Term: Glucose

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**Historical Background and Naming**:
– Glucose was isolated from raisins in 1747 by Andreas Marggraf and discovered in grapes in 1792 by Johann Tobias Lowitz.
– The term ‘glucose’ was coined in 1838 by Jean Baptiste Dumas, while Friedrich August Kekulé proposed the term ‘dextrose’.
– Emil Fischer’s investigations led to an understanding of glucose’s structure.

**Chemical and Physical Properties**:
– Glucose forms white or colorless solids and is highly soluble in water and acetic acid.
– It is poorly soluble in methanol and ethanol, melts at temperatures ranging from 146°C to 150°C, and has a pKa value of 12.16 at 25°C in water.

**Role in Energy Metabolism and Production**:
– Glucose is the primary source of energy in organisms, stored as starch, amylopectin in plants, and glycogen in animals.
– It circulates in the blood as blood sugar and is released from glycogen breakdown in animals.
– Commercially, dextrose is manufactured from starches through pressurized steaming and enzymatic depolymerization.

**Significance in Medicine and Research**:
– Glucose is an essential medicine listed by the World Health Organization and plays a crucial role in metabolism.
– Intravenous sugar solutions are used in medical treatments, and research on glucose metabolism has led to Nobel Prizes in Physiology or Medicine and Chemistry.

**Structural and Functional Properties**:
– Glucose is a monosaccharide with six carbon atoms and an aldehyde group, existing in solid form as a monohydrate with a closed pyran ring.
– Glucose can exist in open-chain and cyclic forms, with over 99% of molecules existing as pyranose forms in solution.
– It exhibits optical activity as d-(+)-glucose and undergoes mutarotation, switching between cyclic and open-chain forms.

Glucose (Wikipedia)

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

d-Glucose

Skeletal formula of d-glucose

Haworth projection of α-d-glucopyranose

Fischer projection of d-glucose
Names
Pronunciation /ˈɡluːkoʊz/, /ɡluːkoʊs/
IUPAC name
Allowed trivial names:
  • ᴅ-Glucose
  • ᴅ-gluco-Hexose
Preferred IUPAC name
PINs are not identified for natural products.
Systematic IUPAC name
  • (2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanal (linear form)
  • (3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol (cyclic form)
Other names
Blood sugars
Dextrose
Corn sugar
d-Glucose
Grape sugar
Identifiers
3D model (JSmol)
3DMet
Abbreviations Glc
1281604
ChEBI
ChEMBL
ChemSpider
EC Number
  • 200-075-1
83256
KEGG
MeSH Glucose
RTECS number
  • LZ6600000
UNII
  • InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6?/m1/s1 checkY
    Key: WQZGKKKJIJFFOK-GASJEMHNSA-N checkY
  • α-d-glucopyranose: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)O)O)O)O
  • β-d-glucopyranose: OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O
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
218.6 J/(K·mol)
209.2 J/(K·mol)
−1271 kJ/mol
2,805 kJ/mol (670 kcal/mol)
Pharmacology
B05CX01 (WHO) V04CA02 (WHO), V06DC01 (WHO)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
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).
checkY verify (what is checkY☒N ?)

In energy metabolism, glucose is the most important source of energy in all organisms. Glucose for metabolism is stored as a polymer, in plants mainly as starch and amylopectin, and in animals as glycogen. Glucose circulates in the blood of animals as blood sugar. The naturally occurring form of glucose is d-glucose, while its stereoisomer l-glucose is produced synthetically in comparatively small amounts and is less biologically active. 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. Glucose is naturally occurring and is found in its free state in fruits and other parts of plants. In animals, glucose is released from the breakdown of glycogen in a process known as glycogenolysis.

Glucose, as intravenous sugar solution, is on the World Health Organization's List of Essential Medicines. It is also on the list in combination with sodium chloride (table salt).

The name glucose is derived from Ancient Greek γλεῦκος (gleûkos, "wine, must"), from γλυκύς (glykýs, "sweet"). The suffix "-ose" is a chemical classifier denoting a sugar.

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