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57-87-4 Usage

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 Amphotericin B, though has been replaced by safer agents in most circumstances, is still used, despite its side effects, for life-threatening fungal or protozoan infections.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

Different sources of media describe the Uses of 57-87-4 differently. You can refer to the following data:
1. Most important of the provitamins D. Usually obtained from yeast which synthesizes it from simple sugars such as glucose. Vitamin (antirachitic).
2. 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.
3. 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

Different sources of media describe the Definition of 57-87-4 differently. You can refer to the following data:
1. ergosterol: A sterol occurring infungi, bacteria, algae, and plants. It isconverted into vitamin D2 by the actionof ultraviolet light.
2. 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.

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.]

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

57-87-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (E0018)  Ergosterol  >95.0%(GC)

  • 57-87-4

  • 5g

  • 355.00CNY

  • Detail
  • TCI America

  • (E0018)  Ergosterol  >95.0%(GC)

  • 57-87-4

  • 25g

  • 995.00CNY

  • Detail
  • Alfa Aesar

  • (B23840)  Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water   

  • 57-87-4

  • 5g

  • 594.0CNY

  • Detail
  • Alfa Aesar

  • (B23840)  Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water   

  • 57-87-4

  • 25g

  • 1408.0CNY

  • Detail
  • Alfa Aesar

  • (B23840)  Ergosterol hydrate, 96% (dry wt.), cont. up to ca 6% water   

  • 57-87-4

  • 100g

  • 2369.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1512)  Ergosterol  pharmaceutical secondary standard; traceable to USP, PhEur

  • 57-87-4

  • PHR1512-200MG

  • 862.41CNY

  • Detail
  • Sigma-Aldrich

  • (E1100000)  Ergosterol  European Pharmacopoeia (EP) Reference Standard

  • 57-87-4

  • E1100000

  • 1,880.19CNY

  • Detail
  • USP

  • (1241007)  Ergosterol  United States Pharmacopeia (USP) Reference Standard

  • 57-87-4

  • 1241007-50MG

  • 4,326.66CNY

  • Detail
  • Sigma

  • (E6510)  Ergosterol  ≥75%

  • 57-87-4

  • E6510-5G

  • 779.22CNY

  • Detail
  • Sigma

  • (E6510)  Ergosterol  ≥75%

  • 57-87-4

  • E6510-10G

  • 1,338.48CNY

  • Detail
  • Sigma

  • (E6510)  Ergosterol  ≥75%

  • 57-87-4

  • E6510-25G

  • 2,788.11CNY

  • Detail

57-87-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Ergosterol

1.2 Other means of identification

Product number -
Other names ERGOSTERIN

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57-87-4 SDS

57-87-4Synthetic route

C42H61N3O6S*C6H15N

C42H61N3O6S*C6H15N

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 16h; Heating;76%
3β-acetoxy-5α,8α-(4-phenyl-1,2,4-triazolidine-3,5-dione-1,2-diyl)ergosta-6,22-diene
28421-56-9

3β-acetoxy-5α,8α-(4-phenyl-1,2,4-triazolidine-3,5-dione-1,2-diyl)ergosta-6,22-diene

A

Ergosterol
57-87-4

Ergosterol

B

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; toluene at 0℃; for 0.166667h;A 70%
B n/a
3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene
10123-90-7

3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene

A

Ergosterol
57-87-4

Ergosterol

B

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

1-Isobutyl-4-phenyl-[1,2,4]triazolidin-3-one

Conditions
ConditionsYield
With diisobutylaluminium hydride In hexane; toluene at 0℃; for 0.166667h;A 51%
B n/a
(24R)-5,7-Ergostadiene-1α,3β,25-triol
131321-88-5

(24R)-5,7-Ergostadiene-1α,3β,25-triol

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether for 0.05h; Irradiation;25%
diethyl ether
60-29-7

diethyl ether

previtamin D2
21307-05-1

previtamin D2

A

Ergosterol
57-87-4

Ergosterol

B

lumisterol
474-69-1

lumisterol

C

tachysterol
115-61-7

tachysterol

Conditions
ConditionsYield
at 0℃; UV-Licht.Irradiation;
(22E,24R)-ergosta-4,7,22-triene-3-one
17398-57-1

(22E,24R)-ergosta-4,7,22-triene-3-one

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With aluminum isopropoxide; isopropyl alcohol
lanosterol
19044-12-3

lanosterol

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
biosynthesis by Botrytis cinerea in the presence of (dl)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;
benzoyloxy-3β (urazolo-1',2')-5α,8α ergostadiene-6,22
87530-75-4

benzoyloxy-3β (urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;10 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;10 % Turnov.
benzoyloxy-3β (benzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22
87530-76-5

benzoyloxy-3β (benzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;53 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;53 % Turnov.
benzoyloxy-3β (p-nitrophenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22
87530-79-8

benzoyloxy-3β (p-nitrophenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;98 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;98 % Turnov.
benzoyloxy-3β (anisalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22
87530-77-6

benzoyloxy-3β (anisalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;29 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;29 % Turnov.
Multi-step reaction with 2 steps
1: 98 percent / NaNO2 (10percent) / tetrahydrofuran; acetic acid
2: 10 percent Turnov. / KOH (0.8N) / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 98 percent / 2,4-dinitro phenylhydrazine, p-toluenesulfonic acid monohydrate / H2O; tetrahydrofuran / 3 h / Heating
2: 18 percent Turnov. / KOH (0.8N) / ethanol / 2 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 98 percent / 2,4-dinitro phenylhydrazine, p-toluenesulfonic acid monohydrate / H2O; tetrahydrofuran / 3 h / Heating
2: 95 percent / PhSeOOH / tetrahydrofuran / 0.33 h / Heating
3: 10 percent Turnov. / KOH (0.8N) / ethanol / 2 h / Heating
View Scheme
benzoyloxy-3β (p-nitrobenzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22
87530-78-7

benzoyloxy-3β (p-nitrobenzalamino-4' urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;67 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;62 % Turnov.
benzoyloxy-3β (amino-4' urazolo-1',2')-5α,8α ergostadiene-6,22
104729-32-0

benzoyloxy-3β (amino-4' urazolo-1',2')-5α,8α ergostadiene-6,22

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;18 % Turnov.
Multi-step reaction with 2 steps
1: 95 percent / PhSeOOH / tetrahydrofuran / 0.33 h / Heating
2: 10 percent Turnov. / KOH (0.8N) / ethanol / 2 h / Heating
View Scheme
(22E)-5α,8α-(4'-phenyl)urazoloergosta-6,22-dien-3β-yl benzoate
28487-73-2, 76035-90-0

(22E)-5α,8α-(4'-phenyl)urazoloergosta-6,22-dien-3β-yl benzoate

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating;37 % Turnov.
With potassium hydroxide In ethanol for 2h; Heating;37 % Turnov.
diethyl ether
60-29-7

diethyl ether

ergosterol peroxide
2061-64-5

ergosterol peroxide

lithium alanate

lithium alanate

A

Ergosterol
57-87-4

Ergosterol

B

5α-ergost-7-ene-3β,5-diol

5α-ergost-7-ene-3β,5-diol

(22E)-3α,5-cyclo-5α-ergosta-6,8(14),22-triene
24352-51-0

(22E)-3α,5-cyclo-5α-ergosta-6,8(14),22-triene

trichloroacetic acid
76-03-9

trichloroacetic acid

A

Ergosterol
57-87-4

Ergosterol

B

isomer(ic) ergostatrienol

isomer(ic) ergostatrienol

Conditions
ConditionsYield
at 80℃; Kochen des Reaktionsprodukts mit aethanol. NaOH;
chloroform
67-66-3

chloroform

(22E)-3α,5-cyclo-5α-ergosta-6,8(14),22-triene
24352-51-0

(22E)-3α,5-cyclo-5α-ergosta-6,8(14),22-triene

trichloroacetic acid
76-03-9

trichloroacetic acid

A

Ergosterol
57-87-4

Ergosterol

B

isomer(ic) ergostatrienol

isomer(ic) ergostatrienol

Conditions
ConditionsYield
at 20℃; Kochen des Reaktionsprodukts mit aethanol. NaOH;
propan-1-ol
71-23-8

propan-1-ol

9(11)-dehydroergosterol
516-85-8

9(11)-dehydroergosterol

sodium

sodium

A

Ergosterol
57-87-4

Ergosterol

B

ergosta-7,9(11),22-triene-3β-ol
516-84-7

ergosta-7,9(11),22-triene-3β-ol

C

(22E)-ergosta-7,22-dien-3β-ol
2465-11-4

(22E)-ergosta-7,22-dien-3β-ol

ethanol
64-17-5

ethanol

9(11)-dehydroergosterol
516-85-8

9(11)-dehydroergosterol

sodium

sodium

A

Ergosterol
57-87-4

Ergosterol

B

ergosta-7,9(11),22-triene-3β-ol
516-84-7

ergosta-7,9(11),22-triene-3β-ol

C

(22E)-ergosta-7,22-dien-3β-ol
2465-11-4

(22E)-ergosta-7,22-dien-3β-ol

(22E,24R)-ergosta-4,7,22-triene-3-one
17398-57-1

(22E,24R)-ergosta-4,7,22-triene-3-one

aluminum isopropoxide
555-31-7

aluminum isopropoxide

isopropyl alcohol
67-63-0

isopropyl alcohol

A

Ergosterol
57-87-4

Ergosterol

B

24βF-methyl-cholestatrien-(4.7.22t)-ol-(3α)
6538-05-2

24βF-methyl-cholestatrien-(4.7.22t)-ol-(3α)

C

ergosta-4,7,22-trien-3-ol
97583-19-2

ergosta-4,7,22-trien-3-ol

D

ergostatrien-(5.7.22t)-ol-(3α)

ergostatrien-(5.7.22t)-ol-(3α)

22-hydroxy-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinorchol-6-ene-1α,3β-diol 1,3-diacetate
125315-55-1

22-hydroxy-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinorchol-6-ene-1α,3β-diol 1,3-diacetate

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: pyridine / 4 h / Ambient temperature
2: 1) NaI / 1) DMF, 30 min, 80 deg C, 2) 30 min, 80 deg C
3: 79 percent / KOH / methanol / 0.5 h / Heating
4: 90 percent / PPTS / CH2Cl2 / 24 h / Ambient temperature
5: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
6: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
7: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
8: 86 percent / LiAlH4 / tetrahydrofuran / Heating
9: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
22-Oxo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl diacetate
125315-53-9

22-Oxo-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl diacetate

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 950 g / NaBH4 / methanol / 0.17 h / Ambient temperature
2: pyridine / 4 h / Ambient temperature
3: 1) NaI / 1) DMF, 30 min, 80 deg C, 2) 30 min, 80 deg C
4: 79 percent / KOH / methanol / 0.5 h / Heating
5: 90 percent / PPTS / CH2Cl2 / 24 h / Ambient temperature
6: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
7: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
8: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
9: 86 percent / LiAlH4 / tetrahydrofuran / Heating
10: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diol
131249-29-1

22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diol

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / PPTS / CH2Cl2 / 24 h / Ambient temperature
2: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
3: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
4: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
5: 86 percent / LiAlH4 / tetrahydrofuran / Heating
6: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl Diacetate
131249-28-0

22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β-diyl Diacetate

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 79 percent / KOH / methanol / 0.5 h / Heating
2: 90 percent / PPTS / CH2Cl2 / 24 h / Ambient temperature
3: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
4: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
5: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
6: 86 percent / LiAlH4 / tetrahydrofuran / Heating
7: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
5α,8α-(4-Phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β,22-triyl 1α,3β-Diacetate 22-p-Toluenesulfonate
131249-26-8

5α,8α-(4-Phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-23,24-dinor-6-cholene-1α,3β,22-triyl 1α,3β-Diacetate 22-p-Toluenesulfonate

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1) NaI / 1) DMF, 30 min, 80 deg C, 2) 30 min, 80 deg C
2: 79 percent / KOH / methanol / 0.5 h / Heating
3: 90 percent / PPTS / CH2Cl2 / 24 h / Ambient temperature
4: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
5: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
6: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
7: 86 percent / LiAlH4 / tetrahydrofuran / Heating
8: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinor-6-cholene
131249-30-4

22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β-bis(tetrahydropyranyloxy)-23,24-dinor-6-cholene

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
2: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
3: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
4: 86 percent / LiAlH4 / tetrahydrofuran / Heating
5: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
(24R)-5α,8α-(4-Phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β,25-tris(tetrahydropyranyloxy)-6-ergostene
131249-35-9, 131321-86-3

(24R)-5α,8α-(4-Phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β,25-tris(tetrahydropyranyloxy)-6-ergostene

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
2: 86 percent / LiAlH4 / tetrahydrofuran / Heating
3: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
(24R)-22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β,25-tris(tetrahydropyranyloxy)-6-ergostene
131249-33-7

(24R)-22-Phenylsulfonyl-5α,8α-(4-phenyl-3,5-dioxo-1,2,4-triazolidine-1,2-diyl)-1α,3β,25-tris(tetrahydropyranyloxy)-6-ergostene

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
2: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
3: 86 percent / LiAlH4 / tetrahydrofuran / Heating
4: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
(3S)-4-iodo-2,3-dimethyl-2-butanol tetrahydropyranyl ether
131249-25-7, 131321-85-2

(3S)-4-iodo-2,3-dimethyl-2-butanol tetrahydropyranyl ether

Ergosterol
57-87-4

Ergosterol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1) BuLi, HMPA / 1) THF, -78 deg C to -20 deg C, 20 min, 2) THF, -20 deg C, 1.5h
2: 53 percent / sodium amalgam (5percent), Na2HPO4 / methanol / 16 h / Ambient temperature
3: 83 percent / p-TsOH*H2O, 95percent EtOH / 4 h / 80 °C
4: 86 percent / LiAlH4 / tetrahydrofuran / Heating
5: 25 percent / diethyl ether; tetrahydrofuran / 0.05 h / Irradiation
View Scheme
Conditions
ConditionsYield
With pyridine at 20℃; for 3h; Inert atmosphere;100%
With pyridine at 20℃; for 24h;96%
With pyridine; dmap In dichloromethane at 20℃;92%
4-Phenylurazole
15988-11-1

4-Phenylurazole

Ergosterol
57-87-4

Ergosterol

3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene
10123-90-7

3β-hydroxy-3',5'-dioxo-4'-phenyl-5,8<1',2'>-1',2',4'-triazolidino-5α,8α-ergosta-6,22-diene

Conditions
ConditionsYield
In acetone at 20℃; for 15h;100%
With (PhSeO)2O In tetrahydrofuran for 2h; Ambient temperature;96%
Dimethoxymethane
109-87-5

Dimethoxymethane

Ergosterol
57-87-4

Ergosterol

O-methoxymethyl-ergosterol
95307-27-0

O-methoxymethyl-ergosterol

Conditions
ConditionsYield
With phosphorus pentoxide100%
With phosphorus pentoxide at 20℃; for 1h;89%
Ergosterol
57-87-4

Ergosterol

(3β,5α)-ergost-8(14)-en-3-ol
632-32-6

(3β,5α)-ergost-8(14)-en-3-ol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol; dichloromethane at 20℃; for 20h;99%
With diethyl ether; palladium at 20℃; Hydrogenation;
With diethyl ether; palladium Hydrogenation;
Ergosterol
57-87-4

Ergosterol

(22E)-ergosta-7,22-dien-3β-ol
2465-11-4

(22E)-ergosta-7,22-dien-3β-ol

Conditions
ConditionsYield
With tert-Amyl alcohol; ammonia; lithium In tetrahydrofuran at -78℃; for 4h;99%
With diisobutylaluminium hydride In toluene at 110℃; for 6h; in sealed flask;94%
With diethyl ether; palladium Hydrogenation;
Ergosterol
57-87-4

Ergosterol

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

ergosterol palmitate
3992-98-1

ergosterol palmitate

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;99%
With enzyme-substance from pig's pancreas
at 190℃;
lauric acid
143-07-7

lauric acid

Ergosterol
57-87-4

Ergosterol

ergosterol laurate
29398-23-0

ergosterol laurate

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;99%
With hydrogenchloride; sodium dodecyl-sulfate Inert atmosphere;
Octanoic acid
124-07-2

Octanoic acid

Ergosterol
57-87-4

Ergosterol

C36H58O2
29398-29-6

C36H58O2

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
1-decanoic acid
334-48-5

1-decanoic acid

Ergosterol
57-87-4

Ergosterol

C38H62O2
29398-30-9

C38H62O2

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
Ergosterol
57-87-4

Ergosterol

n-tetradecanoic acid
544-63-8

n-tetradecanoic acid

C42H70O2
23637-23-2

C42H70O2

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 12h; Reflux;99%
Ergosterol
57-87-4

Ergosterol

stearic acid
57-11-4

stearic acid

ergosteryl stearate
23637-22-1

ergosteryl stearate

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In 1,3,5-trimethyl-benzene for 24h; Reflux;99%
Benzyl N-hydroxycarbamate
3426-71-9

Benzyl N-hydroxycarbamate

Ergosterol
57-87-4

Ergosterol

C35H49NO4

C35H49NO4

Conditions
ConditionsYield
With pyridine; copper(l) chloride In tetrahydrofuran at 20℃; for 2h;99%
Ergosterol
57-87-4

Ergosterol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

methylsulfonylergosterol
15072-98-7

methylsulfonylergosterol

Conditions
ConditionsYield
With pyridine at 10℃; for 1h; Inert atmosphere;98%
With pyridine at 10℃; for 1h;94%
With pyridine at 10℃; for 1h;94%
Conditions
ConditionsYield
With pyridine In dichloromethane98%
With pyridine In dichloromethane at 0 - 20℃; for 18h;94%
Ergosterol
57-87-4

Ergosterol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3β-tert-Butyldimethylsilyloxy-ergosta-5,7,22-triene
95307-26-9

3β-tert-Butyldimethylsilyloxy-ergosta-5,7,22-triene

Conditions
ConditionsYield
With pyridine; 1H-imidazole In toluene at 110℃; for 3h; Inert atmosphere;98%
With pyridine; 1H-imidazole at 25℃; for 2h; Etherification;97%
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 24h; Inert atmosphere;
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

Ergosterol
57-87-4

Ergosterol

ergosterol chloroformate

ergosterol chloroformate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 10℃; for 18h;98%
Ergosterol
57-87-4

Ergosterol

5α,6α-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol
23637-31-2

5α,6α-epoxy-24(R)-methylcholesta-7,22-dien-3β-ol

Conditions
ConditionsYield
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 25℃; for 0.75h; diastereoselective reaction;98%
With potassium carbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 25℃; for 0.75h; Sonication;98%
Ergosterol
57-87-4

Ergosterol

4-(p-nitrophenyl)urazole
13274-45-8

4-(p-nitrophenyl)urazole

(p-nitrophenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22 ol-3β
87530-80-1

(p-nitrophenyl-4' urazolo-1',2')-5α,8α ergostadiene-6,22 ol-3β

Conditions
ConditionsYield
With (PhSeO)2O In tetrahydrofuran for 2h; Ambient temperature;97%
Ergosterol
57-87-4

Ergosterol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

(22E,24R)-5α-ergosta-5,7,22-triene-3-p-toluenesulfonate
51373-27-4

(22E,24R)-5α-ergosta-5,7,22-triene-3-p-toluenesulfonate

Conditions
ConditionsYield
With sodium carbonate In toluene at 10℃; for 2h; Reagent/catalyst; Temperature;96.3%
Ergosterol
57-87-4

Ergosterol

(22E,24R)-ergosta-7,22-dien-3β-ol
17608-76-3

(22E,24R)-ergosta-7,22-dien-3β-ol

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at 110℃; for 60h;96%
With lithium; ethylamine
4-pentynoic acid
6089-09-4

4-pentynoic acid

Ergosterol
57-87-4

Ergosterol

3β‑pentynoyloxy‑ergosta‑5,7,22‑trien

3β‑pentynoyloxy‑ergosta‑5,7,22‑trien

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;96%
hex-5-ynoic acid
53293-00-8

hex-5-ynoic acid

Ergosterol
57-87-4

Ergosterol

3β‑hexynoyloxy‑ergosta‑5,7,22‑trien

3β‑hexynoyloxy‑ergosta‑5,7,22‑trien

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;96%
Ergosterol
57-87-4

Ergosterol

benzoyl chloride
98-88-4

benzoyl chloride

(3β,22E)-ergosta-5,7,22-trien-3-ol benzoate
5035-30-3

(3β,22E)-ergosta-5,7,22-trien-3-ol benzoate

Conditions
ConditionsYield
With pyridine for 6h; Ambient temperature;95%
With pyridine
Ergosterol
57-87-4

Ergosterol

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

3β-bromoacetate-ergosta-5,7,12-triene

3β-bromoacetate-ergosta-5,7,12-triene

Conditions
ConditionsYield
With calcium hydride; N-benzyl-N,N,N-triethylammonium chloride In toluene95%
Ergosterol
57-87-4

Ergosterol

2-nitrosopyridine
79917-37-6

2-nitrosopyridine

C33H48N2O2

C33H48N2O2

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; nitroso-Diels-Alder reaction; stereoselective reaction;95%
Ergosterol
57-87-4

Ergosterol

2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate
151767-11-2

2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)
1354766-16-7

ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside)

Conditions
ConditionsYield
Stage #1: Ergosterol; 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Molecular sieve;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;
95%
hept-6-ynoic acid
30964-00-2

hept-6-ynoic acid

Ergosterol
57-87-4

Ergosterol

3β‑heptynoyloxy‑ergosta‑5,7,22‑trien

3β‑heptynoyloxy‑ergosta‑5,7,22‑trien

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;95%
(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid
2596-47-6, 147677-05-2, 34749-55-8

(E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid

Ergosterol
57-87-4

Ergosterol

3-O-(trans-4-O-acetylferuloyl)ergosterol

3-O-(trans-4-O-acetylferuloyl)ergosterol

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 100℃; under 13501.4 Torr; for 0.25h; Microwave irradiation;94%
Ergosterol
57-87-4

Ergosterol

ergosterol peroxide
2061-64-5

ergosterol peroxide

Conditions
ConditionsYield
With oxygen; phloxine B In methanol at 5℃; for 3h; Irradiation; Inert atmosphere;93%
With oxygen In methanol Diels-Alder Cycloaddition; UV-irradiation;93%
With oxygen; 5,10,15,20-tetraphenylporphyrin In dichloromethane at 0℃; for 4h; Irradiation;70%
Ergosterol
57-87-4

Ergosterol

2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate
203435-09-0

2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate

ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside)
1390620-14-0

ergosterol-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside)

Conditions
ConditionsYield
Stage #1: Ergosterol; 2,3,4,6-tetra-O-benzoyl-α,b-D-galactopyranosyl trichloroacetimidate In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Molecular sieve;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;
93%

57-87-4Relevant articles and documents

v. Christiani,Pailer

, (1938)

Methods for preparing cholesterol, and derivatives and analogs thereof

-

Paragraph 0394-0395; 0406-008, (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.

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.

PREPARATION OF ANTIRACHITIC COMPOUNDS. I. KINETIC MODEL OF THE PHOTOISOMERIZATION PROCESS OF PROVITAMIN D2

Orlov, A. I.,Mikhailova, N. P.,Kosarev, A. A.,Vyunov, K. A.

, p. 829 - 834 (2007/10/02)

-

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