66018-41-5

Basic information

• Product Name: Zeaenol
• Synonyms: LL Z1640-4;Zeaenol
• CAS NO: 66018-41-5
• Molecular Formula: C19H24O7
• Molecular Weight: 364.38966
• Mol File: 66018-41-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 636.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.275±0.06 g/cm3(Predicted)
• Storage Temp.: -20C
• PKA: 7.43±0.70(Predicted)
• CAS DataBase Reference: Zeaenol(CAS DataBase Reference)
• NIST Chemistry Reference: Zeaenol(66018-41-5)
• EPA Substance Registry System: Zeaenol(66018-41-5)

Safety Data

• Hazardous Substances Data: 66018-41-5(Hazardous Substances Data)

Usage

Uses

LL Z1640-4 is a cis-enol resorcylic acid lactone first reported in 1978 exhibiting both antiviral and antiprotozoan activity. More recently, LL Z1640-2, containing the essential cis-enone system that selectively inhibits TAK 1, has gained literature focus. With its "inactive" cis-enol, LL Z1640-4 is an ideal negative control to help dissect the selectivity of the MAP kinases.

General Description

A cell-permeable resorcylic acid lactone compound that may serve as a negative control for TAK1 (TGF-β-Activated Kinase-1) inhibition studies. The active TAK1 inhibitor is also available, (5Z)-7-Oxozeaenol, Curvularia sp. (Cat. No. 499610).

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Relevant articles and documents

14-Membered resorcylic acid lactone derivatives with their anti-inflammatory from the fungus Aspergillus sp. ZJ-65

Two new 14-membered resorcylic acid lactone derivatives, ascarpins A (1) and B (2), together with three related known compounds (3–5) were isolated from the fungus Aspergillus sp. ZJ-65, obtaining from the intestine of grass carp. These structures were elucidated on the basis of extensive spectroscopic methods, chemical conversion, and comparison with literature. All isolates were tested for their inhibitory activity against LPS-induced NO production in RAW 264.7 macrophages. Among them, compounds 1–4 exhibited potential anti-inflammatory activity with IC50 values ranging from 7.6 to 48.3 μM.

Convergent and stereoselective synthesis of (-)-zeaenol

Stereoselective synthesis of (-)-zeaenol has been accomplished from d-xylose as a chiral pool starting material. The key steps of this convergent synthetic strategy involves a Stille coupling, a Noyori reduction, a Julia-Kocienski olefination and a macrolactonization to obtain (-)-zeaenol. We have also explored a Sonogashira coupling along with a Trost protocol for the intramolecular hydrosilylation on the homopropargylic alcohol system as an alternative synthetic approach to this molecule.

The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactoniza