General Description
Watery odorless colorless liquid. Denser than water and soluble in water. Hence sinks in and mixes with water.
Reactivity Profile
A weak reducing agent.
Air & Water Reactions
Water soluble.
Health Hazard
No toxicity
Chemical Properties
White or almost white, crystalline powder.
Originator
Dextrose,Wockhardt Ltd.,India
History
D-Glucose is the most important and predominant monosaccharide found in nature. It
was isolated from raisins by Andreas Sigismund Marggraf (1709–1782) in 1747, and in 1838,
Jean-Baptiste-André Dumas (1800–1884) adopted the name glucose from the Greek word
glycos meaning sweet. Emil Fischer (1852–1919) determined the structure of glucose in the
late 19th century. Glucose also goes by the names dextrose (from its ability to rotate polarized
light to the right), grape sugar, and blood sugar. The term blood sugar indicates that glucose is the primary sugar dissolved in blood. Glucose’s abundant hydroxyl groups enable extensive
hydrogen bonding, and so glucose is highly soluble in water.
Definition
ChEBI: The open chain form of D-glucose.
Definition
Naturally
occurring GLUCOSE belongs to the
stereochemical series D and is dextrorotatory,
indicated by the symbol (+). Thus the
term dextrose is used to indicate D-(+)-glucose.
As other stereochemical forms of glucose
have no significance in biological
systems the term ‘glucose’ is often used interchangeably
with dextrose in biology.
Manufacturing Process
D-Glucose is naturally occurring and is found in fruits and other parts of plants
in its free state. It is used therapeutically in fluid and nutrient replacement.
Dehydration of Dextrose Monohydrate.
1. Dehydration with Fluid-bed Dryer
Dextrose monohydrate was brought in a horizontal-placed turbo-dryer (VOMM,
Mailand, Italy). The dehydration occurred at a temperature of between 90° to
150°C in a stream of air of 5 Normalised m3/kg (i.e volume of gas at 0°C and
1 mbar) dextrose and a rotation speed of 1200 min-1.
Dehydration of Glucose Syrup (Dextrose Content 96%).
A glucose syrup (C*SWEET D 02763 Cerestar) (dry substance ca. 70%) was
sprayed at a flow rate of 7 kg/h at 70°C into a Niro FSD pilot plant spray
dryer. For powdering ca. 9 kg coarsely milled dried product at a ratio
liquid/solid of 1:2 was added. The atomising conditions were as follows:
The drying chamber was operated at:
The fluid bed was adjusted to:
Brand name
Cartose (Sterling Winthrop)
Dextrose.
Therapeutic Function
Sugar supplement
Biotechnological Production
The D-configuration of D-isoascorbic acid at C5 allows a short biosynthetic
pathway from D-glucose, i.e., its 1,5-glucopyranoside, which is oxidized
to D-glucono-1,5-lactone by glucose oxidase followed by oxidation at C2 by
D-gluconolactone oxidase. The immediate oxidation product of
D-glucono-1,5-lactone by gluconolactone oxidase already has reducing activity on,
e.g., 2,6-dichlorphenolindophenol. It is rather stable at pH 4. Upon pH shift, this
compound spontaneously converts to D-isoascorbic acid. The unidentified
immediate oxidation product could be 2-keto-D-glucono-1,5-lactone, which rearranges
via a reversible transesterification reaction to the 1,4-lactone followed by an
irreversible enolization to D-isoascorbic acid. The formation of 2-keto-D-gluconic
acid as the result of 2-keto-D-glucono-1,5-lactone hydrolysis was not reported. The
oxidation of the 1,4-lactone by D-gluconolactone oxidase might also occur to some
extent, since D-glucono-1,5-lactone shows a tendency to slowly rearrange to the
1,4-lactone at pH[4and the D-gluconolactone oxidase of Penicillium
cyaneofulvum accepts both D-glucono-1,5-lactone and the corresponding 1,4-lactone
. This reaction would directly deliver the keto-isomer of D-isoascorbic acid.
The sequence of the reactions from D-glucose to D-isoascorbic acid, first oxidation
at C1, then oxidation at C2 (C1, C2), is similar to the naturally evolved Asc
biosynthesis from L-galactose or L-gulose.
Oxidation of D-gluconolactone at C2 is also afforded by pyranose-2-oxidase
from Polyporus obtusus. In this reaction both D-isoascorbic acid and 2-keto-
D-gluconic acid were obtained in a roughly 1:1 ratio. Obviously, following the
natural C1, C2 oxidation sequence, transesterification and (iso)ascorbic acid formation
are preferred over hydrolysis and 2-keto sugar acid formation or are at least
possible to a significant extent.
If the sequence of oxidation reactions is reversed (C2, C1), i.e., D-glucopyranose
is first oxidized by pyranose-2-oxidase to D-glucosone followed by glucose oxidase
treatment, 2-keto-D-gluconate was reported as the only oxidation product.
Though not explicitly reported, it is safe to assume that the later oxidation occurs
with 2-keto-D-gluco-1,5-pyranose and delivers as the immediate reaction product
2-keto-D-glucono-1,5-lactone, which hydrolyzes affording 2-keto-D-gluconate. It is
unclear why the spontaneous follow-up reaction of 2-keto-D-glucono-1,5-lactone
delivers, at least to some extent, D-isoascorbic acid if obtained according to the C1,
C2 reaction sequence, but only 2-keto-D-gluconate if obtained by the C2, C1
oxidation sequence.
Biochem/physiol Actions
Glycogen phosphorylase, muscle associated (PYGM), is an important contributor to glycogenolysis. Down regulation of PYGM gene is observed in schizophrenia. Mutation in PYGM leads to McArdle disease, a glycogen storage disorder. The PYGM gene is significantly associated with energy production.
Purification Methods
Crystallise -D-glucose from hot glacial acetic acid or pyridine. Traces of solvent are removed by drying in a vacuum oven at 75o for >3hours. [Gottfried Adv Carbohydr Chem 5 127 1950, Kjaer & Lindberg Acta Chem Scand 1 3 1713 1959, Whistler & Miller Methods in Carbohydrate Chemistry I 1301962, Academic Press, Beilstein 1 IV 4306.] [For equilibrium forms see Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972.]
