23537-16-8

Basic information

• Product Name: RUGULOSIN
• Synonyms: (+)-RUGULOSIN;RUGULOSIN;(+)-(1S,1'S,2R,2'R,3S,3'S,9AR,9'AR)-RUGULOSIN;(+)-Rugulosin, (1S,1S,2R,2R,3S,3S,9aR,9aR)-Rugulosin, (2R,2R)-Rugulosin;5H,6H-6,13A,5A,14-[1,2,3,4]Butanetetraylcycloocta[1,2-B:5,6-B']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-;5H,6H-6,13A,5A,14-[1,2,3,4]Butanetetraylcycloocta[1,2-B:5,6-B']dinaphthalene-5,8,13,16(14H)-tetrone, 1,7,9,15,17,20-hexahydroxy-3,11-dimethyl-, [5as-(5ar*,6S*,13ar*,14S*,17R*,18S*,19S*,20R*)]-;Nsc160880;NSC 249990
• CAS NO: 23537-16-8
• Molecular Formula: C30H22O10
• Molecular Weight: 542.49
• Product Categories: Antibiotic
• Mol File: 23537-16-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 293℃ (decomposition)
• Boiling Point: 535.95°C (rough estimate)
• Flash Point: 560.3°C
• Appearance: /
• Density: 1.3164 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5376 (estimate)
• CAS DataBase Reference: RUGULOSIN(CAS DataBase Reference)
• NIST Chemistry Reference: RUGULOSIN(23537-16-8)
• EPA Substance Registry System: RUGULOSIN(23537-16-8)

Safety Data

• Hazardous Substances Data: 23537-16-8(Hazardous Substances Data)

Usage

Description

(+)-Rugulosin is a pigment and mycotoxin produced by certain fungi. It inhibits HIV-1 integrase activity with IC50 values of 19 and 25 μM in coupled and strand transfer assays, respectively. It also inhibits ribonuclease H in rat liver by 83% at a concentration of 157 μM and ribonucleases H1, H2, and H3 in T. pyriformis by 100, 99, and 100%, respectively, at a concentration of 313 μM. (+)-Rugulosin leads to hepatic injury and liver cell hyperplasia in mice when administered in the diet. It is cytotoxic to insect cells but not mammalian C6/36, L929, and HepG2 cells (ID50s = 1.2, >200, 23.7, and >200 μg/ml, respectively).

Uses

Different sources of media describe the Uses of 23537-16-8 differently. You can refer to the following data:
1. (+)-Rugulosin is an intense yellow pigment produced by some species of Penicillium, Aspergillus and the fungal symbiotants of some lichens. (+)-Rugulosin shows antibacterial and insecticidal activity and has found application as a bioinsecticide, notably as the active secondary metabolite in endophytic fungi of seedlings.
2. Rugulosin (+ form) is an intense yellow pigment produced by Penicillium and Aspergillus.

InChI:InChI=1/C30H22O10/c1-7-3-9-13(11(31)5-7)21(33)17-25(37)20-23(35)15-16-24(36)19(29(15,17)27(9)39)26(38)18-22(34)14-10(28(40)30(16,18)20)4-8(2)6-12(14)32/h3-6,15-16,19-20,23-24,31-36H,1-2H3/t15?,16?,19?,20?,23-,24-,29?,30?/m0/s1

Upstream product

• 875926-38-8 C₃₈H₄₀O₁₄ 
• 875926-39-9 C₃₈H₃₈O₁₄ 

Relevant articles and documents

Total syntheses of 2,2′-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin

The total syntheses of 2,2′-epi-cytoskyrin A, rugulosin, and the alleged structure of rugulin are described. These naturally occurring bisanthraquinones and their relatives are characterized by novel molecular architectures at the core, at which lies a mo