92175-42-3

Basic information

• Product Name: (2-METHYL-N-BUTYRYL)SHIKONIN
• Synonyms: ALPHA-METHYL-N-BUTYRYLSHIKONIN;5,8-DIHYDROXY-2-[1-(2-METHYL-N-BUTYRYLOXY)-4-METHYL-3-PENTENYL]-1,4-NAPHTHALENEDIONE;(2-METHYL-N-BUTYRYL)SHIKONIN
• CAS NO: 92175-42-3
• Molecular Formula: C21H24O6
• Molecular Weight: 372.41
• Mol File: 92175-42-3.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 570.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.246±0.06 g/cm3(Predicted)
• PKA: 7.08±0.20(Predicted)
• CAS DataBase Reference: (2-METHYL-N-BUTYRYL)SHIKONIN(CAS DataBase Reference)
• NIST Chemistry Reference: (2-METHYL-N-BUTYRYL)SHIKONIN(92175-42-3)
• EPA Substance Registry System: (2-METHYL-N-BUTYRYL)SHIKONIN(92175-42-3)

Safety Data

• Hazardous Substances Data: 92175-42-3(Hazardous Substances Data)

Usage

Description

(2-METHYL-N-BUTYRYL)SHIKONIN is a shikonin derivative, a class of natural pigments found in the roots of Lithospermum erythrorhizon, a plant used in traditional Chinese medicine. It has demonstrated potential anti-inflammatory, antioxidant, and anticancer properties in preclinical studies.
Used in Pharmaceutical Industry:
(2-METHYL-N-BUTYRYL)SHIKONIN is used as a bioactive compound for its potential therapeutic benefits due to its anti-inflammatory, antioxidant, and anticancer properties. It inhibits the proliferation of cancer cells and induces apoptosis, making it a promising candidate for further research and potential therapeutic applications.
Used in Anti-Inflammatory Applications:
(2-METHYL-N-BUTYRYL)SHIKONIN is used as an anti-inflammatory agent for its ability to inhibit the production of inflammatory mediators, providing potential benefits in managing inflammation-related conditions.
Used in Antioxidant Applications:
(2-METHYL-N-BUTYRYL)SHIKONIN is used as an antioxidant agent for its potential to protect cells from oxidative stress and related damage, contributing to overall health and well-being.

Upstream product

• 1730-91-2 (S)-2-Methylbutyric acid 
• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 

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.