Monacolin J

Monacolin J
Names
Preferred IUPAC name
(4R,6R)-4-Hydroxy-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}oxan-2-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.110.662 Edit this at Wikidata
EC Number
  • 616-759-1
UNII
  • InChI=1S/C19H28O4/c1-11-7-13-4-3-12(2)16(19(13)17(21)8-11)6-5-15-9-14(20)10-18(22)23-15/h3-4,7,11-12,14-17,19-21H,5-6,8-10H2,1-2H3/t11-,12-,14+,15+,16-,17-,19-/m0/s1
    Key: ZDFOBOYQVYMVCW-IRUSZSJRSA-N
  • C[C@@H]1C[C@H](O)[C@@H]2[C@@H](CC[C@@H]3C[C@@H](O)CC(=O)O3)[C@@H](C)C=CC2=C1
Properties
C19H28O4
Molar mass 320.429 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Monacolin J is a statin compound produced by red yeast rice. It is a precursor to simvastatin, and has potential neuroprotective activities.[unreliable medical source?]

Monacolin J can be produced by total mycosynthesis.

References

  1. ↑ Campoy, Sonia; Sierra, Saleta; Suarez, Beatriz; Ramos, Maria C.; Velasco, Javier; Burgos, Javier S.; Adrio, Jose L. (21 July 2010). "Semisynthesis of novel monacolin J derivatives: hypocholesterolemic and neuroprotective activities". J. Antibiot. 63 (8 - August 2010): 499–505. doi:10.1038/ja.2010.76. PMID 20648024.