162283-70-7

Basic information

• Product Name: propionylshikonin
• Synonyms: propionylshikonin;5,8-Dihydroxy-2-[(1R)-4-methyl-1-(1-oxopropoxy)-3-penten-1-yl]-1,4-naphthalenedione
• CAS NO: 162283-70-7
• Molecular Formula: C19H20O6
• Molecular Weight: 344.3585
• Mol File: 162283-70-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 560.2°Cat760mmHg
• Flash Point: 200.9°C
• Appearance: /
• Density: 1.297
• Vapor Pressure: 3.72E-13mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: propionylshikonin(CAS DataBase Reference)
• NIST Chemistry Reference: propionylshikonin(162283-70-7)
• EPA Substance Registry System: propionylshikonin(162283-70-7)

Safety Data

• Hazardous Substances Data: 162283-70-7(Hazardous Substances Data)

Usage

General Description

Propionylshikonin is a natural chemical compound found in the roots of the Lithospermum erythrorhizon plant, also known as red-rooted gromwell. It belongs to the group of naphthoquinone derivatives and has been studied for its potential medicinal properties, including anti-inflammatory, anti-cancer, and anti-microbial effects. Propionylshikonin has shown promising results in inhibiting the growth of various cancer cell lines and reducing the production of inflammatory mediators in immune cells. Additionally, it has demonstrated antibacterial and antifungal activities against several pathogens. These findings suggest that propionylshikonin may have potential therapeutic applications in the treatment of cancer, inflammatory diseases, and infectious illnesses.

InChI:InChI=1/C19H20O6/c1-4-16(23)25-15(8-5-10(2)3)11-9-14(22)17-12(20)6-7-13(21)18(17)19(11)24/h5-7,9,15,20-21H,4,8H2,1-3H3/t15-/m1/s1

Upstream product

• 517-88-4 shikonin 
• 79-03-8 propionyl chloride 
• 517-89-5 shikonin 
• 802294-64-0 propionic acid 
• 24502-78-1 acetylshikonin 

Relevant articles and documents

Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon

Three naphthoquinones were isolated by bioassay-guided fractionation from the CHCl3 extracts of roots of Lithospermum erythrorhizon. They were identified as acetylshikonin (1), isobutyrylshikonin (2), and β-hydroxyisovalerylshikonin (3) on the basis of their spectroscopic analyses. The compounds 1-3 were tested for their inhibitory activities against human ACAT-1 (hACAT-1) or human ACAT-2 (hACAT-2). Compound 2 preferentially inhibited hACAT-2 (IC50 = 57.5 μM) than hACAT-1 (32% at 120 μM), whereas compounds 1 and 3 showed weak inhibitory activities in both hACAT-1 and -2. To develop more potent hACAT inhibitor, shikonin derivatives (5-11) were synthesized by semi-synthesis of shikonin (4), which was prepared by hydrolysis of 1-3. Among them, compounds 5 and 7 exhibited the strong inhibitory activities against hACAT-1 and -2. Furthermore, we demonstrated that compound 7 behaved as a potent ACAT inhibitor in not only in vitro assay system but also cell-based assay system.

Acylshikonin analogues: Synthesis and inhibition of DNA topoisomerase-I

Compounds bearing an acyl group of a various size at 1'-OH of shikonin were synthesized as acyl analogues of shikonin, which was isolated from the root of Lithospermum erythrorhizon, and evaluated for inhibitory effect on topoisomerase-I activity. A selec