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Merck

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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329774840
MDL number:
MFCD00064142
Beilstein/REAXYS Number:
3219887

Key Documents

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Product Name

Chenodeoxycholic acid, European Pharmacopoeia (EP) Reference Standard

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 key

RUDATBOHQWOJDD-BSWAIDMHSA-N

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

grade

pharmaceutical primary standard

API family

ursodiol

manufacturer/tradename

EDQM

mp

165-167 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... NR1H4(9971)

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Application

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

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.

Other Notes

Sales restrictions may apply.

Packaging

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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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
Luciano Adorini et al.
Drug discovery today, 17(17-18), 988-997 (2012-06-02)
Nonalcoholic fatty liver disease (NAFLD) is a highly prevalent chronic liver condition evolving in a proportion of patients into nonalcoholic steatohepatitis (NASH), an aggressive form of NAFLD associated with increased cardiovascular mortality and significant risk of progressive liver disease, including
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
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