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C1050000

Chenodeoxycholic acid

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

3α,7α-Dihydroxy-5β-cholanic acid, 5β-Cholanic acid-3α,7α-diol, Chenodiol

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About This Item

Empirical Formula (Hill Notation):
C24H40O4
CAS Number:
Molecular Weight:
392.57
Beilstein:
3219887
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

ursodiol

manufacturer/tradename

EDQM

mp

165-167 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

C[C@H](CCC(O)=O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1

InChI key

RUDATBOHQWOJDD-BSWAIDMHSA-N

Gene Information

human ... NR1H4(9971)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Chenodeoxycholic acid EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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Cholic acid United States Pharmacopeia (USP) Reference Standard

USP

1133503

Cholic acid

Cholic acid from bovine and/or ovine, ≥98%

Sigma-Aldrich

C1129

Cholic acid

Cholic acid British Pharmacopoeia (BP) Reference Standard

BP618

Cholic acid

Ursodeoxycholic acid ≥99%

Sigma-Aldrich

U5127

Ursodeoxycholic acid

G S Tint et al.
Gastroenterology, 91(4), 1007-1018 (1986-10-01)
Orally administered UDCA dramatically reduces the secretion of cholesterol into the bile. During UDCA therapy cholesterol balance is maintained by a reduction in both the relative and absolute absorption of cholesterol and, perhaps, by a combined moderate enhancement of bile
Fiona D M van Schaik et al.
PloS one, 7(11), e49706-e49706 (2012-11-29)
The bile acid-activated nuclear receptor Farnesoid X Receptor (FXR) is critical in maintaining intestinal barrier integrity and preventing bacterial overgrowth. Patients with Crohn's colitis (CC) exhibit reduced ileal FXR target gene expression. FXR agonists have been shown to ameliorate inflammation
A F Hofmann
Archives of internal medicine, 159(22), 2647-2658 (1999-12-22)
Bile acids, the water-soluble, amphipathic end products of cholesterol metabolism, are involved in liver, biliary, and intestinal disease. Formed in the liver, bile acids are absorbed actively from the small intestine, with each molecule undergoing multiple enterohepatic circulations before being
M Stark et al.
European journal of biochemistry, 266(1), 209-214 (1999-10-29)
Polypeptides were isolated from human bile by extraction with chloroform/methanol, followed by reversed-phase chromatography in methanol/ethylene chloride and gel filtration in chloroform/methanol. Peptides were characterized by SDS/PAGE, sequence analysis and matrix-assisted laser desorption ionization/time-of-flight mass spectrometry. This identified haemoglobin alpha
Francesco Saverio Di Leva et al.
Journal of medicinal chemistry, 56(11), 4701-4717 (2013-05-10)
Here, we report suvanine, a marine sponge sesterterpene, as an antagonist of the mammalian bile acid sensor farnesoid-X-receptor (FXR). Using suvanine as a template, we shed light on the molecular bases of FXR antagonism, identifying the essential conformational changes responsible

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