Glucose
Skeletal formula of d-glucose
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Haworth projection of α-d-glucopyranose
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Fischer projection of d-glucose
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Names | |
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Pronunciation | /ˈɡluːkoʊz/, /ɡluːkoʊs/ |
IUPAC name
Allowed trivial names:[1]
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Preferred IUPAC name
PINs are not identified for natural products. | |
Systematic IUPAC name
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Other names
Blood sugars
Dextrose Corn sugar d-Glucose Grape sugar | |
Identifiers | |
3D model (
JSmol ) |
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3DMet | |
Abbreviations | Glc |
1281604 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
EC Number |
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83256 | |
IUPHAR/BPS |
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KEGG | |
MeSH | Glucose |
PubChem CID
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RTECS number
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UNII |
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Properties | |
C6H12O6 | |
Molar mass | 180.156 g/mol |
Appearance | White powder |
Density | 1.54 g/cm3 |
Melting point | α-d-Glucose: 146 °C (295 °F; 419 K) β-d-Glucose: 150 °C (302 °F; 423 K) |
909 g/L (25 °C (77 °F)) | |
−101.5×10−6 cm3/mol | |
8.6827 | |
Thermochemistry | |
Heat capacity (C)
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218.6 J/(K·mol)[2] |
Std molar
entropy (S⦵298) |
209.2 J/(K·mol)[2] |
Std enthalpy of (ΔfH⦵298)formation |
−1271 kJ/mol[3] |
2,805 kJ/mol (670 kcal/mol) | |
Pharmacology | |
B05CX01 (WHO) V04CA02 (WHO), V06DC01 (WHO) | |
Hazards | |
NFPA 704 (fire diamond) | |
Safety data sheet (SDS) | ICSC 08655 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Glucose is a
In
Glucose, as intravenous sugar solution, is on the World Health Organization's List of Essential Medicines.[8] It is also on the list in combination with sodium chloride (table salt).[8]
The name glucose is derived from Ancient Greek γλεῦκος (gleûkos, "wine, must"), from γλυκύς (glykýs, "sweet").[9][10] The suffix "-ose" is a chemical classifier denoting a sugar.
History
Glucose was first isolated from
Since glucose is a basic necessity of many organisms, a correct understanding of its
For the discovery of the metabolism of glucose
Chemical and physical properties
Glucose forms white or colorless solids that are highly soluble in water and acetic acid but poorly soluble in methanol and ethanol. They melt at 146 °C (295 °F) (α) and 150 °C (302 °F) (beta), decompose starting at 188 °C (370 °F) with release of various volatile products, ultimately leaving a residue of carbon.[24] Glucose has a pKa value of 12.16 at 25 °C (77 °F) in water.[25]
With six carbon atoms, it is classed as a
The term "dextrose" is often used in a clinical (related to patient's health status) or nutritional context (related to dietary intake, such as food labels or dietary guidelines), while "glucose" is used in a biological or physiological context (chemical processes and molecular interactions),[33][34][35][36] but both terms refer to the same molecule, specifically D-glucose.[35][37]
Dextrose monohydrate is the hydrated form of D-glucose, meaning that it is a glucose molecule with an additional water molecule attached.[38] Its chemical formula is C6H12O6 · H2O.[38][39] Dextrose monohydrate is also called hydrated D-glucose, and commonly manufactured from plant starches such as corn starch or potato starch.[38][40] Dextrose monohydrate is utilized as the predominant type of dextrose in food applications, such as beverage mixes—it is a common form of glucose widely used as a nutrition supplement in production of foodstuffs. Dextrose monohydrate is primarily consumed in North America as a corn syrup or high-fructose corn syrup.[35]
Anhydrous dextrose, on the other hand, is glucose that does not have any water molecules attached to it.[40] [41] Anhydrous chemical substances are commonly produced by eliminating water from a hydrated substance through methods such as heating or drying up (desiccation).[42][43][44]Dextrose monohydrate can be dehydrated to anhydrous dextrose in industrial setting.[45][46] Dextrose monohydrate is composed of approximately 9.5% water by mass. Through the process of dehydration, this water content is eliminated to yield anhydrous (dry) dextrose.[40]
Anhydrous dextrose has the chemical formula C6H12O6, without any water molecule attached which is the same as glucose.[38] Anhydrous dextrose on open air tends to absorb moisture and transform to the monohydrate, and it is more expensive to produce.[40] Anhydrous dextrose (anhydrous D-glucose) has increased stability and increased shelf life,[43] has medical applications, such as in oral glucose tolerance test (OGTT).[47]
Whereas molecular weight (molar mass) for D-glucose monohydrate is 198.17 g/mol,[48][49] that for anhydrous D-glucose is 180.16 g/mol[50][51][52] The density of these two forms of glucose is also different.[specify]
In terms of chemical structure, glucose is a monosaccharide containing six carbon atoms and an aldehyde group, and is therefore an aldohexose. The glucose molecule can exist in an open-chain (acyclic) as well as ring (cyclic) form—due to the presence of alcohol and aldehyde or ketone functional groups, the form having the straight chain can easily convert into a chair-like hemiacetal ring structure commonly found in carbohydrates.[53]
Structure and nomenclature
Glucose is usually present in solid form as a
Forms and projections of d-glucose in comparison | ||
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Natta projection | Haworth projection | |
α-d-glucofuranose | β-d-glucofuranose | |
α-d-glucopyranose | β-d-glucopyranose | |
α-d-Glucopyranose in (1) Tollens/Fischer (2) Haworth projection (3) chair conformation (4) Mills projection | ||
Open-chain form
A open-chain form of glucose makes up less than 0.02% of the glucose molecules in an aqueous solution at equilibrium.
Cyclic forms
In solutions, the open-chain form of glucose (either "D-" or "L-") exists in equilibrium with several cyclic isomers, each containing a ring of carbons closed by one oxygen atom. In aqueous solution, however, more than 99% of glucose molecules exist as pyranose forms. The open-chain form is limited to about 0.25%, and furanose forms exist in negligible amounts. The terms "glucose" and "D-glucose" are generally used for these cyclic forms as well. The ring arises from the open-chain form by an intramolecular nucleophilic addition reaction between the aldehyde group (at C-1) and either the C-4 or C-5 hydroxyl group, forming a hemiacetal linkage, −C(OH)H−O−.
The reaction between C-1 and C-5 yields a six-membered
The ring-closing reaction can give two products, denoted "α-" and "β-". When a glucopyranose molecule is drawn in the Haworth projection, the designation "α-" means that the hydroxyl group attached to C-1 and the −CH2OH group at C-5 lies on opposite sides of the ring's plane (a trans arrangement), while "β-" means that they are on the same side of the plane (a cis arrangement). Therefore, the open-chain isomer D-glucose gives rise to four distinct cyclic isomers: α-D-glucopyranose, β-D-glucopyranose, α-D-glucofuranose, and β-D-glucofuranose. These five structures exist in equilibrium and interconvert, and the interconversion is much more rapid with acid catalysis.
The other open-chain isomer L-glucose similarly gives rise to four distinct cyclic forms of L-glucose, each the mirror image of the corresponding D-glucose.
The glucopyranose ring (α or β) can assume several non-planar shapes, analogous to the "chair" and "boat" conformations of cyclohexane. Similarly, the glucofuranose ring may assume several shapes, analogous to the "envelope" conformations of cyclopentane.
In the solid state, only the glucopyranose forms are observed.
Some derivatives of glucofuranose, such as 1,2-O-isopropylidene-D-glucofuranose are stable and can be obtained pure as crystalline solids.[58][59] For example, reaction of α-D-glucose with para-tolylboronic acid H3C−(C6H4)−B(OH)2 reforms the normal pyranose ring to yield the 4-fold ester α-D-glucofuranose-1,2:3,5-bis(p-tolylboronate).[60]
Mutarotation
Mutarotation consists of a temporary reversal of the ring-forming reaction, resulting in the open-chain form, followed by a reforming of the ring. The ring closure step may use a different −OH group than the one recreated by the opening step (thus switching between pyranose and furanose forms), or the new hemiacetal group created on C-1 may have the same or opposite handedness as the original one (thus switching between the α and β forms). Thus, though the open-chain form is barely detectable in solution, it is an essential component of the equilibrium.
The open-chain form is thermodynamically unstable, and it spontaneously isomerizes to the cyclic forms. (Although the ring closure reaction could in theory create four- or three-atom rings, these would be highly strained, and are not observed in practice.) In solutions at room temperature, the four cyclic isomers interconvert over a time scale of hours, in a process called mutarotation.[61] Starting from any proportions, the mixture converges to a stable ratio of α:β 36:64. The ratio would be α:β 11:89 if it were not for the influence of the anomeric effect.[62] Mutarotation is considerably slower at temperatures close to 0 °C (32 °F).
Optical activity
Whether in water or the solid form, d-(+)-glucose is
Note that the d- prefix does not refer directly to the optical properties of the compound. It indicates that the C-5 chiral centre has the same handedness as that of d-glyceraldehyde (which was so labelled because it is dextrorotatory). The fact that d-glucose is dextrorotatory is a combined effect of its four chiral centres, not just of C-5; and indeed some of the other d-aldohexoses are levorotatory.
The conversion between the two anomers can be observed in a polarimeter since pure α-d-glucose has a specific rotation angle of +112.2° mL/(dm·g), pure β-d-glucose of +17.5° mL/(dm·g).[63] When equilibrium has been reached after a certain time due to mutarotation, the angle of rotation is +52.7° mL/(dm·g).[63] By adding acid or base, this transformation is much accelerated. The equilibration takes place via the open-chain aldehyde form.
Isomerisation
In dilute
Biochemical properties
Metabolism of common monosaccharides and some biochemical reactions of glucose |
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Glucose is the most abundant monosaccharide. Glucose is also the most widely used aldohexose in most living organisms. One possible explanation for this is that glucose has a lower tendency than other aldohexoses to react nonspecifically with the
Glucose is produced by plants through photosynthesis using sunlight,
Many of the long-term complications of diabetes (e.g., blindness, kidney failure, and peripheral neuropathy) are probably due to the glycation of proteins or lipids.[73] In contrast, enzyme-regulated addition of sugars to protein is called glycosylation and is essential for the function of many proteins.[74]
Uptake
Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins
In order to get into or out of cell membranes of cells and membranes of cell compartments, glucose requires special transport proteins from the
The glucose transporter
Biosynthesis
In plants and some prokaryotes, glucose is a product of photosynthesis.[69] Glucose is also formed by the breakdown of polymeric forms of glucose like glycogen (in animals and mushrooms) or starch (in plants). The cleavage of glycogen is termed glycogenolysis, the cleavage of starch is called starch degradation.[87]
The metabolic pathway that begins with molecules containing two to four carbon atoms (C) and ends in the glucose molecule containing six carbon atoms is called gluconeogenesis and occurs in all living organisms. The smaller starting materials are the result of other metabolic pathways. Ultimately almost all
Glucose also can be found outside of living organisms in the ambient environment. Glucose concentrations in the atmosphere are detected via collection of samples by aircraft and are known to vary from location to location. For example, glucose concentrations in atmospheric air from inland China range from 0.8 to 20.1 pg/L, whereas east coastal China glucose concentrations range from 10.3 to 142 pg/L.[90]
Glucose degradation
In humans, glucose is metabolized by glycolysis
In other living organisms, other forms of fermentation can occur. The bacterium
Use of glucose as an energy source in cells is by either aerobic respiration, anaerobic respiration, or fermentation.[96] The first step of glycolysis is the phosphorylation of glucose by a hexokinase to form glucose 6-phosphate. The main reason for the immediate phosphorylation of glucose is to prevent its diffusion out of the cell as the charged phosphate group prevents glucose 6-phosphate from easily crossing the cell membrane.[96] Furthermore, addition of the high-energy phosphate group activates glucose for subsequent breakdown in later steps of glycolysis.[97] At physiological conditions, this initial reaction is irreversible.[medical citation needed]
In anaerobic respiration, one glucose molecule produces a net gain of two ATP molecules (four ATP molecules are produced during glycolysis through substrate-level phosphorylation, but two are required by enzymes used during the process).[98] In aerobic respiration, a molecule of glucose is much more profitable in that a maximum net production of 30 or 32 ATP molecules (depending on the organism) is generated.[99]
Click on genes, proteins and metabolites below to link to respective articles.[§ 1]
- ^ The interactive pathway map can be edited at WikiPathways: "GlycolysisGluconeogenesis_WP534".
In yeast, ethanol is fermented at high glucose concentrations, even in the presence of oxygen (which normally leads to respiration rather than fermentation). This is called the Crabtree effect.
Glucose can also degrade to form carbon dioxide through abiotic means. This has been demonstrated to occur experimentally via oxidation and hydrolysis at 22 °C and a pH of 2.5.[103]
Energy source
Glucose is a ubiquitous fuel in
Glucose and oxygen supply almost all the energy for the
The glucose in the blood is called
The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In
Some glucose is converted to
As a result of its importance in human health, glucose is an analyte in
The
Precursor
Organisms use glucose as a precursor for the synthesis of several important substances. Starch, cellulose, and glycogen ("animal starch") are common glucose polymers (polysaccharides). Some of these polymers (starch or glycogen) serve as energy stores, while others (cellulose and chitin, which is made from a derivative of glucose) have structural roles. Oligosaccharides of glucose combined with other sugars serve as important energy stores. These include lactose, the predominant sugar in milk, which is a glucose-galactose disaccharide, and sucrose, another disaccharide which is composed of glucose and fructose. Glucose is also added onto certain proteins and lipids in a process called glycosylation. This is often critical for their functioning. The enzymes that join glucose to other molecules usually use phosphorylated glucose to power the formation of the new bond by coupling it with the breaking of the glucose-phosphate bond.
Other than its direct use as a monomer, glucose can be broken down to synthesize a wide variety of other biomolecules. This is important, as glucose serves both as a primary store of energy and as a source of organic carbon. Glucose can be broken down and converted into
Pathology
Diabetes
To monitor the body's response to blood glucose-lowering therapy, glucose levels can be measured. Blood glucose monitoring can be performed by multiple methods, such as the fasting glucose test which measures the level of glucose in the blood after 8 hours of fasting. Another test is the 2-hour glucose tolerance test (GTT) – for this test, the person has a fasting glucose test done, then drinks a 75-gram glucose drink and is retested. This test measures the ability of the person's body to process glucose. Over time the blood glucose levels should decrease as insulin allows it to be taken up by cells and exit the blood stream.
Hypoglycemia management
Individuals with diabetes or other conditions that result in low blood sugar often carry small amounts of sugar in various forms. One sugar commonly used is glucose, often in the form of glucose tablets (glucose pressed into a tablet shape sometimes with one or more other ingredients as a binder), hard candy, or sugar packet.
Sources
Most dietary carbohydrates contain glucose, either as their only building block (as in the polysaccharides starch and glycogen), or together with another monosaccharide (as in the hetero-polysaccharides sucrose and lactose).[128] Unbound glucose is one of the main ingredients of honey. Glucose is extremely abundant and has been isolated from a variety of natural sources across the world, including male cones of the coniferous tree Wollemia nobilis in Rome,[129] the roots of Ilex asprella plants in China,[130] and straws from rice in California.[131]
Food item |
Carbohydrate, total,[a] including dietary fiber |
Total sugars |
Free fructose |
Free glucose |
Sucrose | Ratio of fructose/ glucose |
Sucrose as proportion of total sugars (%) |
---|---|---|---|---|---|---|---|
Fruits | |||||||
Apple | 13.8 | 10.4 | 5.9 | 2.4 | 2.1 | 2.0 | 19.9 |
Apricot | 11.1 | 9.2 | 0.9 | 2.4 | 5.9 | 0.7 | 63.5 |
Banana | 22.8 | 12.2 | 4.9 | 5.0 | 2.4 | 1.0 | 20.0 |
Fig, dried | 63.9 | 47.9 | 22.9 | 24.8 | 0.9 | 0.93 | 0.15 |
Grapes | 18.1 | 15.5 | 8.1 | 7.2 | 0.2 | 1.1 | 1 |
Navel orange |
12.5 | 8.5 | 2.25 | 2.0 | 4.3 | 1.1 | 50.4 |
Peach | 9.5 | 8.4 | 1.5 | 2.0 | 4.8 | 0.9 | 56.7 |
Pear | 15.5 | 9.8 | 6.2 | 2.8 | 0.8 | 2.1 | 8.0 |
Pineapple | 13.1 | 9.9 | 2.1 | 1.7 | 6.0 | 1.1 | 60.8 |
Plum | 11.4 | 9.9 | 3.1 | 5.1 | 1.6 | 0.66 | 16.2 |
Vegetables | |||||||
Beet , red |
9.6 | 6.8 | 0.1 | 0.1 | 6.5 | 1.0 | 96.2 |
Carrot | 9.6 | 4.7 | 0.6 | 0.6 | 3.6 | 1.0 | 77 |
Red pepper, sweet | 6.0 | 4.2 | 2.3 | 1.9 | 0.0 | 1.2 | 0.0 |
Onion, sweet | 7.6 | 5.0 | 2.0 | 2.3 | 0.7 | 0.9 | 14.3 |
Sweet potato | 20.1 | 4.2 | 0.7 | 1.0 | 2.5 | 0.9 | 60.3 |
Yam | 27.9 | 0.5 | Traces | Traces | Traces | — | Traces |
Sugar cane |
13–18 | 0.2–1.0 | 0.2–1.0 | 11–16 | 1.0 | high | |
Sugar beet | 17–18 | 0.1–0.5 | 0.1–0.5 | 16–17 | 1.0 | high | |
Grains | |||||||
Corn, sweet | 19.0 | 6.2 | 1.9 | 3.4 | 0.9 | 0.61 | 15.0 |
- ^ The carbohydrate value is calculated in the USDA database and does not always correspond to the sum of the sugars, the starch, and the "dietary fiber".
Commercial production
Glucose is produced industrially from starch by
Many crops can be used as the source of starch.
Conversion to fructose
In the US, almost exclusively corn (more precisely, corn syrup) is used as glucose source for the production of
Commercial usage
Glucose is mainly used for the production of fructose and of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel.[133] Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Most soft drinks in the US use HFCS-55 (with a fructose content of 55% in the dry mass), while most other HFCS-sweetened foods in the US use HFCS-42 (with a fructose content of 42% in the dry mass).[143] In Mexico, on the other hand, soft drinks are sweetened by cane sugar, which has a higher sweetening power.[144] In addition, glucose syrup is used, inter alia, in the production of confectionery such as candies, toffee and fondant.[145] Typical chemical reactions of glucose when heated under water-free conditions are caramelization and, in presence of amino acids, the Maillard reaction.
In addition, various organic acids can be biotechnologically produced from glucose, for example by fermentation with
Analysis
When a glucose molecule is to be detected at a certain position in a larger molecule, nuclear magnetic resonance spectroscopy, X-ray crystallography analysis or lectin immunostaining is performed with concanavalin A reporter enzyme conjugate, which binds only glucose or mannose.
Classical qualitative detection reactions
These reactions have only historical significance:
Fehling test
The
Tollens test
In the
Barfoed test
In
Nylander's test
As a reducing sugar, glucose reacts in the Nylander's test.[152]
Other tests
Upon heating a dilute
Instrumental quantification
Refractometry and polarimetry
In concentrated solutions of glucose with a low proportion of other carbohydrates, its concentration can be determined with a polarimeter. For sugar mixtures, the concentration can be determined with a refractometer, for example in the Oechsle determination in the course of the production of wine.
Photometric enzymatic methods in solution
The enzyme glucose oxidase (GOx) converts glucose into gluconic acid and hydrogen peroxide while consuming oxygen. Another enzyme, peroxidase, catalyzes a chromogenic reaction (Trinder reaction)
Photometric test-strip method
The test-strip method employs the above-mentioned enzymatic conversion of glucose to gluconic acid to form hydrogen peroxide. The reagents are immobilised on a polymer matrix, the so-called test strip, which assumes a more or less intense color. This can be measured reflectometrically at 510 nm with the aid of an LED-based handheld photometer. This allows routine blood sugar determination by nonscientists. In addition to the reaction of phenol with 4-aminoantipyrine, new chromogenic reactions have been developed that allow photometry at higher wavelengths (550 nm, 750 nm).[155][156]
Amperometric glucose sensor
The electroanalysis of glucose is also based on the enzymatic reaction mentioned above. The produced hydrogen peroxide can be amperometrically quantified by anodic oxidation at a potential of 600 mV.[157] The GOx is immobilized on the electrode surface or in a membrane placed close to the electrode. Precious metals such as platinum or gold are used in electrodes, as well as carbon nanotube electrodes, which e.g. are doped with boron.[158] Cu–CuO nanowires are also used as enzyme-free amperometric electrodes, reaching a detection limit of 50 μmol/L.[159] A particularly promising method is the so-called "enzyme wiring", where the electron flowing during the oxidation is transferred via a molecular wire directly from the enzyme to the electrode.[160]
Other sensory methods
There are a variety of other chemical sensors for measuring glucose.[161][162] Given the importance of glucose analysis in the life sciences, numerous optical probes have also been developed for saccharides based on the use of boronic acids,[163] which are particularly useful for intracellular sensory applications where other (optical) methods are not or only conditionally usable. In addition to the organic boronic acid derivatives, which often bind highly specifically to the 1,2-diol groups of sugars, there are also other probe concepts classified by functional mechanisms which use selective glucose-binding proteins (e.g. concanavalin A) as a receptor. Furthermore, methods were developed which indirectly detect the glucose concentration via the concentration of metabolized products, e.g. by the consumption of oxygen using fluorescence-optical sensors.[164] Finally, there are enzyme-based concepts that use the intrinsic absorbance or fluorescence of (fluorescence-labeled) enzymes as reporters.[161]
Copper iodometry
Glucose can be quantified by copper iodometry.[165]
Chromatographic methods
In particular, for the analysis of complex mixtures containing glucose, e.g. in honey, chromatographic methods such as
In vivo analysis
Glucose uptake in cells of organisms is measured with
References
- ^ Nomenclature of Carbohydrates (Recommendations 1996) | 2-Carb-2 Archived 2023-08-27 at the Wayback Machine. iupac.qmul.ac.uk.
- ^
- ^ Ponomarev VV, Migarskaya LB (1960), "Heats of combustion of some amino-acids", Russ. J. Phys. Chem. (Engl. Transl.), 34: 1182–83
- ISBN 978-1-4200-4936-7.
- ^ a b "NCATS Inxight Drugs — DEXTROSE, UNSPECIFIED FORM". Archived from the original on 2023-12-11. Retrieved 2024-03-18.
- ISBN 978-0-08-045444-3. Retrieved 13 May 2021.
- ^ a b c d "L-glucose". Biology Articles, Tutorials & Dictionary Online. 2019-10-07. Archived from the original on 2022-05-25. Retrieved 2022-05-06.
- ^ hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
- ^ "Online Etymology Dictionary". Etymonline.com. Archived from the original on 2016-11-26. Retrieved 2016-11-25.
- ^ Thénard, Gay-Lussac, Biot, and Dumas (1838) "Rapport sur un mémoire de M. Péligiot, intitulé: Recherches sur la nature et les propriétés chimiques des sucres". Archived 2015-12-06 at the Wayback Machine (Report on a memoir of Mr. Péligiot, titled: Investigations on the nature and chemical properties of sugars), Comptes rendus, 7 : 106–113. From page 109. Archived 2015-12-06 at the Wayback Machine: "Il résulte des comparaisons faites par M. Péligot, que le sucre de raisin, celui d'amidon, celui de diabètes et celui de miel ont parfaitement la même composition et les mêmes propriétés, et constituent un seul corps que nous proposons d'appeler Glucose (1). ... (1) γλευχος, moût, vin doux." It follows from the comparisons made by Mr. Péligot, that the sugar from grapes, that from starch, that from diabetes and that from honey have exactly the same composition and the same properties, and constitute a single substance that we propose to call glucose (1) ... (1) γλευχος, must, sweet wine.
- ^ ISBN 978-0-12-384953-3. Archivedfrom the original on 2018-02-23.
- ^ Marggraf (1747) "Experiences chimiques faites dans le dessein de tirer un veritable sucre de diverses plantes, qui croissent dans nos contrées" Archived 2016-06-24 at the Wayback Machine [Chemical experiments made with the intention of extracting real sugar from diverse plants that grow in our lands], Histoire de l'académie royale des sciences et belles-lettres de Berlin, pp. 79–90. From page 90: Archived 2014-10-27 at the Wayback Machine "Les raisins secs, etant humectés d'une petite quantité d'eau, de maniere qu'ils mollissent, peuvent alors etre pilés, & le suc qu'on en exprime, etant depuré & épaissi, fournira une espece de Sucre." (Raisins, being moistened with a small quantity of water, in a way that they soften, can be then pressed, and the juice that is squeezed out, [after] being purified and thickened, will provide a sort of sugar.)
- ISBN 978-1-461-21622-3. p. 7.
- from the original on 2019-12-17. Retrieved 2019-07-01.
- ^ Emil Fischer, Nobel Foundation, archived from the original on 2009-09-03, retrieved 2009-09-02
- ^ Fraser-Reid B, "van't Hoff's Glucose", Chem. Eng. News, 77 (39): 8
- ^ "Otto Meyerhof - Facts - NobelPrize.org" Archived 2018-07-15 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Hans von Euler-Chelpin - Facts - NobelPrize.org" Archived 2018-09-03 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Arthur Harden - Facts - NobelPrize.org" Archived 2018-09-03 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Bernardo Houssay - Facts - NobelPrize.org" Archived 2018-07-15 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Carl Cori - Facts - NobelPrize.org" Archived 2018-07-15 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Gerty Cori - Facts - NobelPrize.org" Archived 2018-07-15 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ^ "Luis Leloir - Facts - NobelPrize.org" Archived 2018-07-15 at the Wayback Machine. NobelPrize.org. Retrieved on 5 September 2018.
- ISSN 0040-4020.
- ISBN 978-0-12-369397-6
- ^ "glucose." The Columbia Encyclopedia, 6th ed.. 2015. Encyclopedia.com. 17 Nov. 2015 http://www.encyclopedia.com Archived 2009-04-26 at the Wayback Machine.
- doi:10.1002/efd2.71.
- PMID 29507651.
- ISBN 978-981-15-7304-0. Archivedfrom the original on 2021-04-14. Retrieved 2024-03-18.
- from the original on 2024-02-12. Retrieved 2024-03-18.
- PMID 16863724.
- ^ "Potentially Important Contribution of Dextrose Used as Diluent to Hyperglycemia in Hospitalized Patients | Diabetes Care | American Diabetes Association". Archived from the original on 2022-05-29. Retrieved 2024-03-18.
- ^ "Dextrose: Why is it in food and medicine?". 24 June 2018. Archived from the original on 13 February 2024. Retrieved 18 March 2024.
- ^ a b c "What is Dextrose, How is It Used, and is It Healthy? - the Nutrition Insider". 27 October 2023. Archived from the original on 14 February 2024. Retrieved 18 March 2024.
- ^ "Dextrose vs. Glucose: Are These Sugars Equal?". Archived from the original on 2023-09-29. Retrieved 2024-03-18.
- PMID 938892.
- ^ a b c d "Prakash Chemicals International". Archived from the original on 2023-06-06. Retrieved 2024-03-18.
- ^ "API | glucose monohydrate". Archived from the original on 2023-03-24. Retrieved 2024-03-18.
- ^ a b c d "The difference between dextrose anhydrous and dextrose monohydrate". 28 December 2022. Archived from the original on 18 March 2024. Retrieved 18 March 2024.
- ^ "Dextrose anhydrous". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
- from the original on 2024-03-18. Retrieved 2024-03-18.
- ^ a b "What is the difference between anhydrous glucose and glucose". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
- ^ "Anhydrous vs. Monohydrate - What's the Difference?". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
- from the original on 18 March 2024. Retrieved 18 March 2024.
- from the original on 2024-03-18. Retrieved 2024-03-18.
- ^ "Diabetes & Prediabetes Tests - NIDDK". Archived from the original on 2023-12-16. Retrieved 2024-03-18.
- ^ "Dextrose Monohydrate". Archived from the original on 2023-12-02. Retrieved 2024-03-18.
- ^ "Archived copy". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ "D-Glucose". Archived from the original on 2023-12-15. Retrieved 2024-03-18.
- ^ "Archived copy". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ "Archived copy". Archived from the original on 2024-03-18. Retrieved 2024-03-18.
{{cite web}}
: CS1 maint: archived copy as title (link) - ^ "Glucose (Dextrose)". 2 October 2013. Archived from the original on 21 December 2023. Retrieved 18 March 2024.
- ^ ISBN 978-3-527-30673-2.
- ^ ISBN 9780412630200. p. 316.
- ISBN 9780123849533, Volume 1, p. 76.
- ^ "16.4: Cyclic Structures of Monosaccharides". Chemistry LibreTexts. 2014-07-18. Archived from the original on 2023-04-17. Retrieved 2023-04-17.
- .
- doi:10.1039/A808896I.
- doi:10.1039/B608029D.
- ISBN 0534079687.
- ISBN 978-0-8493-8941-2
- ^ ISBN 978-3-13-160038-7, p. 34 (in German).
- ^ PMID 12192669.
- ISBN 978-3-662-54620-8, p. 531. (German)
- ^ ISBN 978-1-133-10629-6.
- ^ ISBN 978-0-470-57095-1.
- ISBN 0-87901-009-6p. 228.
- ^ a b "Chemistry for Biologists: Photosynthesis". www.rsc.org. Archived from the original on 2016-08-04. Retrieved 2018-02-05.
- ^ ISBN 978-3-642-17972-3, p. 195. (German)
- ^ ISBN 978-8-131-23713-7. p. 674.
- PMID 18840763.
- ISSN 0095-8301, archived from the originalon 2013-10-14, retrieved 2010-05-20
- from the original on 2016-12-06.
- ^ "Showing Compound D-Glucose (FDB012530) - FooDB". Archived from the original on 2022-12-06. Retrieved 2024-03-18.
- ^ ISBN 978-3-642-17972-3, p. 404.
- ISBN 978-3-662-22150-1, p. 641. (in German)
- PMID 28510148.
- ^ ISBN 978-3-642-17972-3, p. 199, 200. (in German)
- (PDF) from the original on 2023-12-02. Retrieved 2024-03-18.
- ^ ISBN 978-3-642-17972-3, p. 214. (in German)
- PMID 17403369.
- PMID 25344989.
- PMID 12504846.
- PMID 30132032.
- PMID 26125647.
- PMID 15862090.
- ^ ISBN 978-1-608-05189-2, p. 46.
- ISBN 978-3-642-17972-3, p. 389. (in German)
- from the original on 2024-03-18. Retrieved 2021-11-09.
- PMID 27707936.
- ISBN 978-3-8273-7312-0; p. 490–496. (German)
- ^ ISBN 978-1-449-61484-3, p. 164.
- PMID 27048250.
- PMID 12981024.
- ^ (PDF) from the original on 2017-03-06. Retrieved March 5, 2017.
- ^ "Glucose". Archived from the original on 2023-12-05. Retrieved 2024-03-18.
- ISBN 978-1-4051-1322-9, archivedfrom the original on 2018-02-23
- ISBN 978-1-4051-1322-9, archivedfrom the original on 2018-02-23
- S2CID 205782021.
- PMID 23266512.
- PMID 22913968.
- from the original on 2024-03-18. Retrieved 2021-11-09.
- ISBN 978-92-5-105014-9, archivedfrom the original on 2010-05-24
- ISBN 978-3-527-66001-8, p. 100 (in German).
- ^ Schmidt, Lang: Physiologie des Menschen, 30. Auflage. Springer Verlag, 2007, p. 907 (in German).
- PMID 10493919.
- ^ Dash P. "Blood Brain Barrier and Cerebral Metabolism (Section 4, Chapter 11)". Neuroscience Online: An Electronic Textbook for the Neurosciences. Department of Neurobiology and Anatomy – The University of Texas Medical School at Houston. Archived from the original on 2016-11-17.
- S2CID 44500072
- (PDF) from the original on 2017-08-18
- S2CID 14380313
- S2CID 38596025
- ^ ISBN 978-0-123-66852-3, p. XIII.
- ^ PMID 29311793.
- ^ S2CID 38764657. Archived from the originalon 2020-07-29. Retrieved 2020-06-07.
- PMID 25410233..
- PMID 25589267.
- ISBN 3-437-23182-0, p. 927, 985 (in German).
- ISBN 978-3-662-22150-1, p. 294.
- S2CID 34263228.
- ^ "Diagnosing Diabetes and Learning About Prediabetes". American Diabetes Association. Archived from the original on 2017-07-28. Retrieved 2018-02-20.
- ^ ISBN 978-1-608-31412-6, p. 366.
- ^ ISBN 978-8-131-23713-7, p. 508.
- PMID 9356547.
- ^ ISBN 978-3-642-17972-3, p. 27. (in German)
- PMID 26964835.
- ^ Estela, Carlos (2011) "Blood Glucose Levels," Undergraduate Journal of Mathematical Modeling: One + Two: Vol. 3: Iss. 2, Article 12.
- ^ "Carbohydrates and Blood Sugar". The Nutrition Source. 2013-08-05. Archived from the original on 2017-01-30. Retrieved 2017-01-30 – via Harvard T.H. Chan School of Public Health.
- from the original on 2024-03-18. Retrieved 2021-11-11.
- from the original on 2024-03-18. Retrieved 2021-11-11.
- from the original on 2024-03-18, retrieved 2021-11-11
- ^ "FoodData Central". fdc.nal.usda.gov. Archived from the original on 2019-12-03. Retrieved 2024-03-18.
- ^ ISBN 978-0-081-00523-1, p. 197.
- ^ ISBN 978-3-527-32943-4. Volume 6, p. 48.
- ^ ISBN 978-1-483-29939-6, p. 195.
- .
- .
- ISBN 978-0-08-092655-1.
- ISBN 978-0-08-092655-1. Retrieved 25 November 2016.
- ISBN 0-19-211579-0.
- ISBN 978-0-191-04072-6, p. 527.
- ^ "Sugar". Learning, Food Resources. food.oregonstate.edu. Oregon State University, Corvallis, OR. 2012-05-23. Archived from the original on 2011-07-18. Retrieved 2018-06-28.
- ^ "High Fructose Corn Syrup: Questions and Answers". US Food and Drug Administration. 2014-11-05. Archived from the original on 2018-01-25. Retrieved 2017-12-18.
- Seattle Times, October 29, 2004.
- ISBN 978-1-118-78014-5, p. 82.
- ISBN 978-1-475-76431-4, p. 938.
- PMID 33083765.
- PMID 33013305.
- ^ H. Fehling: Quantitative Bestimmung des Zuckers im Harn. In: Archiv für physiologische Heilkunde (1848), volume 7, p. 64–73 (in German).
- Berichte der Deutschen Chemischen Gesellschaft(1882), volume 15, p. 1635–1639 (in German).
- from the original on 2020-07-29. Retrieved 2019-07-01.
- Zeitschrift für physiologische Chemie. Volume 8, Issue 3, 1884, p. 175–185 Abstract. Archived 2015-09-23 at the Wayback Machine(in German).
- ^ ISBN 978-3-527-66001-8, p. 102 (in German).
- S2CID 58131350.
- ^ from the original on 2024-03-18. Retrieved 2024-03-18.
- doi:10.1039/A709038B.
- PMID 18154363..
- PMID 18656655.
- S2CID 98567636.
- PMID 8092486.
- ^ PMID 18229952.
- PMID 22027299.
- S2CID 96768832.
- PMID 10826645.
- ^ PMID 26041177.
- PMID 15628134.
- ^ Max Planck Institute of Molecular Plant Physiology in Golm Database (2007-07-19). "Glucose mass spectrum". Golm Metabolome Database. Archived from the original on 2018-09-09. Retrieved 2018-06-04.
- PMID 17177492.
- PMID 24054643.
- Gesellschaft Deutscher Chemiker: wayback=20100331071121 Anlagen zum Positionspapier der Fachgruppe Nuklearchemie Archived 2010-03-31 at the Wayback Machine, February 2000.
- PMID 24991541.