C3045

Cholesterol

Name: Cholesterol
Brand: SIGMA

powder, BioReagent, suitable for cell culture, ≥99%

Synonym(s):

3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₄₆O

CAS Number:

57-88-5

Molecular Weight:

386.65

NACRES:

NA.75

PubChem Substance ID:

24892329

eCl@ss:

39023139

UNSPSC Code:

12352211

EC Number:

200-353-2

MDL number:

MFCD00003646

Beilstein/REAXYS Number:

1915888

Product Name

Cholesterol, powder, BioReagent, suitable for cell culture, ≥99%

InChI key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

InChI

1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

SMILES string

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

biological source

ovine wool

product line

BioReagent

assay

≥99%

form

powder

technique(s)

cell culture | mammalian: suitable

bp

360 °C (lit.)

mp

147-149 °C (lit.)

solubility

H₂O: 0.002 mg/mL
Tween: soluble
ethanol: soluble
serum: soluble

density

1.067 g/mL at 25 °C (lit.)

shipped in

ambient

storage temp.

−20°C

Quality Level

200

Gene Information

human ... POLA1(5422), TOP2A(7153)
rat ... Ar(24208), Polb(29240)

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Related Categories

Biochemicals

Cell Culture & Analysis

Molecular Biology & Functional Genomics

Supplements for Cell Culture

Application

Cholesterol has been used:

as a medium supplement in chorionic villous tissue culture form placenta
as a component of hormone pellet for implantation in mice ovary
for inducing expression of immunity-related GTPase M (IRGM) in human monocytic cell line, THP-1

Biochem/physiol Actions

Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

General description

Cholesterol, a major sterol is the precursor for steroid hormones, bile acid and vitamin in mammals and coordinates endocytosis. It complexes with protein to form lipoproteins for transport in blood. It exists either as high-density lipoprotein (HDL) or low-density lipoprotein (LDL). HDL also called good cholesterol has less lipid content. LDL or bad cholesterol has high lipid content. Statin inhibition of HMG-CoA reductase enzyme in the cholesterol biosynthesis pathway controls elevated cholesterol levels in atherosclerosis and hypercholesterolemia. Low levels of cholesterol results in hypothyroidism, familial hypobetalipoproteinemia and liver disease. Imbalance of cholesterol homeostasis and intracellular cholesterol levels play a key role in cancer development. High cholesterol levels favor breast cancer progression.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Cholesterol biosynthesis: a mechanistic overview

Cerqueira NMFSA, et al.

Biochemistry, 55(39), 5483-5506 (2016)

The role of cholesterol in cancer

Kuzu OF, et al.

Cancer Research, 76(8), 2063-2070 (2016)

Role of cholesterol in the development and progression of breast cancer

Llaverias G et al.

The American Journal of Pathology, 178(1), 402-412 (2011)

The Crohn?s Disease Risk Factor IRGM Limits NLRP3 Inflammasome Activation by Impeding Its Assembly and by Mediating Its Selective Autophagy

Mehto S, et al.

Molecular Cell (2019)

Impact of cholesterol on disease progression

Lin CJ, et al.

BioMedicine, 5(2) (2015)

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