31525-75-4

Usage

General Description

5-Hydroxyseselin is a natural chemical compound derived from the seseli plant, belonging to the sesquiterpenoid family of compounds. It has been identified as a potential anti-inflammatory and anticancer agent due to its ability to inhibit the production of inflammatory cytokines and induce apoptosis in cancer cells. Additionally, 5-Hydroxyseselin has been found to possess antibacterial and antioxidant properties, making it a promising candidate for the development of new pharmaceutical drugs. Research into the potential therapeutic applications of 5-Hydroxyseselin is ongoing, with the goal of harnessing its medicinal properties for the treatment of a variety of diseases and conditions.

Upstream product

• 2732-18-5 5,7-dihydroxy-2H-chromen-2-one 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 76256-29-6 5,7-diacetoxy-8-(3'-methyl-2'-butenyl)coumarin 
• 53017-21-3 5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one 

Downstream Products

• 31525-76-5 5-methoxyseselin 
• 84-99-1 xanthoxyletin 

Relevant academic research and scientific papers

Synthesis and cytotoxicity of coumarin derivatives and nordentatin

Nordentatin and 10 coumarin derivatives were synthesized and evaluated for cytotoxicity. Compounds 6, 7, 9 and 13 showed cytotoxicity against the NCI-H187 cell line with IC50 value ranging of 3-7 μg/mL. Among synthesized coumarins, compounds 4 and 13 demonstrated cytotoxicity against the KB cell line with IC50 values of 3.94 and 6.44 μg/mL, respectively. Fortunately, coumarins 4 and 7 may be one of the new lead compounds for the development of anticancer agents due to reason that they showed weak and inactive against normal cells.

Natural and synthetic 2,2-dimethylpyranocoumarins with antibacterial activity

A new efficient synthetic approach to the natural coumarins 5-hydroxyseselin (5), 5-methoxyseselin (3), and (±) cis-grandmarin (9) is described as well as the synthesis of some new derivatives in the 5-methoxyseselin series (10-15). The natural coumarins 7-hydroxyalloxanthyletin (6), alloxanthoxyletin (8), and dipetalolactone (7) have also been obtained as secondary products. The type of fusion of the pyrano ring in all cases has been established by 2D NMR spectroscopy. The compounds have been studied for their in vitro antibacterial activity, which has been compared with that of some previously synthesized seselin derivatives. The most active compounds were 3, 7, 8, 11, and 14. Some structure-activity relationships are discussed.

SYNTHESIS OF NEW PYRANOCOUMARINS

As a result of condensing 5,7-dihydroxy-4-methylcoumarin with dimethyl acetal-3-methylbuten-2-al, 4-methyl-5-hydroxyseseline, 4-methyldipetalolactone and 5-hydroxy-4,10,10-trimethyl-2H,8H-benzodipyran-2-one have been obtained.Condensation of 5,7-hydroxycoumarin with this acetal leads to 5-hydroxyseseline, dipetalolactone and 5-hydroxy-10,10-dimethyl-2H,8H-benzodipyran-2-one

CLAISEN REARRANGEMENTS-XII SYNHESIS OF THE COUMARINS, 5-METHOXYSESELIN, TRACHYPHYLLIN, COUMURRAYIN AND XANTHOXYLETIN

The structure of the natural coumarins, 5-methoxyseselin 7 and trachyphyllin 14 have been confirmed by total syntheses from 7-acetoxy-5-prenyloxycoumarin 1 in good overall yields.Convenient synthetic routes to the natural coumarins, coumurrayin 4 and xanthoxyletin 10 have also been established.

EFFICIENT SYNTHESES OF THE COUMARINS, COUMURRAYIN, XANTHOXYLETIN AND TRACHYPHYLLIN

The structure of the natural coumarin, trachyphyllin (12) has been confirmed by a total synthesis from 5,7-diacetoxycoumarin (1).Convenient synthetic routes to coumurrayin (5) and xanthoxyletin (10) have been established.