56495-82-0

Basic information

• Product Name: IRISQUINONE
• Synonyms: IRISQUINONE;2-(10-heptadecenyl)-6-methoxy-5-cyclohexadiene- (z)-4-dione;2-(10-heptadecenyl)-6-methoxy-5-cyclohexadiene-(z)-4-dione;6-methoxy-2-delta(sup 10')-cis-heptadecenyl-1,4-benzoquinone;pallasone;2-[(Z)-10-Heptadecenyl]-6-methoxy-2,5-cyclohexadiene-1,4-dione;Irisquinone A
• CAS NO: 56495-82-0
• Molecular Formula: C₂₄H₃₈O₃
• Molecular Weight: 374.56
• Mol File: 56495-82-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 40-43 °C
• Boiling Point: 483.4°Cat760mmHg
• Flash Point: 205.1°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 1.68E-09mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: IRISQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: IRISQUINONE(56495-82-0)
• EPA Substance Registry System: IRISQUINONE(56495-82-0)

Safety Data

• Hazardous Substances Data: 56495-82-0(Hazardous Substances Data)

Usage

General Description

IRISQUINONE is a chemical compound that can be found in the Iris family of plants. It is a naturally occurring phenolic compound that is known for its antioxidant and anti-inflammatory properties. Irisquinone has been studied for its potential use in pharmaceutical and cosmetic applications due to its ability to protect cells from oxidative damage and reduce inflammation. Research has shown that irisquinone has potential as a therapeutic agent for conditions such as cancer, neurodegenerative diseases, and skin disorders. Additionally, its antioxidant properties make it a promising ingredient for skincare products aimed at reducing signs of aging and improving overall skin health. Despite its potential benefits, further research is needed to fully understand the therapeutic potential and safety of irisquinone for various applications.

InChI:InChI=1/C24H38O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21-19-22(25)20-23(27-2)24(21)26/h8-9,19-20H,3-7,10-18H2,1-2H3/b9-8-

Upstream product

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Downstream Products

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Relevant articles and documents

Identification of novel ROS inducers: Quinone derivatives tethered to long hydrocarbon chains

We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 μM) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 μM) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.

A high-yielding synthesis of the naturally occurring antitumour agent irisquinone

A short, high-yielding synthesis of the antitumour agent irisquinone (1) is described. The key steps are the palladium catalysed coupling reaction of dec-9-yn-1-ol with iodide (2) to form alkyne (3) and the Fremy's salt oxidation of phenol (7).

A Practical Preparation of Functionalized Alkylbenzoquinones: Synthesis of Maesanin and Irisquinone

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