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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:
474-25-9
Molecular Weight:
392.57
Beilstein/REAXYS Number:
3219887
MDL number:
MFCD00064142
UNSPSC Code:
41116107
PubChem Substance ID:
329774840
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
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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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 for system suitability European Pharmacopoeia (EP) Reference Standard

Y0001163

Ursodeoxycholic acid for system suitability

Chenodeoxycholic acid-2,2,4,4-d4 98 atom % D, 98% (CP)

Sigma-Aldrich

614122

Chenodeoxycholic acid-2,2,4,4-d4

Ursodeoxycholic acid ≥99%

Sigma-Aldrich

U5127

Ursodeoxycholic acid

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
H Reyes et al.
Annals of medicine, 32(2), 94-106 (2000-04-15)
The pathogenesis of intrahepatic cholestasis of pregnancy (ICP) can be related to abnormalities in the metabolism and disposition of sex hormones and/or bile acids, determined by a genetic predisposition interacting with environmental factors. The total amount of oestrogens and progesterone
Sunder Mudaliar et al.
Gastroenterology, 145(3), 574-582 (2013-06-04)
Obeticholic acid (OCA; INT-747, 6α-ethyl-chenodeoxycholic acid) is a semisynthetic derivative of the primary human bile acid chenodeoxycholic acid, the natural agonist of the farnesoid X receptor, which is a nuclear hormone receptor that regulates glucose and lipid metabolism. In animal
Yongbo Shi et al.
ACS applied materials & interfaces, 5(1), 144-153 (2012-12-14)
Two ruthenium complexes featuring bulky ancillary ligands, XS48 and XS49, were synthesized and studied as dyes in dye-sensitized solar cells (DSCs). Both dyes exhibit higher solar-to-electrical energy conversion efficiency when compared to a commonly used N3 sensitizer under the same
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
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