D-Mannitol
[CAS# 69-65-8]

Identification

• Classification: API >> Urinary system medication >> Dehydrated medicine
• Name: D-Mannitol
• Synonyms: 1,2,3,4,5,6-Hexanehexol; Diosmol; Manicol; Manita; Manna sugar
• Molecular Formula: C₆H₁₄O₆
• Molecular Weight: 182.17
• CAS Registry Number: 69-65-8
• EC Number: 200-711-8
• 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.^*, 1.489 g/mL (Expl.)
• Melting point: 167 - 170 °C (Expl.)
• Boiling point: 494.9 °C 760 mmHg (Calc.)^*, 562.3 - 569.5 °C (Expl.)
• Flash point: 292.5±23.3 °C (Calc.)^*
• Solubility: DMSO 36 mg/mL, Water 36 mg/mL (Expl.)
• Index of refraction: 1.597 (Calc.)^*

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

Safety Data

• Safety Statements: S24/25

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

D-Mannitol is a naturally occurring sugar alcohol that is commonly used as a sweetener, excipient, and in pharmaceutical applications. It has the molecular formula C₆H₁₄O₆ and is a stereoisomer of D-glucose. It is widely found in fruits and vegetables, including mushrooms, asparagus, and seaweed, and is also present in significant quantities in certain plants, such as the mannose-rich fruits of the mannitol tree. D-Mannitol was first isolated from manna, the exudate from the manna ash tree (Fraxinus ornus), hence its name.

The primary discovery of D-mannitol can be attributed to its isolation in the early 19th century. Its role as a sugar alcohol was recognized when it was found to have a structure similar to that of glucose but with reduced caloric content, making it useful as a sugar substitute. D-Mannitol is produced industrially by the hydrogenation of D-glucose, a process in which glucose is reduced to mannitol by the addition of hydrogen in the presence of a catalyst.

D-Mannitol is used primarily as a non-caloric sweetener and is often included in food products, such as sugar-free chewing gums, candies, and baked goods. It has about 60-70% of the sweetness of sucrose but provides fewer calories, making it a popular choice for low-calorie and diabetic-friendly products. Unlike regular sugar, D-mannitol is not easily absorbed in the gastrointestinal tract and thus has a minimal impact on blood sugar levels, making it particularly suitable for individuals with diabetes. As a result, D-mannitol is commonly found in sugar-free and "diet" products.

In addition to its role as a sweetener, D-mannitol is also used extensively in the pharmaceutical industry. It serves as an excipient in tablets and oral dosage forms due to its ability to improve the texture, stability, and shelf-life of the drug. D-Mannitol is also employed as a bulking agent in powdered medications, helping to maintain consistency and uniformity in formulations.

D-Mannitol has a significant role in medical applications, particularly in the treatment of conditions such as kidney failure and elevated intracranial pressure. In intravenous (IV) form, D-mannitol is used as an osmotic diuretic. When administered intravenously, it draws water from the tissues into the bloodstream, increasing urine production and helping to reduce edema (swelling) or to treat patients with acute kidney failure. D-Mannitol is often used in emergency medical situations to reduce intracranial pressure after head trauma or in the treatment of glaucoma.

In addition to its medical applications, D-mannitol is also utilized in laboratory settings. It is used in microbiology for the preparation of culture media and as a protective agent in the preservation of cells and tissues. D-Mannitol has been studied for its role in protecting biological systems during freeze-drying (lyophilization), helping to stabilize proteins, enzymes, and other sensitive compounds.

D-Mannitol has other industrial applications as well. It is used as a stabilizer in the production of certain food ingredients and flavorings. Its ability to retain moisture makes it a useful ingredient in cosmetics and personal care products, including lotions, shampoos, and skin creams. The humectant properties of D-mannitol allow it to maintain moisture and prevent products from drying out.

Despite its many uses, D-mannitol can have some side effects, particularly when consumed in large amounts. Because it is only partially absorbed by the body, it can have a mild laxative effect, leading to gastrointestinal discomfort, including bloating, cramping, and diarrhea. These effects are more pronounced when large quantities of D-mannitol are ingested, particularly in individuals who are sensitive to sugar alcohols.

In conclusion, D-mannitol is a versatile compound with wide-ranging applications in the food, pharmaceutical, and cosmetic industries. It is used as a sweetener, excipient, and therapeutic agent due to its low caloric content, minimal effect on blood sugar, and osmotic diuretic properties. D-Mannitol continues to be a valuable ingredient in various commercial and medical products, particularly in the formulation of sugar-free products and in the treatment of specific medical conditions. Its beneficial properties and low side-effect profile contribute to its continued use and research in multiple fields.

References

2018. Early detection of capping risk in pharmaceutical compacts. International Journal of Pharmaceutics, 553(1-2).
DOI: 10.1016/j.ijpharm.2018.10.052

1962. Zucker und Derivate. Dunnschicht-Chromatographie, 1.
DOI: 10.1007/978-3-642-52704-3_21

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