propionylshikonin

Base Information

• Chemical Name: propionylshikonin
• CAS No.: 162283-70-7
• Molecular Formula: C₁₉H₂₀O₆
• Molecular Weight: 344.364
• Mol file: 162283-70-7.mol

Synonyms:1,4-Naphthalenedione,5,8-dihydroxy-2-[(1R)-4-methyl-1-(1-oxopropoxy)-3-pentenyl]- (9CI);1,4-Naphthalenedione, 5,8-dihydroxy-2-[4-methyl-1-(1-oxopropoxy)-3-pentenyl]-,(R)-; Propionylshikonin

Chemical Property of propionylshikonin

Chemical Property:

• Vapor Pressure: 3.72E-13mmHg at 25°C
• Boiling Point: 560.2°Cat760mmHg
• Flash Point: 200.9°C
• PSA: 100.90000
• Density: 1.297g/cm³
• LogP: 3.08130

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of propionylshikonin

There total 3 articles about propionylshikonin 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: 81.0%

shikonin (517-89-5) + propionic acid (802294-64-0,79-09-4) → propionylshikonin (162283-70-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -10 - 0 ℃; Inert atmosphere;

DOI:10.1002/chir.22209

Reference yield:

acetylshikonin (24502-78-1,34232-27-4,38222-13-8,54984-93-9,106295-33-4) → propionylshikonin (162283-70-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / methanol

2: 67 percent / N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂

With dmap; sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; dichloromethane;

DOI:10.1016/j.bmcl.2006.11.024

Reference yield:

shikonin (517-88-4,517-89-5,11031-58-6,54952-43-1,85921-41-1) + propionyl chloride (79-03-8) → propionylshikonin (84272-99-1,162283-70-7)

Guidance literature:

With hydrogenchloride; In benzene; 1.) 20 min, r.t., 2.) 50 deg C;

upstream raw materials:

shikonin

propionyl chloride

shikonin

propionic acid

Refernces

• 1、 Kong, Wen-Yao,Chen, Xiao-Feng,Shi, Jing,Baloch, Shahla Karim,Qi, Jin-Liang,Zhu, Hai-Liang,Wang, Xiao-Ming,Yang, Yong-Hua. "Design and synthesis of fluoroacylshikonin as an anticancer agent". . p. 757 - 762. Retrieved 2013/11/06.
• 2、 Afzal, M.,Al-Hrif, M. T.. "Cyclisation of Substituted 2-(4-Methyl-pent-3-enyl)-5,8-dihydroxy-1,4-naphthoquinones". . p. 865 - 869. Retrieved 2007/10/02.