Lithocholic acid

Lithocholic acid

Names
IUPAC name (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Other names Lithocholate; Lithocolic acid; 3α-Hydroxy-5β-cholan-24-oic acid; 3α-Hydroxy-5β-cholanic acid; 5β-Cholan-24-oic acid-3α-ol
Identifiers
CAS Number	434-13-9 Y
ChEBI	CHEBI:16325 N
ChEMBL	ChEMBL1478 Y
ChemSpider	9519 Y
EC Number	207-099-1
IUPHAR/BPS	611
Jmol 3D model	Interactive image
PubChem	9903
RTECS number	FZ2275000
InChI InChI=1S/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 Y Key: SMEROWZSTRWXGI-HVATVPOCSA-N Y InChI=1/C24H40O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h15-21,25H,4-14H2,1-3H3,(H,26,27)/t15-,16-,17-,18+,19-,20+,21+,23+,24-/m1/s1 Key: SMEROWZSTRWXGI-HVATVPOCBI
SMILES O=C(O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]4[C@H]2CC[C@@H]3C[C@H](O)CC[C@@]34C)C
Properties
Chemical formula	C24H40O3
Molar mass	376.57 g/mol
Melting point	183 to 188 °C (361 to 370 °F; 456 to 461 K)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Lithocholic acid, also known as 3α-hydroxy-5β-cholan-24-oic acid or LCA, is a bile acid that acts as a detergent to solubilize fats for absorption. Bacterial action in the colon produces LCA from chenodeoxycholic acid by reduction of the hydroxyl functional group at carbon-7 in the "B" ring of the steroid framework.

It has been implicated in human and experimental animal carcinogenesis. Preliminary in vitro research suggests that LCA selectively kills neuroblastoma cells, while sparing normal neuronal cells and is cytotoxic to numerous other malignant cell types at physiologically relevant concentrations.

Dietary fiber can bind to lithocholic acid and aid in its excretion in stool; as such, fiber can protect against colon cancer.

LCA (and LCA acetate and LCA propionate) can activate the vitamin D receptor without raising calcium levels as much as vitamin D itself.