actinorhodin

Base Information

• Chemical Name: actinorhodin
• CAS No.: 1397-77-9
• Molecular Formula: C32H26 O14
• Molecular Weight: 634.55
• Mol file: 1397-77-9.mol

Synonyms:Actinorhodin(7CI,8CI); [8,8'-Bi-1H-naphtho[2,3-c]pyran]-3,3'-diacetic acid,3,3',4,4',5,5',10,10'-octahydro-6,6',9,9'-tetrahydroxy-1,1'-dimethyl-5,5',10,10'-tetraoxo-,[1R-[1a,3b,8(1'R*,3'S*)]]-; 1H-Naphtho[2,3-c]pyran, bimol.deriv.; Actinorhodine

Chemical Property of actinorhodin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 918.5°Cat760mmHg
• PKA: 3.84±0.10(Predicted)
• Flash Point: 299.9°C
• PSA: 242.26000
• Density: 1.632g/cm³
• LogP: 2.83140

Purity/Quality:

99%, ^*data from raw suppliers

ACTINORHODINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Actinorhodin is a benzoisochromanequinone polyketide antibiotic produced from Streptomyces coelicolor (Magnolo et al. 1991). It belongs to a class of aromatic polyketides synthesized by type II PKSs (Manikprabhu and Lingappa 2013). It can be used as a pH indicator, turning red below pH 8.5 and blue above.

Technology Process of actinorhodin

There total 11 articles about actinorhodin 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: 92.0%

C34H30O14 → actinorhodin (1397-77-9)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; at 20 ℃; enantioselective reaction;

DOI:10.1002/anie.201814172

Reference yield:

6-deoxykalafungin (958730-34-2) → 4-deoxykalafunginic acid (52934-83-5,73804-47-4,90761-55-0,142292-63-5,98392-26-8) + actinorhodin (1397-77-9)

Guidance literature:

With ActVA; 5/ActVB; Mechanism; Enzymatic reaction;

DOI:10.1002/cbic.201100571

Reference yield:

C24H24O3 → actinorhodin (1397-77-9)

Guidance literature:

Multi-step reaction with 13 steps

1: bis-[(trifluoroacetoxy)iodo]benzene / acetone; 1,4-dioxane; water / 0 °C / Darkness

2: sodium dithionite; water / Inert atmosphere

3: potassium carbonate / acetone / Reflux

4: triethylamine; silver(l) oxide / dichloromethane / 2 h / 20 °C

5: acetic acid; zinc / chloroform / 1 h / 20 °C

6: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 0 °C

7: osmium(VIII) oxide; 2,6-dimethylpyridine; sodium periodate / 1,4-dioxane; water; tert-butyl alcohol / 3 h / 0 - 20 °C

8: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / tetrahydrofuran; water; tert-butyl alcohol / 1 h / 20 °C

9: hexane; toluene; methanol / 0.25 h / 20 °C

10: palladium 10% on activated carbon; hydrogen / methanol; benzene / 1.5 h / 20 °C / 760.05 Torr

11: ammonium cerium (IV) nitrate / 1,4-dioxane; water; acetonitrile / 3 h / 0 °C

12: magnesium iodide / acetonitrile; diethyl ether / 11 h / 20 °C

13: water; lithium hydroxide monohydrate / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium periodate; osmium(VIII) oxide; sodium dithionite; ammonium cerium (IV) nitrate; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; lithium hydroxide monohydrate; palladium 10% on activated carbon; water; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; magnesium iodide; silver(l) oxide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil; tert-butyl alcohol; benzene;

DOI:10.1002/anie.201814172

upstream raw materials:

6-deoxykalafungin

Refernces

• 1、 Ninomiya, Mamiko,Ando, Yoshio,Kudo, Fumitaka,Ohmori, Ken,Suzuki, Keisuke. "Total Synthesis of Actinorhodin". . p. 4264 - 4270. Retrieved 2019/03/07.