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1553-56-6

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1553-56-6 Usage

Description

DEHYDROLITHOCHOLIC ACID, also known as 3-Oxo-5β-cholanoic Acid, is a steroid compound derived from bile acids. It possesses pharmacological activity and is characterized by its unique molecular structure. DEHYDROLITHOCHOLIC ACID has been found to have various applications in the pharmaceutical and medical fields due to its ability to regulate proteasomes and interact with other biological systems.

Uses

Used in Pharmaceutical Industry:
DEHYDROLITHOCHOLIC ACID is used as a precursor for the synthesis of lithocholic acid derivatives, which are known to have proteasome regulatory functions. These derivatives play a crucial role in the development of drugs targeting various diseases, including cancer and neurodegenerative disorders.
Used in Medical Research:
DEHYDROLITHOCHOLIC ACID is used as a research tool for studying the mechanisms of action of bile acids and their impact on cellular processes. This knowledge can be applied to develop novel therapeutic strategies for various health conditions.
Used in Drug Development:
DEHYDROLITHOCHOLIC ACID is used as a key component in the development of new drugs that target proteasomes, which are essential for cellular protein degradation and regulation. Modulating proteasome activity can have significant implications for the treatment of various diseases, including cancer and inflammatory conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 1553-56-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,5,5 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1553-56:
(6*1)+(5*5)+(4*5)+(3*3)+(2*5)+(1*6)=76
76 % 10 = 6
So 1553-56-6 is a valid CAS Registry Number.
InChI:InChI=1/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-16,18-21H,4-14H2,1-3H3,(H,26,27)/t15-,16?,18+,19-,20+,21+,23+,24-/m1/s1

1553-56-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-oxo-5β-cholanic acid

1.2 Other means of identification

Product number -
Other names 3-oxo-5beta-cholanic acid

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:1553-56-6 SDS

1553-56-6Relevant articles and documents

Preparation method of lithocholic acid and intermediates thereof

-

, (2021/02/20)

The invention discloses a synthesis method of lithocholic acid and an intermediates thereof. According to the preparation method of the lithocholic acid intermediate, a compound I reacts with hydrogento generate a compound II in a mixed solvent by taking palladium on carbon as a catalyst and adding specific alkali; a low-price botanical bulk fermentation product BA is used as a raw material, andlithocholic acid is synthesized through side chain construction, hydrogenation, reduction, hydrolysis and other reactions; and the selectivity of 5beta hydrogen in the hydrogenation reaction is improved, high-toxicity reagents such as hydrazine hydrate are prevented from being used for hydroxyl due to removal of other animal-derived cholic acids, and the method is environmentally friendly, high insafety, simple in route, mild in reaction condition and suitable for industrial mass production.

Vitamin E analogues differentially inhibit human cytochrome P450 3A (CYP3A)-mediated oxidative metabolism of lithocholic acid: Impact of δ-tocotrienol on lithocholic acid cytotoxicity

Wong, Siew Ying,Teo, Josephine Si Min,Chai, Swee Fen,Yeap, Szu Ling,Lau, Aik Jiang

, p. 62 - 74 (2019/05/28)

Lithocholic acid is a cytotoxic bile acid oxidized at the C-3 position by human cytochrome P450 3A (CYP3A) to form 3-ketocholanoic acid, but it is not known whether this metabolite is cytotoxic. Tocotrienols, in their various isomeric forms, are vitamin E analogues. In the present study, the hypothesis to be tested is that tocotrienols inhibit CYP3A-catalyzed lithocholic acid 3-oxidation, thereby influencing lithocholic acid cytotoxicity. Our enzyme catalysis experiments indicated that human recombinant CYP3A5 in addition to CYP3A4, liver microsomes, and intestinal microsomes catalyzed lithocholic acid 3-oxidation to form 3-ketocholanoic acid. Liver microsomes with the CYP3A5*1/*3 and CYP3A5*3/*3 genotypes were associated with decreased lithocholic acid 3-oxidation. α-Tocotrienol, γ-tocotrienol, δ-tocotrienol, and a tocotrienol-rich vitamin E mixture, but not α-tocopherol (a vitamin E analogue), differentially inhibited lithocholic acid 3-oxidation catalyzed by liver and intestinal microsomes and recombinant CYP3A4 and CYP3A5. Compared to lithocholic acid 3-oxidation, CYP3A-catalyzed testosterone 6β-hydroxylation was inhibited to a lesser extent by α-tocotrienol, γ-tocotrienol, δ-tocotrienol, and a tocotrienol-rich vitamin E mixture. δ-Tocotrienol inhibited lithocholic acid 3-oxidation by a mixed mode. Like lithocholic acid, 3-ketocholanoic acid was also cytotoxic in human intestinal and liver cell models. δ-Tocotrienol decreased the extent of lithocholic acid 3-oxidation and this inhibition was associated with enhanced cytotoxicity in LS180 cells treated with δ-tocotrienol and lithocholic acid. Overall, vitamin E analogues inhibited in vitro lithocholic acid 3-oxidation in an isomer-dependent manner, with inhibition occurring with tocotrienols, but not α-tocopherol. The enhanced lithocholic acid toxicity by δ-tocotrienol in a human intestinal cell model warrants future investigations in vivo.

Iron Catalysis for Room-Temperature Aerobic Oxidation of Alcohols to Carboxylic Acids

Jiang, Xingguo,Zhang, Jiasheng,Ma, Shengming

supporting information, p. 8344 - 8347 (2016/07/26)

Oxidation from alcohols to carboxylic acids, a class of essential chemicals in daily life, academic laboratories, and industry, is a fundamental reaction, usually using at least a stoichiometric amount of an expensive and toxic oxidant. Here, an efficient and practical sustainable oxidation technology of alcohols to carboxylic acids using pure O2 or even O2 in air as the oxidant has been developed: utilizing a catalytic amount each of Fe(NO3)3·9H2O/TEMPO/MCl, a series of carboxylic acids were obtained from alcohols (also aldehydes) in high yields at room temperature. A 55 g-scale reaction was demonstrated using air. As a synthetic application, the first total synthesis of a naturally occurring allene, i.e., phlomic acid, was accomplished.

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