Indole-3-acetic acid

Base Information

• Chemical Name: Indole-3-acetic acid
• CAS No.: 87-51-4
• Deprecated CAS: 54692-39-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933.99
• European Community (EC) Number: 201-748-2
• NSC Number: 3787
• UNII: 6U1S09C61L
• DSSTox Substance ID: DTXSID5020738
• Nikkaji Number: J5.156J
• Wikipedia: Indole-3-acetic acid
• Wikidata: Q411208
• Metabolomics Workbench ID: 37131
• ChEMBL ID: CHEMBL82411
• Mol file: 87-51-4.mol

Synonyms:1H-Indole-3-acetic acid;3-indoleacetic acid;3-indolylacetic acid;beta-indoleacetic acid;heteroauxin;IES cpd;indole acetic acid;indole-3-acetic acid;indoleacetate;indoleacetic acid;indoleacetic acid, alpha-(14)C-labeled;indoleacetic acid, calcium salt;indoleacetic acid, monopotassium salt;indoleacetic acid, monosodium salt;indolyl-3-acetic acid

Chemical Property of Indole-3-acetic acid

Chemical Property:

• Appearance/Colour: white to tan crystals
• Vapor Pressure: 1.24E-07mmHg at 25°C
• Melting Point: 165-169 °C(lit.)
• Refractive Index: 1.5460 (estimate)
• Boiling Point: 415.03 °C at 760 mmHg
• PKA: 4.75(at 25℃)
• Flash Point: 204.803 °C
• PSA: 53.09000
• Density: 1.355 g/cm³
• LogP: 1.79500
• Storage Temp.: −20°C
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble in ethanol (50 mg/ml), methanol, DMSO, and chloroform (sparingly). Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

Indole-3-acetic ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)O
• Recent ClinicalTrials: Idarubicin Plus Cytarabine (IA) vs IA Plus Cladribine (IAC) as Induction Regimen to Treat Initially Diagnosed Acute Myeloid Leukemia (AML)
• Uses: Plant growth regulator. It is applied as plant growth hormone. is an inducer of plant cell elongation and division shown to cause uncontrolled growth.
• Biological Functions: 3-Indolylacetic acid (indole-3-acetic acid, IAA) is one of the auxins, which together with the gibberellins and abscisic acid, cyto- kinins and ethylene are hormones regulating the growth and development of plants. IAA is a ubiquitous constituent of higher plants and the most important auxin. Some other, non-indolic compounds, including phenyl- acetic acid biosynthesised in plants from phenylalanine, have similar properties and synthetic auxins have also been prepared. In the plant, IAA conjugates with many compounds, including glucose and other sugars, and with aspartic and glutamic acids. This is probably a way of storing the hormone for future use. IAA initiates many growth effects in plants, including geotropism and phototropism, development of the ovary, division of cells, enlargement in callus tissue, root formation and apical dominance. When fed to plants, the hormone causes growth up to a maximum, which depends on the type of tissue being fed, and thereafter inhibits further growth, probably through the formation of ethylene, which is growth-inhibitory. Stern tissues tolerate the highest levels of IAA and root tissues the lowest. In the plant, the most active sites of IAA synthesis are the young, expanding leaves.

Technology Process of Indole-3-acetic acid

There total 70 articles about Indole-3-acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

indole (120-72-9) → indole-3-acetic acid (87-51-4)

Guidance literature:

With potassium hydroxide; In water; at 250 ℃; for 12h; under 34200 - 38000 Torr;

DOI:10.1007/BF00504405

Reference yield: 52.0%

(5-bromo-1H-indol-3-yl)-acetic acid (40432-84-6) → indole-3-acetic acid (87-51-4)

Guidance literature:

With hydrogen; sodium acetate; nickel; In ethanol; for 4h; under 2327.2 Torr; Ambient temperature;

DOI:10.1016/0031-9422(80)85060-6

Reference yield: 36.0%

→ 3-Methylindole (83-34-1) + indole-3-carbinol (700-06-1) + indole-3-acetic acid (87-51-4) + 3-(3-methylindol-1-yl)methylindole (59027-01-9)

Guidance literature:

With 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide; In acetonitrile; for 0.0833333h; Irradiation;

DOI:10.1248/cpb.37.3239

upstream raw materials:

diazoacetic acid ethyl ester

indole

glycolic Acid

indole-3-acetaldehyde

Downstream raw materials:

N-indol-3-ylacetyl-valine

Indole-3-acetic acid methyl ester

(1-methyl-1H-indol-3-yl)acetic acid methyl ester

ethyl 3-indoleacetate

Refernces

• 1、 Moore. "-". . p. 1109. Retrieved 1969.
• 2、 Eryshev, B. Ya.,Smushkevich, Yu. I.,Suvorov, N. N.. "INDOLE DERIVATIVES. 127. INVESTIGATION OF THE ALKYLATION OF INDOLE BY POLYESTERS". . p. 433 - 435. Retrieved 1985.
• 3、 Alnouti, Yazen,Aretz, Christopher D.,Chhonker, Yashpal S.,Dhuria, Nikilesh V.,Du, Yu,Gautam, Nagsen,Hopkins, Corey R.,Kumar, Sushil,Lesiak, Lauren,Sharma, Swagat,Weaver, C. David. "Discovery, synthesis and biological characterization of a series of: N -(1-(1,1-dioxidotetrahydrothiophen-3-yl)-3-methyl-1 H -pyrazol-5-yl)acetamide ethers as novel GIRK1/2 potassium channel activators". supporting information. p. 1366 - 1373. Retrieved 2021/09/28.
• 4、 Al-Sanea, Mohammad M.,Obaidullah, Ahmad J.,Shaker, Mohamed E.,Chilingaryan, Garri,Alanazi, Mohammed M.,Alsaif, Nawaf A.,Alkahtani, Hamad M.,Alsubaie, Sultan A.,Abdelgawad, Mohamed A.. "A new CDK2 inhibitor with 3-hydrazonoindolin-2-one scaffold endowed with anti-breast cancer activity: Design, synthesis, biological evaluation, and in silico insights". . . Retrieved 2021/02/27.