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E6510 Sigma-Aldrich

Ergosterol

≥75%

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

  • CAS Number 57-87-4

  • Empirical Formula (Hill Notation) C28H44O

  • Molecular Weight 396.65

  •  Beilstein/REAXYS Number 2338604

  •  EC Number 200-352-7

  •  MDL number MFCD00003623

  •  PubChem Substance ID 24894628

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cancer Research, Cell Biology, Chemopreventive Agents,
Quality Level   100
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

Description

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

Packaging

5, 10, 25 g in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E6510.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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 uniq...
Chloe McClanahan
BioFiles 2009, 4.6, 4.
Keywords: Absorption, Angiogenesis, Biofiles, Biological processes, Cancer, Clinical, Gene expression, Growth factors, Hormones, Hydroxylations, Ligands, Metabolites, Transcription, Type, Vitamins

Peer-Reviewed Papers
15

References

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