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Lactitol
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| Clinical data | |
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| Trade names | Importal, Pizensy, Lacty |
| Other names | Lactitol Hydrate (JAN JP) |
| License data | |
| Routes of administration | By mouth |
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| ChEMBL | |
| E number | E966 (glazing agents, ...) |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.008.698 |
| Chemical and physical data | |
| Formula | C12H24O11 |
| Molar mass | 344.313 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 146 °C (295 °F) |
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Lactitol is a disaccharide sugar alcohol produced from lactose. It is used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative.
Production
[edit]Lactitol is produced by hydrogenation of lactose using Raney nickel catalyst. The product can be obtained as an anhydrous, monohydrate, or dihydrate. Two manufacturers, Danisco and Purac Biochem, produce about 10,000 tons/y.[1]
Applications
[edit]Lactitol is used in a variety of low food energy or low fat foods. High stability makes it popular for baking. It is used in sugar-free candies, cookies (biscuits), chocolate, and ice cream, with a sweetness of 30–40% that of sucrose.[2] Lactitol also promotes colon health as a prebiotic. Because of poor absorption, lactitol only has 2–2.5 kilocalories (8.4–10.5 kilojoules) per gram,[2] compared to 4 kilocalories (17 kJ) per gram for typical saccharides. Hence, lactitol is about 60% as caloric as typical saccharides.
Medical
[edit]Lactitol is listed as an excipient in some prescription drugs.[3][4]
Lactitol is a laxative and is used to prevent or treat constipation,[5] e.g., under the trade name Importal.[6][7]
In February 2020, Lactitol was approved for use in the United States as an osmotic laxative for the treatment of chronic idiopathic constipation (CIC) in adults.[8][9][10]
Lactitol in combination with Ispaghula husk is an approved combination for idiopathic constipation as a laxative and is used to prevent or treat constipation.[medical citation needed]
Safety and health
[edit]Lactitol, erythritol, sorbitol, xylitol, mannitol, and maltitol are all classified sugar alcohols (lactitol and maltitol are in fact disaccharide alcohols, since they contain one intact sugar).[1] The U.S. Food and Drug Administration (FDA) classifies sugar alcohols as "generally recognized as safe" (GRAS).[medical citation needed] They are approved as food additives, and are recognized as not contributing to tooth decay or causing increases in blood glucose.[medical citation needed] Lactitol is also approved for use in foods in most countries around the world.[medical citation needed]
Like other sugar alcohols, lactitol causes cramping, flatulence, and diarrhea in some individuals who consume it. These effects arise because humans lack a suitable beta-galactosidase in the upper gastrointestinal (GI) tract, and a majority of ingested lactitol reaches the large intestine,[11] where it then becomes fermentable to gut microbes (prebiotic) and can pull water into the gut by osmosis.[medical citation needed] For these reasons, medical advice is often sought before their use.
History
[edit]The U.S. Food and Drug Administration (FDA) approved Pizensy based on evidence from a clinical trial (Trial 1/ NCT02819297) of 594 subjects with CIC conducted in the United States.[10] The FDA also considered other supportive evidence including data from Trial 2 (NCT02481947) which compared Pizensy to previously approved drug (lubiprostone) for CIC, and Trial 3 (NCT02819310) in which subjects used Pizensy for one year as well as data from published literature.[10]
The benefit and side effects of Pizensy were evaluated in a clinical trial (Trial 1) of 594 subjects with CIC.[10] In this trial, subjects received treatment with either Pizensy or placebo once daily for 6 months.[10] Neither the subjects nor the health care providers knew which treatment was being given until after the trials were completed.[10]
In the second trial (Trial 2) of three months duration, improvement in CSBMs was used to compare Pizensy to the drug lubiprostone which was previously approved for CIC.[10] The third trial (Trial 3) was used to collect the side effects in subjects treated with Pizensy for one year.[10]
References
[edit]- ^ a b Schiweck H, Bär A, Vogel R, Schwarz E, Kunz M, Dusautois C, Clement A, Lefranc C, Lüssem B, Moser M, Peters S (2012). "Sugar Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a25_413.pub3. ISBN 9783527303854.
- ^ a b Gränzle MG (2011). "Lactose and Oligosaccharides | Lactose: Derivatives". Encyclopedia of Dairy Sciences (2nd ed.). Elsevier Ltd. pp. 202–208. doi:10.1016/B978-0-12-374407-4.00275-2. ISBN 9780123744074.
- ^ "Lactitol (Inactive Ingredient)". Drugs.com. 23 September 2018. Retrieved 24 February 2020.
- ^ "Lactitol Monohydrate (Inactive Ingredient)". Drugs.com. 3 October 2018. Retrieved 24 February 2020.
- ^ Miller LE, Tennilä J, Ouwehand AC (2014). "Efficacy and tolerance of lactitol supplementation for adult constipation: a systematic review and meta-analysis". Clinical and Experimental Gastroenterology. 7: 241–248. doi:10.2147/CEG.S58952. PMC 4103919. PMID 25050074.
- ^ "Importal". Drugs.com. 3 February 2020. Archived from the original on 25 February 2020. Retrieved 24 February 2020.
- ^ "Importal® Ex-Lax". FASS.se (the Swedish Medicines Information Engine). 12 February 2003.
- ^ "Pizensy: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 24 February 2020.
- ^ "Pizensy- lactitol powder, for solution". DailyMed. U.S. National Library of Medicine. 21 February 2020. Retrieved 24 February 2020.
- ^ a b c d e f g h "Drug Trial Snapshot: Pizensy". U.S. Food and Drug Administration (FDA). 12 February 2020. Retrieved 4 March 2020.
This article incorporates text from this source, which is in the public domain.
- ^ Grimble GK, Patil DH, Silk DB (December 1988). "Assimilation of lactitol, an 'unabsorbed' disaccharide in the normal human colon". Gut. 29 (12): 1666–1671. doi:10.1136/gut.29.12.1666. PMC 1434111. PMID 3220306.
External links
[edit]
Media related to Lactitol at Wikimedia Commons- "Lactitol". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 20 January 2017.
Lactitol
View on GrokipediaChemical Properties
Molecular Structure
Lactitol is a disaccharide polyol with the molecular formula C12H24O11.[6] It consists of a β-D-galactopyranose unit linked to a D-glucitol (sorbitol) unit through a β-1,4-glycosidic bond, where the anomeric carbon (C1) of the galactose is bonded to the oxygen at the C4 position of the glucitol chain.[6][7] This structure arises from the hydrogenation of lactose, the parent disaccharide with formula C12H22O11, which comprises β-D-galactopyranosyl-(1→4)-D-glucose.[6][8] In lactose, the glucose unit features a reducing aldehyde group at C1; hydrogenation reduces this aldehyde to a primary alcohol (CH2OH), transforming the glucose into an acyclic glucitol moiety and yielding the non-reducing lactitol molecule.[9][10] The resulting structure maintains the intact β-D-galactopyranose ring—characterized by hydroxyl groups at C2, C3, C4 (axial), and C6, with the glycosidic linkage at C1—while the glucitol chain is a linear six-carbon polyol with hydroxyl groups on all carbons, conferring lactitol's polyol properties.[6] This alteration from a reducing to a non-reducing form distinguishes lactitol chemically from lactose.[10]Physical Characteristics
Lactitol appears as a white to off-white crystalline powder, available in both anhydrous and monohydrate forms, with the monohydrate being the most commonly used in commercial applications due to its stability.[11][12] The anhydrous form consists of crystals obtained from absolute ethanol, while the monohydrate is a white, odorless, sweet crystalline solid.[12] Lactitol exhibits high solubility in water, with approximately 206 g dissolving per 100 g water at 25°C for the monohydrate form, making it suitable for aqueous formulations.[12] It is sparingly soluble in ethanol, at about 0.75 g per 100 g solvent at 25°C, and slightly soluble in ether.[12] The melting point varies by hydration state: the anhydrous form melts at 146°C, while the monohydrate form has a melting range of 94–97°C, often accompanied by dehydration.[11][12] Lactitol is hygroscopic in its anhydrous form but non-hygroscopic as the monohydrate, which influences its handling and storage under controlled humidity.[12] The compound exists in various crystal forms, including anhydrous, monohydrate, and dihydrate, each with distinct properties affecting processing.[12] Its density is predicted at 1.69 g/cm³, and it displays a positive optical rotation of +14° (c = 4 in water at 23°C) for the anhydrous form, ranging from +12.3° to +15.0° for hydrated variants.[11][12] These characteristics stem from its disaccharide alcohol structure, contributing to its utility in formulations requiring specific flow and dissolution behaviors.[11]Stability and Reactivity
Lactitol demonstrates high thermal stability, remaining intact during food processing temperatures up to 180°C and decomposing only above 200°C, where it shows only slight color changes without significant breakdown.[2][13] This stability is enhanced by the absence of a reducing carbonyl group, preventing participation in Maillard reactions that would otherwise lead to unwanted flavor or color development during heating.[3] In terms of pH stability, lactitol maintains its structure across a broad range from pH 3 to 9, rendering it suitable for incorporation into acidic food products such as beverages and confectionery without degradation. Its reactivity with other compounds is minimal; unlike reducing sugars, lactitol exhibits a low tendency for browning or caramelization under heat or alkaline conditions, due to its non-reducing polyol nature, which avoids oxidative or condensative reactions common in monosaccharides and disaccharides.[3] For shelf-life considerations, lactitol offers a shelf life exceeding three years under standard conditions of 25°C and 60% relative humidity.[6] It is resistant to fermentation by cariogenic oral bacteria, contributing to its non-cariogenic properties, while being selectively fermented by beneficial gut microbiota such as Bifidobacteria as a prebiotic. This selectivity, combined with its low hygroscopicity compared to other polyols, helps prevent excessive moisture absorption and maintain product crispness in applications like chewing gum and baked goods, supporting extended storage periods. Crystalline forms may still require controlled humidity to avoid hydrate transitions that could affect texture.[14]Production
Synthesis from Lactose
Lactitol is primarily synthesized through the catalytic hydrogenation of lactose, a disaccharide composed of galactose and glucose, where the aldehyde group at the reducing end of the glucose moiety is reduced to a primary hydroxyl group, yielding the corresponding sugar alcohol.[2] This reduction transforms lactose (C₁₂H₂₂O₁₁) into lactitol (C₁₂H₂₄O₁₁) by the addition of hydrogen, as represented by the simplified reaction equation:The process follows the principles of heterogeneous catalysis, adhering to Langmuir-Hinshelwood-Hougen-Watson kinetics, where lactose and hydrogen adsorb onto the catalyst surface, undergo surface reaction (the rate-determining step), and desorb as lactitol. In laboratory-scale experiments, this is typically performed in batch slurry reactors to study kinetics and selectivity, allowing precise control over variables to achieve high conversion rates.[15] Common catalysts for this hydrogenation include Raney nickel (a sponge nickel variant, often promoted with molybdenum) and supported ruthenium catalysts such as Ru/C or Ru/Al₂O₃, with the latter offering superior selectivity and resistance to deactivation compared to nickel-based options.[2] The reaction is conducted under elevated temperatures of 100–130°C and hydrogen pressures of 20–70 bar to facilitate hydrogen activation and solubility in the aqueous lactose solution, ensuring near-complete conversion (yields exceeding 98%) within hours.[16][15] Optimal conditions, such as a catalyst loading of 1.5–2.5 wt% relative to lactose and a lactose concentration of around 40 wt% in water, minimize side reactions while maintaining process efficiency in lab settings. Incomplete hydrogenation or suboptimal conditions can lead to minor byproducts, including sorbitol (from glucose reduction), galactitol (from galactose reduction), lactulose (via isomerization), and lactulitol or lactobionic acid (from partial oxidation or dehydration).[15] These byproducts typically constitute less than 2% of the reaction mixture under controlled laboratory conditions, with selectivity for lactitol enhanced by higher hydrogen pressure and lower temperatures to suppress isomerization pathways. Catalyst deactivation, often due to poisoning by lactobionic acid or protein residues from lactose impurities, is a key consideration in lab-scale studies, necessitating regeneration techniques like alkali washing to restore activity.[2]