85269-25-6

Basic information

• Product Name: (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone
• Synonyms: (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone;Betaenone C
• CAS NO: 85269-25-6
• Molecular Formula: C21H34O5
• Molecular Weight: 366.49166
• Mol File: 85269-25-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone(85269-25-6)
• EPA Substance Registry System: (2S,3R,4R,4aα,8aβ)-3,4,4a,5,6,7,8,8a-Octahydro-2β,7β-dihydroxy-4-[(Z)-3-hydroxy-1-oxo-2-propenyl]-2α,4,5α,7α-tetramethyl-3-[(R)-1-methylpropyl]-1(2H)-naphthalenone(85269-25-6)

Safety Data

• Hazardous Substances Data: 85269-25-6(Hazardous Substances Data)

Upstream product

• 85269-23-4 betaenone B 
• 127718-15-4 (R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-dihydro-furan-2-one 
• 96-17-3 (-)-2-methylbutanal 
• 127760-70-7 (R,E)-2,4-dimethylhex-2-enal 18 
• 116-53-0 (-)-2-methylbutyric acid 
• 76985-26-7 (2S,3R)-3,7-dimethyl-2,3-epoxy-6-octen-1-ol 
• 127718-26-7 (2S,3R,4R,4aS,5R,7R,8aS)-3-((R)-sec-Butyl)-2-hydroxy-7-(2-methoxy-ethoxymethoxy)-4-(3-methoxy-propionyl)-2,4,5,7-tetramethyl-octahydro-naphthalen-1-one 
• 127718-24-5 (4E,10E,12E)-(6R,8S,14R)-1-Methoxy-8-(2-methoxy-ethoxymethoxy)-4,6,8,12,14-pentamethyl-hexadeca-4,10,12-trien-3-one 
• 127718-16-5 (3R,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,5-dimethyl-dihydro-furan-2-one 
• 127718-21-2 C₃₇H₄₄O₆S 
• 127718-20-1 C₃₇H₄₄O₄S 
• 127718-22-3 C₃₉H₅₂O₄ 
• 127718-19-8 tert-Butyl-[(3R,5R)-3-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-6-trityloxy-hexyloxy]-dimethyl-silane 
• 127718-23-4 (6E,8E)-(2R,4S,10R)-4-(2-Methoxy-ethoxymethoxy)-2,4,8,10-tetramethyl-dodeca-6,8-dienal 

Downstream Products

• 85269-22-3 betaenone A 

Relevant articles and documents

Biosynthesis of a Tricyclo[6.2.2.02,7]dodecane System by a Berberine Bridge Enzyme-Like Aldolase

The aldol reaction is one of the most fundamental stereocontrolled carbon–carbon bond-forming reactions and is mainly catalyzed by aldolases in nature. Despite the fact that the aldol reaction has been widely proposed to be involved in fungal secondary metabolite biosynthesis, a dedicated aldolase that catalyzes stereoselective aldol reactions has only rarely been reported in fungi. Herein, we activated a cryptic polyketide biosynthetic gene cluster that was upregulated in the fungal wheat pathogen Parastagonospora nodorum during plant infection; this resulted in the production of the phytotoxic stemphyloxin II (1). Through heterologous reconstruction of the biosynthetic pathway and in vitro assay by using cell-free lysate from Aspergillus nidulans, we demonstrated that a berberine bridge enzyme (BBE)-like protein SthB catalyzes an intramolecular aldol reaction to establish the bridged tricyclo[6.2.2.02,7]dodecane skeleton in the post-assembly tailoring step. The characterization of SthB as an aldolase enriches the catalytic toolbox of classic reactions and the functional diversities of the BBE superfamily of enzymes.