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19-hydroxy Cholesterol

目录号 : GC40417

An oxysterol

19-hydroxy Cholesterol Chemical Structure

Cas No.:561-63-7

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1mg
¥599.00
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5mg
¥2,399.00
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10mg
¥4,506.00
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Sample solution is provided at 25 µL, 10mM.

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产品描述

19-hydroxy Cholesterol is formed during metabolic oxidation of cholesterol. It has been used as an internal standard for the quantitative determination of sterols by mass spectroscopic analysis.[1]

Reference:
[1]. Yamaga, N., Ogura, Y., Islam, A., et al. Utility of 19-hydroxycholesterol as an internal standard compound for the quantitative determination of sterols using capillary gas chromatograph. Yonago Acta medica 45, 27-33 (2002).

Chemical Properties

Cas No. 561-63-7 SDF
化学名 cholest-5-ene-3β,19-diol
Canonical SMILES O[C@@H]1CC2=CC[C@]3([H])[C@@](CC[C@]4([C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C)C)C)C)([H])[C@](CO)2CC1
分子式 C27H46O2 分子量 402.7
溶解度 DMF: 2 mg/ml,DMSO: 0.1 mg/ml,Ethanol: 20 mg/ml,Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml 储存条件 Store at -20°C
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储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.4832 mL 12.4162 mL 24.8324 mL
5 mM 0.4966 mL 2.4832 mL 4.9665 mL
10 mM 0.2483 mL 1.2416 mL 2.4832 mL
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Research Update

A new and improved synthesis of 19-iodocholesterol 3-acetate

Steroids 1978 Apr;31(4):453-61.PMID:663979DOI:10.1016/0039-128x(78)90027-2.

19-Iodocholesterol 3-acetate (VI) was synthesized in a single step by iodo group substitution for hydroxyl using either one of two different reagents: (1) carbodiimidonium methiodide (VIII) or (2) triphenyl-phosphine/N-iodosuccinimide (IX). The yields were as satisfactory as those obtained from the two step iodide replacement of a 19-hydroxy group via the 19-tosyloxy group. The principal intermediate, 19-hydroxy Cholesterol 3-acetate (V), was derived in appreciable quantities, and relatively inexpensively, through the Pb (OCOCH3) 4 photolytic oxidation of the bromohydrin of cholesterol 3-acetate (III) to the epoxide (IV) thence Zn reduction to the 19-hydroxy compound. A specially designed 12 liter flask was of aid in accomplishing the photolysis reaction. Dry column chromatography with the supportive puncture sampling was integral to achieving the good yields and high purity of 19-iodocholesterol (VIII).

Gas chromatographic properties of common cholesterol and phytosterol oxidation products

J Chromatogr A 2004 Nov 5;1055(1-2):169-76.PMID:15560493DOI:10.1016/j.chroma.2004.08.123.

The most common cholesterol and phytosterol oxidation products found in foodstuffs or biological matrices are the 7alpha- and 7beta-hydroxysterol, 7-ketosterol, 5alpha,6alpha- and 5beta,6beta-epoxysterol, and triol derivatives of sterols. This study focused on the preparation and purification of such products derived from campesterol, stigmasterol and beta-sitosterol. The identity of the substances was confirmed by mass spectroscopic analysis. The elution order of a complex mixture composed of the 7alpha- and 7beta-hydroxysterol, 7-ketosterol, 5alpha,6alpha- and 5beta,6beta-epoxysterol, and triol derivatives of cholesterol, campesterol, stigmasterol and beta-sitosterol was recorded on an apolar as well as a medium-polarity capillary column in relation to two commonly used internal standards, i.e. alpha-cholestane and 19-hydroxy Cholesterol. Flame-ionization detector as well as mass spectrometry response factors were derived from a gravimetrically prepared mixture of commercially available cholesterol oxide standards. It was proven that the ionization efficiency of cholesterol and phytosterol oxides are very similar and that response factors obtained for cholesterol oxidation products are also valid for quantitative work regarding phytosterol oxidation products.