125537-93-1

Basic information

• Product Name: (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester
• Synonyms: (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester;Acremoauxin A
• CAS NO: 125537-93-1
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.34104
• Mol File: 125537-93-1.mol

Chemical Properties

• Boiling Point: 621.8°C at 760 mmHg
• Flash Point: 329.8°C
• Appearance: /
• Density: 1.411g/cm³
• Vapor Pressure: 2.55E-16mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester(125537-93-1)
• EPA Substance Registry System: (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester(125537-93-1)

Safety Data

• Hazardous Substances Data: 125537-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester is used as a pharmaceutical compound for its potential therapeutic properties. The indole and carboxylate ester groups in its structure may contribute to its interaction with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, (S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester serves as a valuable compound for studying the synthesis and properties of indolyl carboxylate esters. Its unique structure allows researchers to explore its reactivity, stability, and potential applications in various chemical reactions.
Used in Material Science:
(S)-α-Methyl-1H-indole-3-acetic acid 1-deoxy-D-arabinitol-1-yl ester may also find applications in material science, where its indole and carboxylate ester groups can be utilized to create new materials with specific properties. These materials could have potential uses in various industries, such as electronics, coatings, or adhesives, depending on their characteristics.

InChI:InChI=1/C16H21NO6/c1-9(11-6-17-12-5-3-2-4-10(11)12)16(22)23-8-14(20)15(21)13(19)7-18/h2-6,9,13-15,17-21H,7-8H2,1H3/t9-,13-,14-,15-/m1/s1

Upstream product

• 131768-74-6 1-O-<(2S)-2-(3-indolyl)propionyl>-2,3:4,5-di-O-isopropylidene-D-arabitol 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 21070-37-1 (S)-(+)-α-methyl-3-indolylacetic acid 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 2597-26-4 2-(1H-Indol-3-yl)-propionic acid 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 

Downstream Products

• 5346-78-1 D-arabinitol pentaacetate 
• 21070-37-1 (S)-(+)-α-methyl-3-indolylacetic acid 

Relevant articles and documents

Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: Total synthesis of acremoauxin A and oxazinin 3

Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion.

Synthesis of Acremoauxin A, a New Plant Growth Regulator Produced by Acremonium roseum I 4267

Acremoauxin A, a new fungal auxin derivative produced by A. roseum I 4267, was synthesized from indole, lactic acid, and D-mannitol. (+)-2-(3-Indolyl)propionic acid was prepared from its synthetic racemate by biological resolution using the acremoauxin-producing fungus.The synthetically confirmed structure of acremoauxin A was 1-O--D-arabitol (1).