Determination of the Chemical Structure of the Intense Roasty, Popcom-like Odorant 5-Acetyl-2,3-dihydro-l,4-thiazine

Thomas Hofmann; Rainer Hässner; Peter Schieberle

doi:10.1021/jf00056a043

Determination of the Chemical Structure of the Intense Roasty, Popcom-like Odorant 5-Acetyl-2,3-dihydro-l,4-thiazine

Thomas Hofmann, Rainer Hässner, Peter Schieberle^*

^*Corresponding author for this work

Technical University of Munich

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

34 Scopus citations

Abstract

The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-l,4-thiazine (ADT). A sensory study including 5-propionyl-(PDT) and 5-butanoyl-2,3-dihydro-l,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcom-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).

Original language	English
Pages (from-to)	2195-2198
Number of pages	4
Journal	Journal of Agricultural and Food Chemistry
Volume	43
Issue number	8
DOIs	https://doi.org/10.1021/jf00056a043
State	Published - 1 Aug 1995

Keywords

2,3-butanedione
5-Acetyl-2,3-dihydro-1,4-thiazine
5-butanoyl-2,3-dihydro-l,4-thiazine
5-propionyl-2,3-dihydro-l,4-thiazine
cysteamine
odor threshold
synthesis

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title = "Determination of the Chemical Structure of the Intense Roasty, Popcom-like Odorant 5-Acetyl-2,3-dihydro-l,4-thiazine",

abstract = "The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-l,4-thiazine (ADT). A sensory study including 5-propionyl-(PDT) and 5-butanoyl-2,3-dihydro-l,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcom-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).",

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author = "Thomas Hofmann and Rainer H{\"a}ssner and Peter Schieberle",

year = "1995",

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doi = "10.1021/jf00056a043",

language = "English",

volume = "43",

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journal = "Journal of Agricultural and Food Chemistry",

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T1 - Determination of the Chemical Structure of the Intense Roasty, Popcom-like Odorant 5-Acetyl-2,3-dihydro-l,4-thiazine

AU - Hofmann, Thomas

AU - Hässner, Rainer

AU - Schieberle, Peter

PY - 1995/8/1

Y1 - 1995/8/1

N2 - The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-l,4-thiazine (ADT). A sensory study including 5-propionyl-(PDT) and 5-butanoyl-2,3-dihydro-l,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcom-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).

AB - The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-l,4-thiazine (ADT). A sensory study including 5-propionyl-(PDT) and 5-butanoyl-2,3-dihydro-l,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcom-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).

KW - 2,3-butanedione

KW - 5-Acetyl-2,3-dihydro-1,4-thiazine

KW - 5-butanoyl-2,3-dihydro-l,4-thiazine

KW - 5-propionyl-2,3-dihydro-l,4-thiazine

KW - cysteamine

KW - odor threshold

KW - synthesis

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DO - 10.1021/jf00056a043

M3 - Article

AN - SCOPUS:33751156186

SN - 0021-8561

VL - 43

SP - 2195

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JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 8

ER -

Determination of the Chemical Structure of the Intense Roasty, Popcom-like Odorant 5-Acetyl-2,3-dihydro-l,4-thiazine

Abstract

Keywords

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