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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);PROVITAMINE D2;Ergosterol,98%;Ergosterol (Pr
CBNumber:
CB5763603
Molecular Formula:
C28H44O
Formula Weight:
396.65
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. 
2-8°C
form 
Crystalline Powder or Crystalline Needles
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.
CAS DataBase Reference
57-87-4(CAS DataBase Reference)
NIST Chemistry Reference
Ergosterol(57-87-4)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H300 Fatal if swallowed Acute toxicity,oral Category 1, 2 Danger P264, P270, P301+P310, P321, P330,P405, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H372 Causes damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 1 Danger P260, P264, P270, P314, P501
H413 May cause long lasting harmful effects to aquatic life Hazardous to the aquatic environment, long-term hazard Category 4
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P281 Use personal protective equipment as required.
P311 Call a POISON CENTER or doctor/physician.
P321 Specific treatment (see … on this label).
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

Ergosterol price More Price(17)

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 1241007 Ergosterol United States Pharmacopeia (USP) Reference Standard 57-87-4 50mg $352.8 2018-11-13 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 5g $57 2018-11-22 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 25g $170 2018-11-22 Buy
Alfa Aesar B23840 Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water 57-87-4 25g $197 2018-11-13 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.

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( 235)Suppliers
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Shenzhen Sendi Biotechnology Co.Ltd.
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ATK CHEMICAL COMPANY LIMITED
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View Lastest Price from Ergosterol manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-09 Ergosterol
57-87-4
US $1.00 / KG 1KG 99% 1ton career henan chemical co

Ergosterol Spectrum


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