Synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid for electrochemical protein modification

Varghese John; Jonathan L. Vennerstrom; Thomas J. Holmes

doi:10.1002/jlcr.2580230308

Synthesis of 2,5‐dihydroxy[carboxy‐¹⁴C]benzoic acid for electrochemical protein modification

Varghese John, Jonathan L. Vennerstrom, Thomas J. Holmes

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis of 2,5‐dihydroxy[carboxy‐¹⁴C]benzoic acid (gentisic acid) is described. The procedure utilized [carboxy‐¹⁴C]salicylic acid as a starting material. Salicylic acid was converted to gentisic acid using potassium persulfate hydroxylation. The mixture of hydroxylation products in this reaction was easily separated by UV‐visualized quartz column chromatography to obtain the desired isomer in high purity (overall yield of 38%). This procedure may be used for micro and semimicro preparation of the title compound.

Original language	English (US)
Pages (from-to)	313-316
Number of pages	4
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	23
Issue number	3
DOIs	https://doi.org/10.1002/jlcr.2580230308
State	Published - Mar 1986
Externally published	Yes

Keywords

Carbon‐14
gentisic acid
hydroxylation
quartz column

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Radiology Nuclear Medicine and imaging
Drug Discovery
Spectroscopy
Organic Chemistry

Access to Document

10.1002/jlcr.2580230308

Cite this

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title = "Synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid for electrochemical protein modification",

abstract = "The synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid (gentisic acid) is described. The procedure utilized [carboxy‐14C]salicylic acid as a starting material. Salicylic acid was converted to gentisic acid using potassium persulfate hydroxylation. The mixture of hydroxylation products in this reaction was easily separated by UV‐visualized quartz column chromatography to obtain the desired isomer in high purity (overall yield of 38%). This procedure may be used for micro and semimicro preparation of the title compound.",

keywords = "Carbon‐14, gentisic acid, hydroxylation, quartz column",

author = "Varghese John and Vennerstrom, {Jonathan L.} and Holmes, {Thomas J.}",

year = "1986",

month = mar,

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language = "English (US)",

volume = "23",

pages = "313--316",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "John Wiley and Sons Ltd",

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TY - JOUR

T1 - Synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid for electrochemical protein modification

AU - John, Varghese

AU - Vennerstrom, Jonathan L.

AU - Holmes, Thomas J.

PY - 1986/3

Y1 - 1986/3

N2 - The synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid (gentisic acid) is described. The procedure utilized [carboxy‐14C]salicylic acid as a starting material. Salicylic acid was converted to gentisic acid using potassium persulfate hydroxylation. The mixture of hydroxylation products in this reaction was easily separated by UV‐visualized quartz column chromatography to obtain the desired isomer in high purity (overall yield of 38%). This procedure may be used for micro and semimicro preparation of the title compound.

AB - The synthesis of 2,5‐dihydroxy[carboxy‐14C]benzoic acid (gentisic acid) is described. The procedure utilized [carboxy‐14C]salicylic acid as a starting material. Salicylic acid was converted to gentisic acid using potassium persulfate hydroxylation. The mixture of hydroxylation products in this reaction was easily separated by UV‐visualized quartz column chromatography to obtain the desired isomer in high purity (overall yield of 38%). This procedure may be used for micro and semimicro preparation of the title compound.

KW - Carbon‐14

KW - gentisic acid

KW - hydroxylation

KW - quartz column

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DO - 10.1002/jlcr.2580230308

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VL - 23

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EP - 316

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

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