Graduate University of Groningen. Worked as a chemist in companies such as Wilmar Oleochemicals B.V (Botlek Rotterdam) and SABIC (Bergen op Zoom)

Physical and Chemical Properties of Saccharic Acid

Contents hide

1 Abstract

2 General Information About Saccharic Acid [1-3]

3 Physico-Chemical Properties of Saccharic Acid [1-3]

4 Applications of Saccharic Acid

5 Chemical Reactions [1-5]

6 Synthesis of Saccharic Acid [6]

7 Conclusion

8 Bibliography

Abstract

This article presents a comprehensive overview of saccharic acid, including its general information, physico-chemical properties, applications of saccharic acid, chemical reactions, synthesis of saccharic acid, conclusion and bibliography.

General Information About Saccharic Acid [1-3]

Other synonyms names of Saccharic Acid are: D-glucaric acid; D-glucosaccharic acid; Tetrahydroxyadipic acid

IUPAC Names of Saccharic Acid: (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid; D-Glucaric acid

CAS number are 25525-21-7 and 87-73-0

Physico-Chemical Properties of Saccharic Acid [1-3]

Molecular Formula C₆H₁₀O₈
Molar Weight 210.14 g/mol
Melting Point 125-126 ℃
Solubility: 912 mg/mL in water; very soluble in alcohols; insoluble in diethyl ether
Color/Form: white solid

Structural formula present on Figure 1.

**Figure 1. Structure of** **Saccharic Acid**

Crystalline solid possible of the Saccharic Acid can be seen in the picture provided in Figure 2.

**Figure** **2. Crystalline solid of** **Saccharic Acid**

Applications of Saccharic Acid

Saccharic acid, is a chemical compound with the formula C6H10O8. It is derived by oxidizing a sugar such as glucose with nitric acid. The salts of saccharic acid are called saccharates or glucarates. Saccharic acid and its derivatives are used in the production of environmentally friendly cleaning products due to their biodegradable nature. As an additive, saccharic acid helps stabilize certain formulations and can act as a sequestrant, improving shelf life. Glucaric acid salts (glucarates) are studied for their potential health benefits, including detoxification and anticancer properties.

Calcium saccharate is a calcium salt of saccharic acid, commonly used as a pharmaceutical excipient to enhance drug stability and absorption. It is also utilized as a food additive and firming agent in the food industry. Due to its calcium content, it may contribute to bone health and mineral balance in the body. Additionally, calcium saccharate has been studied for its potential role in detoxification processes, aiding in the elimination of certain toxins. Its solubility properties make it useful in various industrial and medical applications. Calcium D-glucarate, a derivative, is investigated for its ability to support liver function and hormone balance. It serves as a precursor for the synthesis of various polymers, coatings, and bio-based materials, emphasizing its role in sustainable chemistry. Figure 3

Saccharic acid formed the salt with d-amphetamine. This salt is a component of Adderall as a long-lasting amphetamine (Study Candy). Figure 4

Chemical Reactions [1-5]

The salts of saccharic acid (Calcium glucarate; Magnesium glucarate), known as saccharates or glucarates, are formed when the carboxylic acid groups react with bases. Reactions involving KOH presented in Figure 5.

Reaction with carbonates is shown in Figure 6.

**Figure 6. Reaction with potassium carbonate**

Reaction with d-amphetamine free base (component of Adderall) Figure 7

**Figure 7. Dextroamphetamine saccharate formation**

Synthesis of Saccharic Acid [6]

From D-Glucose and Nitric Acid: D-Glucose reacts with 25% nitric acid, resulting in the formation of saccharic acid crystals upon evaporation. Refer to Figure 8 for details.

**Figure 8. Reaction of D-glucose with nitric acid**

In a porcelain cup, 27 g of glucose and 160 ml of 25% nitric acid are mixed. The mixture is heated in a gently boiling water bath while constantly stirring with a glass rod. Heating is continued until the release of nitrogen oxides ceases. Then, the solution is evaporated to a syrup-like consistency, sometimes colored brown. The syrupy mass is dissolved in 5 ml of water, and potassium carbonate is added until the pH becomes alkaline . The solution is then cooled, and glacial acetic acid is added until the pH becomes acidic. The mixture is left overnight. The precipitated crystals of acidic potassium salt are filtered and washed with several milliliters of ice-cold water. The resulting salt (which may be brownish in color) is dissolved in 20 ml of hot water. The solution is cooled, and 0.3 g of activated charcoal is added. The solution is boiled for 5 minutes. The hot solution is filtered, and the filtrate is cooled, forming colorless crystals. The crystals are filtered and dried. The yield of the potassium salt is 10 g. Figure 9

**Figure 9. Scheme of** **saccharic acid** **synthesis**

Conclusion

Saccharic acid, also known as glucaric acid, is an organic compound with the molecular formula C6H10O8. It is produced through the oxidation of sugars like glucose using nitric acid. The resulting salts of saccharic acid are referred to as saccharates or glucarates. Small quantities of saccharic acid occur naturally in various fruits and vegetables, such as apples, oranges, and broccoli. Its role in metabolism and potential detoxification effects have sparked interest in its applications for improving human health and mitigating the effects of harmful substances. Additionally, its biodegradable properties make it an eco-friendly option for reducing chemical waste in the environment.

Bibliography

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