21288-61-9

Basic information

• Product Name: epsilon-pyrromycinone
• Synonyms: epsilon-pyrromycinone;(1R)-2-Ethyl-1,2,3,4,6,11-hexahydro-2α,4α,5,7,10-pentahydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;(1R)-2-Ethyl-2α,4α,5,7,10-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacene-1β-carboxylic acid methyl ester;(1R,2R,4S)-2-Ethyl-1,2,3,4,6,11-hexahydro-2,4,5,7,10-pentahydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;1-Hydroxyaklavinone;ε-Pyrromycinone
• CAS NO: 21288-61-9
• Molecular Formula: C₂₂H₂₀O₉
• Molecular Weight: 428.391
• Mol File: 21288-61-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 213-214 °C(Solv: benzene (71-43-2))
• Boiling Point: 701.2°C at 760 mmHg
• Flash Point: 247.9°C
• Appearance: /
• Density: 1.593g/cm³
• Vapor Pressure: 1.22E-20mmHg at 25°C
• Refractive Index: 1.705
• PKA: 6.30±0.70(Predicted)
• CAS DataBase Reference: epsilon-pyrromycinone(CAS DataBase Reference)
• NIST Chemistry Reference: epsilon-pyrromycinone(21288-61-9)
• EPA Substance Registry System: epsilon-pyrromycinone(21288-61-9)

Safety Data

• Hazardous Substances Data: 21288-61-9(Hazardous Substances Data)

Usage

General Description

Epsilon-pyrromycinone is a natural chemical compound belonging to the pyrromycinone family, which is produced by a strain of Streptomyces bacteria. It is a potent cytotoxic compound and has shown promising anticancer activity in preclinical studies. Epsilon-pyrromycinone has been found to inhibit the growth of various cancer cell lines, including lung cancer, breast cancer, and leukemia. Its mechanism of action involves inducing programmed cell death (apoptosis) in cancer cells, as well as disrupting their DNA replication and repair processes. Research on epsilon-pyrromycinone is ongoing, and it holds potential for the development of novel anticancer therapies.

InChI:InChI=1/C22H20O9/c1-3-22(30)7-12(25)13-8(17(22)21(29)31-2)6-9-14(19(13)27)20(28)16-11(24)5-4-10(23)15(16)18(9)26/h4-6,12,17,23-25,27,30H,3,7H2,1-2H3/t12-,17-,22+/m0/s1

Upstream product

• 88453-81-0 10(R,S)-(methoxycarbonyl)-9(R,S)-ethyl-9(R,S)-hydroxy-7,8,9,10-tetrahydro-1,4,6-trimethoxy-5,12-naphthacenedione 
• 88453-75-2 methyl <3-(3-(benzyloxy)pent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate 
• 88453-73-0 methyl 2-<3-(3-(benzyloxy)pent-1-yl)-5,8-dimethoxy-4-hydroxyanthraquinon-2-yl>acetate 
• 88453-78-5 methyl <3-(3-oxopent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate 
• 88453-76-3 methyl <3-(3-hydroxypent-1-yl)-4,5,8-trimethoxyanthraquinon-2-yl>acetate 
• 641-92-9 (+/-)-ε-deoxypyrromycinone 
• 16234-96-1 (+)-aklavinone 
• 124222-85-1 pyrromycin; hydrochloride 

Downstream Products

• 749-18-8 1-hydroxybisanhydroaklavinone 
• 111233-40-0 ciclamycin 0 
• 167012-88-6 7-O-<(2,3,6-trideoxy-4-ulo-α-L-hexopyranosyl)-(1->4)-<2,6-dideoxy-3-O-(4-methoxybenzyl)-α-L-galactopyranosyl>-(1->4)-2,6-dideoxy-3-O-(4-methoxybenzyl)-1-(2,6-dichlorophenylsulfinyl)-α-L-galactopyranosyl>-ε-pyrromycinone 
• 76069-70-0 daunosaminyl ε-pyrromycinone 
• 129985-41-7 7-O-<4-O-<4-O-(2,3,6-trideoxy-α-L-glycero-hexopyranosid-4-ulosyl)-2,6-dideoxy-3-O-(trimethylsilyl)-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-2-iodo-3-O-(trimethylsilyl)-α-L-talopyranosyl>-ε-pyrromycinone 
• 129985-41-7 7-O-<4-O-<4-O-(2,3,6-trideoxy-α-L-glycero-hexopyranosid-4-ulosyl)-2,6-dideoxy-3-O-(trimethylsilyl)-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-2-iodo-3-O-(trimethylsilyl)-α-L-galactopyranosyl>-ε-pyrromycinone 
• 129985-41-7 7-O-<4-O-<4-O-(2,3,6-trideoxy-α-L-glycero-hexopyranosid-4-ulosyl)-2,6-dideoxy-3-O-(trimethylsilyl)-α-L-lyxo-hexopyranosyl>-2,6-dideoxy-2-iodo-3-O-(trimethylsilyl)-β-L-galactopyranosyl>-ε-pyrromycinone 

Relevant articles and documents

Directed Biosynthesis of Iso-aclacinomycins with Improved Anticancer Activity

A four-enzyme catalyzed hydroxy regioisomerization of anthracycline was integrated into the biosynthetic pathway of aclacinomycin A (ALM-A), to generate a series of iso-ALMs via directed combinatorial biosynthesis combined with precursor-directed mutasynthesis. Most of the newly acquired iso-ALMs exhibit obviously (1-5-fold) improved antitumor activity. Therefore, we not only developed iso-ALMs with potential as clinical drugs but also demonstrated the utility of this tailoring tool for modification of anthracycline antibiotics in drug discovery and development.