Record Information
Version1.0
Creation date2015-10-09 22:29:03 UTC
Update date2017-01-19 02:36:15 UTC
FoodComEx IDPC000176
FoodDB RecordFDB012530
Chemical Information
NameD-Glucose
DescriptionGlucose is a monosaccharide containing six carbon atoms and an aldehyde group. It is referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is a primary source of energy for all living organisms. It is a fundamental metabolite found in all organisms, ranging from bacteria to plants to humans. Most of the glucose generated on the Earth is made by plants and algae during photosynthesis from water and carbon dioxide, where it is used to make cellulose (and other polymeric forms of glucose called polysaccharides) that stabilize plant cell walls. Glucose is also found in fruits and other parts of plants in its free state. In animals, glucose can be generated from the breakdown of glycogen in a process known as glycogenolysis. Glucose can also be synthesized de novo in animals. In particular, it can be synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol (and gluconeogenic amino acids such as glycine, serine and alanine), by a process known as gluconeogenesis. Humans also consume large amounts of glucose as part of their regular diet. Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose-containing food sources. Glucose in the body mainly comes from food - about 300 g per day for the average adult. In humans, the breakdown of glucose-containing polysaccharides happens partly during chewing by means of the enzyme known as amylase, which is contained in saliva, as well as by other enzymes such as maltase, lactase and sucrase on the brush border of the small intestine. 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 blood plasma, the measured values are about 10-15% higher. Dysregulated metabolism of glucose can lead to a number of diseases including diabetes. Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels (called hyperglycemia), through pancreatic burnout and insulin resistance. Persistently elevated levels of glucose (>6 mM or >120 mg/dL) can lead to the formation of covalent adducts of glucose with plasma proteins through a non-enzymatic process known as glycation. This glycation reaction leads to advanced glycation end products or AGEs (PMID: 24634591 ). AGEs are thought to be the major causes of different diabetic complications. High glucose levels may induce glycation of various structural and functional proteins including plasma proteins and collagen. The non-enzymatic modification of plasma proteins such as albumin, fibrinogen, hemoglobin and globulins may produce various deleterious effects including alteration in drug binding in the plasma, platelet activation, generation of oxygen free radicals, impaired fibrinolysis and impairment in immune system regulation (PMID: 24634591 ). Transiently elevated glucose (up to 7.3 mM or 133 mg/dL) is often seen shortly after the consumption of a meal or a food item that is rich in carbohydrates -- even among very healthy people (PMID: 19885137 ). Glucose is also elevated when an individual is fighting viral or bacterial infections or suffering from traumatic injuries (burns, wounds). In fact, glucose can be significantly elevated (>11 mM or 200 mg/dL) when individuals are experiencing sepsis or septic shock (PMID: 16006275 ). On the other hand, low blood glucose levels (hypoglycemia) where blood glucose is <3.9 mM (70 mg/dL) are common among people with type 1 diabetes and people with type 2 diabetes who take certain diabetic medicines. Certain conditions, such as liver disease, may also cause low levels of blood glucose. Hypoglycemia can lead to fatigue, sleepiness, short temper or feeling faint.
CAS Number492-61-5
Structure
Thumb
Synonyms
SynonymSource
(+)-glucosebiospider
Anhydrous dextroseHMDB
CereloseHMDB
Cerelose 2001HMDB
Clearsweet 95HMDB
Clintose LHMDB
Corn sugarHMDB
CPC HydrateHMDB
D-(+)-glucosebiospider
D-GlcChEBI
D-GlcpChEBI
D(+)-glucosebiospider
DextropurHMDB
Dextrosemanual
DextrosolHMDB
GlucodinHMDB
GlucolinHMDB
GlucoseChEBI
GoldsugarHMDB
Grape sugarmanual
MeritoseHMDB
Roferose stHMDB
Staleydex 111HMDB
Staleydex 95mHMDB
Tabfine 097(hs)HMDB
VadexHMDB
Chemical FormulaC6H12O6
IUPAC name(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
InChI IdentifierInChI=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
InChI KeyWQZGKKKJIJFFOK-VFUOTHLCSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-3.24SANGSTER (1994)
Experimental Water Solubility1200 mg/mL at 30 oCMULLIN,JW (1972)
Melting Point146-150 oC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 6 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci 7531AF
Cayman Chemical 16775