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601-57-0

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601-57-0 Usage

Description

Cholestanone is a cholesterol metabolite that has a keto group in place of the 3-hydroxy group on cholesterol. It decreases TGF-β-induced Smad2 phosphorylation and TGF-β expression and prevents inhibition of DNA synthesis by TGF-β in Mv1Lu cells when used at a concentration of 50 μg/ml. Increased fecal excretion of cholestenone is correlated with an increased risk of colorectal cancer. Cholestenone reduces serum cholesterol levels in a variety of animal models but is toxic to rats when administered at doses of 700-1,000 mg/kg per day, inducing hypertrophy in and reducing the activity of the adrenal gland. It has been used as synthetic intermediate in the synthesis of steroids.

Uses

4-Cholesten-3-one is used as a chiral building block for proteomics research. It is an intestinal metabolite of cholesterol and exhibits an anti-obesity effect on animals.

General Description

Cholestenone is a cholesterol metabolite and analog, which substitutes membrane cholesterol and elevates membrane fluidity.

Check Digit Verification of cas no

The CAS Registry Mumber 601-57-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,0 and 1 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 601-57:
(5*6)+(4*0)+(3*1)+(2*5)+(1*7)=50
50 % 10 = 0
So 601-57-0 is a valid CAS Registry Number.
InChI:InChI=1/C27H44O/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/h17-19,22-25H,6-16H2,1-5H3/t19-,22+,23-,24+,25+,26+,27-/m1/s1

601-57-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Packaging
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  • TCI America

  • (C1366)  (+)-4-Cholesten-3-one  >95.0%(GC)

  • 601-57-0

  • 5g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (A11743)  4-Cholesten-3-one, 98+%   

  • 601-57-0

  • 5g

  • 688.0CNY

  • Detail
  • Alfa Aesar

  • (A11743)  4-Cholesten-3-one, 98+%   

  • 601-57-0

  • 25g

  • 2763.0CNY

  • Detail
  • Aldrich

  • (188174)  (+)-4-Cholesten-3-one  98%

  • 601-57-0

  • 188174-1G

  • 331.11CNY

  • Detail
  • Aldrich

  • (188174)  (+)-4-Cholesten-3-one  98%

  • 601-57-0

  • 188174-10G

  • 1,664.91CNY

  • Detail

601-57-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cholest-4-en-3-one

1.2 Other means of identification

Product number -
Other names CHOLESTENONE

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:601-57-0 SDS

601-57-0Relevant articles and documents

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Inhoffen

, p. 1134,1136 (1936)

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Amplifier-mediated activation of cell-penetrating peptides with steroids: Multifunctional anion transporters for fluorogenic cholesterol sensing in eggs and blood

Butterfield, Sara M.,Miyatake, Tomohiro,Matile, Stefan

, p. 325 - 328 (2009)

(Figure Presented). Off-the-shelf, pret-a-porter multianalyte sensing systems are based on the ability of cell-penetrating peptides (CPPs; see picture, blue) to mediate the export of hydrophilic anions (yellow → green) from lipid bilayer vesicles (gray). Covalent capture of hydrophobic analytes (black) with hydrophilic anions (red) produces amphiphilic anions that can activate CPPs.

A One-Step Conversion of Cholest-4-en-3-one to 24-Hydroxychol-4-en-3-one

Manley, Ronald P.,Curry, Kenneth W.,Deno, Norman C.,Meyer, Michael D.

, p. 4385 - 4387 (1980)

Cholest-4-en-3-one has been converted in one step to 24-hydroxychol-4-en-3-one in 17percent yield of crystalline material.The elimination of carbons 25-27 and the introduction of the primary alcohol group at C-24 are accomplished with CF3CO3H-H2SO4 at 0 deg C.

Cascade-Amplified Time-Resolved Fluorescent Assay Driven by an Enzyme-Integrated Catalytic Compartment as an Artificial Multi-Enzyme Complex

Gao, Jie,Wang, Caihong,Wang, Jinhong,Tan, Hongliang

, p. 9629 - 9633 (2019)

We here report a simple and efficient strategy of fabricating artificial multi-enzyme complex (MEC) based on the integration of natural enzyme with catalytic compartment. As a proof of concept, this strategy was demonstrated by selecting cholesterol oxidase (ChOx) and CeIII-based nanoscale coordination polymer (Ce-NCP) with peroxidase-like activity as the models, which forms ChOx@Ce-NCP. Benefitting from the confinement and sheltering effects of Ce-NCP, superior cascade activity and stability in harsh environments were achieved in ChOx@Ce-NCP. Meanwhile, the distinct advantage of ChOx@Ce-NCP has also been highlighted by its negligible substrate inhibition effect and adjustable mass ratio of building blocks. Upon the doping of TbIII in ChOx@Ce-NCP, a luminescent artificial MEC (ChOx@Ce-NCP:Tb) was further fabricated to drive a cascade amplified time-resolved fluorescent assay within a confined space, showing high sensitivity and specificity toward cholesterol.

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Bretschneider,Ajtai

, p. 57 (1943)

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Synthesis and evaluation of cationic lipids bearing cholesteryl groups for gene delivery in vitro

Zhu, Man-Zhou,Wu, Qi-Hua,Zhang, Guisheng,Ren, Tan,Liu, Dexi,Guo, Qing-Xiang

, p. 2207 - 2213 (2002)

A series of cationic lipids were designed and synthesized as vectors for gene delivery. The lipids contain a ketal moiety as a linker and a cholesteryl group as a hydrophobic tail. The framework of cholesteryl derivatives could increase the stability of liposomes by stabilizing the bilayers and their complexes with DNA to improve the transfection efficiency. The ketal bonds in lipids should easily degrade in an acidic environment in a cell (pH = 2-5) after transfection, resulting in little toxicity; in the neutral environment outside of cells (pH = 7), they should be stable as gene carriers. Gene transfer experiments in vitro with BL-6, 3LL, 293, 3T3, and Hela cells were performed. The results show that the gene transfection activity of three lipids is quite high, with least toxicity to cells under the experimental conditions.

Synthesis, NMR and crystal characterization of dimeric terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols

Alarcón-Manjarrez, Carlos,Arcos-Ramos, Rafael,álamo, Marcos Flores,Iglesias-Arteaga, Martín A.

, p. 66 - 72 (2016)

Two dimeric steroidal terephthalates derived from epimeric 4,5-seco-cholest-3-yn-5-ols were prepared starting from cholesterol in a five-step synthetic sequence. X-ray crystallography shows that the obtained compounds display novel supramolecular networks in the solid state in which the facial hydrophobicity of the steroidal skeletons plays an important role. Unambiguous NMR characterization of the obtained dimers is also provided.

4alpha-methyl-24beta-ethyl-5alpha-cholesta-14,25-dien-3beta-ol and 24beta-ethylcholesta-5, 9(11), 22E-trien-3beta-ol, sterols from Clerodendrum inerme.

Pandey, Richa,Verma, Ram K,Singh, Subhash C,Gupta, Madan M

, p. 415 - 420 (2003)

From the aerial parts of Clerodendrum inerme, two new sterols (4alpha-methyl-24beta-ethyl-5alpha-cholesta-14, 25-dien-3beta-ol and 24beta-ethylcholesta-5, 9(11), 22E-trien-3beta-ol) and a new aliphatic ketone (11-pentacosanone) were isolated together with another known aliphatic ketone (6-nonacosanone) and a diterpene (clerodermic acid). The structure elucidations were based on analyses of physical and spectroscopic data.

Ruthenium-Catalyzed Dehydrogenation of Alcohols with Carbodiimide via a Hydrogen Transfer Mechanism

Sueki, Shunsuke,Matsuyama, Mizuki,Watanabe, Azumi,Kanemaki, Arata,Katakawa, Kazuaki,Anada, Masahiro

, p. 4878 - 4885 (2020/06/02)

Ruthenium-catalyzed oxidative dehydrogenation of alcohols using carbodiimide as an efficient hydrogen acceptor has been developed. The protocol exhibits wide substrate scope with good to excellent yields. The results of the kinetic analysis indicated that the reaction mechanism includes the hydrogen transfer process and that the addition of carbodiimide is essential for the reaction system, and the resulting amidine also could react as a hydrogen acceptor.

ENABLING CHOLESTEROL CATABOLISM IN HUMAN CELLS

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Paragraph 0016; 0028; 0036; 0046-0047, (2020/07/05)

Compositions, methods, and systems for modifying sterol metabolism in a subject is disclosed. In some embodiments, the subjects may be administered one or more mammalian cells modified to express at least one sterol degrading enzyme derived from a bacterium. In many embodiments, the cell is a macrophage or monocyte stably expressing three or more enzymes that aid in opening the β ring of cholesterol. The disclosed compositions and methods may be useful in lowering cholesterol levels in a subject in need thereof. In some embodiments, the subject may have a genetic predisposition to atherosclerosis.

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