Citreomontanin

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Citreomontanin
Category Others
Catalog number BBF-05570
CAS 74474-66-1
Molecular Weight 352.47
Molecular Formula C23H28O3
Purity 95%

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Description

A metabolite of penicillium pedemontanum.

Specification

Synonyms all-E-citreomontanin; Citreomontanine; 2H-Pyran-2-one, 4-methoxy-5-methyl-6-(7,9,11-trimethyl-1,3,5,7,9,11-tridecahexaenyl)-, (all-E)-; 4-methoxy-5-methyl-6-((1E,3E,5E,7E,9E,11E)-7,9,11-trimethyltrideca-1,3,5,7,9,11-hexaen-1-yl)-2H-pyran-2-one
IUPAC Name 4-methoxy-5-methyl-6-[(1E,3E,5E,7E,9E,11E)-7,9,11-trimethyltrideca-1,3,5,7,9,11-hexaenyl]pyran-2-one
Canonical SMILES CC=C(C)C=C(C)C=C(C)C=CC=CC=CC1=C(C(=CC(=O)O1)OC)C
InChI InChI=1S/C23H28O3/c1-7-17(2)14-19(4)15-18(3)12-10-8-9-11-13-21-20(5)22(25-6)16-23(24)26-21/h7-16H,1-6H3/b9-8+,12-10+,13-11+,17-7+,18-15+,19-14+
InChI Key OYWYCUVDFLSMOF-JLQIEDEZSA-N

Properties

Appearance Orange Crystal
Boiling Point 540.7°C at 760 mmHg
Melting Point 165-166°C
Density 1.02 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Structures and biomimetic synthesis of novel α-pyrone polyketides of an endophytic Penicillium sp. in Catharanthus roseus
Teigo Asai, Dan Luo, Kouwa Yamashita, Yoshiteru Oshima Org Lett. 2013 Mar 1;15(5):1020-3. doi: 10.1021/ol303506t. Epub 2013 Feb 13.
Novel polyketides, citreoviripyrone A (1) and B (2), known citreomontanin (3), and (-)-citreoviridin (4) were isolated from the mycelium of the endophytic fungus. The endophytic fungus, which belongs to the genus Penicillium, was separated from surface-sterilized healthy leaves of Catharanthus roseus. The structures of 1 and 2 were determined on the basis of NMR data, and 1 was characterized as an α-pyrone polyketide featuring bicyclo[4.2.0]octadiene. The biomimetic synthesis of 1 and 2 from 3 elucidated a plausible biosynthetic pathway. Both Zn(II)-type and NAD(+)-dependent histone deacetylase inhibitors significantly enhanced the production of 1 and 3.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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