC ACID3-(3-Indole)propionic acidbeta-(3-Indolyl)propionic acid
名称をさらに表示
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-プロパン酸インド-ル-3-プロピオン酸インドール-3-プロピオン酸インドール‐3‐プロピオン酸インドール-3-プロピオン酸, 98%PROPAN-2-OL3-(1H-INDOL-3-YL)PROPANOIC ACIDISOPROPYL ALCOHOISOPROPANEFEMA 2929ISOPROPANOISOPROPANOL ALCOHOL2-PPROPANOL
3-Indolepropionicacidindole-3-propanoic acidJF49U1Q7KN1H-Indole-3-proponoic acidVP-20629NSC-3252NSC-47831SHP622

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

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP1.75
Melting Point134 - 135 °C
Physical DescriptionSolid

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.)

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 · 5 件

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

Regulatory Information1H-Indole-3-propanoic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (18.2%)

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

化学と産業

薬理情報

Cellular LocationsMembrane

用途と製造

General Manufacturing Information1H-Indole-3-propanoic acid: INACTIVE
応用分野 · 3 件

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.]

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

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

63 件

関連ノート

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