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Hydroxy acids
 Organic compound containing both hydroxyl and carboxy groups are known as
hydroxy acids.
 They may be mono or polybasic and may contain one or more hydroxyl groups
 Based on position of hydroxyl group the monohydroxy acids may be classified as
α,β,γ,δ, etc hydroxy acids
Lactic acid (α-Hydroxy propanoic acid/ 2-hydroxy propanoic acid)
 Lactic Acid is α-hydroxy acid with the chemical formula C3H6O3.
 It is also known as milk acid.

 Lactic acid occurs in sour milk, yogurt, cottage cheese, gastric juice, cucumbers ,
opium and also a muscle metabolite of the carbohydrate metabolism
 In the year 1780, Carl Wilhelm Scheele a Swedish chemist isolated lactic acid from
sour milk for the first time.
Properties of Lactic Acid
 Lactic acid is colorless crystalline solid.
 The commercial lactic acid is colourless or yellow syrupy liquid having sour taste.
 The molecular weight or molar mass of lactic acid is 90.08 g/mol and it’s pH level is
3.51 per 1 mM of lactic acid.
 The melting point of lactic acid is 530C, and the boiling point is 1220 C.
 L-lactic acid has a specific rotation of + 3.820 and D-lactic acid – 3.820
 It is soluble in water and ethanol.
 Lactic acid is corrosive to any metals and tissue.
 Thus, overuse and overconsumption of the lactic acid can come with severe side
effects.
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Chemical properties:
Action of heat:
 α-Hydroxy acid on heating forms cyclic diester known as lactide.
 The OH group and COOH group of two separate molecules combine with each other
with the elimination of water.

Oxidation:
1. When oxidized with a weak oxidizing agent like Ag2O or Fentons reagent (FeSO4 +
H2O2),lactic acid forms Pyruvic acid

2. Lactic acid with dilute and acidified KMnO4 is oxidized to acetaldehyde, CO2 and H2O

Biological Importance:
 Lactic acid is a fuel for cell in intense exercise or when O2 level is low.
 It is converted to glucose in our body and provides energy needed for work.
 It attracts immune system cells to help heal wound and fight infection
 It is used as calcium and iron lactate in medicine to make up the deficiency of
Calcium and Iron in body
 Silver lactate is used as antiseptic.
 Lactic acid is used for deliming of hides in tanning industry
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Tartaric acid (2, 3-dihydroxy butan-1, 4-dioic acid)

 Tartaric acid is α -hydroxy acid with a chemical formula C4H6O6.
 It is also known as 2, 3-dihydroxysuccinic acid or racemic acid.
Occurrence: Tartaric acid occurs in Tamarind and various fruits such as grapes, berries,
plums, oranges, bananas, apricots, avocados etc.

Physical Properties

 It is a white crystalline solid.

 Readily soluble in water and alcohol but insoluble in ether.
 Tartaric acid occurs in three form dextro (d), laevo (l), and meso.
 The molecular mass of tartaric acid is 150.087 grams per mole.
 The density of tartaric acid is 1.79g/cm3.
 The melting point of the acid is between 171-174°C.

Chemical properties:
Salt formation: Tartaric acid being a dibasic acid forms two series of salt- acid and normal
salt, when heated with alkalies.
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Biological Importance:
 It act as an antioxidant and boost immunity
 It helps in digestion by regulating flatulence and improve absorption power of the
intestine
 It act as antibacterial agent by changing the pH of the environment
 In skin products tartaric acid is used as it reduces line and wrinkles,
hyperpigmentation, acne and large pours
 Potassium antimonyl tartarate is used as an eliminant for poisons in stomach by
causing nausea and vomiting
 It is used as leavening agent in baking powder

Citric acid
 β-hydroxy tricarboxylic acid/ 3-carboxy-3-hydroxyl pentan - 1,5- dioic acid
 It is β-hydroxy acid.Citric acid is a weak acid with a chemical formula C6H8O7.
 This organic acid was isolated for the first time by chemist Carl Wilhelm Scheele in
the year 1784.

Occurrence: Fruits such tomato, citrus fruits- lemon, orange, lime. It is also an
biochemical intermediate of TCA cycle
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Physical Properties of citric acid:

 It is a colourless, odourless and crystalline compound.

 It is soluble in water, alcohol, and acetone but sparingly soluble in ether.
 It is optically inactive molecule because it does not have an asymmetric carbon atom.
 The molar mass of citric acid is 192.124g/mol.
 Its density is 1.665g/cm3.
 Its melting point is 153°C.

Chemical properties:
Effect of heat in presence of Conc. H2SO4:
 When heated to 150oC in presence of Conc.H2SO4 citric acid loses a molecule of
water and forms an unsaturated acid known as aconitic acid.
 Aconitic acid on further heating undergoes decarboxylation to form citraconic acid
and itaconic acid.
 Citraconic acid and itaconic acid on heating loses a molecule of water and forms
citraconic anhydride and itaconic anhydride.

Effect of heat in presence of fuming H2SO4: When heated in presence of fuming

H2SO4 citric acid is decarboxylated and form acetone dicarboxylic acid which further
decarboxylate to acetoacetic acid and then to acetone.
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Salt formation:
Citric acid when treated with alkalies form three series of salt- monosodium citrate, disodium
citrate and tri- sodium citrate

Biological Importance:
 It is an important biochemical intermediate of TCA cycle which can be utilized for the
biosynthesis of fatty acids
 It helps supply calcium and vitamin C to the body and, thus, assists in bone
maintenance.
 It enhances antioxidant properties and improve health from diseases such as
osteoporosis, bone health, etc.
 Citric acid is used as a natural preservative because it lowers the pH and makes the
oxidative enzymes lethargic in frozen foods. As a result the growth of bacteria in
foods is prevented.
 It is used as an emulsifying agent in ice creams
 It is used to add a sour taste to synthetic fruit drinks /soft drinks and other food items
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 Sodium citrate used in baby food – prevent curdling of milk in stomach

 It is used to produce detergents and soaps

Dicarboxylic acids– The dicarboxylic acids contain two carboxyl groups. They may
be saturated or unsaturated.
Examples; Succinic acids, Fumaric acid, Maleic acid etc.

Succinic acid (Butane-1, 4-dioic acid)

 Succinic acid is a dicarboxylic saturated acid
 It occurs widely in nature in numerous plants and unripe fruits.
 It is also an intermediate of TCA cycle

Biological importance:
 It is an important intermediate of TCA cycle and serves an electron donor in the
production of fumaric acid and FADH2
 It is a precursor for the synthesis of heme
 It increases resistance to adverse environmental effects and accelerates flowering and
increases productivity.

Fumaric acid (Trans-butenedioic acid)

 It is unsaturated dicarboxylic acid

 It occurs in many moulds and also present in the sap of the plant Fumaria officianilis,
hence named as fumaric acid.
 It is also an intermediate of TCA cycle

Biological importance:
 It is an important biochemical intermediate of TCA cycle
 Fumaric acid is used as a food acidulant in beverages and baking powders.
 Fumaric acid is a pharmaceutically active substance that is used to
treat psoriasis or multiple sclerosis

Keto acids: Carboxylic acids containing ketonic group and carboxyl group are known
as ketoacids
Example; Pyruvic acid, α-ketoglutaric acid, oxaloacetic acid

Pyruvic acid (2-oxy propanoic acid)

 It is the product of aerobic glycolysis ie; On oxidation of glucose pyruvic acid is
obtained

Biological importance:
 Pyruvic acid is the product of aerobic glycolysis
 In the body it is converted to glucose which on oxidation provides energy to do work
 It is precursor for synthesis of amino acids such as alanine
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 It is an important intermediate molecule in protein, fat and carbohydrate metabolism

 Pyruvate functions as an antioxidant.

α-Ketoglutaric acid (2-oxy pentane-1- dioic acid)

 It is a dicarboxylic keto acid
 It is an intermediate metabolite of TCA cycle

Biological importance:
 It is an intermediate of TCA cycle
 α-ketoglutaric (AKG) acid plays an important role in maintaining physiological
functions and cell metabolism.
 It is a nitrogen scavenger.
 It is a precursor for biosynthesis of amino acid Glutamate and glutamine
 AKG can decrease protein catabolism and increase protein synthesis to enhance bone
tissue formation in the skeletal muscles.
 It is an important metabolic fuel for cells of the gastrointestinal tract

Oxaloacetic acid (2-oxy butane-1, 4-dioic acid)

 It is also a dicarboxylic keto acid
 It is an intermediate metabolite of TCA cycle

Biological importance:
 It is an intermediate of TCA cycle
 It is a precursor for biosynthesis of amino acid aspartate
 It is also involved in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid
and fatty acid synthesis.
 Oxaloacetate is a critical component in the production of ATP and must be constantly
regenerated in order for the citric acid cycle and the electron transport chain to
continue.