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E2634

Sigma-Aldrich

Ergosta-5,7,9(11),22-tetraen-3β-ol

~96% (HPLC)

Synonym(s):

Dehydroergosterol

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About This Item

Empirical Formula (Hill Notation):
C28H42O
CAS Number:
516-85-8
Molecular Weight:
394.63
MDL number:
MFCD00083319
UNSPSC Code:
12352200
PubChem Substance ID:
24894479
NACRES:
NA.77

assay

~96% (HPLC)

Quality Level

200

storage temp.

−20°C

SMILES string

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

InChI

1S/C28H42O/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/h7-10,14,18-20,22,24-25,29H,11-13,15-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,27-,28+/m0/s1

InChI key

QSVJYFLQYMVBDR-CMNOFMQQSA-N

Related Categories

General description

Ergosta-5,7,9(11),22-tetraen-3β-ol is an analogue of ergosterol. It comprises of three conjugated double bonds in a steroid ring system. Ergosta-5,7,9(11),22-tetraen-3β-ol possesses anti-inflammatory property. It is used as a cholesterol reporter.

Application

A fluorescent cholesterol analog useful as a probe in membrane research.
Ergosta-5,7,9(11),22-tetraen-3β-ol has been used to examine the acyltransferase activity of lecithin:cholesterol acyltransferase (LCAT). It has also been used for liposome preparation.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351,H373

Hazard Classifications

Carc. 2 - STOT RE 2

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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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Alexander G Georgiev et al.
Traffic (Copenhagen, Denmark), 12(10), 1341-1355 (2011-06-22)
Sterol transport between the endoplasmic reticulum (ER) and plasma membrane (PM) occurs by an ATP-dependent, non-vesicular mechanism that is presumed to require sterol transport proteins (STPs). In Saccharomyces cerevisiae, homologs of the mammalian oxysterol-binding protein (Osh1-7) have been proposed to
Fluorescent sterols: probe molecules of membrane structure and function.
F Schroeder
Progress in lipid research, 23(2), 97-113 (1984-01-01)
Fischer, R.T., et al.
J. Biol. Physics, 13, 13-13 (1985)
Tim P Levine
The Journal of cell biology, 195(6), 927-929 (2011-12-14)
A new study in this issue (De Saint-Jean et al. 2011. J. Cell Biol. http://dx.doi.org/jcb.201104062) reveals that the sterol transfer protein Osh4p can also transport the signaling phospholipid phosphatidylinositol 4-phosphate (PI(4)P), which binds to the same site in Osh4p as
Peter Kohut et al.
Biochemical and biophysical research communications, 404(1), 233-238 (2010-11-30)
Uptake of external sterols in the yeast Saccharomyces cerevisiae is a multistep process limited to anaerobiosis or heme deficiency. It includes crossing the cell wall, insertion of sterol molecules into plasma membrane and their internalization and integration into intracellular membranes.
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