Lithocholic acid

Lithocholic acid^[1]

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
PubChem	9903
ChemSpider	9519^Y
EC number	207-099-1
ChEBI	CHEBI:16325^N
ChEMBL	CHEMBL1478^Y
IUPHAR ligand	611
RTECS number	FZ2275000
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₂₄H₄₀O₃
Molar mass	376.57 g/mol
Melting point	183-188 °C
Hazards
S-phrases	S22 S24/25
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lithocholic acid (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.^[2]

Dietary fiber can bind to lithocholic acid and aid in its excretion in stool;^[3] 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.^[4]

References

^ Lithocholic acid at Sigma-Aldrich
^ http://carcin.oxfordjournals.org/cgi/content/full/21/5/999 The effect of lithocholic acid on proliferation and apoptosis during the early stages of colon carcinogenesis: differential effect on apoptosis in the presence of a colon carcinogen . Kozoni. 1999
^ http://content.nejm.org/cgi/content/full/329/1/21/F2 Effect on Blood Lipids of Very High Intakes of Fiber in Diets Low in Saturated Fat and Cholesterol. 1993
^ http://www.jlr.org/content/49/4/763.short Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia. Mikishima. 2008

Lithocholic acid

References

Further reading