134615-37-5

Basic information

• Product Name: REVEROMYCIN A
• Synonyms: REVEROMYCIN A;ZESGNAJSBDILTB-OXVOKJAASA-N
• CAS NO: 134615-37-5
• Molecular Formula: C36H52O11
• Molecular Weight: 660.79
• Product Categories: Antineoplastic and Immunosuppressive AntibioticsReceptor Tyrosine Kinase Biology;Epidermal Growth Factor Receptor (EGFR)Antibiotics;Interferes with Protein Synthesis;Antibiotics;Antibiotics A to;Antibiotics by Application;Antibiotics N-SAntibiotics;AntifungalAntibiotics;Mechanism of Action;Receptor Tyrosine Kinase Inhibitors;Spectrum of Activity
• Mol File: 134615-37-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 849°Cat760mmHg
• Flash Point: 258.7°C
• Appearance: /solid
• Density: 1.21g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: −20°C
• Solubility: DMF: soluble
• PKA: 4.36±0.17(Predicted)
• CAS DataBase Reference: REVEROMYCIN A(CAS DataBase Reference)
• NIST Chemistry Reference: REVEROMYCIN A(134615-37-5)
• EPA Substance Registry System: REVEROMYCIN A(134615-37-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 134615-37-5(Hazardous Substances Data)

Usage

Description

REVEROMYCIN A is a complex spiroketal antibiotic derived from a Streptomyces sp. It is characterized by its ability to inhibit the mitogenic activity of epidermal growth factor (EGF) and selectively target isoleucyl-tRNA synthetase. REVEROMYCIN A exhibits antiproliferative properties against various human cell lines and demonstrates potent antifungal activity. Additionally, it has been shown to induce apoptosis in osteoclasts, thereby inhibiting bone resorption.

Uses

Used in Pharmaceutical Industry:
REVEROMYCIN A is used as an inhibitor of EGF mitogenic activity for its potential role in treating cancer. By inhibiting the signal transduction of epidermal growth factor, it may help in controlling the growth and proliferation of cancer cells.
Used in Antifungal Applications:
REVEROMYCIN A is used as an antifungal agent due to its potent antifungal activity. It can be employed in the development of treatments for various fungal infections.
Used in Bone Resorption Inhibition:
REVEROMYCIN A is used as an agent to induce apoptosis in osteoclasts, which helps in inhibiting bone resorption. This property can be utilized in the development of therapies for conditions related to excessive bone resorption, such as osteoporosis.
Used in Cell Cycle Regulation:
As a G1 phase cell cycle inhibitor, REVEROMYCIN A is used to selectively inhibit isoleucyl-tRNA synthetase. This application can be relevant in the study and treatment of cell cycle-related disorders and diseases.

InChI:InChI=1/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29+,30-,35+,36-/m0/s1

Upstream product

• 297741-51-6 succinic acid allyl ester 2-(4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-8-[6-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-8-triethylsilanyloxy-octa-2,4-dienyl]-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-53-8 succinic acid allyl ester 8-[9-allyloxycarbonyl-6-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-nona-2,4,8-trienyl]-2-(4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-52-7 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-8-[(2E,4E)-(6S,7R)-6-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-8-oxo-octa-2,4-dienyl]-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-50-5 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-8-[(E)-4-(benzothiazole-2-sulfonyl)-3-methyl-but-2-enyl]-3-butyl-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-54-9 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-8-[(E)-4-(benzothiazol-2-ylsulfanyl)-3-methyl-but-2-enyl]-3-butyl-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-44-7 Succinic acid allyl ester (2S,3R,6R,8R,9S)-3-butyl-2-(tert-butyldiphenylsilanyloxymethyl)-8-[2-(4-methoxybenzyloxy)ethyl]-9-methyl-1,7-dioxaspiro[5.5]undec-3-yl ester 
• 297741-49-2 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-8-((E)-4-hydroxy-3-methyl-but-2-enyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 1053612-90-0 tert-Butyl-{(2S,3R,6R,8R,9S)-3-butyl-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-3-methylsulfanylmethoxy-1,7-dioxa-spiro[5.5]undec-2-ylmethoxy}-diphenyl-silane 
• 297741-48-1 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-9-methyl-8-((E)-3-methyl-4-oxo-but-2-enyl)-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-46-9 (2S,3R,6R,8R,9S)-3-Butyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-8-[2-(4-methoxy-benzyloxy)-ethyl]-9-methyl-1,7-dioxa-spiro[5.5]undecan-3-ol 
• 297741-45-8 Succinic acid allyl ester (2S,3R,6R,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-8-(2-hydroxy-ethyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 297741-43-6 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-8-(2-hydroxy-ethyl)-9-methyl-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 1045798-76-2 Succinic acid allyl ester (2S,3R,6S,8R,9S)-2-((1E,3E)-4-allyloxycarbonyl-3-methyl-buta-1,3-dienyl)-3-butyl-9-methyl-8-(2-oxo-ethyl)-1,7-dioxa-spiro[5.5]undec-3-yl ester 
• 250379-08-9 Triethyl-{(1R,2S)-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-methyl-but-3-ynyloxy}-silane 

Related news

Stabilization of tooth movement by administration of REVEROMYCIN A (cas 134615-37-5) to osteoprotegerin-deficient knockout mice07/30/2019

IntroductionIn this study, mechanical stress in the form of tooth movement was applied to osteoprotegerin-deficient knockout mice, which served as an animal model for juvenile Paget’s disease. To compare and evaluate bone turnover and response of the surrounding bony tissue, we administered rev...detailed

Relevant articles and documents

Total synthesis of (-)-reveromycin A via a hetero-Diels-Alder approach

The asymmetric total synthesis of (-)-reveromycin A is described which utilizes a Lewis acid catalyzed inverse electron demand hetero-Diels-Alder reaction followed by hydroboration/oxidation to afford the labile [6,6]-spiroketal core in a highly stereosel

Total synthesis of reveromycin A

matrix presented The stereoselective total synthesis of reveromycin A (1), a potent inhibitor of eukaryotic cell growth, has been accomplished on the basis of the stereocontrolled construction of the 6,6-spiroketal system, efficient succinylation of the t