251091-29-9

Basic information

• Product Name: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-3-hydroxy-2,6-dimethyl-4-[(2E,4E)-1-oxo-2,4-hexadienyl]-
• CAS NO: 251091-29-9
• Molecular Formula: C16H18O5
• Molecular Weight: 290.316
• Mol File: 251091-29-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-3-hydroxy-2,6-dimethyl-4-[(2E,4E)-1-oxo-2,4-hexadienyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-3-hydroxy-2,6-dimethyl-4-[(2E,4E)-1-oxo-2,4-hexadienyl]-(251091-29-9)
• EPA Substance Registry System: 2,4-Cyclohexadien-1-one, 6-(acetyloxy)-3-hydroxy-2,6-dimethyl-4-[(2E,4E)-1-oxo-2,4-hexadienyl]-(251091-29-9)

Safety Data

• Hazardous Substances Data: 251091-29-9(Hazardous Substances Data)

Upstream product

• 79950-85-9 sorbicillin 
• 64-19-7 acetic acid 
• 2614-88-2 sorbinyl chloride 
• 110-44-1 sorbic Acid 
• 6248-20-0 2,4-dihydroxy-3-methylbenzaldehyde 
• 108-24-7 acetic anhydride 
• 608-25-3 2-methylbenzene-1,3-diol 
• 634-65-1 2,4-dimethylbenzene-1,3-diol 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 251091-33-5 (6S)-6-acetoxy-4-(2,4-hexadienoyl)-3-hydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one 
• 1569266-62-1 C₂₀H₂₀O₆ 
• 388079-06-9 (+/-)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one 
• 79950-85-9 sorbicillin 

Relevant articles and documents

Biomimetic explorations towards the bisorbicillinoids: Total synthesis of bisorbicillinol, bisorbibutenolide, and trichodimerol

Strikingly simple cascade dimerization sequences can be used to assemble the complex frameworks of bisorbicillinoids such as bisorbicillinol (1), bisorbibutenolide (2), and trichodimerol (3). The mechanistic facets of the biomimetic total syntheses of these bioactive natural products were also explored. Inspection of the unique molecular architecture of these compounds reveals that they are likely to be assembled in nature by a dimerization of two oxidized forms of sorbicillin.

Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization

Natural products are a virtually inexhaustible source of small molecules with spectacular molecular architectures and biomedical potential. Their structural complexity generates formidable challenges to total synthesis but often also precludes time- and resource-efficient, stereoselective synthetic access. Biosynthetically, nature frequently uses dimerization and oligomerization reactions to produce highly challenging frameworks from simple starting materials. Impressive examples are the bisorbicillinoids, a family of fungal natural products thought to originate from the polyketide precursor sorbicillin. Utilizing the recombinant oxidoreductase SorbC from the sorbicillin biosynthetic gene cluster, a robust, fully stereoselective synthesis of bisorbicillinoid natural products and unnatural side-chain analogues was developed.

Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.

In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative) analysis for 1 gave m/z 247 as the (M-1)- ion peak. The hydrolysis of synthetic 6-O-acetylsorbicillinol (+/- -2) by 0.05 M KOH and acetylation of product 1 in an aqueous solution indicated that the structure of 1 was (6S)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one, designated sorbicillinol, a quinol that has been postulated to be important in bisorbicillinoid biosynthesis.