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Ergosterol

Overview A target for antifungal drugs Reference
Ergosterol
Ergosterol structure
CAS No.
57-87-4
Chemical Name:
Ergosterol
Synonyms
ERGOSTERIN;ERGOSTEROL;provitamind;ERGOSTERINE;Provitamin D;PROVITAMIN D2;ERGOSTEROL(P);Ergosterol>PROVITAMINE D2;Ergosterol,98%
CBNumber:
CB5763603
Molecular Formula:
C28H44O
Formula Weight:
396.66
MOL File:
57-87-4.mol

Ergosterol Properties

Melting point:
156-158 °C(lit.)
Boiling point:
250 °C (1.3 mmHg)
alpha 
-120 º (c=1, CHC13)
Density 
0.9784 (rough estimate)
refractive index 
-112.5 ° (C=1, THF)
storage temp. 
-20°C
form 
Crystalline Powder or Crystalline Needles
pka
14.91±0.70(Predicted)
color 
White to off-white
optical activity
[α]20/D 120±10°, c = 1% in chloroform
Water Solubility 
PRACTICALLY INSOLUBLE
Sensitive 
Light Sensitive
Merck 
14,3659
BRN 
2338604
Stability:
Stable, but may be light or air sensitive. Incompatible with acids, strong oxidizing agents.
InChIKey
DNVPQKQSNYMLRS-APGDWVJJSA-N
CAS DataBase Reference
57-87-4(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
Z30RAY509F
NIST Chemistry Reference
Ergosterol(57-87-4)
EPA Substance Registry System
Ergosta-5,7,22-trien-3-ol, (3.beta.,22E)- (57-87-4)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H300-H413-H302-H315-H319-H331-H336-H351-H361d-H372
Precautionary statements  P264-P270-P301+P310a-P321-P405-P501a-P261-P281-P305+P351+P338-P311
Hazard Codes  T+,T,Xn
Risk Statements  28-48/20/22-40-38-25-67-36/38-22-20-63
Safety Statements  28-36/37-45-26
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
1-3-8-10
HazardClass  6.1
PackingGroup  II
HS Code  29334900
NFPA 704
0
1 0

Ergosterol price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 45480 Ergosterol ≥95.0% (HPLC) 57-87-4 10g-f $125 2018-11-20 Buy
Sigma-Aldrich E1100000 Ergosterol European Pharmacopoeia (EP) Reference Standard 57-87-4 $190 2021-03-22 Buy
Sigma-Aldrich 1241007 Ergosterol United States Pharmacopeia (USP) Reference Standard 57-87-4 50mg $366 2021-03-22 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 5g $50 2021-03-22 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 25g $177 2021-03-22 Buy

Ergosterol Chemical Properties,Uses,Production

Overview

Sterols are essential structural and regulatory components of eukaryotic cell membranes. Mammals, plants and fungi produce similar sterols, which differ in the number and location of double bonds and methyl side chains. Ergosterol (ergosta-5, 7, 22-trien-3β-ol) is a sterol found in fungi, and named for ergot, the common name of members of the fungal genus Claviceps from which ergosterol was first isolated. Ergosterol is the end product of the sterol biosynthetic pathway and is the major sterol in yeasts. Like cholesterol in mammalian cells, it is responsible for membrane fluidity and permeability[6]. Ergosterol is a very important component of yeast and other fungal cell membranes, playing many important roles as that cholesterol plays in animal cells.[1] Its specificity in higher fungi is thought to be related to the climatic instabilities (highly varying humidity and moisture conditions) encountered by these organisms in their typical ecological niches (plant and animal surfaces, soil). Thus, despite the added energy requirements of ergosterol synthesis (if compared to cholesterol), ergosterol is thought to have evolved as a nearly ubiquitous, evolutionarily advantageous fungal alternative to cholesterol.

Figure 1 the chemical structure of ergosterol

A target for antifungal drugs

Since ergosterol is a key component in cell membranes of fungi, yet absent in those of animals. It has become a very useful target for antifungal drugs. Ergosterol is also present in the cell membranes of some protists, such as trypanosomes. This also becomes the basis for the use of some antifungals against West African sleeping sickness.
Antifungal drugs targeting ergosterol includes Amphotericin B[2, 3], fluconazole, miconazole, itraconazole, and clotrimazole. Amphotericin B acts by binding to sterols (ergosterol) in the cell membrane of susceptible fungi[2, 3]. This creates a transmembrane channel, and the resultant change in membrane permeability allowing leakage of intracellular components. Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of amphotericin B and the azoles. Amphotericin B, a polyene, binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death[2, 3]. Amphotericin B, though has been replaced by safer agents in most circumstances, is still used, despite its side effects, for life-threatening fungal or protozoan infections.
Fluconazole, miconazole, itraconazole, and clotrimazole work in a different way, take effect through inhibiting synthesis of ergosterol from lanosterol by interfering with14α-demethylase[4, 5]. Fluconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Fluconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.

Reference

  1. Ruzicka, S., Edgerton, D., Norman, M., & Hill, T. (2000). The utility of ergosterol as a bioindicator of fungi in temperate soils. Soil Biology & Biochemistry, 32(7), 989-1005.
  2. Vertut-Croquin, A, et al. "Differences in the interaction of the polyene antibiotic amphotericin B with cholesterolor ergosterol-containing phospholipid vesicles. A circular dichroism and permeability study." Biochemistry 22.12(1983): 2939-44.
  3. Baginski, M, H. Resat, and E. Borowski. "Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels." Biochim Biophys Acta 1567.1-2(2002): 63-78.
  4. Ballard, S. A., et al. "A novel method for studying ergosterol biosynthesis by a cell-free preparation of Aspergillus fumigatus and its inhibition by azole antifungal agents." J Med Vet Mycol 28.4(1990):335-344.
  5. Lv, Quan-Zhen; Yan, Lan; Jiang, Yuan-Ying (2016). "The synthesis, regulation, and functions of sterols in Candida albicans: Well-known but still lots to learn". Virulence. 7 (6): 649–659.
  6. Parks, L. W., Smith, S. J. & Crowley, J. H. (1995). Biochemical and physiological effects of sterol alterations in yeast – a review. Lipids 30, 227–230.

Description

Ergosterol is a membrane component and with few exceptions is restricted to eumycotic fungi (101). As a constituent of intact membranes, its abundance should reflect the amount of living fungal biomass in an environment. This membrane component has been related to biomass by a number of investigators and the values range from 1.9 to 11.5 mg ergosterol g?1 mycelium (102). These conversion factors yield very high values for fungal biomass, and seem unrealistic (102) when compared with independent measures of bacterial biomass. It is likely that the ergosterol assay detects nonliving hyphae and these measures may overestimate viable fungal biomass. Similarly, chitin is a dominant cell wall component in most fungi and has been proposed as a unique marker for total fungal biomass.

Chemical Properties

solid

Uses

Most important of the provitamins D. Usually obtained from yeast which synthesizes it from simple sugars such as glucose. Vitamin (antirachitic).

Uses

Ergosterol is a steroid alcohol that when irradiated with ultraviolet light yields calciferol (vitamin d2). irradiated ergosterol is added to milk for vitamin d fortification.

Definition

ergosterol: A sterol occurring infungi, bacteria, algae, and plants. It isconverted into vitamin D2 by the actionof ultraviolet light.

Definition

ChEBI: A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group.

Hazard

Due to its ability to catalyze calcium deposition in the bony structure (thus preventing rickets), overdosage of vitamin D may be harmful.

Purification Methods

Crystallise ergosterol from EtOAc, then from ethylene dichloride or EtOH/*C6H6 (3:1). It has been purified by conversion to the isobutyl ester which crystallises from Et2O/Me2CO (1:3) with m: turbid at 148o, melts at 159o and becomes clear at 162o, followed by hydrolysis, [Bill & Honeywell J Biol Chem 80 15 1938]. When crystallised from EtOH, it forms the 1.5-hydrate m 168o. The water is difficult to remove giving an amorphous solid m 166-183o, b 250o/high vacuum. It is light sensitive. The benzoate has m 169-171o, after crystallisation from Me2CO/*C6H6 (4:1) after prolonged standing at 0o and becomes highly charged, with [] D20 -177o (c 1, CHCl3). [UV of sterols: Hogness et al. J Biol Chem 120 239 1937, Beilstein 6 IV 4407.]

Ergosterol Preparation Products And Raw materials

Raw materials

Preparation Products


Ergosterol Suppliers

Global( 378)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
ATK CHEMICAL COMPANY LIMITED
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+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 26762 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
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career henan chemical co
+86-371-86658258
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Chengdu Biopurify Phytochemicals Ltd.
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Hubei Jusheng Technology Co.,Ltd.
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View Lastest Price from Ergosterol manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-03 Ergosterol
57-87-4
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-11-02 Ergosterol
57-87-4
US $10.00 / Kg/Bag 1KG 99% 20 Tons Hebei Zhanyao Biotechnology Co. Ltd
2021-09-29 Ergosterol
57-87-4
US $1.00 / KG 1KG ≥97% 100kg/month WUHAN FORTUNA CHEMICAL CO., LTD

Ergosterol Spectrum


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