585-86-4

Basic information

• Product Name: LACTITOL
• Synonyms: LACTITOL;4-O-(beta-D-galacto-hexopyranosyl)-D-glucitol;4-O-?D-Galactopyranosyl-D-glucitol monohydrate;4-O-(β-Galactosyl)-D-glucitol;D-Glucitol, 4-O-.beta.-D-galactopyranosyl-;4-O-B-D-GALACTOPYRANOSYL-D-GLUCITOL MONOHYDRATE;Lactnol;4-β-D-galactopyranosyl-D-glucito1
• CAS NO: 585-86-4
• Molecular Formula: C12H24O11
• Molecular Weight: 344.31
• EINECS: 209-566-5
• Mol File: 585-86-4.mol

Chemical Properties

• Melting Point: 146°
• Boiling Point: 788.5 °C at 760 mmHg
• Flash Point: 430.7 °C
• Appearance: /
• Density: 1.69 g/cm³
• Vapor Pressure: 9.8E-29mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Slightly soluble in ethanol (95%) and ether. Soluble 1 in 1.75 of water at 20°C; 1 in 1.61 at 30°C; 1 in 1.49 at 40°C; 1 in 1.39 at 50°C.
• PKA: 12.84±0.70(Predicted)
• CAS DataBase Reference: LACTITOL(CAS DataBase Reference)
• NIST Chemistry Reference: LACTITOL(585-86-4)
• EPA Substance Registry System: LACTITOL(585-86-4)

Safety Data

• Hazardous Substances Data: 585-86-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Lactitol is used as an excipient in some prescription drugs, such as Adderall, due to its slow digestion and minimal assimilation properties.
Used in Food Industry:
Lactitol is used as a replacement bulk sweetener for low-calorie foods, taking advantage of its lower sweetness compared to sucrose and its slow fermentation properties.
Used in Medical Applications:
Lactitol is used medically as a laxative, benefiting from its slow digestion and fermentation in the gut, leading to the production of short-chain fatty acids as major fermentation end products.
Used in Dental Applications:
Lactitol has been found to be less cariogenic than sucrose, making it a suitable sweetener for candies and chocolates that are hypoacidogenic in humans.
Chemical Properties:
Lactitol occurs as white orthorhombic crystals, odorless with a sweet taste that imparts a cooling sensation. It is available in powdered form and in a range of crystal sizes, with the directly compressible form being a water-granulated product of microcrystalline aggregates. However, due to its lower sweetness compared to sucrose, additional sweetening agents may be needed for palatability in sweets.

Production Methods

Lactitol is produced by the catalytic hydrogenation of lactose.

Pharmaceutical Applications

Lactitol is used as a noncariogenic replacement for sucrose. It is also used as a diluent in solid dosage forms.(1) A direct-compression form is available,(2,3) as is a direct-compression blend of lactose and lactitol. Lactitol is also used therapeutically in the treatment of hepatic encephalopathy and as a laxative.

Safety

Lactitol is regarded as a nontoxic and nonirritant substance. It is not fermented significantly in the mouth, and is not cariogenic.It is not absorbed in the small intestine, but is broken down by microflora in the large intestine, and is metabolized independently of insulin. In large doses it has a laxative effect; therapeutically, 10–20 g daily in a single oral dose is administered for this purpose. LD50 (mouse, oral): >23 g/kg LD50 (rat, oral): 30 g/kg

storage

Lactitol as the monohydrate is nonhygroscopic and is stable under humid conditions. It is stable to heat and does not take part in the Maillard reaction. In acidic solution, lactitol slowly hydrolyzes to sorbitol and galactose. Lactitol is very resistant to microbiological breakdown and fermentation. Store in a well-closed container. When the compound is stored in an unopened container at 25°C and 60% relative humidity, a shelf-life in excess of 3 years is appropriate.

Regulatory Status

GRAS listed. Accepted for use as a food additive in Europe. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2/t4-,5+,6+,7+,8-,9-,10+,11+,12-/m0/s1

Upstream product

• 5965-65-1 lactobionolactone 
• 7732-18-5 water 
• 5965-66-2 LACTOSE 
• 67-56-1 methanol 
• 13360-52-6 Cellobiose 
• 3616-19-1 1,2,3,6-tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-altropyranosyl)-D-glucopyranose 
• 584-30-5 3-O-β-galactopyranosyl-D-galactose 
• 107333-59-5 1-propenyl O(4,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 88862-57-1 allyl O-(4,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 106238-74-8 O-(4,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>3)-2,4,6-tri-O-benzyl-D-galactopyranoside 
• 81713-25-9 2,3-di-O-benzoyl-4,6-di-O-benzyl-α-D-galactopyranosyl chloride 
• 61236-87-1 allyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside 

Downstream Products

• 867197-73-7 β-D-galactopyranosyl-(1->4)-(1-deoxy-D-glucityl)-(1->N)-S²-(trityl)cysteamine 
• 230286-11-0 2-azidoethyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside 
• 37091-07-9 lactitol nonaacetate 
• 5346-71-4 Acetic acid (2R,3S,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(1R,2R,3S)-2,3,4-triacetoxy-1-((R)-1,2-diacetoxy-ethyl)-butoxy]-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Method of preparing lacitol monohydrate and dihydrate

The invention relates to the new product lactitol monohydrate and to a method for the production of crystalline lactitol. The crystalline lactitol monohydrate can be obtained bij seeding an aqueous lactitol solution of a special concentration under special conditions causing the lactitol monohydrate to crystallize and recovering the product. From the mother liquor a further amount of lactitol dihydrate can be recovered. Crystalline lactitol dihydrate can be obtained using different special conditions. Lactitolmonohydrate can further be obtained by mixing one part bij weight of an aqueous lactitol solution of a suited concentration with 1 tot 3 parts bij weight of methanol or ethanol and cooling the mixture to 15° tot 25° C.

Sequential removal of monosaccharides from the reducing end of oligosaccharides and uses thereof

Methods are provided for the sequential removal of monosaccharides from the reducing end of oligosaccharides. The present invention also discloses the use of such methods for structural determinations of oligosaccharides and to enable new structures to be generated from pre-existing oligosaccharides. In addition, the methods of the present invention may be automated by the incorporation into systems.

Hydrolysis of Substrate Analogues Catalysed by β-D-Glucosidase from Aspergillus niger. Part III. Alkyl and Aryl β-D-Glucopyranosides

The hydrolysis of eighteen alkyl and aryl β-D-glucopyranosides and the disaccharides methyl β-cellobioside (reference substrate), cellobitol, methyl β-gentiobioside, and methyl α-C-gentiobioside catalysed by β-D-glucosidase from Aspergillus niger has been studied using 1H NMR spectroscopy and progress-curve enzyme kinetics in both single-substrate and competition experiments.The influence of chain length and stereochemistry of alkyl groups and substitutions of phenyl groups revealed that this enzyme has evolved preferentially to hydrolyse cellobiose despite low aglycone specificity.The implications of steric and polar or non-polar effects, which were shown to be important for the active site interactions on the energetics of the enzymatic activity as inferred from the kinetic experiments, are discussed.

SYNTHESIS OF A CLOSE ANALOG OF THE REPEATING UNIT OF THE ANTIFREEZE GLYCOPROTEINS OF POLAR FISH

The protected glycopeptide N-(benzyloxycarbonyl)-L-alanyl-3)-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)>-L-threonyl-L-alanine 2,2,2-trichloroethyl ester (21) was made by coupling the respective disaccharide and tripeptide blocks.The disaccharide block was generated by coupling tetra-O-benzoyl-α-D-galactopyranosyl bromide to allyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside and converting the product into O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranosyl chloride (6) via the 1-propenyl glycoside and the free (1-OH) sugar.Alternatively, the 1-propenyl intermediate was obtained directly by using 1-propenyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside (10) as the acceptor in the initial coupling reaction.An efficient 3-step synthesis of 10 was accomplished by the dibutyltin oxide-assisted, selective crotylation of allyl α-D-galactopyranoside at O-3, followed by benzylation and treatment of the product with potassium tert-butoxide.The N-benzyloxycarbonyl (Z) and N-tert-butoxycarbonyl (Boc) 2,2,2-trichloroethyl esters of Thr-Ala and Ala-Thr-Ala were formed by sequential coupling.The silver triflate-promoted glycosylation of the Z-protected dipeptide and tripeptide by 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl chloride, and of the tripeptide by 6, proceeded with excellent α-stereoselectivity.From the disaccharide tripeptide 21, the carboxyl-deprotected and fully deproptected derivatives were prepared.

The assembly of oligosaccharides from "standardized intermediates": beta-(1----3)-linked oligomers of D-galactose.

Several 2-O-benzoyl-4,6-di-O-benzyl-3-O-R-alpha-D-galactopyranosyl chlorides, designed as general precursors of beta-linked, interior D-galactopyranosyl residues in oligosaccharides, were tested in a sequential synthesis of the galactotriose beta-D-Galp-(1----3)-beta-D-Galp-(1----3)-D-Gal (19). The chlorides having R = tetrahydro-2-pyranyl and tert-butyldimethylsilyl gave excellent results, whereas those having R = 3-benzoylpropionyl and chloroacetyl were unsatisfactory. An activated disaccharide block (17), having R = 2,3-di-O-benzoyl-4,6-di-O-benzyl-beta-D-galactopyranosyl, was also prepared and tested as a glycosyl donor. The coupling of 17 to 1-propenyl 2-O-benzoyl-4,6-di-O-benzyl-alpha-D-galactopyranoside (14), in the molar ratio 1.13:1, gave 64% of a trisaccharide derivative (18) that could be converted into 19. This latter synthesis of 19 is efficient because all three galactose units are derived from 14 or its immediate precursor.