66513-28-8

Basic information

• Product Name: INDANOMYCIN FROM STREPTOMYCES*ANTIBIOTIC US
• Synonyms: 2h-pyran-2-aceticacid,6-(1-ethyl-4-(1-ethyl-2,3,3a,4,5,7a-hexahydro-4-(1h-pyr;3-alpha,beta,4-beta,5-beta(1e(2s*(s*),5r*,6s*),3e),7a-alpha))-(1s-(1-alph;5-dimethyl-rol-2-ylcarbonyl)-1h-inden-5-yl)-3-butadienyl)tetrahydro-alpha;antibioticx14547;antibioticx14547a;x14547;x14547a;INDANOMYCIN FROM STREPTOMYCES*ANTIBIOTIC US
• CAS NO: 66513-28-8
• Molecular Formula: C31H43NO4
• Molecular Weight: 493.684
• Mol File: 66513-28-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 654°C at 760 mmHg
• Flash Point: 349.3°C
• Appearance: /
• Density: 1.115g/cm³
• Vapor Pressure: 5.36E-18mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C
• CAS DataBase Reference: INDANOMYCIN FROM STREPTOMYCES*ANTIBIOTIC US(CAS DataBase Reference)
• NIST Chemistry Reference: INDANOMYCIN FROM STREPTOMYCES*ANTIBIOTIC US(66513-28-8)
• EPA Substance Registry System: INDANOMYCIN FROM STREPTOMYCES*ANTIBIOTIC US(66513-28-8)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1 / PGIII
• RTECS: UP6100000
• Hazardous Substances Data: 66513-28-8(Hazardous Substances Data)

Usage

Description

Indanomycin is an antibiotic of the pyrroloketoindane class, which includes an unusual indane ring structure. It has bactericidal activity against Gram-positive bacteria, with minimum inhibitory concentration (MIC) values of ≤0.2 μg/ml, and insecticidal activity.

Uses

Different sources of media describe the Uses of 66513-28-8 differently. You can refer to the following data:
1. Indanomycin is an unusual pyrollic ionophore active against Gram positive bacteria and insects. Interestingly, indanomycin has antihypertensive properties. Indanomycin possesses affinity for both mono- and divalent ions, and has been reported as a growth promotor in ruminants.
2. Indanomycin is an unusual pyrollic ionophore active against Gram +ve bacteria and insects.

InChI:InChI=1/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23-,24+,25+,27?,28+,30+/m0/s1

Upstream product

• 153868-68-9 (αR,2R,5S,6R)-α,5-Dimethyl-6-<(1E)-1-ethyl-2-iodovinyl>tetrahydropyran-2-acetic acid 
• 80109-54-2 (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 
• 80109-51-9 (R)-2-[(2R,5S,6R)-6-((E)-3-Bromo-1-ethyl-propenyl)-5-methyl-tetrahydro-pyran-2-yl]-propionic acid methyl ester 
• 80109-58-6 (R)-2-((2R,5S,6R)-6-{(1E,3E)-1-Ethyl-4-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(pyridin-2-ylsulfanylcarbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-buta-1,3-dienyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 
• 80109-57-5 (1S,3aR,4S,5S,7aS)-1-Ethyl-5-{(1E,3E)-4-[(2R,3S,6R)-6-((R)-1-methoxycarbonyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-hexa-1,3-dienyl}-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carboxylic acid 
• 80109-56-4 (R)-2-{(2R,5S,6R)-6-[(1E,3E)-1-Ethyl-4-((1S,3aR,4S,5S,7aS)-1-ethyl-4-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl)-buta-1,3-dienyl]-5-methyl-tetrahydro-pyran-2-yl}-propionic acid methyl ester 
• 80109-55-3 (R)-2-{(2R,5S,6R)-6-[(1E,3E)-1-Ethyl-4-((1S,3aR,4S,5S,7aS)-1-ethyl-4-hydroxymethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl)-buta-1,3-dienyl]-5-methyl-tetrahydro-pyran-2-yl}-propionic acid 
• 95588-48-0 (+/-)-tert-butyl<<(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanyl>methoxy>dimethylsilane 
• 95588-47-9 (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylsulfonyl)methyl>-4-indanmethanol 
• 95532-30-2 (+/-)-methyl (1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylate 
• 81331-47-7 (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indancarboxylic acid 
• 80109-50-8 methyl (2R)-2-[(2R,5S,6R)-6-(3-Hydroxypent-1-en-3-yl)-5-methyltetrahydro-2H-pyran-2-yl]propanoate 
• 95588-46-8 (+/-)-(1S,3aR,4S,5R,7aS)-1-ethyl-3a,4,5,7a-tetrahydro-5-<(phenylthio)methyl>-4-indanmethanol 
• 105182-68-1 ((2E,4E)-(S)-8-Cyano-6-ethyl-octa-2,4-dienyl)-triphenyl-phosphonium; bromide 

Downstream Products

• 80109-54-2 (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1R,3aS,4R,5S,7aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 
• 80109-54-2 (R)-2-((2R,5S,6R)-6-{(E)-4-Benzenesulfonyl-4-[(1S,3aR,4S,5R,7aS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-ethyl-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]-1-ethyl-but-1-enyl}-5-methyl-tetrahydro-pyran-2-yl)-propionic acid methyl ester 

Relevant articles and documents

Total Synthesis of Ionophore Antibiotic X-14547A (Indanomycin)

A convergent, enantioselective total synthesis of ionophore antibiotic X-14547A (indanomycin, 1) is described.The dioxanone-to-dihydropyran variant of the lactonic Ireland-Claisen rearrangement establishes the hydropyran nucleus of the "left wing" fragment 2.Elaboration to the target synthon utilizes a new methodology for the preparation of stereodefined vinylsilanes (24 -> 25 -> 26) via net SN2' coupling of silanes with Grignard reagents catalyzed by CuCN.Salient features in the construction of the "right wing" subunit 3 include a modification of the Noyori three-component coupling procedure (32 -> 33) and the application of a retro hetero Diels-Alder/intramolecular Diels-Alder ("mock Claisen") process (5 -> 39).Palladium-mediated cross coupling of "left wing" and "right wing" synthons using Stille's method tolerates a free carboxylic acid and an unprotected acyl pyrrole, affording indanomycin directly in its natural absolute configuration.

Total synthesis of the ionophore antibiotic X-14547A (Indanomycin)

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Total synthesis of ionophore antibiotic X-14547A. II. Coupling of the tetrahydropyran and tetrahydroindan systems and construction of the butadienyl and ketopyrrole moieties

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