76348-95-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one,2,3-dihydro-6,7-dihydroxy-2,2-dimethyl-(9CI)
• Synonyms: 4H-1-Benzopyran-4-one,2,3-dihydro-6,7-dihydroxy-2,2-dimethyl-(9CI);6,7-dihydroxy-2,2-dimethylchroman-4-one
• CAS NO: 76348-95-3
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21058
• Product Categories: ALCOHOL
• Mol File: 76348-95-3.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1-Benzopyran-4-one,2,3-dihydro-6,7-dihydroxy-2,2-dimethyl-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one,2,3-dihydro-6,7-dihydroxy-2,2-dimethyl-(9CI)(76348-95-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one,2,3-dihydro-6,7-dihydroxy-2,2-dimethyl-(9CI)(76348-95-3)

Safety Data

• Hazardous Substances Data: 76348-95-3(Hazardous Substances Data)

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 533-73-3 1,2,4-Trihydroxybenzene 
• 613-03-6 1,2,4-triacetoxybenzene 
• 118948-72-4 1-(2',4',5'-trihydroxyphenyl)-3-methyl-1-oxo-2-butene 
• 20628-06-2 2-hydroxy-4,5-dimethoxyacetophenone 
• 65383-61-1 6,7-dimethoxy-2,2-dimethyl-4-chromanone 

Downstream Products

• 130208-77-4 C₂₃H₂₀O₈S₂ 
• 130208-93-4 C₂₃H₂₀O₇S₂ 
• 130208-85-4 C₂₃H₂₂O₈S₂ 
• 130208-94-5 C₂₃H₁₈Br₂O₇S₂ 

Relevant articles and documents

Discovery of Small Molecules as Multi-Toll-like Receptor Agonists with Proinflammatory and Anticancer Activities

Therapies based on activation of multiple Toll-like receptors (TLRs) may offer superior therapeutic profiles than that of single TLR activation. To discover new small molecules that could activate multiple TLRs, we performed a cell-based high-Throughput screening of a small-molecule library based on TLR3-mediated NF-B activation. Subsequent structural optimization and counterscreening of other TLRs produced the first small molecule 17e (CU-CPT17e) capable of simultaneously activating TLRs 3, 8, and 9. Biochemical studies demonstrated that 17e could induce a strong immune response via the production of various cytokines in human monocytic THP-1 cells. Furthermore, 17e inhibited the proliferation of HeLa cancer cells by triggering apoptosis and arresting the cell cycle at the S phase. These results showcase potential therapeutic applications of 17e in both vaccine adjuvants and anticancer therapies based on multi-TLR activation.

A Novel Synthesis of Precocenes. Efficient Synthesis and Regioselective O-Alkylation of Dihydroxy-2,2-dimethyl-4-chromanones

The reactions of trihydroxybenzenes 1a-c and 3-methylbut-2-enoic acid (2) in a zinc chloride/water/phosphoryl chloride system afford either the new trihydroxyphenylbutenone derivatives 3b,c or dihydroxy-2,2-dimethyl-4-chromanones 4a-c in good yields.Compounds 3b,c can be cyclized in high yields to 4b,c in 5percent sodium hydroxide solution.Regioselective O-alkylation of 4a-c leads to 5a-f in good yields.O-Alkylation of 5a-f, followed by reduction and dehydration, results in the formation of precocene 3 (7d) and its regioisomer 7a-c,e,f.Methylation of 4a-c gives 6g-i.Subsequent reduction and dehydration affords precocene 2 (7h) and its regiosiomers 7g,i.