585-86-4 Usage
Description
Lactitol (4-o-(|3-D-Galactopyranosyl)-D-glucitol) is a disaccharide
sugar alcohol derived from lactose by reduction of its glucose
moiety. Lactitol has not been found in nature. It is about 0.4 times
as sweet as sucrose.In vitro studies with galactosidase-containing enzyme preparations
have demonstrated that lactitol is hydrolyzed only very slowly. In
incubations with human intestinal biopsies, it has been shown that
the human intestinal mucosa does not exhibit any significant dis accharidase activity with lactitol as a substrate. The hydrolytic
activities towards lactitol and isomalt were only 1.3% of those
towards lactose and isomaltulose, respectively. Corresponding exper iments with intestinal preparations of germ-free pigs and convention ally kept minipigs gave similar results. These observations indicate that lactitol is the most slowly digested disaccharide sugar alcohol.
However, in vitro investigations with intestinal enzyme prepara tions provide only relative figures on hydrolysis rates. Experiments
with humans and 14C-labeled lactitol during jejunal perfusion indi cate that lactitol is virtually not assimilated by the human small
intestine. After passage through the small intestine, ingested lac titol reaches the bacterially colonized segments of the gut where
intensive fermentation takes place. Short-chain fatty acids (acetate,
propionate, butyrate) are the major fermentation end products
which are subsequently further metabolized by the host.Lactitol is slowly fermented in growing cultures by some strepto cocci, actinomyces and lactobacilli. When fed at 25% of the diet
to rats that had been inoculated with Streptococcus mutans, lactitol
was about equally as cariogenic as sorbitol and significantly less
cariogenic than sucrose. Test candies and chocolates sweetened
by lactitol are hypoacidogenic in humans tested by plaque pH
telemetry. Boiled sweets made with 100% lactitol are rough in
texture owing to crystallization, and caused some gastrointestinal
upsets in human volunteers. Since lactitol has only one-third the
sweetness of sucrose, sweets need an additional sweetening agent
for palatability.
Chemical Properties
Lactitol occurs as white orthorhombic crystals. It is odorless with a
sweet taste that imparts a cooling sensation. It is available in
powdered form and in a range of crystal sizes. The directly
compressible form is a water-granulated product of microcrystalline
aggregates.
Uses
Lactitol is listed as an excipient in some prescription drugs, such as Adderall. Lactitol is a sugar alcohol used as a replacement bulk sweetener for low calorie foods. It is also used medically as a laxative.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 585-86-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 5 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 585-86:
(5*5)+(4*8)+(3*5)+(2*8)+(1*6)=94
94 % 10 = 4
So 585-86-4 is a valid CAS Registry Number.
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
585-86-4Relevant articles and documents
Method of preparing lacitol monohydrate and dihydrate
-
, (2008/06/13)
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.
Hydrolysis of Substrate Analogues Catalysed by β-D-Glucosidase from Aspergillus niger. Part III. Alkyl and Aryl β-D-Glucopyranosides
Sigurskjold, Bent W.,Haunstrup, Ib,Bock, Klaus
, p. 451 - 458 (2007/10/02)
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.
The assembly of oligosaccharides from "standardized intermediates": beta-(1----3)-linked oligomers of D-galactose.
Chowdhary,Navia,Anderson
, p. 173 - 185 (2007/10/02)
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.