40790-12-3

Basic information

• Product Name: (3S,7R,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one
• Synonyms: .alpha.-Zearalenol; 1H-2-benzoxacyclotetradecin-1-one, 3,4,5,6,7,8,9,10-octahydro-7,14,16-trihydroxy-3-methyl-, (3S,7R,11E)-; alpha zearalenol; a-Zearalenol
• CAS NO: 40790-12-3
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.3802
• Mol File: 40790-12-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 599°C at 760 mmHg
• Flash Point: 217.9°C
• Density: 1.174g/cm³
• Vapor Pressure: 3.4E-15mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: (3S,7R,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,7R,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one(40790-12-3)
• EPA Substance Registry System: (3S,7R,11E)-7,14,16-trihydroxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclotetradecin-1-one(40790-12-3)

Safety Data

• Hazardous Substances Data: 40790-12-3(Hazardous Substances Data)

Upstream product

• 3187-58-4 methyl orsellinate 
• 6110-37-8 methyl 2,4-dimethoxy-6-methylbenzoate 
• 17846-90-1 methyl 2-formyl-4,6-dimethoxybenzoate 
• 1204755-29-2 4,6-dimethoxy-2-vinyl-benzoic acid 
• 393109-13-2 (S)-tert-butyl(hept-6-en-2-yloxy)dimethylsilane 
• 1604028-37-6 (2R,6S)-6-(tert-butyldimethylsilyloxy)heptane-1,2-diol 
• 445380-26-7 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-bis(tert-butyldimethylsilyloxy)undec-1'-en-1'-yl]benzoate 
• 445380-27-8 methyl 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoate 
• 445380-28-9 4,6-bis[(2-methoxyethoxy)methyloxy]-2-[(1'E,6'R,10'S)-6',10'-dihydroxyundec-1'-en-1'-yl]benzoic acid 
• 311805-54-6 (5R,9S)-5,9-bis(tert-butyldimethylsilyloxy)decan-1-ol 
• 311805-75-1 (5S,9S)-5,9-bis(tert-butyldimethylsilyloxy)decanal 
• 311805-71-7 diethyl (6-benzyloxy-2-oxo-1-hexyl)phosphonate 
• 445380-24-5 (1'E,4R,5S)-4-(7'-benzyloxy-3'-oxohept-1'-en-1'-yl)-2,2,5-trimethyl-1,3-dioxolane 
• 311805-52-4 (1'E,2RS,4S,5S)-4-(7'-benzyloxy-3'-oxohept-1'-en-1'-yl)-5-methyl-1,3-dioxa-2-thiolane 2-oxide 

Downstream Products

• 38055-76-4 7β-cis-zearalenol 
• 36455-71-7 Z-7α-zearalenol 

Relevant articles and documents

Enantioselective total synthesis of β-zearalenol from (s)-propylene oxide

The total synthesis of 14-membered resorcylic acid macrolide, β-zearalenol, was accomplished starting from commercially available enantiomerically pure propylene oxide and methyl 2,4-dihydroxy-6-methylbenzoate using Grignard reaction, asymmetric dihydroxy

In vitro phase i metabolism of cis -zearalenone

The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (trans-ZEN). Upon the influence of (UV-) light, trans-ZEN isomerizes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive metabolization of cis-ZEN is observed for rat and human liver microsomes as analyzed by HPLC-MS/MS and high-resolution MS. Kinetic investigations based on the substrate depletion approach showed no significant difference in rate constants and half-lives for cis- and trans-ZEN in rat microsomes. In contrast, cis-ZEN was depleted about 1.4-fold faster than trans-ZEN in human microsomes. The metabolite pattern of cis-ZEN revealed a total of 10 phase I metabolites. Its reduction products, α- and β-cis-zearalenol (α- and β-cis-ZEL), were found as metabolites in both species, with α-cis-ZEL being a major metabolite in rat liver microsomes. Both compounds were identified by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was monohydroxylated cis-ZEN. In human microsomes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolites of cis-ZEN reported in this study, in particular α-cis-ZEL, might also show higher estrogenicity.

The use of π-allyltricarbonyliron lactone complexes in the synthesis of the resorcylic macrolides α- and β-zearalenol

A highly stereoselective synthesis of the natural products α- and β-zearalenol 1 and 2 has been achieved using π-allyltricarbonyliron lactone complexes to control the 1,5-stereochemical relationship of the oxygen functionalities found in these resorcylic macrolides.