5739-85-5

Basic information

• Product Name: Pyrenophorin
• Synonyms: Pyrenophorin;(3E,8R,11E,16R)-8,16-Dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,5,10,13-tetrone
• CAS NO: 5739-85-5
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.33
• Mol File: 5739-85-5.mol
• Article Data: 18

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 5.91E-12mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: Pyrenophorin(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrenophorin(5739-85-5)
• EPA Substance Registry System: Pyrenophorin(5739-85-5)

Safety Data

• Hazardous Substances Data: 5739-85-5(Hazardous Substances Data)

Usage

General Description

Pyrenophorin is a phytotoxic sesquiterpene produced by the fungus Pyrenophora avenae, which causes diseases in various cereal crops. The chemical has been found to inhibit seedling growth in various plant species and is thought to be a key factor in the pathogenicity of the fungus. Pyrenophorin has been shown to interfere with cellular processes, including disrupting mitochondrial function and inhibiting ATP production. It is also known to induce oxidative stress and cell death in plants. Research on pyrenophorin is ongoing, as understanding its mode of action and developing strategies to mitigate its effects could potentially lead to improved disease management in agricultural settings.

InChI:InChI=1/C16H20O6/c1-11-3-5-13(17)8-10-16(20)22-12(2)4-6-14(18)7-9-15(19)21-11/h7-12H,3-6H2,1-2H3/b9-7-,10-8+/t11-,12-/m1/s1

Upstream product

• 78174-85-3 Trifluoro-acetic acid 8,16-dimethyl-2,5,10,13-tetraoxo-11-(2,2,2-trifluoro-acetoxy)-1,9-dioxa-cyclohexadec-3-yl ester 
• 71171-69-2 (E)-7-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-oct-2-enoic acid methyl ester 
• 80736-31-8 (+/-)-7-hydroxyoct-2-enoic acid 
• 84771-72-2 (3E,11E)-8,16-Dimethyl-5,13-bis-trimethylsilanyloxy-1,9-dioxa-cyclohexadeca-3,11-diene-2,10-dione 
• 80708-14-1 (4E,12E)-8,16-Dimethyl-1,9-dioxacyclohexadeca-4,12-diene-2,10-dione 
• 80708-19-6 5,14-Dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione 
• 78174-83-1 4,13-Dimethyl-3,9,12,18-tetraoxa-8,17-diaza-tricyclo[14.2.1.1^7,10]icosa-7,16-diene-2,11-dione 
• 78174-84-2 3,11-Dihydroxy-8,16-dimethyl-1,9-dioxa-cyclohexadecane-2,5,10,13-tetraone 
• 87518-76-1 dl- and meso-5,5:13,13-bis(ethylenedioxy)pyrenophorine 
• 87921-22-0 (3E,11E)-5,5,13,13-Tetrakis-ethylsulfanyl-8,16-dimethyl-1,9-dioxa-cyclohexadeca-3,11-diene-2,10-dione 
• 97911-78-9 10,22-Dimethyl-1,4,9,14,17,21-hexaoxa-dispiro[4.7.4.7]tetracosane-8,20-dione 
• 61989-64-8 (7E,20E)-(11R,24R)-11,24-Dimethyl-10,23-dioxa-1,5,15,19-tetrathia-dispiro[5.7.5.7]hexacosa-7,20-diene-9,22-dione 
• 22248-41-5 (3E,8R,11E,16R)-5,13-Dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione 
• 80736-32-9 (3E,8R,11E,16R)-(-)-8,16-Dimethyl-1,9-dioxacyclohexadeca-3,11-diene-2,10-dione 

Relevant articles and documents

Stereoselective total synthesis of (?)-pyrenophorin

Abstract: Stereoselective total synthesis of (?)-pyrenophorin was accomplished from commercially available starting material 2-bromo epoxide using regioselective ring opening and the intermolecular Mitsunobu cyclization as key steps. Graphic abstract: [Figure not available: see fulltext.].

Macrodiolide Diversification Reveals Broad Immunosuppressive Activity That Impairs the cGAS-STING Pathway

The development of new immunomodulatory agents can impact various areas of medicine. In particular, compounds with the ability to modulate innate immunological pathways hold significant unexplored potential. Herein, we report a modular synthetic approach to the macrodiolide natural product (?)-vermiculine, an agent previously shown to possess diverse biological effects, including cytotoxic and immunosuppressive activity. The synthesis allows for a high degree of flexibility in modifying the macrocyclic framework, including the formation of all possible stereoisomers. In total, 18 analogues were prepared. Two analogues with minor structural modifications showed clearly enhanced cancer cell line selectivity and reduced toxicity. Moreover, these compounds possessed broad inhibitory activity against innate immunological pathways in human PBMCs, including the DNA-sensing cGAS-STING pathway. Initial mechanistic characterization suggests a surprising impairment of the STING-TBK1 interaction.

Formation of macrocycles via ring-closing olefin metathesis

The enhanced metathesis activity of 1,3-dimesityl-4,5-dihydroimidazole-2-ylidene ruthenium carbene catalyst 3 significantly increases the feasibility of synthesizing macrocyclic compounds. Catalyst 3 exhibits sufficient activity in RCM to dimerize α,β-unsaturated ester substrates and afford the corresponding head-to-tail (E,E)-dimeric (and trimeric) macrocycles. The dimerization appears to be under thermodynamic control with the product mixture dependent not only on the electronic and steric nature of the substrate but also on concentration.