74285-61-3

Basic information

• Product Name: (+/-)-3-Hydroxy-4-oxo-β-jonon
• Synonyms: (+/-)-3-Hydroxy-4-oxo-β-jonon
• CAS NO: 74285-61-3
• Molecular Weight: 222.284
• Mol File: 74285-61-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (+/-)-3-Hydroxy-4-oxo-β-jonon(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-3-Hydroxy-4-oxo-β-jonon(74285-61-3)
• EPA Substance Registry System: (+/-)-3-Hydroxy-4-oxo-β-jonon(74285-61-3)

Safety Data

• Hazardous Substances Data: 74285-61-3(Hazardous Substances Data)

Upstream product

• 79-77-6 (E)-β-ionone 
• 29790-29-2 (E)-2,4,4-trimethyl-3-(3-oxobut-1-en-1-yl)cyclohex-2-enone 
• 69659-83-2 4-Oxo-β-jonon-9-(aethylenacetal) 
• 80713-56-0 4-Oxo-β-jonon-4,9-bis(aethylenacetal) 
• 472-61-7 (3RS,3'RS)-Astaxanthin 
• 942419-98-9 4-trimethylsilyloxy-β-ionone 9-ethylene ketal 
• 74285-60-2 (+/-)-3-Acetoxy-4-oxo-β-jonon-9-(aethylenacetal) 
• 74285-59-9 (E)-3,5,5-trimethyl-2-oxo-4-(3-oxobut-1-en-1-yl)cyclohex-3-en-1-yl acetate 

Downstream Products

• 74311-44-7 (S)-3-Hydroxy-4-oxo-β-jonon 
• 80779-52-8 (R)-3-Hydroxy-4-oxo-β-jonon 
• 882491-37-4 (6S)-6-hydroxy-3-[(1E)-3-hydroxy-3-methylpenta-1,4-dienyl]-2,4,4-trimethylcyclohex-2-en-1-one 
• 74311-42-5 (S)-3-Acetoxy-4-oxo-β-jonon 
• 942420-01-1 3-(4-chlorobenzoyloxy)-4-oxo-β-ionone 

Relevant articles and documents

Analysis of palmitoyl apo-astaxanthinals, apo-astaxanthinones, and their epoxides by UHPLC-PDA-ESI-MS

Food products enriched with fatty acid-esterified xanthophylls may result in deviating dietary apo-carotenoids. Therefore, free astaxanthin and its mono- and dipalmitate esters were subjected to two degradation processes in a methanolic model system: light-accelerated autoxidation and hypochlorous acid/hypochlorite (HOCl/OCl-) bleaching. Reversed phase ultrahigh-performance liquid chromatography photodiode array with in-line electrospray ionization mass spectrometry (RP-UHPLC-PDA-ESI-MS) was used for assessment of degradation products. Apo-astaxanthinals and -astaxanthinones containing 3 (apo-9) to 10 (apo-8′) conjugated double bonds were found upon autoxidation for all three types of astaxanthin (except free apo-8′-astaxanthinal). Fragmentation of [M + H]+ and [M + Na]+ parent masses of apo-astaxanthins from dipalmitate astaxanthin indicated palmitate esterification. Astaxanthin monopalmitate degradation resulted in a mixture of free and palmitate apo-astaxanthins. HOCl/OCl- rapidly converted the astaxanthins into a mixture of epoxy-apo-9- and epoxy-apo-13-astaxanthinones. The palmitate ester bond was hardly affected by autoxidation, whereas for HOCl/OCl- the ester bond of the apo-astaxanthin palmitoyl esters was degraded.

Synthese von Astaxanthin aus β-Jonon. I. Erschliessung der enantiomeren C15-Wittigsalze durch chemische und mikrobiologische Racematspaltung von (+/-)-3-Acetoxy-4-oxo-β-jonon

Racemic 3-acetoxy-4-oxo-β-ionone (10) was synthesized from the industrially accessible intermediate β-ionone (5).Resolution of 10 into its enantiomers was achieved via the corresponding diastereometric camphanates and by microbial resolution.Site-selective alkylation of racemic and of optically pure 3-acyloxy-4-oxo-β-ionones with vinyl magnesium chloride at -70 deg furnished the corresponding 3-acyloxy-4-oxo-9-vinyl-β-ionols which could be transformed to the Wittig salts 1, 3 and 4, respectively, following known procedures .