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Cholic acid

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-C3008

  • Specification : 98%

  • CAS number : 81-25-4

  • Formula : C24H40O5

  • Molecular Weight : 408.58

  • PUBCHEM ID : 221493

  • Volume : 25mg

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Catalogue Number

BF-C3008

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

408.58

Appearance

White granular crystal

Botanical Source

bile of Pig

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CC(CCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C

Synonyms

Cholalic acid/Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,12α)- (9CI)/cholic acid/17b-(1-Methyl-3-carboxypropyl)etiocholane-3a,7a,12a-triol/3a,7a,12a-Trihydroxycholanic acid/5β-Cholic acid/3a,7a,12a-Trihydroxy-5b-cholanoic acid/(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-Trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid/5b-Cholic acid/3a,7a,12a-Trihydroxy-5b-cholanic Acid/3α,7α,12α-trihydroxy-5β-cholan-24-oic acid/CHOLALIN/Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,8ξ,12α,20R)-/Cholbam/Cholic&Cyclosphorine/3a,7a,12a-Trihydroxy-b-cholanic acid/3a,7a,12a-Trihydroxy-β-cholanic acid/Cholic acd/5b-Cholanic acid-3a,7a,12a-triol/AHR 3053-13C3/(3α,5β,7α,12α)-3,7,12-Trihydroxycholan-24-oic acid/3a,7a,12a-Trihydroxy-5b-cholan-24-oic Acid/5β-Cholanic acid, 3α,7α,12α-trihydroxy- (7CI)/CHOLATE/Kolbam/Orphacol/Cholic acid, 5β-/(3a,5b,7a,12a)-3,7,12-Trihydroxycholan-24-oic acid/Cholan-24-oic acid, 3,7,12-trihydroxy-, (3α,5β,7α,12α)-/Cholan-24-oic acid, 3,7,12-trihydroxy-, (3-α,5-β,7-α,12-α)-/(3α,5β,7α,8ξ,12α,20R)-3,7,12-Trihydroxycholan-24-oic acid

IUPAC Name

(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid

Density

1.2±0.1 g/cm3

Solubility

Ethanol; DMSO

Flash Point

321.0±26.6 °C

Boiling Point

583.9±50.0 °C at 760 mmHg

Melting Point

197-202 ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918190000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:81-25-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

29032641

Abstract

Coxsackievirus Type B3 (CVB3) is an enterovirus that belongs to the Picornaviridae and causes various diseases such as myocarditis and hand-foot-mouth disease. However, an effective antiviral drug is still not developed. In this study, we looked for potential inhibitors of CVB3 replication by examining the survival of CVB3-infected HeLa cells. We detected an antiviral effect by cholic acid and identified it as a candidate inhibitor of CVB3 replication. Cholic acid circulates in the liver and intestines, and it helps the digestion and absorption of lipids in the small intestine. HeLa cells were cultured in 12-well plates and treated with cholic acid (1 and 10 μg/ml) and 10⁶ PFU/ml of CVB3. After 16 h post-infection, the cells were lysed and subjected to western blot analysis and RT-PCR. The production of the viral capsid protein VP1 was dramatically decreased, and translation initiation factor eIF4G1 cleavage was significantly inhibited by treatment with 10 μg/ml cholic acid. Moreover, cholic acid inhibited ERK signaling in CVB3-infected HeLa cells. RT-PCR showed that the amounts of the CVB3 RNA genome and mRNA for the ER stress-related transcription factor ATF4 were significantly reduced. These results showed that cholic acid strongly reduced ER stress and CVB3 proliferation. This compound can be developed as a safe natural therapeutic agent for enterovirus infections.

KEYWORDS

Coxsackievirus B3; ER stress; cholic acid; myocarditis; proliferation

Title

Cholic Acid Attenuates ER Stress-Induced Cell Death in Coxsackievirus-B3 Infection.

Author

Han JY1, Jeong HI2, Park CW1, Yoon J2, Ko J3, Nam SJ2, Lim BK1.

Publish date

2018 Jan 28

PMID

30373615

Abstract

BACKGROUND:
Oral cholic acid (CA) replacement has been shown to be an effective therapy in children with primary bile acid synthesis defects, which are rare and severe genetic liver diseases. To date there has been no report of the effects of this therapy in children reaching adulthood. The aim of the study was to evaluate the long-term effectiveness and safety of CA therapy.

METHODS:
Fifteen patients with either 3β-hydroxy-Δ5-C27-steroid oxidoreductase (3β-HSD) (n = 13) or Δ4-3-oxosteroid 5β-reductase (Δ4-3-oxo-R) (n = 2) deficiency confirmed by mass spectrometry and gene sequencing received oral CA and were followed prospectively.

RESULTS:
The median age at last follow-up and the median time of follow-up with treatment were 24.3 years (range: 15.3-37.2) and 21.4 years (range: 14.6-24.1), respectively. At last evaluation, physical examination findings and blood laboratory test results were normal in all patients. Liver sonograms were normal in most patients. Mean daily CA dose was 6.9 mg/kg of body weight. Mass spectrometry analysis of urine showed that excretion of the atypical metabolites remained low or traces in amount with CA therapy. Liver fibrosis scored in liver biopsies or assessed by elastography in 14 patients, after 10 to 24 years with CA therapy, showed a marked improvement with disappearance of cirrhosis (median score < F1; range: F0-F2). CA was well tolerated in all patients, including five women having 10 uneventful pregnancies during treatment.

CONCLUSIONS:
Oral CA therapy is a safe and effective long-term treatment of 3β-HSD and Δ4-3-oxo-R deficiencies and allows affected children to reach adulthood in good health condition without the need for a liver transplantation.

KEYWORDS

AKR1D1; Bile acid; Genetic cholestasis; HSD3B7

Title

Cholic acid for primary bile acid synthesis defects: a life-saving therapy allowing a favorable outcome in adulthood.

Author

Gonzales E1,2,3,4, Matarazzo L5, Franchi-Abella S2,6, Dabadie A7, Cohen J1, Habes D1, Hillaire S8, Guettier C2,9, Taburet AM10, Myara A11, Jacquemin E12,13,14.

Publish date

2018 Oct 29

PMID

30389306

Abstract

A novel synthetic route of producing ursodeoxycholic acid (UDCA) and obeticholic acid (OCA) was developed through multiple reactions from cheap and readily-available cholic acid. The reaction conditions of the key elimination reaction of mesylate ester group were also investigated and optimized, including solvent, base and reaction temperature. In the straightforward synthetic route for preparation of UDCA and OCA, most of the reaction steps have high conversions with average yields of 94% and 92%, and overall yield up to 65% (7 steps) and 36% (11 steps) from cholic acid, respectively. This promising route offers economical and efficient strategies for potential large-scale production of UDCA and OCA.

Copyright © 2018 Elsevier Inc. All rights reserved.

KEYWORDS

Cholic acid; Obeticholic acid; Synthesis; Ursodeoxycholic acid

Title

A facile synthesis of ursodeoxycholic acid and obeticholic acid from cholic acid.

Author

He XL1, Wang LT1, Gu XZ2, Xiao JX1, Qiu WW3.

Publish date

2018 Dec


Description :

Cholic acid is a major primary bile acid produced in the liver and usually conjugated with glycine or taurine. It facilitates fat absorption and cholesterol excretion.