41653-78-5

Basic information

• Product Name: (3aS,9aβ,9bα)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-6α,8α-dihydroxy-5aα-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one
• Synonyms: Ridentin B
• CAS NO: 41653-78-5
• Molecular Formula: C15H20O4
• Molecular Weight: 264.3169
• Mol File: 41653-78-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aS,9aβ,9bα)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-6α,8α-dihydroxy-5aα-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,9aβ,9bα)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-6α,8α-dihydroxy-5aα-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one(41653-78-5)
• EPA Substance Registry System: (3aS,9aβ,9bα)-3a,4,5,5a,6,7,8,9,9a,9b-Decahydro-6α,8α-dihydroxy-5aα-methyl-3,9-bis(methylene)naphtho[1,2-b]furan-2(3H)-one(41653-78-5)

Safety Data

• Hazardous Substances Data: 41653-78-5(Hazardous Substances Data)

Upstream product

• 3668-04-0 ludovicin A 
• 60268-40-8 hanphyllin 

Relevant articles and documents

TRANSANNULAR CYCLIZATION OF THE E,E-GERMACRADIENOLIDE HANPHYLLIN

The results are reported of the interaction of the trans,trans-germacradienolide hanphyllin with m-chloroperbenzoic acid and with 50percent sulfuric acid.This leads to a cyclization reaction with the formation of eudesmanolides: 1β-hydroxy-3-oxo-1,4,5,7α(H),6β(H)-eudesm-11(13)-en-6,12-olide, ridentin B, and 3β-hydroxy-5,7α(H),6β(H)-eudesma-4(15),11(13)-dien-6,12-olide; and also products of the opening of the lactone ring as a consequence of transeterification.The structures of the compounds obtained are discussed on the basis of spectral results (IR, PMR, and mass spectra) and of x-ray structural analysis.

Transformations of Some Sesquiterpene Lactones by Filamentous Fungi and Cytotoxic Evaluations

Biotransformation is an economically and ecologically viable technology which has been used to modify the structures of many classes of biologically active products. Some fungi may be useful for the biotransformation of sesquiterpene lactones (SLs), leading to unusual structural changes that modify their biological activities, and other transformations mimic their biosynthetic pathways, generating evidences for the proposed biogenesis. Eight filamentous fungi were screened for their ability to transform different SLs (1?–?9), and microbial reactions yielded compounds 10?–?17, which in turn have been isolated as natural products, thus mimicking their biosynthesis. Their structures were identified based on NMR and MS spectroscopic analyses. The cytotoxicities of SLs 1, 4, 6, 7 and 9, and their biotransformed produts (10, 14, 15 and 17) against human cancer cell lines U251 (glia), PC3 (prostate), K562 (leukemia), HCT-15 (colon), MCF7 (breast), and SKLU-1 (lung), were determined, confirming that the presence of Michael acceptor is an important feature for the bioactivity.