5545. Lithocholic Acid
Nomenclature
CAS number: 434-13-9
(3α,5β)-3-Hydroxycholan-24-oic acid; 3α-hydroxycholanic acid; 17β-(1-methyl-3-carboxypropyl)etiocholan-3α-ol. C24H40O3; mol wt 376.57.
C 76.55%, H 10.71%, O 12.75%.
Description and references
Found in ox bile, human bile, rabbit bile, and in ox and pig gallstones. Isoln: Fischer, Z. Physiol. Chem. 73, 234 (1911). Characterization: Wieland, Weyland, ibid. 110, 123 (1920). Prepn from cholic or from desoxycholic acid: Hoehn, Mason, J. Am. Chem. Soc. 62, 569 (1940); Sarel, Yanuka, J. Org. Chem. 24, 2018 (1959). Crystal and molecular structure by x-ray diffraction: S. K. Arora et al., Acta Crystallogr. 32B, 415 (1976).
Properties
Hexagonal leaflets from alcohol, prisms from acetic acid, mp 184-186°. [α]D20 +33.7° (c = 1.5 in abs ethanol); [α]D19 +23.3° (Wieland); [α]D20 +32.1° (Fischer). Freely sol in hot alc. More sol in ether than cholic or desoxycholic acid. Sol in about 10 times its weight of ethyl acetate. Slightly sol in glacial acetic acid (about 0.2 g in 3 ml). More sol in benzene than desoxycholic acid. Insol in petr ether, gasoline, ligroin, water.Derivative
Methyl ester.C25H42O3; mol wt 390.60.
C 76.87%, H 10.84%, O 12.29%.
Properties
Crystallizes with mol methanol, mp 125-127°.Derivative
Ethyl ester.C26H44O3; mol wt 404.63.
C 77.18%, H 10.96%, O 11.86%.
Properties
Crystals, mp 92-93°.Derivative
Benzyl ester.C31H46O3; mol wt 466.70.
C 79.78%, H 9.93%, O 10.28%.
Properties
Crystals, mp 145-148°.Derivative
Acetyllithocholic acid.C26H42O4; mol wt 418.61.
C 74.60%, H 10.11%, O 15.29%.
Properties
Crystals, mp 169°.Derivative
Acetyllithocholic acid methyl ester.C27H44O4; mol wt 432.64.
C 74.96%, H 10.25%, O 14.79%.
Properties
Flat needles from pentane, mp 123-130°.Derivative
Acetyllithocholic acid ethyl ester.C28H46O4; mol wt 446.66.
C 75.29%, H 10.38%, O 14.33%.