Lithocholic Acid
Title: Lithocholic Acid
CAS Registry Number: 434-13-9
CAS Name: (3a,5b)-3-Hydroxycholan-24-oic acid
Additional Names: 3a-hydroxycholanic acid; 17b-(1-methyl-3-carboxypropyl)etiocholan-3a-ol
Molecular Formula: C24H40O3
Molecular Weight: 376.57
Percent Composition: C 76.55%, H 10.71%, O 12.75%
Literature 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°. [a]D20 +33.7° (c = 1.5 in abs ethanol); [a]D19 +23.3° (Wieland); [a]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.
Melting point: mp 184-186°
Optical Rotation: [a]D20 +33.7° (c = 1.5 in abs ethanol); [a]D19 +23.3° (Wieland); [a]D20 +32.1° (Fischer)
 
Derivative Type: Methyl ester
Molecular Formula: C25H42O3
Molecular Weight: 390.60
Percent Composition: C 76.87%, H 10.84%, O 12.29%
Properties: Crystallizes with ½ mol methanol, mp 125-127°.
Melting point: mp 125-127°
 
Derivative Type: Ethyl ester
Molecular Formula: C26H44O3
Molecular Weight: 404.63
Percent Composition: C 77.18%, H 10.96%, O 11.86%
Properties: Crystals, mp 92-93°.
Melting point: mp 92-93°
 
Derivative Type: Benzyl ester
Molecular Formula: C31H46O3
Molecular Weight: 466.70
Percent Composition: C 79.78%, H 9.93%, O 10.28%
Properties: Crystals, mp 145-148°.
Melting point: mp 145-148°
 
Derivative Type: Acetyllithocholic acid
Molecular Formula: C26H42O4
Molecular Weight: 418.61
Percent Composition: C 74.60%, H 10.11%, O 15.29%
Properties: Crystals, mp 169°.
Melting point: mp 169°
 
Derivative Type: Acetyllithocholic acid methyl ester
Molecular Formula: C27H44O4
Molecular Weight: 432.64
Percent Composition: C 74.96%, H 10.25%, O 14.79%
Properties: Flat needles from pentane, mp 123-130°.
Melting point: mp 123-130°
 
Derivative Type: Acetyllithocholic acid ethyl ester
Molecular Formula: C28H46O4
Molecular Weight: 446.66
Percent Composition: C 75.29%, H 10.38%, O 14.33%
Properties: Crystals, mp 90-91°.
Melting point: mp 90-91°

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