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Merck
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SML3096

Sigma-Aldrich

Obeticholic acid

≥98% (HPLC)

Sinónimos:

(3α,5β, 6α,7α)-6-ethyl-3,7-dihydroxy-cholan-24-oic acid, 6-ECDCA, 6a-Ethyl-Chenodeoxycholic Acid, OCA

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About This Item

Fórmula empírica (notación de Hill):
C26H44O4
Número de CAS:
459789-99-2
Peso molecular:
420.63
MDL number:
MFCD16621104
UNSPSC Code:
12352106
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +4 to +6°, c = 1.0 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

C[C@@H]([C@@]1([H])CC[C@@]([H])([C@@]2([C@@H]([C@@H]([C@@]3(C[C@@H](CC[C@@]3([C@]2(CC4)[H])C)O)[H])CC)O)[H])[C@@]14C)CCC(O)=O

InChI

1S/C26H44O4/c1-5-17-21-14-16(27)10-12-26(21,4)20-11-13-25(3)18(15(2)6-9-22(28)29)7-8-19(25)23(20)24(17)30/h15-21,23-24,27,30H,5-14H2,1-4H3,(H,28,29)/t15-,16-,17-,18-,19+,20+,21+,23+,24-,25-,26-/m1/s1

InChI key

ZXERDUOLZKYMJM-ZWECCWDJSA-N

Biochem/physiol Actions

Obeticholic acid (6-ECDCA) is a is a semi-synthetic bile acid analogue used to treat used to treat primary biliary cholangitis. Obeticholic acid is an orally available, potent and selective FXR agonist that exhibits anticholeretic and anti-inflammation effects.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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Botao Gao et al.
Tissue engineering and regenerative medicine, 18(2), 217-224 (2021-02-01)
Ballooned hepatocytes (BH) are a key histological hallmark of nonalcoholic steatohepatitis (NASH), yet their consequences for liver-specific functions are unknown. In our previous study, an experimental model of human induced-BHs (iBH) has been successfully developed based on cell sheet technology. This
Roberto Pellicciari et al.
Journal of medicinal chemistry, 45(17), 3569-3572 (2002-08-09)
A series of 6alpha-alkyl-substituted analogues of chenodeoxycholic acid (CDCA) were synthesized and evaluated as potential farnesoid X receptor (FXR) ligands. Among them, 6alpha-ethyl-chenodeoxycholic acid (6-ECDCA) was shown to be a very potent and selective FXR agonist (EC(50) = 99 nM)
Lulu Sun et al.
Nature reviews. Gastroenterology & hepatology, 18(5), 335-347 (2021-02-12)
Farnesoid X receptor (FXR) is a ligand-activated transcription factor involved in the control of bile acid (BA) synthesis and enterohepatic circulation. FXR can influence glucose and lipid homeostasis. Hepatic FXR activation by obeticholic acid is currently used to treat primary

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