52438-12-7

Basic information

• Product Name: ISOBUTYRYLSHIKONIN
• Synonyms: ISOBUTYRYLSHIKONIN;5,8-DIHYDROXY-2-(1-ISOBUTYRYLOXY-4-METHYL-3-PENTENYL)-1,4-NAPHTHALENEDIONE;2-[1-(Isobutyryloxy)-4-methyl-3-pentenyl]-5,8-dihydroxy-1,4-naphthoquinone;(R)-1-(1,4-Dihydro-5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methyl-3-pentenyl=isobutyrate;2-Methylpropanoic acid (R)-1-[(1,4-dioxo-5,8-dihydroxy-1,4-dihydronaphthalene)-2-yl]-4-methyl-3-pentenyl ester;Isobutylshikonin;(R)-2-Methyl-propanoic acid 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester;Isobutyroylshikonin
• CAS NO: 52438-12-7
• Molecular Formula: C20H22O6
• Molecular Weight: 358.39
• EINECS: 932-567-3
• Mol File: 52438-12-7.mol

Chemical Properties

• Melting Point: 88 °C
• Boiling Point: 561.9±50.0 °C(Predicted)
• Appearance: /
• Density: 1.269±0.06 g/cm3(Predicted)
• PKA: 7.05±0.20(Predicted)
• CAS DataBase Reference: ISOBUTYRYLSHIKONIN(CAS DataBase Reference)
• NIST Chemistry Reference: ISOBUTYRYLSHIKONIN(52438-12-7)
• EPA Substance Registry System: ISOBUTYRYLSHIKONIN(52438-12-7)

Safety Data

• Hazardous Substances Data: 52438-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Isobutyrylshikonin is used as an anti-inflammatory agent for its capacity to reduce inflammation, which is beneficial in managing various conditions and diseases.
Used in Skincare Industry:
Isobutyrylshikonin is used as a therapeutic ingredient for skin disorders such as psoriasis and atopic dermatitis, leveraging its anti-inflammatory properties to alleviate symptoms and promote skin health.
Used in Anticancer Applications:
Isobutyrylshikonin is used as a potential anti-cancer agent due to its ability to inhibit the growth of cancer cells and induce apoptosis, offering a novel approach to cancer treatment strategies.
Used in Cosmetic Industry:
Isobutyrylshikonin is used as an antioxidant in cosmetic products to protect the skin from oxidative stress and environmental damage, thereby promoting overall skin health and longevity.

Upstream product

• 517-88-4 shikonin 
• 79-30-1 isobutyryl chloride 
• 517-89-5 shikonin 
• 79-31-2 isobutyric Acid 
• 517-88-4 (S)-5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-enyl)naphthalene-1,4-dione 

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.

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