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Related Concept Videos

Polyprotic Acids03:38

Polyprotic Acids

25.6K
Acids are classified by the number of protons per molecule that they can give up in a reaction. Acids such as HCl, HNO3, and HCN that contain one ionizable hydrogen atom in each molecule are called monoprotic acids. Their reactions with water are:
25.6K
Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

7.8K
Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in water and readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion.
7.8K
Composition of Polyprotic Acid Solutions as a Function of pH01:19

Composition of Polyprotic Acid Solutions as a Function of pH

1.2K
Polyprotic acids of the type H2M constitute two ionizable protons. As a result, on titration with a base, they exhibit two equivalence points in the titration curve. During titration, the species H2M, HM−, and M2− will be present in the solution at different points. The fractions of H2M, HM−, and M2− present at the various instances of the titration are denoted by α0, α1, and α2, respectively.
A graph with the alpha values is plotted against the volume of...
1.2K
Brønsted-Lowry Acids and Bases02:16

Brønsted-Lowry Acids and Bases

20.0K
In 1923, the Brønsted–Lowry definition of acids and bases was proposed by Johannes Brønsted and Thomas Lowry. According to this theory, a Brønsted acid is defined as a species that donates a proton in a chemical reaction and gets converted to its conjugate base. A Brønsted base is defined as a species that accepts a proton in a chemical reaction and gets converted into its conjugate acid. These transfers of protons are caused by the displacement of electrons in these...
20.0K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

9.1K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
9.1K
Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.2K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
3.2K

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Determination of the Gas-phase Acidities of Oligopeptides
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Determination of the Gas-phase Acidities of Oligopeptides

Published on: June 24, 2013

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Asparagusic acid.

Stephen C Mitchell1, Rosemary H Waring2

  • 1Computational and Systems Medicine, Department of Surgery and Cancer, Faculty of Medicine, Imperial College London, South Kensington, London SW7 2AZ, United Kingdom.

Phytochemistry
|October 9, 2013
PubMed
Summary
This summary is machine-generated.

Asparagusic acid, unique to asparagus, causes odorous urine after consumption. This sulfurous compound may substitute for alpha-lipoic acid in metabolic processes.

Keywords:
1,2-Dithiolane-4-carboxylic acidAsparagaceae familyAsparagusAsparagus officinalis L.Asparagusic acidShort reviewSulphur heterocycleUrine odour

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Food Science

Background:

  • Asparagusic acid (1,2-dithiolane-4-carboxylic acid) is a unique sulfur-containing heterocyclic compound found in asparagus.
  • Other dithiolane derivatives exist in non-food species, but asparagusic acid is notable for its presence in a common food.
  • Despite its unique origin, asparagusic acid is considered non-toxicologically significant for humans.

Purpose of the Study:

  • To review existing literature on asparagusic acid.
  • To highlight its chemical properties, biological activity, and metabolic pathways.
  • To explore potential applications of asparagusic acid.

Main Methods:

  • Literature review of scattered data on asparagusic acid.
  • Analysis of chemical structure and reactivity.
  • Investigation of biological properties and metabolic roles.

Main Results:

  • Asparagusic acid's unique structure with adjacent sulfur atoms confers high chemical reactivity.
  • It is the likely cause of the characteristic odor in urine after asparagus consumption.
  • The compound exhibits biological properties, including potential substitution for alpha-lipoic acid in key metabolic oxidation systems.

Conclusions:

  • Asparagusic acid is a chemically reactive, biologically active compound unique to asparagus.
  • Its role in urine odor and potential metabolic functions warrants further investigation.
  • Exploratory applications of asparagusic acid may exist, meriting additional research.