Emodin anthrone

Base Information

• Chemical Name: Emodin anthrone
• CAS No.: 491-60-1
• Molecular Formula: C15H12O4
• Molecular Weight: 256.258
• UNII: 77C500W1A2
• DSSTox Substance ID: DTXSID80197684
• Nikkaji Number: J540.469J
• Wikidata: Q27266578
• Metabolomics Workbench ID: 122866
• ChEMBL ID: CHEMBL122192
• Mol file: 491-60-1.mol

Synonyms:1,3,8-trihydroxy-6-methylanthrone;emodin anthrone;emodinanthrone

Chemical Property of Emodin anthrone

Chemical Property:

• Vapor Pressure: 5.6E-13mmHg at 25°C
• Melting Point: 254-258 °C (decomp)
• Refractive Index: 1.723
• Boiling Point: 556.2 °C at 760 mmHg
• PKA: 7.34±0.20(Predicted)
• Flash Point: 304.2 °C
• PSA: 77.76000
• Density: 1.471 g/cm³
• LogP: 2.24700
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 369

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,4,5-TRIHYDROXY-7-METHYLANTHRACEN-10(9H)-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2)C=C(C=C3O)O
• Uses: Emodinanthrone is a useful intermediate in the preparation of emodin anthrone for dermatological applications.

Technology Process of Emodin anthrone

There total 15 articles about Emodin anthrone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone (518-82-1) → emodinanthrone (491-60-1)

Guidance literature:

With hydrogenchloride; acetic acid; tin(ll) chloride; at 120 ℃; for 24h;

Reference yield: 86.0%

6-formyl-1,3,8-trihydroxyanthracene-9,10-dione (33770-95-5) → emodinanthrone (491-60-1)

Guidance literature:

With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; In water; at 100 ℃; for 3h;

DOI:10.1007/s12272-012-0307-4

Reference yield:

→ emodinanthrone (491-60-1)

Guidance literature:

With hydrogen iodide; acetic acid;

upstream raw materials:

citreorosein

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

hydrogen iodide

acetic acid

Downstream raw materials:

1,8-dihydroxy-3-methylanthracen-9(10H)-one

1,6,8-trihydroxy-3-methyl-9,10-anthraquinone

germichrysone

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

Refernces

• 1、 Gon?alves, Renato Sonchini,César, Gabriel Batista,Barbosa, Patrícia Magalh?es,Hioka, Noboru,Nakamura, Celso Vataru,Bruschi, Marcos Luciano,Caetano, Wilker. "Optimized protocol for multigram preparation of emodin anthrone, a precursor in the hypericin synthesis". . p. 1 - 4. Retrieved 2018.
• 2、 Zhang, Ying,Shang, Kun,Wu, Xiaowen,Song, Siyu,Li, Zebo,Pei, Zhichao,Pei, Yuxin. "Highly efficient green synthesis and photodynamic therapeutic study of hypericin and its derivatives". . p. 21786 - 21792. Retrieved 2018.
• 3、 Kamuhabwa, Appolinary R.,Geboes, Karel R.,De Witte, Peter A.. "Investigation of the absorption of hypericin into the skin of hairless mice". . p. 487 - 494. Retrieved 2000.
• 4、 Zhang, Dongjian,Jiang, Cuihua,Yang, Shengwei,Gao, Meng,Huang, Dejian,Wang, Xiaoning,Shao, Haibo,Feng, Yuanbo,Sun, Ziping,Ni, Yicheng,Zhang, Jian,Yin, Zhiqi. "Effects of skeleton structure on necrosis targeting and clearance properties of radioiodinated dianthrones". . p. 566 - 577. Retrieved 2016.
• 5、 Jalab, Murhaf,Critchley, Megan E.,Taylor, Charlotte M.,Lawrence, Clare L.,Smith, Robert B.. "1,8-Substituted anthraquinones, anthrones and bianthrones as potential non-azole leads against fungal infections". . . Retrieved 2019/08/01.