19254-69-4

Basic information

• Product Name: Ergosta-4,6,8(14),22-tetraen-3-one
• Synonyms: Ergosta-4,6,8(14),22-tetraen-3-one;22-tetraen-3-one;Ergosta-4,6,8(14)
• CAS NO: 19254-69-4
• Molecular Formula: C28H40O
• Molecular Weight: 393
• Mol File: 19254-69-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 523.5 °C at 760 mmHg
• Flash Point: 263.5 °C
• Appearance: /
• Density: 1.01 g/cm³
• Vapor Pressure: 4.68E-11mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ergosta-4,6,8(14),22-tetraen-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: Ergosta-4,6,8(14),22-tetraen-3-one(19254-69-4)
• EPA Substance Registry System: Ergosta-4,6,8(14),22-tetraen-3-one(19254-69-4)

Safety Data

• Hazardous Substances Data: 19254-69-4(Hazardous Substances Data)

Usage

Definition

ChEBI: An ergostanoid that is (22E)-ergosta-4,6,8(14),22-tetraene substituted by an oxo group at position 3. It has been isolated from the mycelia of Cordyceps sinensis.

InChI:InChI=1/C28H40O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,17-20,24,26H,11-16H2,1-6H3/b8-7+/t19-,20+,24+,26-,27-,28+/m0/s1

Upstream product

• 2061-65-6 5-hydroxy-5α-ergosta-6,8(14)-22-trien-3β-yl acetate 
• 2061-64-5 ergosterol peroxide 
• 17398-57-1 (22E,24R)-ergosta-4,7,22-triene-3-one 
• 104729-39-7 ergosta-4,6,8(14),22-tetraene-3β-ol 
• 57-87-4 Ergosterol 
• 556-91-2 aluminum tri-tert-butoxide 
• 108-88-3 toluene 
• 106-51-4 p-benzoquinone 
• 10088-64-9 ergosta-5,7,14,22t-tetraen-3β-ol 
• 474-69-1 lumisterol 

Downstream Products

• 20817-91-8 lumista-4,6,8⁽¹⁴⁾,22t-tetraen-3-one-(2,4-dinitro-phenylhydrazone) 

Related news

Effect of ergosta-4,6,8(14),22-tetraen-3-one (ergone) on adenine-induced chronic renal failure rat: A serum metabonomic study based on ultra performance liquid chromatography/high-sensitivity mass spectrometry coupled with MassLynx i-FIT algorithm08/04/2019

BackgroundErgosta-4,6,8(14),22-tetraen-3-one (ergone) has been proven to prevent the progression of renal injury and the subsequent renal fibrosis. We investigated the therapeutic effects and mechanism of ergone on a chronic renal failure model of rats induced by adenine.detailed

Urinary metabonomics study on the protective effects of ergosta-4,6,8(14),22-tetraen-3-one on chronic renal failure in rats using UPLC Q-TOF/MS and a novel MSE data collection technique08/02/2019

Ergosta-4,6,8(14),22-tetraen-3-one (ergone), isolated from the medicinal fungus Polyporus umbellatus, has been proven to prevent the progression of renal injury and the subsequent renal fibrosis. UPLC Q-TOF/MS was employed to investigate the metabonomic characteristics of adenine-induced chronic...detailed

Ergosta-4,6,8(14),22-tetraen-3-one induces G2/M cell cycle arrest and apoptosis in human hepatocellular carcinoma HepG2 cells07/31/2019

BackgroundMushrooms have been used in Asia as traditional foods and medicines for a long time. Ergosta-4,6,8(14),22-tetraen-3-one (ergone) is one of the well-known bioactive steroids, which exists widely in various medicinal fungi such as Polyporus umbellatus, Russula cyanoxantha, and Cordyceps ...detailed

Folate-functionalized nanoparticles for controlled ergosta-4,6,8(14),22-tetraen-3-one delivery07/30/2019

To improve the therapeutic effect of ergosta-4,6,8(14),22-tetraen-3-one (ergone), a folate–decorated ergone–bovine serum albumin nanoparticles (abbreviated FA–ergone–BSANPs) was prepared. The properties were extensively studied by Zetasizer Nano Particle Size Analyzer and TEM, which indicate...detailed

Relevant articles and documents

STEROIDS FROM CALVATIA CYATHIFORMIS

Cyathisterone (ergosta-7,22-diene-3,6-dione) and cyanthisterol (8β-hydroxyergosta-4,6,22-trien-3-one), two new steroids, have been isolated from Calvatia cyanthiformis along with two known ergosterol derivatives, ergosta-4,7,22-triene-3,6-dione and ergosta-4,6,8(14),22-tetraen-3-one.Their molecular structures were defined by spectroscopic means and chemical correlations. - Key words: Calvatia cyathiformis; lycoperdaceae; sterois; cyanthisterone; ergosta-7,22-diene-3,6-dione; cyathisterol; 8β-hydroxyergosta-4,6,22-trien-3-one.

Reactive oxygen species altering the metabolite profile of the marine-derived fungus Dichotomomyces cejpii F31-1

To investigate the influence of reactive oxygen species (ROS) on the secondary metabolites of the marine-derived fungus Dichotomomyces cejpii F31-1, hydrogen peroxide (H2O2) was added to the GPY culture medium. The HPLC chromatogram of the EtOAc extract of the culture broth was distinct from that of the H2O2 free GPY medium. Further study of the metabolites in the GPY medium with H2O2 resulted in the discovery of eight known compounds. Among them, (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) and ergosta-4,6,8(14),22-tetraene-3-one (3) were present in the highest concentration, while ergosterol and diketopiperazines are abundant in the H2O2 free medium. Additionally, a new compound, dichocetide D (1) containing a chlorine element and a known ergosterol (10) were isolated from the H2O2 free medium. (22E)-5α, 8α-epidioxyergosta-6, 22-dien-3β-ol (2) exhibited moderate cytotoxic activity against human prostate cancer cell line LNCaP-C4-2B.

An anti-aldosteronic diuretic component (drain dampness) in polyporus sclerotium

Polyporus Sclerotium, botanically from the Polyporus umbellatus (PERS.) FRIES, was traditionally used for the purpose of promoting diuresis. The present study investigated the diuretic effect of ergosta-4,6,8(14),22-tetraen-3-one (ergone) which is a maker component according to the chemical assay for its quality standardization. It resulted in a reversion to ordinary value of the urinary ratio of Na/K in deoxycoricosterone acetate (DOCA)-treated and adrenalectomized rats, although it had no this effect on the Na or K contents as well as Na/K value both in normal rats and in adrenalectomized rats without DOCA. These data indicate that ergone possesses an anti-aldosteronic diuretic effect. Moreover, it was identified in the blood and bile of rats after its administration to the gastrointestinal tract. The above results demonstrate that it is an active component of Polyporus Sclerotium.

Synthesis of fluorescent 4,6,8(14)-trien-3-one steroids via 3,5,7-trien- 3-ol ethers. Important probes for steroid-protein interactions

A general synthesis of fluorescent 4,6,8(14)-trien-3-one steroids with and without an aliphatic side chain is described via 3-alkoxy-3,5,7-trienes as intermediates. The advantages of this method are general applicability, good yields, limited number of reaction steps (up to four), and ready availability of starting materials (at low cost). a) Starting from ergosterol (1) or cholesta-5,7-dien-3-ol (2) and oxidizing them to ergosta-4,7,22-trien-3-one (3) or cholesta-4,7-dien-3-one (4) we synthesized the enol ethers (5) and (6). Subsequent treatment with DDQ gave the 4,6,8(14),22-tetraen-3-one (7) and the 4,6,8(14)-trien-3-one (8). b) Similarly 17β-(I-oxopropoxy)-androsta- 4,6,8(14)-trien-3-one (13) was obtained, but the required enol ether was synthesized via the 4,6-dien-3-one (11).