Tartaric acid is a naturally occurring organic acid found in many fruits and vegetables, commonly used in food and beverage industries as a flavor enhancer, preservative, and acidity regulator.
| IUPAC Name | 2,3-dihydroxybutanedioic acid |
| Molecular Formula | C4H6O6 |
| CAS Number | 87-69-4 |
| Synonyms | 2,3-dihydroxysuccinic acid; 2,3-dihydroxybutanedioic acid; alpha-hydroxy-beta-oxosuccinic acid; 2-hydroxy-2,3-dihydroxybutanedioic acid; 2-hydroxybutane-1,2,3-tricarboxylic acid; 2-hydroxy-1,2,3-propanetricarboxylic acid; racemic acid; natural tartaric acid; L-(+)-tartaric acid; D-(-)-tartaric acid; mesotartaric acid; tartrate; tartronic acid |
| InChI | InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10) |
Tartaric Acid Formula
The chemical formula for tartaric acid is C4H6O6. The formula shows the number and types of atoms present in a single molecule of tartaric acid. The molecule contains four carbon atoms, six oxygen atoms, and six hydrogen atoms. The formula is important in determining the stoichiometry of reactions involving tartaric acid and in calculating its molar mass.
Tartaric Acid Molar Mass
2,3-dihydroxysuccinic acid has a molar mass of 150.09 g/mol, which is the sum of the atomic weights of all the atoms in a single molecule of 2,3-dihydroxysuccinic acid. This organic acid has two carboxyl groups and two hydroxyl groups, which makes it a dicarboxylic acid. Its molar mass is important in determining the amount of 2,3-dihydroxysuccinic acid needed in different applications.
Tartaric Acid Boiling Point
2,3-dihydroxysuccinic acid has a relatively high boiling point of 214°C (417°F) at standard pressure. This temperature is much higher than the boiling point of water, which makes 2,3-dihydroxysuccinic acid very stable at high temperatures. This property is important for its use in the food and beverage industry as it can withstand the high temperatures used in food processing and can be used as a natural preservative.
Tartaric Acid Melting Point
2,3-dihydroxysuccinic acid has a melting point of 170-172°C (338-342°F). Its melting point is important in determining its physical properties, such as its solubility and viscosity, and in the manufacturing of different products that require 2,3-dihydroxysuccinic acid.
Tartaric Acid Density g/ml
The density of 2,3-dihydroxysuccinic acid is 1.79 g/ml, which means that one milliliter of 2,3-dihydroxysuccinic acid weighs 1.79 grams. This property is important in determining the concentration of 2,3-dihydroxysuccinic acid in different solutions and is crucial in the production of 2,3-dihydroxysuccinic acid salts.
Tartaric Acid Molecular Weight
The molecular weight of 2,3-dihydroxysuccinic acid is 150.09 g/mol. This property is important in determining the amount of 2,3-dihydroxysuccinic acid needed in different applications and the stoichiometry of reactions involving 2,3-dihydroxysuccinic acid.
Tartaric Acid Structure
Tartaric acid has a chiral carbon, which means that it exists in two different stereoisomers L-(+)-2,3-dihydroxysuccinic acid and D-(-)-2,3-dihydroxysuccinic acid. Both isomers have the same molecular formula and the same functional groups but differ in their spatial arrangement. 2,3-dihydroxysuccinic acid has two carboxylic acid groups and two hydroxyl groups, which makes it a dicarboxylic acid. The molecule has a central carbon atom that is bonded to two hydroxyl groups and two carboxyl groups.
| Appearance | White crystalline powder or colorless crystals |
| Specific Gravity | 1.79 |
| Color | Colorless |
| Odor | Odorless |
| Molar Mass | 150.09 g/mol |
| Density | 1.79 g/mL at 25°C |
| Melting Point | 170-172°C (338-342°F) |
| Boiling Point | 214°C (417°F) |
| Flash Point | Not applicable |
| Water Solubility | 133 g/L (20°C) |
| Solubility | Soluble in water, ethanol, and ether |
| Vapor Pressure | 0.00013 mmHg at 25°C |
| Vapor Density | Not applicable |
| pKa | pKa1 = 2.98; pKa2 = 4.34; pKa3 = 5.40 |
| pH | 2.2 (0.1 M solution) |
Note: Physico-chemical properties of 2,3-dihydroxysuccinic acid may vary depending on the specific form of the compound, such as the stereoisomer, salt form, or concentration. These values are for the standard form of 2,3-dihydroxysuccinic acid.
Tartaric Acid Safety and Hazards
2,3-dihydroxysuccinic acid is generally recognized as safe (GRAS) by the US Food and Drug Administration (FDA) and is widely used in the food and beverage industry. However, as with any chemical substance, 2,3-dihydroxysuccinic acid can pose certain hazards if not handled properly. Direct contact with 2,3-dihydroxysuccinic acid can cause skin and eye irritation, and ingestion can cause gastrointestinal discomfort. Inhaling 2,3-dihydroxysuccinic acid dust can cause respiratory irritation. 2,3-dihydroxysuccinic acid is also a combustible substance and may pose a fire hazard if exposed to high temperatures or flames. Proper safety precautions, such as wearing protective gear and handling 2,3-dihydroxysuccinic acid in well-ventilated areas, should be taken when working with this chemical.
Tartaric Acid Synthesis Methods
2,3-dihydroxysuccinic acid can be synthesized through several methods. One common method is the hydrolysis of potassium acid tartrate, which is obtained from the residues of grape juice and wine production. Potassium acid tartrate is first mixed with water and heated to produce 2,3-dihydroxysuccinic acid and potassium hydroxide. The resulting solution is then neutralized with hydrochloric acid to yield 2,3-dihydroxysuccinic acid crystals.
Another method involves the oxidation of certain carbohydrates, such as glucose or sucrose, using nitric acid. The resulting mixture is then treated with calcium carbonate to precipitate calcium tartrate, which is subsequently acidified with sulfuric acid to produce 2,3-dihydroxysuccinic acid.
A third method involves the reaction of maleic anhydride with glycolic acid or glycine to produce 2,3-dihydroxysuccinic acid. This method is often used for the production of high-purity 2,3-dihydroxysuccinic acid for use in pharmaceuticals or other sensitive applications.
Tartaric Acid Uses
2,3-dihydroxysuccinic acid has a wide range of uses in various industries.
- The food and beverage industry utilizes tartaric acid as a natural acidulant to provide a sour taste to their products. 2,3-dihydroxysuccinic acid is also used in food and beverage products as a pH control agent, stabilizer, and flavor enhancer, such as in soft drinks, candies, and baked goods.
- The pharmaceutical industry uses 2,3-dihydroxysuccinic acid as an excipient in the production of tablets and capsules, and as a chelating agent to improve the solubility and bioavailability of certain drugs.
- Cosmetic products such as facial masks and peels contain 2,3-dihydroxysuccinic acid due to its exfoliating and brightening properties. 2,3-dihydroxysuccinic acid is used as a buffering agent in hair dyes and bleaches in the cosmetic industry.
- Industrial applications of 2,3-dihydroxysuccinic acid include its use as a sequestering agent in metal plating, a scale inhibitor in water treatment, and a component in the production of adhesives, textiles, and paper products.
Questions:
How many stereoisomers are possible for tartaric acid?
Tartaric acid has two chiral centers, meaning it has the potential to have four stereoisomers. However, due to its internal symmetry, only three of these stereoisomers are actually possible. The three stereoisomers are: meso-tartaric acid (achiral), L-(+)-tartaric acid (dextrorotatory), and D-(-)-tartaric acid (levorotatory).
Is tartaric acid a strong acid?
Tartaric acid is a weak organic acid, meaning it does not completely dissociate in water and has a relatively low acid dissociation constant (pKa). Its pKa values are approximately 2.98 and 4.34, which indicate that it is a weak acid. In comparison, a strong acid, such as hydrochloric acid (HCl), has a much lower pKa value, indicating that it is completely dissociated in water and is a much stronger acid than 2,3-dihydroxysuccinic acid. However, while 2,3-dihydroxysuccinic acid may be considered a weak acid, it still has many practical applications in various industries, including food and beverage, pharmaceutical, and cosmetic, due to its natural origin, safe status, and diverse functionality.
What is the pH of tartaric acid?
The pH of tartaric acid depends on the concentration of the solution and the dissociation constant (pKa) of 2,3-dihydroxysuccinic acid. 2,3-dihydroxysuccinic acid is a weak acid and has two pKa values of approximately 2.98 and 4.34. At low concentrations, 2,3-dihydroxysuccinic acid is only partially dissociated and the pH of its solution is slightly acidic, typically ranging from 2.8 to 3.5. However, at higher concentrations, the pH of 2,3-dihydroxysuccinic acid solution can decrease due to increased ionization, resulting in a more acidic solution. It is important to note that the pH of a 2,3-dihydroxysuccinic acid solution also depends on the presence of other acids and bases in the solution, as well as the temperature and other environmental factors.