| Identification | Back Directory | [Name]
Soraphen A | [CAS]
122547-72-2 | [Synonyms]
C11300
Soraphen A
(1S,2S,3Z,5R,6S,11S,14S,15R,16R,17S,18S)-15,17-dihydroxy-5,6,16-trimethoxy-2,14,18-trimethyl-11-phenyl-12,19-dioxabicyclo[13.3.1]nonadec-3-en-13-one
4,19-Dioxabicyclo[13.3.1]nonadec-12-en-3-one,1,17-dihydroxy-10,11,18-triMethoxy-2,14,16-triMethyl-5-phenyl-,(1R,2S,5S,10S,11R,12E,14S,15S,16S,17S,18R)- | [Molecular Formula]
C29H44O8 | [MOL File]
122547-72-2.mol | [Molecular Weight]
520.65 |
| Hazard Information | Back Directory | [Description]
Soraphen A was originally isolated from the culture broth of Sorangium cellulosum, a soil-dwelling myxobacterium, for its potent antifungal activity (Gerth et al. 1994, Gerth et al. 2003). This polyketide natural product contains an unsaturated 18-membered lactone ring, an extracyclic phenyl ring, 2 hydroxyl groups, 3 methyl groups, and 3 methoxy groups (Bedorf et al. 1993, Ligon et al. 2002) . There is also a 6-membered ring within the macrocycle formed by a hemiketal between the C3 carbonyl and C7 hydroxyl. | [Uses]
Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation. It has demonstrated strong promise as a broad-spectrum fungicide against various plant pathogenic fungi (Pridzun et al. 1995). | [Definition]
ChEBI: A macrolide and an agent highly effective against plant-pathogenic fungi. It was extensively researched for agricultural use until it was discovered to be a teratogen. | [References]
Total Synthesis of the Acetyl CoA Carboxylase Inhibitor Soraphen A: Asymmetric Tsuji Reduction Enables Successive Olefin Metathesis. DOI:10.1021/jacs.1c12063
Soraphen A, an inhibitor of acetyl CoA carboxylase activity, interferes with fatty acid elongation. DOI:10.1016/j.bcp.2010.12.014
https://www.cell.com/fulltext/S1097-2765(04)00725-7 |
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