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C3045

Sigma-Aldrich

Cholesterol

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

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Synonym(s):
3β-Hydroxy-5-cholestene, 5-Cholesten-3β-ol
Empirical Formula (Hill Notation):
C27H46O
CAS Number:
57-88-5
Molecular Weight:
386.65
Beilstein:
1915888
EC Number:
200-353-2
MDL number:
MFCD00003646
UNSPSC Code:
12352211
eCl@ss:
39023139
PubChem Substance ID:
24892329
NACRES:
NA.75

biological source

ovine wool

Quality Level

200

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

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

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

InChI key

HVYWMOMLDIMFJA-DPAQBDIFSA-N

Gene Information

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

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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.

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.

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Cholesterol biosynthesis: a mechanistic overview
Cerqueira NMFSA, et al.
Biochemistry, 55(39), 5483-5506 (2016)
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)
Patient-derived xenograft model for uterine leiomyoma by sub-renal capsule grafting
Serna VA and Kurita T
Journal of biological methods, 5(2), 84-94 (2018)
Impact of cholesterol on disease progression
Lin CJ, et al.
BioMedicine, 5(2) (2015)
The role of cholesterol in cancer
Kuzu OF, et al.
Cancer Research, 76(8), 2063-2070 (2016)
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