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Merck

E6510

Ergosterol

≥75%

Synonym(s):

3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol, Provitamin D2

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About This Item

Empirical Formula (Hill Notation):
C28H44O
CAS Number:
57-87-4
Molecular Weight:
396.65
UNSPSC Code:
12352205
NACRES:
NA.77
PubChem Substance ID:
24894628
EC Number:
200-352-7
Beilstein/REAXYS Number:
2338604
MDL number:
MFCD00003623

Key Documents

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InChI key

DNVPQKQSNYMLRS-APGDWVJJSA-N

InChI

1S/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

SMILES string

[H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)\C=C\[C@H](C)C(C)C

biological source

microbial

assay

≥75%

form

powder

color

white to off-white

mp

156-158 °C (lit.)

storage temp.

2-8°C

Quality Level

100

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Application

Ergosterol has been used:
  • as a component of yeast cell monolayer models, to study the effects of steroidal and triterpenoid saponins on the monolayers
  • as a standard sample, to isolate and identify a fungal metabolite fraction containing ergosterol
  • as a component of the culture medium to isolate the CYP51RNAi phenotype of Trypanosoma brucei gambiense, to verify ergosterol biosynthesis

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.

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.

hcodes

H413

pcodes

P273

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB0617
MKCX4618
MKCS7680
MKCS7130
MKCM7027

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Combination treatment of ergosterol followed by amphotericin B induces necrotic cell death in human hepatocellular carcinoma cells
Lin Yu-Chun, et al.
Testing (2017)
Ameeta K Agarwal et al.
Eukaryotic cell, 7(2), 387-400 (2007-12-25)
Sampangine, a plant-derived alkaloid found in the Annonaceae family, exhibits strong inhibitory activity against the opportunistic fungal pathogens Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus. In the present study, transcriptional profiling experiments coupled with analyses of mutants were performed in
Major antifungal drugs
Bell AS
Medicinal Chemistry (2007)
Trypanosoma brucei CYP51: essentiality and targeting therapy in an experimental model
PLoS Neglected Tropical Diseases (2016)
Marek CL
Pediatric Dentistry (2019)
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