Lithocholic acid

Lithocholic acid^[1]
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 Registry Number	434-13-9^Y
ChEBI	CHEBI:16325^N
ChEMBL	ChEMBL1478^Y
ChemSpider	9519^Y
EC number	207-099-1
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
IUPHAR ligand	611
Jmol-3D images	Image
PubChem	9903
RTECS number	FZ2275000
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)
Hazards
S-phrases	S22 S24/25
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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.^[2] 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.^[3]

Dietary fiber can bind to lithocholic acid and aid in its excretion in stool;^[4] 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.^[5]

References

↑ Lithocholic acid at Sigma-Aldrich
↑ Kozoni, V.; Tsioulias, G; Shiff, S; Rigas, B (2000). "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". Carcinogenesis 21 (5): 999–1005. doi:10.1093/carcin/21.5.999. PMID 10783324.
↑ Goldberg, AA; Beach, A; Davies, GF; Harkness, TA; Leblanc, A; Titorenko, VI (2011). "Lithocholic bile acid selectively kills neuroblastoma cells, while sparing normal neuronal cells". Oncotarget 2 (10): 761–82. PMC 3248158. PMID 21992775.
↑ Jenkins, DJ; Wolever, TM; Rao, AV; Hegele, RA; Mitchell, SJ; Ransom, TP; Boctor, DL; Spadafora, PJ et al. (1993). "Effect on blood lipids of very high intakes of fiber in diets low in saturated fat and cholesterol". The New England Journal of Medicine 329 (1): 21–6. doi:10.1056/NEJM199307013290104. PMID 8389421.
↑ Ishizawa, M.; Matsunawa, M.; Adachi, R.; Uno, S.; Ikeda, K.; Masuno, H.; Shimizu, M.; Iwasaki, K.-i. et al. (2008). "Lithocholic acid derivatives act as selective vitamin D receptor modulators without inducing hypercalcemia". The Journal of Lipid Research 49 (4): 763. doi:10.1194/jlr.M700293-JLR200.

Lithocholic acid

References

Further reading