Deoxycholic acid

Deoxycholic acid

Names
IUPAC name (3α,5β,12α,20R)-3,12-Dihydroxycholan-24-oic acid
Other names Deoxycholic acid Deoxycholate Kybella Celluform Plus
Identifiers
CAS Number	83-44-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28834 Y
ChEMBL	ChEMBL406393 Y
ChemSpider	193196 Y
DrugBank	DB07690 Y
ECHA InfoCard	100.001.344
IUPHAR/BPS	610
PubChem	222528
UNII	005990WHZZ Y
InChI InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1 Y Key: KXGVEGMKQFWNSR-LLQZFEROSA-N Y InChI=1/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16-,17+,18-,19+,20+,21+,23+,24-/m1/s1 Key: KXGVEGMKQFWNSR-LLQZFEROBK
SMILES C[C@H](CCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C
Properties
Chemical formula	C24H40O4
Molar mass	392.58 g·mol−1
Melting point	174–176 °C (345–349 °F; 447–449 K)
Solubility in water	0.024%
Acidity (pKa)	6.58
Magnetic susceptibility (χ)	-272.0·10−6 cm3/mol
Pharmacology
ATC code	D11AX24 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Deoxycholic acid (conjugate base deoxycholate), also known as cholanoic acid , Kybella , Celluform Plus and 3α,12α-dihydroxy-5β-cholan-24-oic acid, is a bile acid. Deoxycholic acid is one of the secondary bile acids, which are metabolic byproducts of intestinal bacteria. The two primary bile acids secreted by the liver are cholic acid and chenodeoxycholic acid. Bacteria metabolize chenodeoxycholic acid into the secondary bile acid lithocholic acid, and they metabolize cholic acid into deoxycholic acid. There are additional secondary bile acids, such as ursodeoxycholic acid. Deoxycholic acid is soluble in alcohol and acetic acid. When pure, it comes in a white to off-white crystalline powder form.

Deoxycholic acid has been used since its discovery in various fields of human medicine. In the human body deoxycholic acid is used in the emulsification of fats for the absorption in the intestine. It has, in some countries (including Switzerland) been licensed as an emulsifier in food industry, but it is no longer common. Outside the body it is used in experimental basis of cholagogues and is also in use to prevent and dissolve gallstones.

In research deoxycholic acid is used as a mild detergent for the isolation of membrane associated proteins. The critical micelle concentration for deoxycholic acid is approximately 2.4-4 mM.

Sodium deoxycholate, the sodium salt of deoxycholic acid, is often used as a biological detergent to lyse cells and solubilise cellular and membrane components. Sodium deoxycholate mixed with phosphatidylcholine, is used in mesotherapy injections to produce lipolysis, and has been used as an alternative to surgical excision in the treatment of lipomas.