53277-19-3

Basic information

• Product Name: Benzaldehyde, 2,4,6-tris(acetyloxy)-
• Synonyms: 2,4,6-Triacetoxy-benzaldehyd;Benzaldehyde,2,4,6-tris(acetyloxy);2,4,6-triacetoxybenzaldehyde
• CAS NO: 53277-19-3
• Molecular Formula: C13H12O7
• Molecular Weight: 280.234
• Mol File: 53277-19-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 151 °C
• Boiling Point: 419.3±45.0 °C(Predicted)
• Density: 1.309±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Benzaldehyde, 2,4,6-tris(acetyloxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2,4,6-tris(acetyloxy)-(53277-19-3)
• EPA Substance Registry System: Benzaldehyde, 2,4,6-tris(acetyloxy)-(53277-19-3)

Safety Data

• Hazardous Substances Data: 53277-19-3(Hazardous Substances Data)

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 60-29-7 diethyl ether 
• 487-70-7 2,4,6-trihydroxybenzaldehyde 
• 108-24-7 acetic anhydride 

Downstream Products

• 3067-10-5 7-hydroxy-5-methoxychromene-2-one 
• 31525-76-5 5-methoxyseselin 
• 1151-98-0 apigeninidin chloride 
• 15402-08-1 5,7-dihydroxyflavylium chloride 
• 1154-78-5 3′,4′,5,7-tetrahydroxyflavylium chloride 
• 164329-24-2 2,4-diacetoxyl-6-hydroxybenzaldehyde 

Relevant articles and documents

(±)-Diinsininone: made nature's way

We report the synthesis of diinsininone (33), the aglycone of (±)-diinsinin (2). Thereby, we complete the first construction of a proanthocyanidin (PA) type-A compound incorporating a [3.3.1]-bicyclic ketal as its characteristic core. Our strategy utilizes a coupling between a benzopyrilium salt and a flavanone that proves applicable to other PA type-A compounds. During this undertaking, treatment of naringenin (9) with 2-iodoxybenzoic acid (IBX) followed by reductive work-up affords eriodictyol (10). This reactivity mirrors that of catechol hydroxylase (F3H) found in the flavonoid pathway. Other interesting transformations include the formation of flavonoids through an ortho-quinone methide (o-QM) cycloaddition-oxidation sequence and regioselective β-glycosidations of several unprotected flavanones suggesting a likely synthesis of 2 from the aglycone 33.

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.

Ortho Effect in the Fragmentation of 2-Acetoxychalcones under Electron Impact

2-Acetoxychalcones decompose under electron impact conditions by loss of an acetoxy fragment to form flavylium ions.The effect is restricted to the ortho position and is reduced after hydrogenation of the chalcone double bond.The intense flavylium ion originates as shown by specific labelling with 18O-from two different fragmentation lines: (a) direct loss of an acetoxy radical by cleavage of the phenolic Ar-O bond and (b) sequential elimination of ketene and a hydroxy radical.