D-fructose

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  • Name: D-fructose
  • Description: Fructose, or levulose, is a levorotatory monosaccharide and an isomer of glucose (C6H12O6). The chemical composition of fructose is (C6H12O6). Pure fructose has a sweet taste similar to cane sugar,... but with a "fruity" aroma. Although fructose is a hexose (6-carbon sugar) with a keto group, also called a keto-hexose, it generally exists as a 5-member hemiketal ring (a furanose) and rarely as pyran or straight chain. When fructose forms a ring an additional “anomeric” asymmetric carbon is created which is denoted as “alpha” or “beta”. D-fructopyranose is also a cyclic hemiketal that has a role as a sweetening agent. In the acyclic form, aside from the keto group, each of the 5 remaining carbons of D-fructose has one hydroxyl group, in the S, R and R configuration counting from the first hydroxyl containing asymmetric carbon next to the ketone.The D-fructofuranose structure is responsible for the long metabolic pathway and high reactivity compared to glucose. Fructose is found in many foods and is one of the three most important blood sugars along with glucose and galactose. Honey, tree fruits, berries, melons, and some root vegetables, such as beets, sweet potatoes, parsnips, and onions contain fructose, usually in combination with sucrose and glucose. Fructose is also derived from the digestion of sucrose, a disaccharide consisting of glucose and fructose that is broken down by enzymes during digestion. Fructose is the sweetest naturally occurring sugar, estimated to be twice as sweet as sucrose. Fructose is soluble in water, alcohol, or ether.It is used as a preservative and an intravenous infusion in parenteral feeding. The spontaneous addition of single sugar molecules to proteins, known as glycation, is a significant cause of damage in diabetics. Fructose appears to be as dangerous as glucose in this regard, and therefore does not seem to be the answer for diabetes (McPherson et al, 1988). This may be an important contribution to senescence and many age-related chronic diseases (HMDB ID:HMDB0000660)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
23838602 Age [17–85], Gender ⚥ 0.012 (β) UPLC-MS/MS; GC-MS serum, plasma
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    Fru; levulose;D-fructopyranose
  • Chemical Formula:
    C6H12O6
  • Exact Mass g/mol:
    180.0630000
  • Systematic name:
    (3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
  • SMILES:
    C1[C@H]([C@H]([C@@H](C(O1)(CO)O)O)O)O
  • InChI:
    InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4-,5+,6?/m1/s1
  • InChI Key:
    LKDRXBCSQODPBY-VRPWFDPXSA-N
  • CAS number:
    57-48-7
Related resources
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Plasma, Serum, Tissue
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Linear regression
Method: UPLC-MS/MS; GC-MS
Sample: serum; plasma
PubMed PMID: 23838602
β = 0.012 (y = βx + α)
p-value < 0.05
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