5162-01-6

Basic information

• Product Name: beta, beta-dimethylacrylshikonin
• Synonyms: 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester;Arnebin 1;Arnebin i;Crotonic acid, 3-methyl-, ester with 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone;Alkannin beta,beta-dimethylacrylate
• CAS NO: 5162-01-6
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.4
• Mol File: 5162-01-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 587.3°Cat760mmHg
• Flash Point: 206.4°C
• Appearance: /
• Density: 1.269g/cm³
• Vapor Pressure: 2.16E-14mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: beta, beta-dimethylacrylshikonin(CAS DataBase Reference)
• NIST Chemistry Reference: beta, beta-dimethylacrylshikonin(5162-01-6)
• EPA Substance Registry System: beta, beta-dimethylacrylshikonin(5162-01-6)

Safety Data

• Hazardous Substances Data: 5162-01-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3/t17-/m0/s1

Upstream product

• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 517-88-4 shikonin 
• 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 articles and documents

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.