50-99-7 Usage
Uses
1. Used in Biological Respiration:
D(+)-Glucose is used as the primary fuel for biological respiration, providing energy in the form of ATP for living organisms. During digestion, complex sugars and starches are broken down into glucose, which is then transported to the liver and metabolized through glycolysis, producing pyruvate as the final product.
2. Used in Skincare:
D(+)-Glucose has moisture-binding properties and provides a soothing effect on the skin. It is a sugar obtained by the hydrolysis of starch and is used in various skincare products.
3. Used in Food Industry:
D(+)-Glucose is used as a corn sweetener in the food industry, commercially made from starch by the action of heat and acids or enzymes. It is used in ice cream, bakery products, and confections, and is also known as corn sugar.
4. Used in Pharmaceutical Industry:
Labelled D(+)-Glucose is a simple sugar that plays a vital role in various metabolic processes, including enzymic synthesis. It is used as a diagnostic tool in the detection of type 2 diabetes mellitus and potentially Huntington's disease through the analysis of blood-glucose in type 1 diabetes mellitus.
5. Used as an Energy Source:
D(+)-Glucose is a primary source of energy for living organisms and is used in the production of oral rehydration salts (ORS) and intravenous (IV) fluids to provide nutrients to patients under intensive care who are unable to receive them by the oral route.
6. Used in Biochemistry:
D(+)-Glucose anhydrous is used for biochemistry reagents, with the CAS number 50-99-7 and a molar mass of 180.16 g/mol.
7. Used in the Production of Biomolecules:
D(+)-Glucose polymerizes to form several important classes of biomolecules, including cellulose, starch, and glycogen. It also combines with other compounds to produce common sugars such as sucrose and lactose.
8. Used in Research and Analysis:
D(+)-Glucose has been used as a standard for the estimation of total sugar in hydrolyzed starch by the phenol-sulfuric acid method and in the preparation of liquid media for culturing some yeast cells.
References
1. http://www.sigmaaldrich.com/catalog/product/sigma/g8270?lang=en®ion=CA
2. https://pubchem.ncbi.nlm.nih.gov/compound/D-glucose#section=Top
3. http://www.hmdb.ca/metabolites/HMDB00122
4. http://www.biology-online.org/dictionary/D-glucose
5. http://www3.hhu.de/biodidaktik/zucker/sugar/glukose.html
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.
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 DryerDextrose 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:
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.
Air & Water Reactions
Water soluble.
Reactivity Profile
A weak reducing agent.
Health Hazard
No toxicity
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.
Safety Profile
Mildly toxic by ingest ion. An experimental teratogen. Experi mental reproductive effects. Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. Potentially
explosive reaction with potassium nitrate +
sodium peroxide when heated in a sealed
container. Uxtures with alkali release
carbon monoxide when heated. When
heated to decomposition it emits acrid
smoke and irritating fumes.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 50-99-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 50-99:
(4*5)+(3*0)+(2*9)+(1*9)=47
47 % 10 = 7
So 50-99-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6+/m0/s1
50-99-7Relevant articles and documents
A new secoiridoid glycoside and a new sesquiterpenoid glycoside from Valeriana jatamansi with neuroprotective activity
Tan, Yu-Zhu,Yong, Yan,Dong, Yan-Hong,Wang, Ru-Jing,Li, Hong-Xiang,Zhang, Hai,Guo, Da-Le,Zhang, Shi-Jin,Dong, Xiao-Ping,Xie, Xiao-Fang
, p. 177 - 180 (2016)
A new secoiridoid glycoside, isopatrinioside (1) and a new sesquiterpenoid glycoside, valeriananoid F (2), together with nine known compounds, were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of spectroscopic analysis. Compound 1 was an unusual monocyclic iridoid glycoside ring-opened between C-1 and C-2 produced by the cleavage of the pyran ring. Of the eleven isolates, compounds 1 and 4 exhibited moderate neuroprotective effects against CoCl2-induced neuronal cell death in PC12 cells.
Anthraquinone glycosides from Cassia roxburghii and evaluation of its free radical scavenging activity
El-Toumy, Sayed A.,El Souda, Sahar S.,Mohamed, Tahia K.,Brouard, Inaki,Bermejo, Jame
, p. 47 - 51 (2012)
The methanolic extract of the leaves of Cassia roxburghii DC., was investigated for its anthraquinone glycosides and antioxidant activity. Two new anthraquinone glycosides named emodin 1-O-β-d-glucopyranosyl-(1→2)- glucopyranoside (1) and aloemodin 8-O-β-
A new triterpene glycoside from fruit of Phytolacca americana
Getiya,Gabelaya,Mshvildadze,Pichette,Lavoie,Dekanosidze
, p. 764 - 766 (2011)
Glycosides H and I, the structures of which were established by modern physicochemical analytical methods (PMR, 13C NMR, COSY, TOCSY, HMBC, MS) and acid-base hydrolysis, were isolated from the purified total saponins from fruit of Phytolacca americana containing at least 10 triterpene glycosides by rechromatography of enriched fractions over a column of silica gel. Glycoside H was a bidesmoside of phytolaccageninic acid, which was isolated earlier from cell culture of Phytolacca acinosa. Glycoside I was 3-O-(β-D-xylopyranosyl- (1 → 3)-β-D-galactopyranosyl-(1 → 3-β-D-xylopyranosyl)-28-O- β-D-glucopyranosyl phytolaccagenin, which was isolated by us for the first time.
New phenolic glycosides from Polygonum cuspidatum
Jiang, Jian-Shuang,Li, Fu-Shuang,Feng, Zi-Ming,Yang, Ya-Nan,Zhang, Pei-Cheng
, p. 17 - 23 (2020)
Two new isobenzofuranone derivatives, polyphthaliside A (1) and polyphthaliside B (2), and a new isocoumarin derivative, polyisocoumarin (3), were isolated from Polygonum cuspidatum. Their structures were elucidated by detailed spectroscopic analysis and chemical methods. The cytotoxicity activity and PTP1B inhibitory activity of compounds 1–3 were estimated and none of them exhibited activities at a concentration of 10 μM.
Substrate control through per-O-methylation of cyclodextrin acids
Fenger, Thomas H.,Bols, Mikael
, p. 7769 - 7771 (2010)
Per-O-methylated cyclodextrins containing a single 2-O-(2-acetate), 2-O-(3-propanoate) or a 6-carboxylate were investigated for glycosidase activity on p-nitrophenyl glycosides. The former two compounds displayed enzyme catalysis giving rate accelerations of 500-1000, while the latter compound gave marginal catalysis. These results show that per-O-methylated cyclodextrins direct substrate binding from the secondary face leading to better catalysis. The Royal Society of Chemistry.
Three new glycosides from Hylocereus undatus
Wu, Xin,Wang, Ying,Huang, Xiao-Jun,Fan, Chun-Lin,Wang, Guo-Cai,Zhang, Xiao-Qi,Zhang, Qin-Wen,Ye, Wen-Cai
, p. 728 - 733 (2011)
Three new glycosides, undatusides A-C (1-3), and 11 known compounds (4-14) were isolated from the flowers of Hylocereus undatus. Their structures were elucidated on the basis of spectroscopic data and chemical method.
Polysciosides J and K, two new oleanane-type triterpenoid saponins from the leaves of Polyscias fruticosa (L.) harms. cultivating in An Giang Province, Viet Nam
Do, Van Mai,Tran, Cong Luan,Nguyen, Tan Phat
, p. 1250 - 1255 (2020)
For the first time, the phytochemical constituents of the leaves of Polyscias fruticosa (L.) Harms. cultivating in An Giang Province, Viet Nam were investigated and led to purify two new oleanane-type triterpenoid saponins, named polyscioside J (1) and polyscioside K (2) together with two known saponins, ladyginoside A (3) and chikusetsusaponin IVa (4) using variously chromatographic methods. Saponin (4) was reported for the first time from this species. Their structures were verified by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and compared with previous literatures.
NMR-Based Investigation of Hydrogen Bonding in a Dihydroanthracen-1(4 H)one from Rubia philippinensis and Its Soluble Epoxide Hydrolase Inhibitory Potential
Oh, Joonseok,Quan, Khong Trong,Lee, Ji Sun,Park, Inwha,Kim, Chung Sub,Ferreira, Daneel,Thuong, Phuong Thien,Kim, Young Ho,Na, Minkyun
, p. 2429 - 2435 (2018)
Hydrogen bonding is a vital feature of a large ensemble of chemical structures. Soluble epoxide hydrolase (sEH) has been targeted for development of the treatment for inflammation-associated diseases. Compounds 1 and 2 were purified from Rubia philippinensis, and their structures were established via physical data analysis. Compound 1 possesses intramolecular hydrogen bonding, sufficiently robust to transfer heteronuclear magnetization via a nonbonded interaction. The bonding strength was assessed using the 1H NMR chemical shift temperature coefficients (-1.8 ppb/K), and the heteronuclear coupling constants were measured. The stereochemical details were investigated using interproton distance analysis and ECD. Purified compounds displayed moderate sEH-inhibitory activity.
A membrane-bound trehalase from Chironomus riparius larvae: Purification and sensitivity to inhibition
Forcella, Matilde,Cardona, Francesca,Goti, Andrea,Parmeggiani, Camilla,Cipolla, Laura,Gregori, Maria,Schirone, Raffaella,Fusi, Paola,Parenti, Paolo
, p. 1186 - 1195 (2010)
A preparation of a membrane-bound trehalase from the larvae of the midge Chironomus riparius (Diptera: Chironomidae) was obtained by detergent solubilization, ion-exchange chromatography and concanavalin A affinity chromatography. Trehalase was purified 1080-fold to a specific activity of 75 U mg-1. The initial rate of trehalase activity followed Henri-Michaelis-Menten kinetics with a Km of 0.48 ± 0.04 mM. Catalytic efficiency was maximal at pH 6.5. The activity was highly inhibited by mono-and bicyclic iminosugar alkaloids such as (in order of potency) casuarine (IC50 = 0.25 ± 0.03 μM), deoxynojirimycin (IC50 = 2.83 ± 0.34 μM) and castanospermine (IC50 = 12.7 ± 1.4 μM). Increasing substrate concentration reduced the inhibition. However, in the presence of deoxynojirimycin, Lineweaver-Burk plots were curvilinear upward. Linear plots were obtained with porcine trehalase. Here, we propose that deoxynojirimycin inhibits the activity of trehalase from C. riparius according to a ligand exclusion model. Inhibition was further characterized by measuring enzyme activity in the presence of a series of casuarine and deoxynojirimycin derivatives. For comparison, inhibition studies were also performed with porcine trehalase. Results indicate substantial differences between midge trehalase and mammalian trehalase suggesting that, in principle, inhibitors against insect pests having trehalase as biochemical targets can be developed.
New cycloartane glycosides from the rhizomes of Cyperus rotundus and their antidepressant activity
Zhou, Zhong-Liu,Lin, San-Qing,Yin, Wen-Qing
, p. 662 - 668 (2016)
Two new cycloartane glycosides, cyprotusides A (1) and B (2), were isolated from the rhizomes of Cyperus rotundus. Their chemical structures were elucidated on the basis of IR, MS, NMR spectroscopic analyses coupled with chemical degradation. The potential antidepressant activity of the two compounds was evaluated. In the despair mice models, compounds 1 and 2 showed significant antidepressant activity.
