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Related Concept Videos

Amines: Introduction01:07

Amines: Introduction

Amines are organic derivatives of ammonia. They are formed by replacing one or more ammonia protons with alkyl or aryl groups. Depending upon the number of organyl groups bonded to nitrogen, amines are classified as primary, secondary, or tertiary. Primary amines have one organyl group attached to the nitrogen atom, while secondary and tertiary amines have two and three organyl groups attached to the nitrogen atom, respectively.
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Physical Properties of Amines01:26

Physical Properties of Amines

Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
Amino Acid Biosynthetic Pathways01:29

Amino Acid Biosynthetic Pathways

Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which provide...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

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Extraction of Non-Protein Amino Acids from Cyanobacteria for Liquid Chromatography-Tandem Mass Spectrometry Analysis
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Biogenic amines in natural ciders.

G Garai1, M T Dueñas, A Irastorza

  • 1Departamento de Química Aplicada, Facultad de Ciencias Químicas, Universidad del País Vasco, Box 1072, 20080 San Sebastián, Spain.

Journal of Food Protection
|December 26, 2006
PubMed
Summary

Biogenic amines, found in fermented foods like cider, can cause toxic effects. This study measured amine levels in natural ciders, finding putrescine, histamine, and tyramine were most common, suggesting a need to control lactic acid bacteria.

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Area of Science:

  • Food Science
  • Analytical Chemistry
  • Microbiology

Background:

  • Biogenic amines are physiologically important but can be toxic in high dietary amounts.
  • These compounds are prevalent in fermented foods, including cider.
  • Understanding biogenic amine levels in cider is crucial for food safety.

Purpose of the Study:

  • To quantify biogenic amine levels in natural ciders.
  • To identify the predominant biogenic amines present.
  • To investigate correlations between cider composition and biogenic amine content.

Main Methods:

  • Analyzed 24 commercial natural cider samples.
  • Utilized reverse-phase high-performance liquid chromatography (RP-HPLC) with fluorescence detection.
  • Employed precolumn derivatization with o-phthaldialdehyde for amine analysis.
  • Applied cluster analysis and principal component analysis for data evaluation.

Main Results:

  • Biogenic amine levels varied significantly, from undetected to 23 mg/liter, with an average of 5.94 +/- 8.42 mg/liter.
  • Putrescine, histamine, and tyramine were the most frequently detected amines.
  • Higher histamine, tyramine, and putrescine levels correlated with lower glycerol and higher 1,3-propanediol content.

Conclusions:

  • Lactic acid bacteria activity significantly influences biogenic amine formation in cider.
  • Specific cider parameters (glycerol, 1,3-propanediol) indicate potential for high biogenic amine levels.
  • Effective control of lactic acid bacteria during cider production is recommended to manage biogenic amine content.