24502-79-2

Usage

Uses

Used in Pharmaceutical Industry:
(BETA,BETA-DIMETHYLACRYL)SHIKONIN is used as a compound for the discovery and study of FFA4 agonists. It plays a crucial role in the development of new drugs targeting the free fatty acid receptor 4 (FFA4), which is involved in various physiological processes, including glucose homeostasis, inflammation, and cardiovascular function.
Used in Research and Development:
(BETA,BETA-DIMETHYLACRYL)SHIKONIN is used as a research tool for understanding the structure-activity relationship of FFA4 agonists. It helps researchers to design and synthesize more potent and selective FFA4 agonists, which can be used for the treatment of various diseases, such as type 2 diabetes, obesity, and inflammatory disorders.

InChI:InChI=1/C17H14O6/c1-3-5-13(23-14(21)4-2)9-8-12(20)15-10(18)6-7-11(19)16(15)17(9)22/h3-4,6-8,13,18-19H,1-2,5H2/t13-/m1/s1

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 
• 36883-11-1 3-Methyl-but-2-enoic acid (S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-4-hydroxy-4-methyl-pentyl ester 

Relevant academic research and scientific papers

Antimicrobial activities of naphthazarins from Arnebia euchroma

Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of α-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 μg/mL] than alkannin or shikonin (MIC = 6.25 μg/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC ≤ 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 μg/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.