ChemicalBook > CAS DataBase List > Ergosterol

Ergosterol

Product Name:
Ergosterol
CAS No.
57-87-4
Chemical Name:
Ergosterol
CBNumber:
CB5763603
Molecular Formula:
C28H44O
Formula Weight:
396.65
MOL File:
57-87-4.mol
More
Less

Ergosterol Property

Melting point:
156-158 °C(lit.)
alpha 
-120 º (c=1, CHC13)
Boiling point:
250 °C (1.3 mmHg)
Density 
0.9784 (rough estimate)
refractive index 
-112.5 ° (C=1, THF)
storage temp. 
2-8°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)
NIST Chemistry Reference
Ergosterol(57-87-4)
EPA Substance Registry System
Ergosta-5,7,22-trien-3-ol, (3.beta.,22E)- (57-87-4)
More
Less

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
1-3-8-10
HazardClass 
6.1
PackingGroup 
II
HS Code 
29334900
Hazardous Substances Data
57-87-4(Hazardous Substances Data)
More
Less

N-Bromosuccinimide Price More Price(17)

Sigma-Aldrich Gold
Product number:
45480
Product name :
Ergosterol
Purity:
≥95.0% (HPLC)
Packaging:
10g-f
Price:
$125
Updated:
2018/11/20
Buy:
Buy
Sigma-Aldrich Gold
Product number:
1241007
Product name :
Ergosterol
Purity:
United States Pharmacopeia (USP) Reference Standard
Packaging:
50mg
Price:
$352.8
Updated:
2019/12/02
Buy:
Buy
TCI Chemical Gold
Product number:
E0018
Product name :
Ergosterol
Purity:
>95.0%(GC)
Packaging:
5g
Price:
$49
Updated:
2019/12/02
Buy:
Buy
TCI Chemical Gold
Product number:
E0018
Product name :
Ergosterol
Purity:
>95.0%(GC)
Packaging:
25g
Price:
$175
Updated:
2019/12/02
Buy:
Buy
Alfa Aesar Gold
Product number:
B23840
Product name :
Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water
Packaging:
25g
Price:
$203
Updated:
2019/12/02
Buy:
Buy
More
Less

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.

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

Raw materials

Preparation Products

Less

Ergosterol Suppliers

Global(276)Suppliers
Chengdu RunZeBenTu Chemical Co., Ltd
Tel:
13096311329 028-88469284 qq:616445927
Fax:
028-88469284
Email:
616445927@qq.com
Country:
China
ProdList:
2893
Advantage:
50
Nanjing Bermuda Biotechnology Co., Ltd.
Tel:
173-40521416- ;
Fax:
17340521416
Email:
1757224788@qq.com;1757224788@qq.com
Country:
China
ProdList:
1190
Advantage:
58
Watson Biotechnology Co.,Ltd
Tel:
027-59207879-
Fax:
QQ:1972026995
Email:
kf@3600chem.com
Country:
China
ProdList:
3960
Advantage:
55
-
Tel:
029-81629930-
Email:
1048433815@qq.com
Country:
China
ProdList:
270
Advantage:
58
Kono Chem Co.,Ltd
Tel:
29-86107037-8015
Fax:
029-86107037
Email:
info@konochemical.com
Country:
China
ProdList:
2356
Advantage:
55
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Fax:
86-10-82849933
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Country:
China
ProdList:
96815
Advantage:
76
future industrial shanghai co., ltd
Tel:
400-0066-400;021-60496031
Fax:
021-55660885
Email:
sales@jonln.com;sales@jonln.com
Country:
China
ProdList:
2000
Advantage:
65
Chembest Research Laboratories Limited
Tel:
021-20908456-
Fax:
021-58180499
Email:
sales@BioChemBest.com
Country:
China
ProdList:
5997
Advantage:
61
Alfa Aesar
Tel:
400-610-6006; 021-67582000
Fax:
021-67582001/03/05
Email:
saleschina@alfa-asia.com
Country:
China
ProdList:
30163
Advantage:
84

57-87-4, ErgosterolRelated Search:

ISOQUERCITRIN Diosgenin FERULIC ACID METHYL ESTER Ceftiofur hydrochloride Betulin LYSERGOL Terbinafine hydrochloride Vitamin D2 ergotamine Ergosterol STIGMASTEROL Cholesterol Triethylenetetramine 9,10-DIDEHYDRO-6-METHYL-ERGOLINE-8-CARBOXYLIC ACID ERGOSTEROL [3-3H] ERGOSTERYL-3-O-BETA-D-GLUCOPYRANOSIDE ASTASIN ERGOSTEROL ACETATE
  • Ergocalciferol EP Impurity B
  • Ergocalciferol Impurity 2(Ergocalciferol EP Impurity B)
  • (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
  • (3β,22E)-ergosta-5,7,22-trien-3-ol
  • (22E)-5,7,22-Ergostatrien-3β-ol
  • 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)
  • Ergosterol (Provitamin D2)
  • Ergosterol, 98% 25GR
  • Ergosterol, 98% 5GR
  • (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)-
  • Ganoderma lucidum Polysaccharide
  • Provitamin D
  • provitamind
  • 24-METHYLCHLOLESTA-5,7,22-TRIEN-3BETA-OL
  • (22E)-Ergosta-5,7,22-trien-3beta-ol
  • 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
  • (3BETA,22E)-ERGOSTA-5,7,22-TRIEN-3-OL
  • 3BETA-HYDROXY-5,7,22-ERGOSTATRIENE
  • 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
Overview A target for antifungal drugs Reference