52387-14-1

Basic information

• Product Name: ISOVALERYLSHIKONIN
• Synonyms: ISOVALERYLSHIKONIN;5,8-DIHYDROXY-2-(1-ISOVALERYLOXY-4-METHYL-3-PENTENYL)-1,4-NAPHTHALENEDIONE;3-Methylbutanoic acid (R)-1-[(1,4-dioxo-5,8-dihydroxy-1,4-dihydronaphthalen)-2-yl]-4-methyl-3-pentenyl ester;5,8-Dihydroxy-2-[(R)-1-isovaleryloxy-4-methyl-3-pentenyl]-1,4-naphthalenedione
• CAS NO: 52387-14-1
• Molecular Formula: C21H24O6
• Molecular Weight: 372.41
• Product Categories: Miscellaneous Natural Products
• Mol File: 52387-14-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 107 °C
• Boiling Point: 570.1°C at 760 mmHg
• Flash Point: 198.6°C
• Appearance: /
• Density: 1.246g/cm³
• Vapor Pressure: 1.34E-13mmHg at 25°C
• Refractive Index: 1.578
• PKA: 7.08±0.20(Predicted)
• CAS DataBase Reference: ISOVALERYLSHIKONIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOVALERYLSHIKONIN(52387-14-1)
• EPA Substance Registry System: ISOVALERYLSHIKONIN(52387-14-1)

Safety Data

• Hazardous Substances Data: 52387-14-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H24O6/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/h5-7,10,12,17,22-23H,8-9H2,1-4H3

Upstream product

• 517-88-4 shikonin 
• 108-12-3 isopentanoyl chloride 
• 503-74-2 3-methylbutyric acid 
• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 
• 517-89-5 shikonin 
• 24502-78-1 acetylshikonin 

Relevant articles and documents

Synthesis and pharmacological in vitro investigations of novel shikonin derivatives with a special focus on cyclopropane bearing derivatives

Melanoma is the deadliest form of skin cancer and accounts for about three quarters of all skin cancer deaths. Especially at an advanced stage, its treatment is challenging, and survival rates are very low. In previous studies, we showed that the constitu

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.