| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:09:02 -0700 |
| HMDB ID |
HMDB00660 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common 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), it generally exists as a 5-member hemiketal ring (a furanose). This 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. It is used as a preservative and an intravenous infusion in parenteral feeding. Fructose is a reducing sugar, as are all monosaccharides. 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 so 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 (Levi & Werman 1998). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- beta-D-Arabino-hexulose
- beta-D-Fructofuranose
- beta-D-Fructose
- beta-delta-Arabino-hexulose
- beta-delta-Fructofuranose
- beta-delta-Fructose
- beta-Fruit sugar
- beta-Levulose
- D-(-)-Fructose
- D-Fructose
- delta-(-)-Fructose
- delta-Fructose
- FRU
- Fructon
- Fructose
- Levulose
|
| Chemical Formula |
C6H12O6 |
| Average Molecular Weight |
180.1559 |
| Monoisotopic Molecular Weight |
180.063388116 |
| IUPAC Name |
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol |
| Traditional IUPAC Name |
fructose |
| CAS Registry Number |
53188-23-1 |
| SMILES |
OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O |
| InChI Identifier |
InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1 |
| InChI Key |
RFSUNEUAIZKAJO-ARQDHWQXSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Carbohydrates and Carbohydrate Conjugates |
| Class |
Monosaccharides |
| Sub Class |
Pentoses |
| Other Descriptors |
- Aliphatic Heteromonocyclic Compounds
- D-fructofuranose(ChEBI)
|
| Substituents |
- 1,2 Diol
- Hemiacetal
- Oxolane
- Primary Alcohol
- Secondary Alcohol
|
| Direct Parent |
Pentoses |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
119 - 122 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
778 mg/mL at 20 °C |
YALKOWSKY,SH & DANNENFELSER,RM (1992) |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Urine
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| Tissue Location |
|
| Pathways |
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| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
31.0 +/- 3.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
48.0 +/- 16.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
240.0 (220.0 -260.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
160 +/- 91 uM |
Not Specified |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and Quantified |
|
70.38 +/- 107.54 umol/mmol creatinine |
Infant (0-1 year old) |
Not Specified |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
12.00 +/- 3.8 uM |
Adult (>18 years old) |
Both |
Diabetes |
Not Available |
| Urine |
Detected and Quantified |
|
8.4 +/- 7.0 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Diabetes |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Diabetes mellitus type 2 |
|---|
- Kawasaki T, Akanuma H, Yamanouchi T: Increased fructose concentrations in blood and urine in patients with diabetes. Diabetes Care. 2002 Feb;25(2):353-7.
Pubmed: 11815509
|
|
| Associated OMIM IDs |
- 125853 (Diabetes mellitus type 2)
|
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB012528 |
| KNApSAcK ID |
C00033848 |
| Chemspider ID |
388775 |
| KEGG Compound ID |
C02336 |
| BioCyc ID |
CPD-535 |
| BiGG ID |
33835 |
| Wikipedia Link |
FRU |
| NuGOwiki Link |
HMDB00660 |
| Metagene Link |
HMDB00660 |
| METLIN ID |
135 |
| PubChem Compound |
439709 |
| PDB ID |
FRU |
| ChEBI ID |
28645 |
| References |
|---|
| Synthesis Reference |
Liu, Hong; Han, Dong; Meng, Xiang-bao; Li, Zhong-jun. Improved synthesis of fructose-derived 1,3,4-oxadiazole as novel antitumor agents. Journal of Chinese Pharmaceutical Sciences (2005), 14(4), 209-212. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Vicari E, La Vignera S, Castiglione R, Calogero AE: Sperm parameter abnormalities, low seminal fructose and reactive oxygen species overproduction do not discriminate patients with unilateral or bilateral post-infectious inflammatory prostato-vesiculo-epididymitis. J Endocrinol Invest. 2006 Jan;29(1):18-25.
Pubmed: 16553029
- Bar A: Characteristics and significance of D-tagatose-induced liver enlargement in rats: An interpretative review. Regul Toxicol Pharmacol. 1999 Apr;29(2 Pt 2):S83-93.
Pubmed: 10341166
- Andrade-Rocha FT: Semen analysis in an infertile man with seminal vesicles cysts associated with ipsilateral renal agenesis. Int Urol Nephrol. 2006;38(1):101-3.
Pubmed: 16502061
- Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11.
Pubmed: 10408311
- Gonzales GF, Villena A: True corrected seminal fructose level: a better marker of the function of seminal vesicles in infertile men. Int J Androl. 2001 Oct;24(5):255-60.
Pubmed: 11554981
- Buemann B, Gesmar H, Astrup A, Quistorff B: Effects of oral D-tagatose, a stereoisomer of D-fructose, on liver metabolism in man as examined by 31P-magnetic resonance spectroscopy. Metabolism. 2000 Oct;49(10):1335-9.
Pubmed: 11079825
- Koca Y, Ozdal OL, Celik M, Unal S, Balaban N: Antioxidant activity of seminal plasma in fertile and infertile men. Arch Androl. 2003 Sep-Oct;49(5):355-9.
Pubmed: 12893512
- Williams AC, Ford WC: The role of glucose in supporting motility and capacitation in human spermatozoa. J Androl. 2001 Jul-Aug;22(4):680-95.
Pubmed: 11451366
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.
Pubmed: 19212411
|
