(2E)-3-(1H-indol-3-yl)prop-2-enoic acid

• ChemBase编号: 34851
• 分子式: C11H9NO2
• 平均质量: 187.19466
• 单一同位素质量: 187.06332853
• SMILES: [nH]1cc(/C=C/C(=O)O)c2c1cccc2
• Canonical SMILES: OC(=O)/C=C/c1c[nH]c2c1cccc2
• InChI: InChI=1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+
• InChIKey: PLVPPLCLBIEYEA-AATRIKPKSA-N

名称和登记号

名称

• IUPAC标准名: (2E)-3-(1H-indol-3-yl)prop-2-enoic acid; 3-(1H-indol-3-yl)prop-2-enoic acid
• IUPAC传统名: (2E)-3-(1H-indol-3-yl)prop-2-enoic acid; 3-indoleacrylic acid
• 别名: 反式-3-吲哚丙烯酸; 反式吲哚-3-丙烯酸; (2E)-3-(1H-Indol-3-yl)acrylic acid; 3-(3-Indolyl)acrylic acid; IAA; INDOLE-3-ACRYLIC ACID; trans-3-(1H-Indol-3-yl)prop-2-enoic acid; trans-3-Indoleacrylic acid; 3-Indoleacrylic acid; trans-3-(3-Indolyl)-2-propenoic acid; trans-Indolyl-3-acrylic acid; trans-Indole-3-acrylic acid; 3-(1H-Indol-3-yl)prop-2-enoic acid; 3-(1H-Indol-3-yl)acrylic acid

登记号

• CAS号: 1204-06-4; 29953-71-7
• EC号: 214-872-7
• MDL号: MFCD00005633
• Beilstein号: 6317
• PubChem SID: 24896048; 160998158; 24880662; 24895938; 24880663; 24895972
• PubChem CID: 5375048

理论计算性质

• Acid pKa: 4.650101
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.3284619
• LogD (pH = 7.4): -0.44907793
• Log P: 2.2348483
• 摩尔折射率: 54.1464 cm^3
• 极化性: 21.407972 Å^3
• 极化表面积: 53.09 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: powder; white to off-white, faint gray or faint yellow to light yellow
• 熔点: ~190 °C (dec.); 183-185°C; 185 °C (dec.)(lit.); 185°C; ca 185°Cdec.

安全信息

• 保存条件: 2-8°C
• 保存注意事项: IRRITANT; Irritant; Irritant/Light Sensitive
• RTECS编号: NL3680000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36; 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥97.0% (HPLC); ≥98% (HPLC); ≥99.0% (HPLC); 98%; 98+%
• 级别: matrix substance for MALDI-MS; puriss. p.a.; purum
• 痕量阳离子: Ba: ≤5 mg/kg; Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤100 mg/kg; K: ≤20 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• abs.: absorption/337 nm ≥2000 (mol. absorption)
• Empirical Formula (Hill Notation): C11H9NO2

详细说明

MP Biomedicals - 02102040

Crystalline
Light yellow crystals.
A metabolite of tryptophan.

Sigma Aldrich - I2273

Application
3-indoleacrylic acid may be used in various microbiology studies to induce transcription of genes under the control of the trpE promoter.
Biochem/physiol Actions
Induces transcription of genes under the control of the trpE promoter.1 IAA also transcriptionally activates gene expression in plants.2,3 Some of the genes that are induced by IAA encode a family of proteins that contain nuclear localization signals that direct a β-glucuronidase reported protein into the nucleus.4

Sigma Aldrich - I1625

Application
3-indoleacrylic acid may be used in various microbiology studies to induce gene expression.1,2

Sigma Aldrich - 57290

Other Notes
Tryptophan anti-metabolite, inhibits the conversion of indole to tryptophan by tryptophan synthetase in Sacchamomyces cerevisiae1

Sigma Aldrich - I3807

包装
1, 10 g in glass bottle
Application
色氨酸代谢产物。1