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14606

Sigma-Aldrich

Cholesterol

tested according to Ph. Eur.

Synonym(s):

Cholesterolum, 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
Beilstein:
1915888
EC Number:
200-353-2
MDL number:
MFCD00003646
UNSPSC Code:
41141804
PubChem Substance ID:
329750548
NACRES:
NA.21
Pricing and availability is not currently available.

Agency

USP/NF
tested according to Ph. Eur.

Quality Level

100

form

powder

bp

360 °C (lit.)

mp

147-149 °C (lit.)

solubility

chloroform: soluble 1 gm in 4.5 ml
diethyl ether: soluble 1 gm in 2.8 ml
pyridine: soluble 1 gm in 1.5 ml
H2O: insoluble
acetone: soluble
alcohol: slightly soluble
alcohol: very soluble (Hot)
benzene: soluble
dioxane: soluble
ethyl acetate: soluble
hexane: soluble
oil: soluble
petroleum ether: soluble

density

1.067 g/mL at 25 °C (lit.)

application(s)

pharmaceutical (small molecule)

storage temp.

2-8°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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Application

Cholesterol was used for preparing ISCOMS containing ovalbumin (OVA) for studying whether the incorporation of the protein antigen ovalbumin (OVA) in lipophilic immune-stimulating complexes (ISCOMS) induces very strong primary immune responses. It was incorporated in animal feed to study the effect of cholesterol-rich diet.[1][2]

Biochem/physiol Actions

Cholesterol is a lipid that makes up about 20-25% of the structural components of the cell membranes. It determines the fluidity and permeability of the membrane, making it permeable to water but not to ions and protons. Cholesterol also regulates the functions of the transporters and signaling proteins present on the plasma membrane.[3] The major sites of cholesterol synthesis are small intestine and liver.[4]
Major component of all biological membranes; ~25% of total brain lipid is cholesterol.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6298
BCCK5493
BCCH3789
BCCG1852
BCCF4488

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Ricardo L F Guerra et al.
Lipids in health and disease, 6, 16-16 (2007-07-04)
Exercise has been prescribed in the treatment and control of dyslipidemias and cholesterolemia, however, lipid responses to different training frequencies in hypercholesterolemic men have been inconsistent. We sought to verify if different frequencies of continuous moderate exercise (2 or 5
Daniela C U Cavallini et al.
Lipids in health and disease, 8, 1-1 (2009-01-09)
Much attention has been drawn to different alternative strategies for cardiovascular disease prevention. The aim of the present study was to observe and compare the effects of Enterococcus faecium CRL183 (probiotic microorganism), an isoflavones mixture and simvastatin (drug used to
John M Dietschy et al.
Journal of lipid research, 45(8), 1375-1397 (2004-07-16)
Unesterified cholesterol is an essential structural component of the plasma membrane of every cell. During evolution, this membrane came to play an additional, highly specialized role in the central nervous system (CNS) as the major architectural component of compact myelin.
R R Grummer et al.
Journal of animal science, 66(12), 3160-3173 (1988-12-01)
Cholesterol utilized for steroid synthesis by ovarian tissue may be derived from de novo synthesis or cellular uptake of lipoprotein cholesterol. The majority of blood cholesterol is transported by either low (LDL) or high (HDL) density lipoproteins, depending on the
F Sheedfar et al.
International journal of obesity (2005), 39(2), 331-338 (2014-05-23)
In the context of obesity, epigenetic mechanisms regulate cell-specific chromatin plasticity, perpetuating gene expression responses to nutrient excess. MacroH2A1, a variant of histone H2A, emerged as a key chromatin regulator sensing small nutrients during cell proliferation and differentiation. Mice genetically
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Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Dear Madam or Sir, can you please tell me what is the purity grade of this cholesterol batch? Unfortunately, I could not find it on your website. Thank you.

    1 answer

    1. The exact purity value is listed on the lot specific Certificate of Analysis. Please navigate to the DOCUMENTATION part of the Product Detail Page to access a certificate under ‘Certificate of Analysis’: https://www.sigmaaldrich.com/product/sial/14606#product-documentation

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