491-60-1

Basic information

• Product Name: emodin anthrone
• Synonyms: emodin anthrone;1,3,8-Trihydroxy-6-methyl-10H-anthracen-9-one;1,6,8-Trihydroxy-3-methyl-10-hydroanthracen-9-one;9(10H)-Anthracenone, 1,3,8-trihydroxy-6-methyl-;Aids002046;Aids-002046
• CAS NO: 491-60-1
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25
• Mol File: 491-60-1.mol
• Article Data: 18

Chemical Properties

• Melting Point: 254-258 °C (decomp)
• Boiling Point: 556.2 °C at 760 mmHg
• Flash Point: 304.2 °C
• Appearance: /
• Density: 1.471 g/cm³
• Vapor Pressure: 5.6E-13mmHg at 25°C
• Refractive Index: 1.723
• PKA: 7.34±0.20(Predicted)
• CAS DataBase Reference: emodin anthrone(CAS DataBase Reference)
• NIST Chemistry Reference: emodin anthrone(491-60-1)
• EPA Substance Registry System: emodin anthrone(491-60-1)

Safety Data

• Hazardous Substances Data: 491-60-1(Hazardous Substances Data)

Usage

Uses

Emodinanthrone is a useful intermediate in the preparation of emodin anthrone for dermatological applications.

InChI:InChI=1/C15H12O4/c1-7-2-8-4-9-5-10(16)6-12(18)14(9)15(19)13(8)11(17)3-7/h2-3,5-6,16-18H,4H2,1H3

Upstream product

• 481-73-2 citreorosein 
• 10034-85-2 hydrogen iodide 
• 64-19-7 acetic acid 
• 517-48-6 2,4,5,2',4',5'-hexahydroxy-7,7'-dimethyl-9H,9'H-[1,1']bianthryl-10,10'-dione 
• 96822-98-9 1,3,8-triacetoxyanthracene-9,10-dione-6-carbaldehyde 
• 33770-95-5 6-formyl-1,3,8-trihydroxyanthracene-9,10-dione 
• 6030-60-0 1,6,8-triacetoxy-3-methyl-9,10-anthraquinone 
• 1373404-37-5 1,8-diacetoxy-3-hydroxyanthracene-9,10-dione-6-carbaldehyde 
• 21871-90-9 physcion-10,10'-bianthrone 
• 108-24-7 acetic anhydride 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 

Downstream Products

• 491-58-7 1,8-dihydroxy-3-methylanthracen-9(10H)-one 
• 548-03-8 protohypericin 
• 428854-25-5 10-[2-(4-dimethylamino-phenyl)-vinyl]-1,3,4,6,8,15-hexahydroxy-13-methyl-dibenzo[a,o]perylene-7,16-dione 
• 23310-12-5 oxyskyrin 
• 18693-31-7 Aurantioskyrin 
• 225662-66-8 hypericin 
• 518-82-1 1,6,8-trihydroxy-3-methyl-9,10-anthraquinone 
• 196865-20-0 1,3,4,6,8,15-Hexahydroxy-10-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxymethyl)-13-methyl-dibenzo[a,o]perylene-7,16-dione 
• 61419-08-7 germichrysone 

Relevant articles and documents

Biosynthesis of Actinorhodin and Related Antibiotics: Discovery of Alternative Routes for Quinone Formation Encoded in the act Gene Cluster

All known benzoisochromanequinone (BIQ) biosynthetic gene clusters carry a set of genes encoding a two-component monooxygenase homologous to the ActVA-ORF5/ActVB system for actinorhodin biosynthesis in Streptomyces coelicolor A3(2). Here, we conducted molecular genetic and biochemical studies of this enzyme system. Inactivation of actVA-ORF5 yielded a shunt product, actinoperylone (ACPL), apparently derived from 6-deoxy-dihydrokalafungin. Similarly, deletion of actVB resulted in accumulation of ACPL, indicating a critical role for the monooxygenase system in C-6 oxygenation, a biosynthetic step common to all BIQ biosyntheses. Furthermore, in vitro, we showed a quinone-forming activity of the ActVA-ORF5/ActVB system in addition to that of a known C-6 monooxygenase, ActVA-ORF6, by using emodinanthrone as a model substrate. Our results demonstrate that the act gene cluster encodes two alternative routes for quinone formation by C-6 oxygenation in BIQ biosynthesis.

Accumulation and Photocytotoxicity of Hypericin and Analogs in Two- and Three-Dimensional Cultures of Transitional Cell Carcinoma Cells

The aim of this study was to investigate the in vitro cellular accumulation, distribution and photocytotoxic effect of hypericin in two-dimensional (2-D) and three-dimensional (3-D) cultured RT-112 transitional cell carcinoma cells of the bladder. In addition, two iodinated derivatives of hypericin were incorporated to investigate whether these analogs, with their increased lipophilicity and heavy-atom effect, display a different biological behavior and optimized photodynamic effect. The results indicate that hypericin and mono-iodohypericin behave similarly in terms of cellular accumulation, spheroidal distribution and photocytotoxic effect. In contrast, di-iodohypericin concentrated to a higher extent in monolayers and spheroids, but the accumulation was restricted to the outermost part of the spheroid. An inverse correlation therefore seems to exist between the extent of cellular uptake under 2-D conditions and the penetration of the compounds in multicellular systems. Moreover, a less pronounced photocytotoxic effect was observed for di-iodohypericin in both 2-D and 3-D cell culture systems. It can be concluded that iodinated derivatives of hypericin do not show an increased cytotoxic effect upon irradiation in either monolayers or spheroids. Moreover, this study shows that when new photosensitizers are preclinically developed, the use of 3-D cell aggregates is critical for a correct evaluation of their efficacy.

An Efficient Multigram Synthesis of Hypericin Improved by a Low Power LED Based Photoreactor

In this work, an improved synthesis process was developed for the multigram production of hypericin. An inexpensive and efficient low power Light Emission Diode (LED) based photoreactor was designed and employed to perform the protohypericin photocyclization reaction allowing its photoconversion in hypericin. This closed system overcomes safety issues related to scale-up hypericin preparation typically described in the literature which combines the use of open systems, organic solvents, and high-power light sources. The photoreactor designed allows a solution to, mainly, the intrinsic effect of hypericin photobleaching inherent to the protohypericin photocyclization reaction, implying an increase in the yield of the final product and consequently the final cost. Using a red-LED based photoreactor, a safety protocol was carried out in a 5-g scale hypericin preparation with quantitative yield.

A Convenient Semisynthetic Route to Hypericin

A semisynthetic route to produce hypericin was established using Cortex frangulae as the starting point.The emodin isolated from it easily and in good yield was reduced to emodin anthrone by means of SnCl2.The latter was reacted via a known oxidative dimerization and photocyclization reaction into hypericin. Keywords: Emodin; Emodin anthrone; Hypericin; Cortex frangulae.

Tautomers of anthrahydroquinones: Enzymatic reduction and implications for chrysophanol, monodictyphenone, and related xanthone biosyntheses

Reduction of emodin by sodium dithionite resulted in the formation of two tautomeric forms of emodin hydroquinone. Subsequent conversion by the short-chain dehydrogenase/reductase (SDR) MdpC into the corresponding 3-hydroxy-3,4-dihydroanthracen-1(2H)-one implies that deoxygenation is the first step in monodictyphenone biosynthesis. Implications for chrysophanol formation as well as reaction sequences in the related xanthone, ergochrome, and bianthraquinone biosyntheses are discussed.

Clamping device anthraquinone compound in the preparation of antineoplastic application

The invention relates to application of dianthraquinonyl, in particular to application of dianthraquinonyl compounds to preparing anti-tumor medicine. Radioactive therapeutic nuclides are labeled on dianthraquinonyl medicine, and accordingly the labeled medicine with excellent tumor targeting can be obtained. The application has the advantages that the compounds can be gathered on dead cells and tissues in tumors and are provided with instable chemical elements or isotopes, accordingly, radiation can occur, surrounding cells and tissues can be destroyed, and the purpose of treating tumors can be achieved.