57-87-4 Usage
Uses
1. Used in the Food Industry:
Ergosterol is used as a source of Vitamin D2 for fortification, particularly in milk products. When irradiated with ultraviolet light, it yields calciferol (vitamin D2), which is essential for maintaining healthy bones and immune system function.
2. Used in Pharmaceutical Research:
Ergosterol serves as a valuable compound for studying the function of anti-fungal drugs such as Amphotericin B and its analogues. It also aids in understanding the ergosterol biosynthesis pathway within various fungi, acting as a useful indicator of living fungal biomass.
3. Used in Environmental Science:
As a membrane component, ergosterol is used to estimate the amount of living fungal biomass in an environment. Its abundance in intact membranes reflects the presence of living fungi, making it a reliable marker for ecological studies.
4. Used in Chemical Research:
Ergosterol is a phytosterol consisting of ergostane with double bonds at the 5,6-, 7,8-, and 22,23-positions, as well as a 3beta-hydroxy group. Its unique chemical structure makes it an interesting subject for research in the field of chemical properties and potential applications.
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 Amphotericin B, though has been replaced by safer agents in most circumstances, is still used, despite its side effects, for life-threatening fungal or protozoan infections.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
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.
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.
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.
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.
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.
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 57-87-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 7 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57-87:
(4*5)+(3*7)+(2*8)+(1*7)=64
64 % 10 = 4
So 57-87-4 is a valid CAS Registry Number.
InChI:InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19?,20?,22-,24+,25?,26-,27-,28+/m0/s1
57-87-4Relevant articles and documents
Methods for preparing cholesterol, and derivatives and analogs thereof
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, (2021/04/07)
The present invention relates to the field of pharmaceutical chemistry, and in particular to methods of preparing cholesterol,and derivatives and analogs thereof. The cholesterol derivatives include, but not limited to, 7-dehydrocholesterol, 25-hydroxycholesterol, 25- hydroxy7dehydrocholesterol and ergosterol. In the invention, phytosterol can be used as a raw material to prepare the compound shown in the formula I through microbial conversion, and then cholesterol and the derivatives and analogues thereof are prepared.
MOLECULARLY IMPRINTED POLYMERS
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, (2012/03/12)
The present invention provides methods of designing molecularly imprinted polymers (MIPs) which have applications in extracting bioactive compounds from a range of bioprocessing feedstocks and wastes. The present invention is further directed to MIPs designed by the methods of the present invention.
METHODS AND COMPOSITIONS FOR THE TREATMENT OF ESTROGEN-DEPENDENT HYPERPROLIFERATIVE UTERINE DISORDERS
-
, (2010/04/30)
The present invention relates to the treatment of estrogen-dependent hyperproliferative uterine disorders including endometriosis, uterine fibroids, endometrial hyperplasia, uterine cancer, and their related symptoms by intravaginally administering at least two active agents selected from an aromatase inhibitor,an antiinflammatory agent, and a uterine-selective estrogen receptor antagonist. This combination therapy reduces local estrogen production, blocks local estrogen action, and suppresses inflammation locally, resulting in starvation of the estrogen-dependent diseased tissues, relief of related symptoms, and retardation of disease progression. Intravaginal delivery maximizes local inhibition of estrogen production without significantly affecting systemic circulating estogen levels. This results in enhanced clinical ellicacy and reduced side effects.
Facile retro-cycloaddition of adducts derived from steroidal 5,7-diene and 4-phenyl-1,2,4-triazoline-3,5-dione by diisobutylaluminium hydride
Kondo, Fumihiro,Miyashita, Misako,Konno, Katsuhiro,Takayama, Hiroaki
, p. 2679 - 2680 (2007/10/02)
Facile retro-cycloaddition of adducts derived from a steroidal 5,7-diene and 4-phenyl-1,2,4-triazoline-3,5-dione was achieved by diisobutylaluminium hydride under mild conditions.
EFFECT ON ERGOSTEROL BIOSYNTHESIS OF A FUNGICIDE, SSF-109, IN BOTRYTIS CINEREA
Shirane, Noboru,Murabayashi, Akira,Masuko, Michio,Uomori, Atsuko,Yoshimura, Yohko,et al.
, p. 2513 - 2520 (2007/10/02)
Treatment of Botrytis cinerea with a novel fungicide SSF-109, (dl)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cyclo-heptanol (0.45 μg ml-1), gave five 14α-methyl sterols, 24-methylene-24(25)-dihydrolanosterol, 24-methylene-24(25)-dihydrolanosten-3-one, obtusifoliol, obtusifolione, and 14α-methylfecosterol, together with ergosterol and ergosta-5,8,22-trien-3β-ol.SSF-109 was found to inhibit the biosynthesis of ergosterol at the 14α-demethylation step.
IMPROVED SYNTHESIS OF 1,2,4-TRIAZOLINE-3,5-DIONE DERIVATIVES OF ERGOSTEROL AND A NEW METHOD FOR THEIR RECONVERSION TO ERGOSTEROL
Barton, Derek H. R.,Lusinchi, Xavier,Ramirez, Jesus Sandoval
, p. 2995 - 2998 (2007/10/02)
The ergosterol diene system reacts in excellent yield with a series of 4-substituted 1,2,4-triazoline-3,5-diones generated by in situ oxidation of the appropriate hydrazides with phenylseleninic anhydride or phenylseleninic acid.Diaryltelluroxide and diphenylselenoxide are also efficient oxidants.The diene system can be smoothly regenerated by alkaline hydrolysis.
Potent Hydrophylic Dienophiles. Synthesis and Aqueous Stability of Several 4-Aryl- and Sulfonated 4-Aryl-1,2,4-triazoline-3,5-diones and Their Immobilization on Silica Gel
Keana, John F.W.,Guzikowski, Anthony P.,Ward, David D.,Morat, Claude,Nice, Faith L. Van
, p. 2654 - 2660 (2007/10/02)
The purpose of this investigation is the development of a series of sulfonated 4-aryl-1,2,4-triazoline-3,5-diones (TADs) useful as potent dienophiles for Diels-Alder reactions in aqueous solution and capable of providing a TAD moiety immobilized on an insoluble support.TADs 4, 5, 23, 24, and 29 were all prepared by oxidation of the corresponding urazoles with N2O4.The urazole precursors were prepared by chlorosulfonation of the appropriate 4-arylurazole, followed in some cases by hydrolysis and neutralization.While TAD sulfonic acids 5 and 29 were not stable toward isolation, the presence of the bulky isopropyl groups in 23 and 24 rendered these TADs isolable in pure form and sufficiently stable in water to allow Diels-Alder reactions to compete successfully with attack on the TAD moiety by the solvent (see following paper).Urazolesulfonyl chlorides 2, 18, and 19 reacted with aminopropylsilylated silica gel 31 to give the corresponding immobilized sulfonamides, which were readily oxidized to TAD silica gels 33 (red) and 34 (purple).TAD acid 23 and 31 gave silica gel 35 in which the TAD moiety was attached to the gel via an ionic bond. 1,3-Dienes were selectively and quantitatively removed from solution by these silica gels and could be recovered quantitatively therefrom.
