53811-56-6

Basic information

• Product Name: 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one
• Synonyms: 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one;7-Hydroxy-6-methylcoumarin
• CAS NO: 53811-56-6
• Molecular Formula: C₁₀H₈O₃
• Molecular Weight: 176.17
• Mol File: 53811-56-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one(53811-56-6)
• EPA Substance Registry System: 7-Hydroxy-6-methyl-2H-1-benzopyran-2-one(53811-56-6)

Safety Data

• Hazardous Substances Data: 53811-56-6(Hazardous Substances Data)

Upstream product

• 617-48-1 malic acid 
• 496-73-1 4-methyl resorcinol 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 39828-37-0 2,4-dihydroxy-5-methylbenzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 53811-55-5 6-methyl-7-acetoxycoumarin 
• 881-61-8 6-formyl umbelliferone 

Downstream Products

• 109029-00-7 6-Methyl-7-(2'-oxocyclohexyloxy)coumarin 
• 90370-11-9 6,5'-dimethylangelicin 
• 90370-14-2 6-methylangelicin 
• 4444-74-0 crenulatin 

Relevant articles and documents

Anti-AIDS agents. 37. Synthesis and structure-activity relationships of (3'R,4'R)-(+)-cis-khellactone derivatives as novel potent anti-HIV agents

To explore the structural requirements of (+)-cis-khellactone derivatives as novel anti-HIV agents, 24 monosubstituted 3',4'-di-O-(S)- camphanoyl-(+)-cis-khellactone (DCK) derivatives were synthesized asymmetrically. These compounds included 4 isomeric monomethoxy analogues (3- 6), 4 isomeric monomethyl analogues (7-10), 4 4-alkyl/aryl-substituted analogues (11-14), and 12 4-methyl-(+)-cis-khellactone derivatives (15-26) with varying 3',4'-substituents. These (+)-cis-khellactone derivatives were screened against HIV-1 replication in acutely infected H9 lymphocytes. The results demonstrated that the (3'R,4'R)-(+)-cis-khellactone skeleton, two (S)-(-)-camphanoyl groups at the 3'- and 4'-positions, and a methyl group on the coumarin ring, except at the 6-position, were optimal structural moieties for anti-HIV activity. 3-Methyl- (7), 4-methyl- (8), and 5-methyl- (9) 3',4'- di-O-(S)-camphanoyl-(3'R,4'R)-(+)-cis-khellactone showed EC50 and therapeutic index values of -5 μM and >2.15 x 106, respectively, in H9 lymphocytes, which are much better than those of DCK and AZT in the same assay. Furthermore, 8 and 9 also showed potent inhibitory activity against HIV-1 replication in the CEM-SS cell line, and most monosubstituted DCK analogues were less toxic than DCK in both assays.

Synthesis of Naturally Occurring 6-Acyl-7-methoxycoumarins

A convenient synthesis of 6-azyl-7-methoxy coymarins (2a-e) is described sterting from 6-alkyl-7-methoxycoumarins (1a-e), using cerium(IV) ammonium nitrate (CAN) as an oxidizing agent.

Photochemotherapic method of treating psoriasis by using methylangelicin compounds

The alkylangelicins according to the invention are obtained starting from an umbelliferone, in which the 6-position is already substituted by an alkyl group; in such a way the 7-allyloxy or 7-acyloxy umbelliferone intermediates can form by transposition of the allyl or acyl group only the 8-allyl and 8-acyl derivatives, and therefore the presence, even in traces, of psoralens is absolutely excluded in the subsequent synthetic steps. The 6-alkylangelicins thus obtained are particularly usable for the photochemotherapy of psoriasys and of other skin diseases characterized by cellular hyperproliferation, as well as for the photochemotherapy of vitiligo and of alopecia aerata.