Overview A target for antifungal drugs Reference
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Ergosterol

Overview A target for antifungal drugs Reference
Product Name
Ergosterol
CAS No.
57-87-4
Chemical Name
Ergosterol
Synonyms
PROVITAMIN D2;Ganoderma lucidum Polysaccharide;ERGOSTERIN;ERGOSTERINE;Provitamin D;(3β，22E)-ergosta-5，7，22-trien-3-ol;24-Methylcholesta-5,7,22-trien-3β-ol;ERGOSTEROL;provitamind;ERGOSTEROL(P)
CBNumber
CB5763603
Molecular Formula
C28H44O
Formula Weight
396.66
MOL File
57-87-4.mol
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Ergosterol Property

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
solubility 
Acetone (Slightly, Heated), Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
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
LogP
9.300 (est)
CAS DataBase Reference
57-87-4(CAS DataBase Reference)
NIST Chemistry Reference
Ergosterol(57-87-4)
EPA Substance Registry System
Ergosta-5,7,22-trien-3-ol, (3.beta.,22E)- (57-87-4)
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Safety

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
F 
1-3-8-10
HazardClass 
6.1
PackingGroup 
II
HS Code 
29334900
Hazardous Substances Data
57-87-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H413May cause long lasting harmful effects to aquatic life

Precautionary statements

P273Avoid release to the environment.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1241007
Product name
Ergosterol
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
50mg
Price
$393
Updated
2024/03/01
Sigma-Aldrich
Product number
45480
Product name
Ergosterol
Purity
≥95.0% (HPLC)
Packaging
10g-f
Price
$125
Updated
2021/12/16
TCI Chemical
Product number
E0018
Product name
Ergosterol
Purity
>95.0%(GC)
Packaging
5g
Price
$72
Updated
2024/03/01
TCI Chemical
Product number
E0018
Product name
Ergosterol
Purity
>95.0%(GC)
Packaging
25g
Price
$207
Updated
2024/03/01
Alfa Aesar
Product number
B23840
Product name
Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water
Packaging
5g
Price
$61.65
Updated
2024/03/01
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Ergosterol Chemical Properties,Usage,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

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.

Uses

Ergosterol may be used to study the function of anti-fungal drugs such as Amphotericin B and its analogues and to study the ergosterol biosynthesis pathway within various fungi. It acts as a useful indicator of living fungal biomass.

Uses

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

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.

General Description

Ergosterol or provitamin D2 is a biological precursor of Vitamin D2. It is found predominantly in cell membranes of fungi and protists such as trypanosomes.

Hazard

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

Biochem/physiol Actions

Ergosterol has a role in maintaining the integrity of the cell membrane and its fluidity. The sterol has anti-tumor and anti-inflammatory properties.

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

Ribonucleic acid ZYMOSAN A Yeast extract

Preparation Products

22(S),23(S)-Homobrassinolide Vitamin D2
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View Lastest Price from Ergosterol manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Ergosterol 57-87-4
Price
US $1.00/KG
Min. Order
1KG
Purity
≥97%
Supply Ability
100kg/month
Release date
2021-06-21
Changsha Staherb Natural Ingredients Co., Ltd.
Product
Ergosterol 57-87-4
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
≥98% HPLC
Supply Ability
1000kg
Release date
2022-10-10
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Ergosterol 57-87-4
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2021-03-03

57-87-4, ErgosterolRelated Search:

Ergosterol STIGMASTEROL Triethylenetetramine ISOQUERCITRIN Diosgenin FERULIC ACID METHYL ESTER Ceftiofur hydrochloride Betulin LYSERGOL Terbinafine hydrochloride Vitamin D2 ergotamine Cholesterol 9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID ERGOSTEROL [3-3H] ERGOSTERYL-3-O-BETA-D-GLUCOPYRANOSIDE ASTASIN ERGOSTEROL ACETATE

  • (22E)-Ergosta-5,7,22-trien-3-ol
  • (22E,24R)-Ergosta-5,7,22-trien-3-ol
  • (3beta)-Ergosta-5,7,22- trien-3-ol
  • ergosta-5:6,7:8,22:23-trien-3-ol
  • 7,22-trien-3-ol, (3.beta.)-Ergosta-5 delta-5,7,22-ergostatrien-3beta-ol
  • Ergosterol (22E)-Ergosta-5,7,22-trien-3β-ol
  • Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water
  • 3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol, Provitamin D2
  • ERGOSTEROL (ERG)
  • ErgosterolProvitamine D2
  • 3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol
  • 5,7,22-Ergostatrien-3β-ol
  • Ergosterol,3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol, Provitamin D2
  • Ergosterol (50 mg)
  • (3β，22E)-ergosta-5，7，22-trien-3-ol
  • (22E)-5,7,22-Ergostatrien-3β-ol
  • Ergosterol (Provitamin D2)
  • (24R)-Ergosta-5,7,22-trien-3β-ol
  • 24-Methylcholesta-5,7,22-trien-3β-ol
  • 24R-Methylcholesta-5,7,22E-trien-3β-ol
  • 24α-Methyl-22E-dehydrocholesterol
  • 3β-Hydroxyergosta-5,7,22-triene
  • ergosta-5,7,22-trien-3β-ol
  • 22-trien-3-ol,(3beta,22e)-ergosta-7
  • 3-Hydroxy-(22E,24R)-ergosta-5,7,22-triene
  • 7,22-trien-3-ol,(3.beta.)-Ergosta-5
  • delta-5,7,22-ergostatrien-3beta-ol
  • ergosta-5,7,22-trien-3beta-ol
  • Ergosta-5,7,22-trien-3-ol, (3beta,22E)-
  • Ergosterol, 98% 25GR
  • Ergosterol, 98% 5GR
  • Ganoderma lucidum Polysaccharide
  • Ergocalciferol EP Impurity B
  • 24-METHYLCHLOLESTA-5,7,22-TRIEN-3BETA-OL
  • (22E)-Ergosta-5,7,22-trien-3beta-ol
  • Provitamin D
  • provitamind
  • (3BETA,22E)-ERGOSTA-5,7,22-TRIEN-3-OL
  • 3BETA-HYDROXY-5,7,22-ERGOSTATRIENE
  • 5,7,22-CHOLESTATRIEN-24-METHYL-3-OL
  • 5,7,22-ERGOSTATRIEN-3BETA-OL
  • 5,7,22-CHOLESTATETRIEN-24BETA-METHYL-3BETA-OL
  • 5,7,22-CHOLESTATRIEN-24-BETA-METHYL-3-BETA-OL
  • ERGOSTERIN
  • ERGOSTERINE
  • ERGOSTEROL
  • PROVITAMIN D2
  • PROVITAMINE D2
  • ERGOSTEROL USP STANDARD
  • ERGOSTEROL 95% (HPLC)
  • ERGOSTEROL 95+%
  • ERGOSTEROL EP STANDARD
  • Ergosterol std.
  • Ergosterol,98%
  • Provitamin D<sub>2</sub>
  • 3β-hydroxy-5,7,22-ergostatriene
  • (3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
  • ERGOSTEROL(P)