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

Saccharic Acid

Contents hide

1 Abstract Physical and Chemical Properties of Saccharic Acid

1.1 Abstract

1.2 General Information About Saccharic Acid [1-3]

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

1.4 Applications of Saccharic Acid

1.5 Chemical Reactions [1-5]

1.6 Synthesis of Saccharic Acid [6, 7]

1.7 Conclusion

1.8 Bibliography

Abstract Physical and Chemical Properties of Saccharic Acid

Abstract

This article presents a comprehensive overview of saccharic acid, including its general information, physico-chemical properties, applications of D-glucaric acid, chemical reactions, synthesis of (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid, conclusion and bibliography.

General Information About Saccharic Acid [1-3]

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

IUPAC Names: (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

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

Crystalline solid of the D-glucaric acid can be seen in the picture

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

Applications of Saccharic Acid

(2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic 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 D-Tetrahydroxyadipic are called saccharates or glucarates. D-glucaric acid and its derivatives are used in the production of environmentally friendly cleaning products due to their biodegradable nature. As an additive, the 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 (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic 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. Calcium D-glucarate. Saccharic Acid — **Figure 3. Calcium D-glucarate**. **Saccharic Acid**

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

Figure 4. Adderall. Saccharic Acid — **Figure 4. Adderall**. **Saccharic Acid**

Chemical Reactions [1-5]

The salts of (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid (Calcium glucarate; Magnesium glucarate), known as saccharates or glucarates, are formed when the carboxylic acid groups react with bases.

Figure 5. Reactions with KOH. Saccharic Acid — **Figure 5. Reactions with KOH**. **Saccharic Acid**

Reaction with carbonates is shown.

Figure 6. Reaction with potassium carbonate. Saccharic Acid — **Figure 6. Reaction with potassium carbonate**. **Saccharic Acid**

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

Figure 7. Dextroamphetamine saccharate formation. Saccharic Acid — **Figure 7. Dextroamphetamine saccharate formation**. **Saccharic Acid**

Synthesis of Saccharic Acid [6, 7]

Saccharic Acid Synthesis

From D-Glucose and Nitric Acid: D-Glucose reacts with 25% nitric acid, resulting in the formation of (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid crystals upon evaporation.

Figure 8. Reaction of D-glucose with nitric acid. Saccharic Acid — **Figure 8. Reaction of D-glucose with nitric acid**. **Saccharic 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. Scheme of saccharic acid synthesis. — **Figure 9. Scheme of** **saccharic acid** **synthesis**.

Conclusion

(2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic 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 this acid are referred to as saccharates or glucarates. Small quantities of glucaric 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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