Chemical Properties |
white crystals or powder |
Chemical Properties |
Citric acid monohydrate occurs as colorless or translucent crystals, or as a white crystalline, efflorescent powder. It is odorless and has a strong acidic taste. The crystal structure is orthorhombic. |
Production Methods |
Citric acid occurs naturally in a number of plant species and may be extracted from lemon juice, which contains 5–8% citric acid, or pineapple waste. Anhydrous citric acid may also be produced industrially by mycological fermentation of crude sugar solutions such as molasses, using strains of Aspergillus niger . Citric acid is purified by recrystallization; the anhydrous form is obtained from a hot concentrated aqueous solution and the monohydrate from a cold concentrated aqueous solution. |
Pharmaceutical Applications |
Citric acid (as either the monohydrate or anhydrous material) is widely used in pharmaceutical formulations and food products, primarily to adjust the pH of solutions. It has also been used experimentally to adjust the pH of tablet matrices in enteric-coated formulations for colon-specific drug delivery. Citric acid monohydrate is used in the preparation of effervescent granules, while anhydrous citric acid is widely used in the preparation of effervescent tablets. Citric acid has also been shown to improve the stability of spray-dried insulin powder in inhalation formulations.
In food products, citric acid is used as a flavor enhancer for its tart, acidic taste. Citric acid monohydrate is used as a sequestering agent and antioxidant synergist. It is also a component of anticoagulant citrate solutions. Therapeutically, preparations containing citric acid have been used to dissolve renal calculi. |
Safety |
Citric acid is found naturally in the body, mainly in the bones, and is commonly consumed as part of a normal diet. Orally ingested citric acid is absorbed and is generally regarded as a nontoxic material when used as an excipient. However, excessive or frequent consumption of citric acid has been associated with erosion of the teeth.
Citric acid and citrates also enhance intestinal aluminum absorption in renal patients, which may lead to increased, harmful serum aluminum levels. It has therefore been suggested that patients with renal failure taking aluminum compounds to control phosphate absorption should not be prescribed citric acid or citrate-containing products. |
storage |
Citric acid monohydrate loses water of crystallization in dry air or when heated to about 408℃. It is slightly deliquescent in moist air. Dilute aqueous solutions of citric acid may ferment on standing. |
Purification Methods |
Crystallise it from hot H2O solution (w/w solubility is 54% at 10o, 71% at 50o and 84% at 100o. The monohydrate (softens at ~75o and melts at ~100o) dehydrates in air or when heated gently above 40o . The triethylester ( M 276.3, b 127o/1mm, 294o/atm, d 4 1.137, n D 1.4420.) is a bitter tasting oil. [Beilstein 3 H 556 and 568, 3 IV 1272.] |
Incompatibilities |
Citric acid is incompatible with potassium tartrate, alkali and alkaline earth carbonates and bicarbonates, acetates, and sulfides. Incompatibilities also include oxidizing agents, bases, reducing agents, and nitrates. It is potentially explosive in combination with metal nitrates. On storage, sucrose may crystallize from syrups in the presence of citric acid. |
Regulatory Status |
GRAS listed. The anhydrous form is accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (inhalations; IM, IV, and other injections; ophthalmic preparations; oral capsules, solutions, suspensions and tablets; topical and vaginal preparations). Included in nonparenteral and parenteral medicines licensed in Japan and the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients. |