Lanosterol Solubility in Organic Solvents

Abstract

Lanosterol is a sterol derivative that plays a crucial role in the biosynthesis pathway of cholesterol. Recently, it has been found to reverse the formation of cataracts. The physicochemical properties of lanosterol are poorly understood. Pure lanosterol (>95%) was isolated from a crude product (54.6%) by a newly developed C18 reverse-phase high-performance liquid chromatography (HPLC) method. Purity and structure were confirmed by gas chromatography-mass spectrometry (GC-MS). Ultraviolet-visible spectroscopy shows lanosterol has a maximum absorption peak at 202 nm and the extinction coefficient calculated to be 38280 M-1 ∙cm-1 . The melting temperature and fusion enthalpy were determined to be 407.22 K and 15.37 kJ∙mol-1, respectively, by differential scanning calorimeter (DSC). The solubility of lanosterol was measured in methanol, ethanol, acetonitrile, acetone, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and ethyl acetate using a static equilibrium set up from 284.65 K to 321.65 K. The solubility of lanosterol increases with an increase in temperature. The solubility of lanosterol has a minimum of 0.11mol∙L-1 in acetonitrile at 291.6 K and a maximum of 1.27 mol∙L-1 in ethylene acetate at 320.8 K. The solubilities of lanosterol in selected solvents were correlated by the modified Apelblat equation, Wilson model, NRTL model and UNIQUAC model.

Meeting Name

Engineering Sciences and Fundamentals 2018 - Core Programming Area at the 2018 AIChE Annual Meeting (2018: Oct. 28-Nov. 2, Pittsburgh, PA)

Department(s)

Chemical and Biochemical Engineering

Keywords and Phrases

Acetone; Acetonitrile; Biochemistry; Differential scanning calorimetry; Dimethyl sulfoxide; Dimethylformamide; Drug products; Ethylene; Gas chromatography; High performance liquid chromatography; Mass spectrometry; Physicochemical properties; Solubility; Ultraviolet visible spectroscopy, Biosynthesis pathways; Differential scanning calorimeters; Dimethyl sulfoxide (DMSO); Extinction coefficients; Gas chromatography-mass spectrometries (GC-MS); N ,N-Dimethylformamide; Reverse phase high performance liquid chromatography; Static equilibrium, Organic solvents

International Standard Book Number (ISBN)

978-151087632-3

Document Type

Article - Conference proceedings

Document Version

Citation

File Type

text

Language(s)

English

Rights

© 2018 American Institute of Chemical Engineers (AIChE), All rights reserved.

Publication Date

01 Nov 2018

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