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80-97-7

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80-97-7 Usage

Description

Cholestanol is a cholesterol metabolite formed by oxidation and an intermediate in the biosynthesis of chenodeoxycholic acid . Cholestanol (10 μg/ml) induces apoptosis in cornea and lens epithelial cells and increases the activity of IL-1β converting enzyme (ICE) and CPP32 proteases. Dietary administration of 1% cholestanol to mice increases serum and liver cholestanol levels and leads to corneal opacities and gallstones and in rats it leads to cholestanol deposition in the cerebellum. Cholestanol levels are increased in plasma of patients with cerebrotendinous xanthomatosis (CTX), a disease characterized by a deficiency in the mitochondrial enzyme sterol 27-hydrolylase (CYP27A1) that leads to progressive neurological symptoms.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 80-97-7 differently. You can refer to the following data:
1. 5α-Cholestan-3β-ol is a carbon stanol formed from biohydrogenation of Cholesterol (C432501) in the gut. Studies have also examined the conversion of 5α-Cholestan-3β-ol catalyzed by 3-β-hydroxysteroid dehydrogenase of rat liver.
2. 5alpha-Cholestan-3beta-ol is used as a standard in lipid analysis using HPLC. It acts as a derivitized steroid compound. It is used in agrochemical, pharmaceutical and dyestuff field .

Definition

ChEBI: A cholestanoid that is (5alpha)-cholestane substituted by a beta-hydroxy group at position 3.

General Description

Cholestanol is a 5α-dihydro derivative of cholesterol. It acts as a marker for cholesterol absorption. Cholestanol is a steroid with 27 carbon atoms.

Biochem/physiol Actions

5α-Cholestan-3β-ol is derived from cholesterol by the action of intestinal microorganisms. It is known to induce the formation of gall stones in rabbits in the presence of sodium ions.

Purification Methods

Purify 5--cholestan-3-ol via acetylation, crystallisation and de-acetylation, then recrystallisation from EtOH or slightly aqueous EtOH, or MeOH. Its solubility is: 0.5% (MeOH) and 1% (EtOH) at 25o. [Mizutani & Whitten J Am Chem Soc 107 3621 1985.] The acetate has m 114-115o from EtOAc/MeOH and, [] D 20 +13o (c 2, CHCl3). [Bruce & Ralls Org Synth Col Vol II 191 1943, Beilstein 6 IV 3577.]

Check Digit Verification of cas no

The CAS Registry Mumber 80-97-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 0 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 80-97:
(4*8)+(3*0)+(2*9)+(1*7)=57
57 % 10 = 7
So 80-97-7 is a valid CAS Registry Number.
InChI:InChI=1/C27H48O/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/h18-25,28H,6-17H2,1-5H3/t19-,20?,21?,22+,23-,24+,25+,26+,27-/m1/s1

80-97-7 Well-known Company Product Price

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  • TCI America

  • (C0317)  β-Cholestanol (contains α-Cholestanol)  >95.0%(GC)

  • 80-97-7

  • 25g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (L08624)  5alpha-Cholestan-3beta-ol, 98%   

  • 80-97-7

  • 5g

  • 307.0CNY

  • Detail
  • Alfa Aesar

  • (L08624)  5alpha-Cholestan-3beta-ol, 98%   

  • 80-97-7

  • 25g

  • 1181.0CNY

  • Detail
  • Sigma

  • (D6128)  5α-Cholestan-3β-ol  ≥95%

  • 80-97-7

  • D6128-10G

  • 863.46CNY

  • Detail
  • Sigma

  • (D6128)  5α-Cholestan-3β-ol  ≥95%

  • 80-97-7

  • D6128-25G

  • 1,903.59CNY

  • Detail

80-97-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (5α)-cholestan-3β-ol

1.2 Other means of identification

Product number -
Other names Cholestanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80-97-7 SDS

80-97-7Relevant articles and documents

Ruthenium-decorated lipid vesicles: Light-induced release of [Ru(terpy)(bpy)(OH2)]2+ and thermal back coordination

Bonnet, Sylvestre,Limburg, Bart,Meeldijk, Johannes D.,Gebbink, Robertus J. M. Klein,Killian, J. Antoinette

, p. 252 - 261 (2011)

Electrostatic forces play an important role in the interaction between large transition metal complexes and lipid bilayers. In this work, a thioether-cholestanol hybrid ligand (4) was synthesized, which coordinates to ruthenium(II) via its sulfur atom and intercalates into lipid bilayers via its apolar tail. By mixing its ruthenium complex [Ru(terpy)(bpy)(4)]2+ (terpy = 2,2′;6′,2′′-terpyridine; bpy = 2,2′-bipyridine) with either the negatively charged lipid dimyristoylphosphatidylglycerol (DMPG) or with the zwitterionic lipid dimyristoylphosphatidylcholine (DMPC), large unilamellar vesicles decorated with ruthenium polypyridyl complexes are formed. Upon visible light irradiation the ruthenium-sulfur coordination bond is selectively broken, releasing the ruthenium fragment as the free aqua complex [Ru(terpy)(bpy)(OH 2)]2+. The photochemical quantum yield under blue light irradiation (452 nm) is 0.0074(8) for DMPG vesicles and 0.0073(8) for DMPC vesicles (at 25 °C), which is not significantly different from similar homogeneous systems. Dynamic light scattering and cryo-TEM pictures show that the size and shape of the vesicles are not perturbed by light irradiation. Depending on the charge of the lipids, the cationic aqua complex either strongly interacts with the membrane (DMPG) or diffuses away from it (DMPC). Back coordination of [Ru(terpy)(bpy)(OH2)]2+ to the thioether-decorated vesicles takes place only at DMPG bilayers with high ligand concentrations (25 mol %) and elevated temperatures (70 °C). During this process, partial vesicle fusion was also observed. We discuss the potential of such ruthenium-decorated vesicles in the context of light-controlled molecular motion and light-triggered drug delivery.

Electrochemical Borylation of Alkyl Halides: Fast, Scalable Access to Alkyl Boronic Esters

Cao, Yangmin,Hu, Ping,Huang, Cheng,Liu, Zhao,Lu, Qingquan,Ma, Wan,Peng, Pan,Qi, Xiaotian,Wang, Bingbing

supporting information, p. 12985 - 12991 (2021/09/03)

Herein, a fast, scalable, and transition-metal-free borylation of alkyl halides (X = I, Br, Cl) enabled by electroreduction is reported. This process provides an efficient and practical access to primary, secondary, and tertiary boronic esters at a high current. More than 70 examples, including the late-stage borylation of natural products and drug derivatives, are furnished at room temperature, thereby demonstrating the broad utility and functional-group tolerance of this protocol. Mechanistic studies disclosed that B2cat2 serves as both a reagent and a cathodic mediator, enabling electroreduction of difficult-to-reduce alkyl bromides or chlorides at a low potential.

Copper-Catalyzed and Indium-Mediated Methoxycarbonylation of Unactivated Alkyl Iodides with Balloon CO

Chen, Yanchi,Su, Lei,Gong, Hegui

supporting information, p. 4689 - 4693 (2019/06/27)

This work emphasizes the synthesis of alkyl esters via Cu-catalyzed and In-mediated alkoxycarbonylation of unactivated alkyl iodides in the presence of In or InI. The reactions were suitable for the preparation of primary, secondary, and even tertiary alkyl esters, representing an exceptionally rare example for the creation of quaternary carbon centers upon formation of esters. The preliminary mechanistic studies indicated that alkyl radicals were involved, and Cu/In/CO played a cooperative role in the carbonylation event.

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