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3-吲哚丙酸(IPA)

3-吲哚丙酸(IPA)用途

3-Indolepropionic acid 是一个强效的抗氧化剂,有治疗阿尔兹海默症 (Alzheimer’s) 的潜能。

3-吲哚丙酸(IPA)名称

[ CAS 号 ]:
830-96-6

[ 中文名 ]:
3-吲哚丙酸

[ 英文名 ]:
3-Indolepropionic acid

[中文别名 ]:

[英文别名 ]:

3-Indolepropionic acid
MFCD00005660
1H-Indole-3-propanoic acid
3-(1H-Indol-3-yl)propanoic acid
b-(3-Indolyl)propionic acid
Indole-3-propionic acid
EINECS 212-600-1
3-(1H-Indol-3-yl)propionic acid
IPA

3-吲哚丙酸(IPA)生物活性

[ 描述 ]:

3-Indolepropionic acid 是一个强效的抗氧化剂,有治疗阿尔兹海默症 (Alzheimer’s) 的潜能。

[ 相关类别 ]:

天然产物 >> 糖和糖苷

研究领域 >> 代谢疾病

研究领域 >> 神经疾病

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

3-吲哚丙酸被证明是一种强大的抗氧化剂,具有治疗阿尔茨海默病的潜力[1]。 3-吲哚丙酸是比褪黑激素更有效的羟基自由基清除剂。与褪黑激素类似,但与其他抗氧化剂不同,3-吲哚丙酸清除自由基而不随后产生反应性和促氧化的中间体化合物[2]。还有人提出,吲哚丙酸是一种肠道微生物群产生的代谢产物,是2型糖尿病(T2D)发展的潜在生物标志物,可通过保持β细胞功能来介导其保护作用[3]。

[参考文献]

[1]. Wikoff WR, et al. Metabolomics analysis reveals large effects of gut microflora on mammalian blood metabolites. Proc Natl Acad Sci U S A. 2009 Mar 10;106(10):3698-703.

[2]. Reiter RJ, et al. Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin. Ann N Y Acad Sci. 1998 Nov 20;854:410-24.

[3]. de Mello VDet al. Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study. Sci Rep. 2017 Apr 11;7:46337. doi: 10.1038/srep46337.

[相关活性小分子]

3-吲哚丙酸(IPA)物理化学性质

[ 密度 ]:
1.3±0.1 g/cm3

[ 沸点 ]:
417.6±20.0 °C at 760 mmHg

[ 熔点 ]:
134-135 °C(lit.)

[ 分子式 ]:
C₁₁H₁₁NO₂

[ 分子量 ]:
189.210

[ 闪点 ]:
206.4±21.8 °C

[ 精确质量 ]:
189.078979

[ PSA ]:
53.09000

[ LogP ]:
1.76

[ 外观性状 ]:
灰白色晶体

[ 蒸汽密度 ]:
2.1 (vs air)

[ 蒸汽压 ]:
0.0±1.0 mmHg at 25°C

[ 折射率 ]:
1.667

[ 储存条件 ]:
−20°C

[ 水溶解性 ]:
slightly soluble

3-吲哚丙酸(IPA)MSDS

3-吲哚丙酸(IPA)毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NM1329000

CHEMICAL NAME :: 1H-Indole-3-propionic acid

CAS REGISTRY NUMBER :: 830-96-6

BEILSTEIN REFERENCE NO. :: 0147733

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C11-H11-N-O2

MOLECULAR WEIGHT :: 189.23

WISWESSER LINE NOTATION :: T56 BMJ D2VQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 34,138,1936

3-吲哚丙酸(IPA)安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xi:Irritant;

[ 风险声明 (欧洲) ]:
R22;R36/37/38

[ 安全声明 (欧洲) ]:
S7-S16-S24/25-S26-S36/37-S37/39-S22

[ 危险品运输编码 ]:
UN 1987 3/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
NT8050000

[ 海关编码 ]:
29339990

3-吲哚丙酸(IPA)合成路线

3-吲哚丙酸(IPA)上下游产品

3-吲哚丙酸(IPA)上游产品

3-吲哚丙酸(IPA)下游产品

3-吲哚丙酸(IPA)制备

制备方法：将苯胺盐酸盐在酸性条件下加亚硝酸钠重氮化，然后与环戊酮-2-羧酸乙酯反应，制得α-羰基乙二酸苯腙。将所得苯腙溶于含20%硫酸的乙醇溶液中，回流反应4h，生成吲哚-2-羧酸-3-丙酸。将其加热至225-230℃，约半小时反应结束，将反应物溶于沸水中，加活性炭脱色，过滤。滤液浓缩，结晶，用热水重结晶，得3-吲哚丙酸。

3-吲哚丙酸(IPA)海关

[ 海关编码 ]: 2933990090

[ 中文概述 ]:
2933990090. 其他仅含氮杂原子的杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-吲哚丙酸(IPA)文献

Metabolomics Approach Reveals Integrated Metabolic Network Associated with Serotonin Deficiency.

Sci. Rep. 5 , 11864, (2015)

Serotonin is an important neurotransmitter that broadly participates in various biological processes. While serotonin deficiency has been associated with multiple pathological conditions such as depre...

QSAR study on permeability of hydrophobic compounds with artificial membranes.

Bioorg. Med. Chem. 15 , 3756-67, (2007)

We previously reported a classical quantitative structure-activity relationship (QSAR) equation for permeability coefficients (P(app-pampa)) by parallel artificial membrane permeation assay (PAMPA) of...

Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K.

J. Med. Chem. 52 , 2786-93, (2009)

Human kynurenine aminotransferase I (hKAT I) catalyzes the formation of kynurenic acid, a neuroactive compound. Here, we report three high-resolution crystal structures (1.50-1.55 A) of hKAT I that ar...

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