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Structure Database (LMSD)

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Common Name

Cholesteryl acetate

Systematic Name

3β-acetoxycholest-5-ene

Synonyms

LM ID

LMST01010245

Formula

C₂₉H₄₈O₂

Exact Mass

Calculate m/z

428.36543

Sum Composition

ST 29:2;O2

Status

Curated

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Classification

Biological Context

Cholesteryl acetate is a cholesterol ester.¹ It has been used as an internal standard for the quantification of cholesterol, as well as cholesterol derivatives, by GC or GLC.^2,3 Cholesteryl acetate has also been derivatized from, and used for the quantification of, cholesterol by ESI-MS/MS.⁴ It has also been used in the manufacturing of liquid crystal displays (LCDs), wrist watches, and thermometers.⁵

This information has been provided by Cayman Chemical

References

1. Vijayakumar, V.N., Rajasekaran, T.R., and Baskar, K. Influence of hydrogen bond on thermal and phase transitions of binary complex liquid crystals. Russ. J. Phys. Chem. A 91(13), 2578-2584 (2017).

2. Liebisch, G., Binder, M., Schifferer, R., et al. High throughput quantification of cholesterol and cholesteryl ester by electrospray ionization tandem mass spectrometry (ESI-MS/MS). Biochim. Biophys. Acta 176(1), 121-128 (2006).

3. Gray, G.M., and Yardley, H.J. Lipid compositions of cells isolated from pig, human, and rat epidermis. J. Lipid Res. 16(6), 434-440 (1975).

4. Jones Owen, V.M., Ho, F.K., Mazzuchin, A., et al. Cholesterol in amniotic fluid, determined by gas chromatography. Clin. Chem. 22(2), 224-226 (1976).

5. Huang, Z., Kawi, S., and Chiew, Y.C. Solubility of cholesterol and its esters in supercritical carbon dioxide with and without cosolvents. J. Supercrit. Fluids 30(1), 25-39 (2004).

String Representations

InChiKey (Click to copy)

XUGISPSHIFXEHZ-VEVYEIKRSA-N

InChi (Click to copy)

InChI=1S/C29H48O2/c1-19(2)8-7-9-20(3)25-12-13-26-24-11-10-22-18-23(31-21(4)30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-20,23-27H,7-9,11-18H2,1-6H3/t20-,23+,24+,25-,26+,27+,28+,29-/m1/s1

SMILES (Click to copy)

O(C(=O)C)[C@@H]1CC2=CC[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@](C)([H])CCCC(C)C)[C@@]4(C)CC[C@]3([H])[C@@]2(C)CC1