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2H-1-Benzopyran-2-one, 5-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy- (CAS No. 7380-39-4): A Comprehensive Overview

2H-1-Benzopyran-2-one, 5-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy- (CAS No. 7380-39-4) is a complex organic compound that has garnered significant attention in the fields of medicinal chemistry and natural product research. This compound, commonly known as dihydrocoumarin, is a derivative of coumarin and exhibits a wide range of biological activities, making it a valuable molecule for both academic and industrial applications.

The structure of dihydrocoumarin is characterized by a benzopyran core with specific functional groups that contribute to its unique properties. The presence of the 5-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy] and 7-methoxy substituents imparts significant structural complexity and biological activity. These substituents are derived from natural sources and are known to play crucial roles in the compound's pharmacological effects.

Recent studies have highlighted the diverse biological activities of dihydrocoumarin. One of the most notable applications is its use as an anticoagulant. The compound has been shown to inhibit the vitamin K epoxide reductase complex (VKORC1), which is essential for the synthesis of clotting factors in the liver. This mechanism of action makes dihydrocoumarin a potential candidate for the development of new anticoagulant drugs, particularly in the treatment of thrombotic disorders.

In addition to its anticoagulant properties, dihydrocoumarin has been investigated for its anti-inflammatory and antioxidant activities. Research has demonstrated that the compound can effectively reduce inflammation by inhibiting the production of pro-inflammatory cytokines such as interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-α). Furthermore, its antioxidant properties have been attributed to its ability to scavenge free radicals and protect cells from oxidative damage.

The natural occurrence of dihydrocoumarin in various plant species has also been extensively studied. It is found in high concentrations in plants such as Melilotus officinalis (sweet clover) and Cassia alata (candle bush). These plants have been used in traditional medicine for centuries due to their therapeutic properties. The presence of dihydrocoumarin in these plants contributes to their medicinal value and has led to increased interest in their potential use in modern drug discovery.

From a synthetic perspective, the preparation of dihydrocoumarin involves several steps that require precise control over reaction conditions. One common synthetic route involves the condensation of salicylaldehyde with malonic acid followed by reduction and functionalization steps to introduce the desired substituents. Recent advancements in synthetic chemistry have led to more efficient and environmentally friendly methods for the production of dihydrocoumarin, making it more accessible for large-scale applications.

The pharmacokinetic properties of dihydrocoumarin have also been studied in detail. The compound has been shown to have good oral bioavailability and a favorable pharmacokinetic profile, which makes it suitable for oral administration. However, like many other coumarin derivatives, it can interact with certain drugs and dietary components, leading to potential drug-drug interactions. Therefore, careful consideration is required when using dihydrocoumarin in therapeutic settings.

In conclusion, 2H-1-Benzopyran-2-one, 5-[[(2E)-3,7-dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy- (CAS No. 7380-39-4) is a multifaceted compound with a wide range of biological activities. Its anticoagulant, anti-inflammatory, and antioxidant properties make it a valuable molecule for both research and development in the pharmaceutical industry. Ongoing studies continue to explore new applications and mechanisms of action, further solidifying its importance in the field of medicinal chemistry.

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• 495-02-3(Auraptene)
• 30413-87-7(2H-1-Benzopyran-2-one,7-[(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy]-)
• 532-16-1(2H-1-Benzopyran-2-one,7-[(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy]-)
• 15334-19-7(4-Hexenal,4-methyl-6-[(2-oxo-2H-1-benzopyran-7-yl)oxy]-, (4E)-)
• 74156-47-1(6-[[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]oxy]-7-methoxy-2H-1-benzopyran-2-one)
• 108354-46-7(2H-1-Benzopyran-2-one, 7-[[(2E,6E)-8-hydroxy-3,7-dimethyl-2,6-octadien-1-yl]oxy]-)
• 1228175-65-2(8-((3,7-Dimethylocta-2,6-dien-1-yl)oxy)-5,7-dimethoxy-2H-chromen-2-one)