Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin

Jin Woo Jhoo; Ming Chi Lin; Shengmin Sang; Xiaofang Cheng; Nanqun Zhu; Ruth E. Stark; Chi Tang Ho

doi:10.1021/jf011591v

Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin

Jin Woo Jhoo, Ming Chi Lin, Shengmin Sang, Xiaofang Cheng, Nanqun Zhu, Ruth E. Stark, Chi Tang Ho

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

Abstract

Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (¹H NMR, ¹³C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.

Original language	English
Pages (from-to)	4055-4058
Number of pages	4
Journal	Journal of Agricultural and Food Chemistry
Volume	50
Issue number	14
DOIs	https://doi.org/10.1021/jf011591v
State	Published - Jul 3 2002
Externally published	Yes

Keywords

2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine
Thermal degradation
Thiamin

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10.1021/jf011591v

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title = "Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin",

abstract = "Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (1H NMR, 13C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.",

keywords = "2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine, Thermal degradation, Thiamin",

author = "Jhoo, \{Jin Woo\} and Lin, \{Ming Chi\} and Shengmin Sang and Xiaofang Cheng and Nanqun Zhu and Stark, \{Ruth E.\} and Ho, \{Chi Tang\}",

year = "2002",

month = jul,

day = "3",

doi = "10.1021/jf011591v",

language = "English",

volume = "50",

pages = "4055--4058",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

number = "14",

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TY - JOUR

T1 - Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin

AU - Jhoo, Jin Woo

AU - Lin, Ming Chi

AU - Sang, Shengmin

AU - Cheng, Xiaofang

AU - Zhu, Nanqun

AU - Stark, Ruth E.

AU - Ho, Chi Tang

PY - 2002/7/3

Y1 - 2002/7/3

N2 - Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (1H NMR, 13C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.

AB - Thiamin hydrochloride was thermally degraded in phosphate buffer (pH 6.5) at 110 °C for 2 h. A major decomposition product was isolated by column chromatography and structurally identified by spectrometric techniques (1H NMR, 13C NMR, 2D NMR, and MS) as 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine (MAMP). The possible formation pathway of MAMP was studied using two model systems. It is proposed that MAMP is formed by nucleophilic attack of 2-methyl-3-furanthiol on the thiamin.

KW - 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine

KW - Thermal degradation

KW - Thiamin

UR - https://www.scopus.com/pages/publications/0037014314

U2 - 10.1021/jf011591v

DO - 10.1021/jf011591v

M3 - Article

SN - 0021-8561

VL - 50

SP - 4055

EP - 4058

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 14

ER -

Characterization of 2-methyl-4-amino-5-(2-methyl-3-furylthiomethyl)pyrimidine from thermal degradation of thiamin

Abstract

Keywords

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