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1204-06-4

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1204-06-4 Usage

Chemical Properties

light yellow to yellow-beige crystalline powder

Uses

3-Indoleacrylic acid has been used in the induction of ribokinase expression in E. coli.

Synthesis Reference(s)

Synthesis, p. 236, 1984 DOI: 10.1055/s-1984-30787

General Description

3-Indoleacrylic acid (IAA) is a chemical used for the induction of gene transcription. This expression system requires that the gene of interest is cloned in plasmids containing the trpE promoter.

Biochem/physiol Actions

3-Indoleacrylic acid helps to block the mycelial growth of?Neurospora crassa. As a result, the cells accumulate indoleglycerol phosphate, which influences the rate of tryptophan synthetase.

Purification Methods

Recrystallise the acid from AcOH, H2O or EtOAc/cyclohexane. UV in MeOH has at 225, 274 and 325nm. [Shaw et al. J Org Chem 23 1171 1958, constitution: Rappe Acta max Chem Scand 18 818 1964, Moffatt J Chem Soc 1442 1957, Kimming et al. Hoppe Seyler's Z Physiol Chem 371 234 1958, Beilstein 22 V 249.]

Check Digit Verification of cas no

The CAS Registry Mumber 1204-06-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,0 and 4 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1204-06:
(6*1)+(5*2)+(4*0)+(3*4)+(2*0)+(1*6)=34
34 % 10 = 4
So 1204-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C39H38N4O14/c1-17-18(2-6-33(44)45)26-14-30-23(11-38(54)55)20(4-8-35(48)49)28(42-30)16-32-24(12-39(56)57)21(5-9-36(50)51)29(43-32)15-31-22(10-37(52)53)19(3-7-34(46)47)27(41-31)13-25(17)40-26/h13-16,41-42H,2-12H2,1H3,(H,44,45)(H,46,47)(H,48,49)(H,50,51)(H,52,53)(H,54,55)(H,56,57)/b25-13-,26-14-,27-13-,28-16-,29-15-,30-14-,31-15-,32-16-

1204-06-4 Well-known Company Product Price

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  • Sigma

  • (I2273)  3-Indoleacrylic acid  BioReagent, ≥98% (HPLC)

  • 1204-06-4

  • I2273-1G

  • 765.18CNY

  • Detail
  • Sigma

  • (I2273)  3-Indoleacrylic acid  BioReagent, ≥98% (HPLC)

  • 1204-06-4

  • I2273-5G

  • 2,851.29CNY

  • Detail

1204-06-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Indoleacrylic acid

1.2 Other means of identification

Product number -
Other names 2-Propenoic acid, 3-(1H-indol-3-yl)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1204-06-4 SDS

1204-06-4Relevant articles and documents

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Suvorov et al.

, (1968)

-

Induction of Apoptosis in Hepatocellular Carcinoma Cell Lines by Novel Indolylacrylamide Derivatives: Synthesis and Biological Evaluation

Hawash, Mohammed,Kahraman, Deniz Cansen,Cetin-Atalay, Rengul,Baytas, Sultan Nacak

, (2021/04/28)

Hepatocellular carcinoma (HCC) is the most prevalent primary liver cancer and one of the leading causes of cancer associated death worldwide. This is due to the highly resistant nature of this malignancy and the lack of effective treatment options for advanced stage HCC patients. The hyperactivity of PI3K/Akt and Ras/Raf/MEK/ERK signaling pathways contribute to the cancer progression, survival, motility, and resistance mechanisms, and the interaction of these two pathways are responsible for the regulation of cancer cell growth and development. Therefore, it is vital to design and develop novel therapeutic options for HCC treatment targeting these hyperactive pathways. For this purpose, novel series of trans-indole-3-ylacrylamide derivatives originated from the lead compound, 3-(1H-indole-3-yl)-N-(3,4,5-trimethoxyphenyl)acrylamide, have been synthesized and analyzed for their bioactivity on cancer cells along with the lead compound. Based on the initial screening, the most potent compounds were selected to elucidate their effects on cellular signaling activity of HCC cell lines. Cell cycle analysis, immunofluorescence, and Western blot analysis revealed that lead compound and (E)-N-(4-tert-butylphenyl)-3-(1H-indole-3-yl)acrylamide induced cell cycle arrest at the G2/M phase, enhanced chromatin condensation and PARP-cleavage, addressing induction of apoptotic cell death. Additionally, these compounds decreased the activity of ERK signaling pathway, where phosphorylated ERK1/2 and c-Jun protein levels diminished significantly. Relevant to these findings, the lead compound was able to inhibit tubulin polymerization as well. To conclude, the novel trans-indole-3-ylacrylamide derivatives inhibit one of the critical pathways associated with HCC which results in cell cycle arrest and apoptosis in HCC cell lines.

Synthesis and antiinflammatory activity of indolylacrylic and methylacrylic acids

Andreani,Rambaldi,Locatelli,Pifferi

, p. 903 - 906 (2007/10/02)

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