Ergosterol

Details:

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
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)
Safety Information
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)
MSDS Information
Provider    Language
Provitamine D2    English
ACROS    English
SigmaAldrich    English
ALFA    English
Ergosterol Usage And Synthesis
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    
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.
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    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    Ribonucleic acid-->Yeast extract-->ZYMOSAN A-->4a,13b-Etheno-1H,9H-benzo[c]cyclopenta[h][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione, 5,6,7,8,8a,8b,10,10a,11,12,13,13a-dodecahydro-6-hydroxy-8a,10a-dimethyl-2-phenyl-11-[(1R,2E,4R)-1,4,5-trimethyl-2-hexenyl]-, (4aS,6S,8aR,8bR,10aR,11R,13aR,13bS)--->Ergosta-4,7,22-trien-3-one, (22E)-
Preparation Products    Vitamin D2-->22(S),23(S)-Homobrassinolide-->Stellasterol