Dehydration of Cholic Acid

Devor, Arthur W.; Marlow, H. W.

doi:10.1021/ja01214a066

Cited by 13 publications

(5 citation statements)

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“…Oxidation of this crude olefin 5 (10 g) as per Scheme I, yielded 4.5 g of enone 6. Prolonged (2.5 h) refluxing of cholic acid with fused ZnCI2 in acetone followed by acetylation and esterification did result in the corresponding ester 10 of the reported apocholic acid 8 (3). These experiments emphasize the importance of the duration of refluxing (not reported in ref 3) in order to completely dehydrate and subsequently isomerize cholic acid to apocholic acid.…”

Section: Resultssupporting

confidence: 50%

“…An ether solution (2 L) of acid 1 (82 g of crude material) was treated with diazomethane. The ether was removed by evaporation and the residue was eluted through silica gel (800 g deactivated with 15% H20) with CHCI3 containing 5% CH3OH to yield 60 g of pure methyl ester Methyl 3 ,12 --5ß•^ -7-ß -24-ß ß (3). A solution of ester 2 (36 g) in pyridine (500 mL) was treated with POCI3 while chilling on an ice bath.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 5.beta.-chol-7-en-6-one analogs of ecdysone from cholic acid

Dias¹

1977

J. Chem. Eng. Data

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Section: Resultssupporting

confidence: 50%

Section: Methodsmentioning

confidence: 99%

Synthesis of 5.beta.-chol-7-en-6-one analogs of ecdysone from cholic acid

Dias¹

1977

J. Chem. Eng. Data

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“…This compound was prepared by the action of ZnCL on choiic acid (24). Isolation of the product gave a crystalline compound melting at 168-17QsC; reported (24) mp 166-168°C.…”

Section: Ah2ar-dlhydr~xy-a~~~~)-cl~olenoie (Apochslic) Acidmentioning

confidence: 99%

Preparation and mass spectral behaviour of some 5β-cholenoic acids

Child¹,

Kuksis²,

Marai³

1979

Can. J. Biochem.

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Monounsaturated 5 beta-cholanoic acids with double bonds in rings A, B, and C were prepared by POCl3 and ZnCl2 dehydration from natural bile acids with selectively blocked hydroxyl functions. The yields ranged from 15 to 100%. The products were purified by thin-layer and AgNO3 thin-layer chromatography and the structures were confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. The methyl ester acetates of the unsaturated 5 beta-cholanoic acids possessed chromatographic properties closely similar to those of the corresponding saturated bile acids. Several characteristic fragments were seen in the mass spectra which, in conjunction with the chromatographic properties, permitted an unambiguous distinction between different monounsaturated acids, and between saturated and unsaturated bile acids of the same number and configuration of functional groups. The 20 5 beta-cholenoic acids examined represent all of the simple chemical and enzymatic dehydration products of natural bile acids and can be completely identified by their combined chromatographic and mass spectral properties.

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“…For example, dehydration in children might concentrate the bile. [ 2 ] In addition, some underlying genetic diseases such as hemoglobinopathies might alter the component of the bile. [ 3 ] These factors have to be considered in bile analysis; however, it is not well assessed and mentioned in the report by Verma et al .…”

mentioning

confidence: 99%