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

• ChemBase ID: 34851
• Molecular Formular: C11H9NO2
• Molecular Mass: 187.19466
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-3-(1H-indol-3-yl)prop-2-enoic acid; 3-(1H-indol-3-yl)prop-2-enoic acid
• IUPAC Traditional name: (2E)-3-(1H-indol-3-yl)prop-2-enoic acid; 3-indoleacrylic acid
• Synonyms: (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; 反式-3-吲哚丙烯酸; 反式吲哚-3-丙烯酸

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 4.650101
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.3284619
• LogD (pH = 7.4): -0.44907793
• Log P: 2.2348483
• Molar Refractivity: 54.1464 cm^3
• Polarizability: 21.407972 Å^3
• Polar Surface Area: 53.09 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: IRRITANT; Irritant; Irritant/Light Sensitive
• RTECS: NL3680000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (HPLC); ≥99.0% (HPLC); 98%; 98+%
• Grade: matrix substance for MALDI-MS; puriss. p.a.; purum
• Cation Traces: 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

DETAILS

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

Packaging
1, 10 g in glass bottle
Application
Metabolite of tryptophan.1