L-Sorbitol
[CAS# 6706-59-8]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: L-Sorbitol
• Synonyms: (2R,3S,4S,5S)-hexane-1,2,3,4,5,6-hexol
• Molecular Formula: C₆H₁₄O₆
• Molecular Weight: 182.17
• CAS Registry Number: 6706-59-8
• SMILES: C([C@H]([C@@H]([C@H]([C@H](CO)O)O)O)O)O

Properties

• Density: 1.6±0.1 g/cm³ Calc.^*
• Boiling point: 494.9 ºC 760 mmHg (Calc.)^*
• Flash point: 292.5±23.3 ºC (Calc.)^*
• Index of refraction: 1.597 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

L-Sorbitol is a naturally occurring sugar alcohol that is widely used in the food, pharmaceutical, and cosmetic industries due to its sweetening, humectant, and stabilizing properties. The molecular formula of L-sorbitol is C₆H₁₄O₆, and it is chemically known as (2S,3S,4S,5S)-hexane-1,2,3,4,5-pentol. It is an isomer of D-sorbitol, which is more commonly used, and is primarily derived from the reduction of glucose. L-sorbitol is considered a non-caloric sweetener because it is metabolized more slowly in the body compared to regular sugars like sucrose or glucose.

The discovery of sorbitol dates back to the early 20th century when it was isolated from fruits such as apples and pears. However, it became more commercially relevant when it was synthesized from glucose via reduction, which was a more cost-effective method. L-sorbitol is commonly found in various fruits, such as apples, peaches, and prunes, which contribute to its natural occurrence.

L-sorbitol is widely used as a sugar substitute due to its ability to provide sweetness without the high caloric content of traditional sugars. As a sugar alcohol, it is less likely to cause tooth decay because it is not fermented by the bacteria in the mouth. This makes it particularly valuable in sugar-free or reduced-calorie products such as chewing gums, candies, and baked goods.

In addition to its role as a sweetener, L-sorbitol is also used as a humectant in the cosmetic and pharmaceutical industries. Its ability to retain moisture makes it useful in the formulation of lotions, creams, and other skincare products. It is also utilized in oral care products, such as toothpaste and mouthwashes, as it helps to prevent dryness and maintain texture.

L-sorbitol has other notable applications in the pharmaceutical industry. It is used as a stabilizer in the formulation of various medicines, including syrups and chewable tablets. Additionally, L-sorbitol is often included in parenteral formulations because of its safety profile and ability to act as an osmotic agent. It can also be used as a laxative, as it draws water into the colon and aids in relieving constipation.

In industrial applications, L-sorbitol is involved in the production of biodegradable plastics. It is used as a component in the manufacturing of polylactic acid (PLA), a sustainable polymer that is used in the production of eco-friendly packaging materials. The increasing demand for environmentally friendly and biodegradable products has led to a rise in the use of L-sorbitol in the development of sustainable plastics.

Despite its numerous benefits, L-sorbitol can have some side effects when consumed in large quantities. It is poorly absorbed by the gastrointestinal tract, and excessive intake can lead to gastrointestinal discomfort, including bloating, gas, and diarrhea. These side effects are typically mild and occur when large amounts are consumed at once, as L-sorbitol is slowly absorbed and metabolized by the body.

The industrial production of L-sorbitol typically involves the hydrogenation of glucose. This process reduces glucose to sorbitol by adding hydrogen in the presence of a catalyst. The reaction results in a mixture of L- and D-sorbitol, with L-sorbitol being isolated and purified for use in various applications.

In summary, L-sorbitol is a versatile compound with widespread use across various industries. Its properties as a sweetener, humectant, and stabilizer make it valuable in food products, pharmaceuticals, and cosmetics. The growing demand for low-calorie and sugar-free alternatives, as well as biodegradable plastics, has further expanded its applications. Despite potential side effects at high doses, L-sorbitol remains an essential ingredient in many commercial products.

References

2018. Enzymes in Sweeteners Production. Energy, Environment, and Sustainability, 1.
DOI: 10.1007/978-981-13-3263-0_9

2018. Enhancing the Production of d-Mannitol by an Artificial Mutant of Penicillium sp. T2-M10. Applied Biochemistry and Biotechnology, 186(4).
DOI: 10.1007/s12010-018-2791-6

1909. Uber die Konfiguration des Traubenzuckers und seiner Isomeren. I. Untersuchungen Uber Kohlenhydrate und Fermente (1884-1908), 1.
DOI: 10.1007/978-3-642-99501-9_47