MilliporeSigma
All Photos(4)

Documents

C2394

Sigma-Aldrich

5-Cholesten-3β-ol-7-one

≥90%

Sign Into View Organizational & Contract Pricing

Synonym(s):
3β-Hydroxy-5-cholesten-7-one, 7-Ketocholesterol
Empirical Formula (Hill Notation):
C27H44O2
CAS Number:
Molecular Weight:
400.64
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

assay

≥90%

form

powder

functional group

ketone

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@@]([C@](CC[C@H](O)C3)(C)C3=CC4=O)([H])[C@]4([H])[C@]1([H])CC[C@]2([H])[C@]([H])(C)CCCC(C)C

InChI

1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1

InChI key

YIKKMWSQVKJCOP-ABXCMAEBSA-N

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
D6128P9129H6891
5-Cholesten-3β-ol-7-one ≥90%

C2394

5-Cholesten-3β-ol-7-one

5α-Cholestan-3β-ol ≥95%

D6128

5α-Cholestan-3β-ol

5-Pregnen-3β-ol-20-one ≥98%

P9129

5-Pregnen-3β-ol-20-one

7β-Hydroxycholesterol ≥95%

H6891

7β-Hydroxycholesterol

functional group

ketone

functional group

-

functional group

ketone

functional group

hydroxyl

assay

≥90%

assay

≥95%

assay

≥98%

assay

≥95%

form

powder

form

powder

form

powder

form

powder

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

Application

5-Cholesten-3β-ol-7-one was used as a standard in the determination of cholesterol derivatives by GC-MS and HPLC.

Biochem/physiol Actions

5-Cholesten-3β-ol-7-one is a cholesterol derivative that decreases the membrane potential of lipid bilayers. It reportedly accumulates in atherosclerotic plaques that leads to apoptosis of vascular cells.

Preparation Note

5-Cholesten-3β-ol-7-one yields clear to slightly hazy, colorless to faint yellow solution in chloroform at 250 mg/5 ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Rapid analysis of oxidized cholesterol derivatives by high-performance liquid chromatography combined with diode-array ultraviolet and evaporative laser light-scattering detection
Osada K et al
Journal of the American Oil Chemists' Society, 76, 863-871 (1999)
Thomas Starke-Peterkovic et al.
Biophysical journal, 90(11), 4060-4070 (2006-03-04)
The effect of cholesterol removal by methyl-beta-cyclodextrin on the dipole potential, psi(d), of membrane vesicles composed of natural membrane lipids extracted from the kidney and brain of eight vertebrate species was investigated using the voltage-sensitive fluorescent probe di-8-ANEPPS. Cyclodextrin treatment
E Boselli et al.
Journal of chromatography. A, 917(1-2), 239-244 (2001-06-14)
Pressurized liquid extraction (PLE, ASE) was compared with the Folch procedure (a solid-liquid extraction with chloroform/methanol 2:1, v/v) for the lipid extraction of egg-containing food; the accuracy of PLE for the quantitative determination of oxysterols in whole egg powder was
C Adcox et al.
Journal of agricultural and food chemistry, 49(4), 2090-2095 (2001-04-20)
The cytotoxicity of cholesterol and a mixture of beta-sitosterol/campesterol (50%/40%) and their oxides was examined in a cultured-derived macrophage cell line, C57BL/6. Cell numbers, lactate dehydrogenase (LDH) leakage, protein content, lipid uptake, and mitochondria dehydrogenase activity were determined after exposure
Anne Pilotelle-Bunner et al.
Biochimica et biophysica acta, 1787(8), 1039-1049 (2009-03-25)
Three different cholesterol derivatives and phloretin, known to affect the local electric field in phospholipid membranes, have been introduced into Rhodobacter sphaeroides reaction centre-containing phospholipid liposomes. We show that cholesterol and 6-ketocholestanol significantly slow down the interquinone first electron transfer

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service