ChemicalBook >> CAS DataBase List >>Ergosterol

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
Molecular Weight:
396.66
MDL Number:
MFCD00003623
MOL File:
57-87-4.mol
MSDS File:
SDS
Last updated:2024-03-14 18:29:10

Ergosterol Properties

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. -20°C
solubility Acetone (Slightly, Heated), Chloroform (Slightly), Ethyl Acetate (Slightly, Heated)
pka 14.91±0.70(Predicted)
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.
InChIKey DNVPQKQSNYMLRS-APGDWVJJSA-N
LogP 9.300 (est)
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)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H413
Precautionary statements  P273
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(46)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1241007 Ergosterol United States Pharmacopeia (USP) Reference Standard 57-87-4 50mg $393 2024-03-01 Buy
Sigma-Aldrich 45480 Ergosterol ≥95.0% (HPLC) 57-87-4 10g-f $125 2021-12-16 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 5g $72 2024-03-01 Buy
TCI Chemical E0018 Ergosterol >95.0%(GC) 57-87-4 25g $207 2024-03-01 Buy
Alfa Aesar B23840 Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water 57-87-4 5g $61.65 2024-03-01 Buy
Product number Packaging Price Buy
1241007 50mg $393 Buy
45480 10g-f $125 Buy
E0018 5g $72 Buy
E0018 25g $207 Buy
B23840 5g $61.65 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.
the chemical structure of ergosterol
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

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.

Definition

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

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.]

125315-55-1
57-87-4
Synthesis of Ergosterol from 4a,13b-Etheno-1H,9H-benzo[c]cyclopenta[h][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 6,8-bis(acetyloxy)-5,6,7,8,8a,8b,10,10a,11,12,13,13a-dodecahydro-11-(2-hydroxy-1-methylethyl)-8a,10a-dimethyl-2-phenyl-, [4aS-[4aα,6α,8β,8aα,8bβ,10aα,11α(R*),13aβ,13bα]]- (9CI)
Global( 503)Suppliers
Supplier Tel Email Country ProdList Advantage
XuZhou Magic Biotechnology Co., Ltd.
+undefined13921770081 SVP01@magicbiotech.cn China 92 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21703 55
Firsky International Trade (Wuhan) Co., Ltd
+8615387054039 admin@firsky-cn.com China 436 58
Hangzhou ICH Biofarm Co., Ltd
+undefined8613073685410 sales@ichemie.com China 985 58
Shanghai Affida new material science and technology center
+86-15081010295 +86-15081010295 jan@oudaxin.com China 332 58
Shanghai Daken Advanced Materials Co.,Ltd
+86-371-66670886 info@dakenam.com China 14770 58
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32480 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038 zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58

View Lastest Price from Ergosterol manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ergosterol pictures 2024-03-16 Ergosterol
57-87-4
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Ergosterol pictures 2024-03-15 Ergosterol
57-87-4
US $0.00-0.00 / kg 1kg 99 20 Tons Shanghai Affida new material science and technology center
Ergosterol pictures 2024-03-01 Ergosterol
57-87-4
US $10.00 / kg 1kg 98%HPLC 10000 Changsha Staherb Natural Ingredients Co., Ltd.
  • Ergosterol pictures
  • Ergosterol
    57-87-4
  • US $0.00 / KG
  • 98%+
  • WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
  • Ergosterol pictures
  • Ergosterol
    57-87-4
  • US $0.00-0.00 / kg
  • 99
  • Shanghai Affida new material science and technology center
  • Ergosterol pictures
  • Ergosterol
    57-87-4
  • US $10.00 / kg
  • 98%HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
(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) (22E)-5,7,22-Ergostatrien-3β-ol Ergosterol (Provitamin D2) (24R)-Ergosta-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 24-METHYLCHLOLESTA-5,7,22-TRIEN-3BETA-OL (22E)-Ergosta-5,7,22-trien-3beta-ol 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 ERGOSTEROL PROVITAMINE D2 ERGOSTEROL USP STANDARD ERGOSTEROL 95% (HPLC) ERGOSTEROL 95+% ERGOSTEROL EP STANDARD Ergosterol std. Ergosterol,98% Provitamin D2 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) (3S,9S,10R,13R,14R,17R)-17-((2R,5R,E)-5,6-diMethylhept-3-en-2-yl)-10,13-diMethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol Ergosterol (Pr Ergosterol hydrate Ergosterol hydrate, 96% dry weight Ergosta-5,7,22-trien-3-ol,(3b,22E)- ERGOSTEROL, >=95.0% HPLC Ergocalciferol EP Impurity B Ergocalciferol Impurity 2(Ergocalciferol EP Impurity B)