14. Hydroxycarboxilic acids and ketocarboxylic acids – overview. Comparison of their chemical properties. Important compounds of this group and their biological significance – lactic acid, salicylic acid, malic acid, tartaric acid, citric acid; pyruvic acid, acetoacetic acid, oxaloacetic acid, α -ketoglutaric acid. Ketone bodies.
Topic 14 of 25 in the MU Plovdiv syllabus for Chemistry (Dental Medicine, Year 1). The free AceMed note covers it in 11 sections, about 1,565 words (11 min of reading), with 28 flashcards.
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Hydroxycarboxylic acids (aliphatic and aromatic acids).
Stereoisomerism in saturated hydroxy carboxylic acids.
Chemical properties.
Reactions on heating and complex formation.
Medicines derived from salicylic acid.
Oxo carboxylic acids.
Structure and Nomenclature of Oxo Carboxylic Acids
Major examples: glyoxylic, pyruvic, acetoacetic and oxaloacetic acid. Keto-enol tautomerism.
Hydroxycarboxylic acids (aliphatic and aromatic acids).
Definition:
Hydroxycarboxylic acids contain both a hydroxyl group (-OH) and a carboxyl group (-COOH) in their structure.
Classification:
1. Aliphatic Hydroxycarboxylic Acids:
Can be further categorized into:
Saturated: No carbon-carbon double bonds.
Unsaturated: Contain one or more carbon-carbon double bonds.
2. Aromatic Hydroxycarboxylic Acids:
Contain an aromatic ring in their structure along with -OH and -COOH groups.
Examples:
Saturated Aliphatic: Lactic acid
Unsaturated Aliphatic: Citric acid
Aromatic: Salicylic acid
Sources:
Found naturally in fruits, vegetables, and microorganisms.
Applications:
Used in food, pharmaceuticals, cosmetics, and chemical synthesis.
Stereoisomerism in saturated hydroxy carboxylic acids.
L-lactic acid is the L stereoisomer, commonly found in the L-form in biological systems and is often produced during anaerobic respiration in muscle cells. Hence, it's often referred to as "L-muscle."D-lactic acid is the D stereoisomer, and it's found in D-form in certain fermented dairy products like milk. Hence, it's often referred to as "D-milk." These terms, L and D, denote the configuration of the asymmetric carbon atom in the molecule. L refers to the "levorotatory" configuration (meaning it rotates plane-polarized light counterclockwise), while D refers to the "dextrorotatory" configuration (rotating plane -polarized light clockwise). The L and D forms are not related to the terms "left" and "right" but rather originate from Latin terms for "left" and "right" handedness in terms of optical activity.
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