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E6510

Sigma-Aldrich

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
Beilstein:
2338604
EC Number:
200-352-7
MDL number:
MFCD00003623
UNSPSC Code:
12352205
PubChem Substance ID:
24894628
NACRES:
NA.77

biological source

microbial

Assay

≥75%

form

powder

color

white to off-white

mp

156-158 °C (lit.)

storage temp.

2-8°C

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

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

InChI key

DNVPQKQSNYMLRS-APGDWVJJSA-N

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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.

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.

Hazard Statements

H413

Precautionary Statements

P273

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Trypanosoma brucei CYP51: essentiality and targeting therapy in an experimental model
PLoS Neglected Tropical Diseases (2016)
Insect deterrent and nematicidal screening of microfungi from Mexico and anti-aphid compounds from Gliomastix masseei
Ruiz-Jimenez
Revista Brasileira de Zootecnia (2017)
Cheuk Hei Ho et al.
Nature biotechnology, 27(4), 369-377 (2009-04-08)
We present a yeast chemical-genomics approach designed to identify genes that when mutated confer drug resistance, thereby providing insight about the modes of action of compounds. We developed a molecular barcoded yeast open reading frame (MoBY-ORF) library in which each
Marek CL
Pediatric Dentistry (2019)
The influence of steroidal and triterpenoid saponins on monolayer models of the outer leaflets of human erythrocytes, E. coli and S. cerevisiae cell membranes
Orczyk M, et al.
Journal of Colloid and Interface Science (2020)
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Articles

Vitamin D and Prevention of Human Disease

Vitamin D2 (ergocalciferol) is naturally synthesized from ergosterol by invertebrates, fungi, and plants in response to ultraviolet B irradiation, while vitamin D3 synthesis (cholecalciferol) is uniquely initiated in the skin of vertebrates. During sun exposure, ultraviolet B photons are absorbed by 7-dehydrocholesterol, which is found within the plasma membranes of epidermal and dermal skin layers. This reaction yields an unstable derivative of 7-dehydrocholesterol, named precholecalcitrol, which rapidly rearranges to vitamin D3. Vitamin D binding protein (DBP) is a carrier protein responsible for drawing vitamin D3 from the plasma membrane into the dermal capillaries within the extracellular space.

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