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E6510

Sigma-Aldrich

Ergosterol

≥75%

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Synonym(s):
3β-Hydroxy-5,7,22-ergostatriene, 5,7,22-Ergostatrien-3β-ol, Provitamin D2
Empirical Formula (Hill Notation):
C28H44O
CAS Number:
Molecular Weight:
396.65
Beilstein:
2338604
EC Number:
MDL number:
PubChem Substance ID:

biological source

microbial

Quality Level

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

Precautionary Statements

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Articles

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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