ContaminantDB: D-Fructose

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:30:41 UTC

Update Date

2026-04-06 04:22:16 UTC

Accession Number

CHEM003305

Identification

Common Name

D-Fructose

Class

Small Molecule

Description

Fructose, or fruit sugar, is a simple monosaccharide found in many plants, where it is often covalently linked to glucose to form the disaccharide sucrose. Fructose is one of three common dietary monosaccharides, along with glucose and galactose, that are absorbed directly into the bloodstream during digestion. Fructose is found naturally in many fruits and vegetables and honey. It is frequently derived from sugar cane, sugar beets, and corn. High-fructose corn syrup (HFCS), which is widely used as a sweetener in beverages and foods, is a mixture of glucose and fructose. The primary reason that fructose is used commercially in foods and beverages is because of its low cost and is its high relative sweetness. It is the sweetest of all naturally occurring carbohydrates being 1.73 times as sweet as sucrose. Fructose consumption in the U.S. has more than doubled in the past 30 years. Americans' fructose intake climbed from 15 grams per day in the early 1900s to 55 grams per day in 1994. This increase is largely due to an increase in soft drink consumption.

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Animal Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
beta-D-Arabino-hexulose	ChEBI
beta-D-Fructose	ChEBI
beta-Fruit sugar	ChEBI
beta-Levulose	ChEBI
FRUCTOSE	ChEBI
b-D-Arabino-hexulose	Generator
Β-D-arabino-hexulose	Generator
b-D-Fructose	Generator
Β-D-fructose	Generator
b-Fruit sugar	Generator
Β-fruit sugar	Generator
b-Levulose	Generator
Β-levulose	Generator
beta-D-Fructofuranose	HMDB
beta-delta-Arabino-hexulose	HMDB
beta-delta-Fructofuranose	HMDB
beta-delta-Fructose	HMDB
D-(-)-Fructose	HMDB
delta-(-)-Fructose	HMDB
delta-Fructose	HMDB
FRU	HMDB
Fructon	HMDB
Levulose	HMDB
Braun brand OF fructose	HMDB
Fleboplast levulosa	HMDB
Fresenius kabi brand OF fructose	HMDB
Instituto farmacologico brand OF fructose	HMDB
Levulosa	HMDB
Levulosa ife	HMDB
Grifols brand OF fructose	HMDB
Levulosa baxter	HMDB
Levulosado braun	HMDB
Ern brand OF fructose	HMDB
Levulosa grifols	HMDB
Levulosa mein	HMDB
Levulosado vitulia	HMDB
Apir levulosa	HMDB
Baxter brand OF fructose	HMDB
Bieffe brand OF fructose	HMDB
Levulosa braun	HMDB
Levulosa ibys	HMDB
Levulosa, apir	HMDB
Levulosa, fleboplast	HMDB
Levulosado bieffe medit	HMDB
Plast apyr levulosa mein	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Mass

180.156 g/mol

Monoisotopic Mass

180.063 g/mol

CAS Registry Number

53188-23-1

IUPAC Name

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol

Traditional Name

fructose

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

Description

belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose (CHEBI:28645 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular

Biofluid Locations

Not Available

Tissue Locations

All Tissues

Pathways

Name	SMPDB Link	KEGG Link
Amino Sugar Metabolism	SMP00045	map00520
Fructose and Mannose Degradation	SMP00064	map00051
Galactose Metabolism	SMP00043	map00052
Starch and Sucrose Metabolism	SMP00058	map00500
Fructose intolerance, hereditary	SMP00725	Not Available
Fructosuria	SMP00561	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White crystals

Experimental Properties

Property	Value
Melting Point	103°C
Boiling Point	440°C
Solubility	778 mg/mL at 20°C

Predicted Properties

Property	Value	Source
Water Solubility	1110 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-2.8	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.26 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-076r-9600000000-f2c06850d0c3db9ec103	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0fb9-5614950000-6ef14e948d063026f7ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_6) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0002-0900000000-2ce9036c30158be73d60	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9600000000-a826b29724713036f579	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9200000000-7621d8d96132cc999f4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-00di-9000000000-a6de82c4270a43535ef4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-00di-9000000000-f9fa2c446096028a62b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-a6de82c4270a43535ef4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f9fa2c446096028a62b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2afc98a319bf6041adf0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-1dd0cdea93f529e6ccb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9100000000-d0f08ad6c9dee008067a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-74b62c8ea3678afcff8a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-1900000000-5a0f3f01ddf8c11c6370	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-93c2b00aa44481aa8630	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-9800000000-b033c19e1db6b17bf7cf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-01306ef5e3c5a271dfb2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-4e87bfc49b1664133053	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-6aefe19f3e63c1b3fbef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03gm-9500000000-d2f178dbda765758ef3d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btd-9000000000-62631cc26542b523e7d7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion

Mechanism of Toxicity

Fructose is distinct from other sugars in its ability to cause intracellular ATP depletion, nucleotide turnover, and the generation of uric acid. Uric acid is generated via fructose due to its rapid phosphorylation (to fructose-1-phosphate) in the liver, leading to a rapid drop in free phosphate and ATP. This drop in ATP leads to the stimulation of adenosine monophosphate (AMP) deaminase which deaminates AMP to produce IMP, which is subsequently converted to uric acid (10). Uric acid is normally an anti-oxidant but without sufficient amounts of ascorbic acid (vitamin C) present in the plasma, it functions as a pro-oxidant. Because many soft drinks and foods that are sweetened with high fructose corn syrup do not contain vitamin C, the resulting uric acid can lead to a number of harmful effects, including gout, chronic inflammation, hypertension, increased adiposity, fatty liver disease and obesity (10). Many studies have shown that elevated uric acid levels are associated with several metabolic and cardiovascular conditions, including diabetes and coronary artery disease (10). Elevated serum uric acid has also been shown to be the most reliable predictor for the development of hypertension and incident renal disease (11) as well as fatty liver disease (12). Fructose-induced uric acid generation also causes mitochondrial oxidative stress that stimulates fat accumulation independent of excessive caloric intake (13). Several studies have demonstrated that oxidative stress is one of the earliest phenomena observed in vascular, renal, liver cells and adipocytes exposed to uric acid (11). High fructose consumption is also associated with more severe depletion of liver ATP, which may impair liver "energy balance”. High-fructose beverages have also been shown to lead to lower circulating insulin and leptin levels, and higher ghrelin levels. Since leptin and insulin decrease appetite and ghrelin increases appetite, some researchers suspect that eating large amounts of fructose increases the likelihood of weight gain.

Metabolism

Free fructose is absorbed directly by the intestine. When fructose is consumed in the form of sucrose, it is digested (broken down) and then absorbed as free fructose. Fructose absorption occurs on the mucosal membrane via facilitated transport involving GLUT5 and GLUT2 transport proteins. Fructose is phosphorylated in the liver by fructokinase (Km= 0.5 mM). Fructokinase initially produces fructose 1-phosphate, which is split by aldolase B to produce the trioses dihydroxyacetone phosphate (DHAP) and glyceraldehyde. DHAP is then converted to glycerol-3-phophate which stimulates production of triglycerides. Nearly half (45%) of all pure fructose consumed is used up within 3-6 hours by the body for energy. If fructose is consumed with glucose (as it typically is in nature), up to 66% of it is used for energy within the same time frame. Roughly a third (29%) to a half (54%) of all fructose consumed is converted to glucose. Less than 1% of fructose appears to be directly converted to triglycerides.

Toxicity Values

Consuming more than 100 g a day of pure fructose may lead to a modest but statistically significant rise in body weight of 0.44 kg a week. Consuming 100 g or more of fructose a day also significantly increases fasting levels of serum triglycerides. LD50: 15000 mg/kg (intravenous, rabbit)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Acute consumption of fructose or high fructose corn syrup is essentially non-toxic. Chronic, excess fructose consumption has been shown to be a cause (or indirect cause) of gout, insulin resistance, hypertension, obesity, fatty liver disease, elevated LDL cholesterol and elevated triglycerides, leading to metabolic syndrome. In Wistar rats, a laboratory model of diabetes, 10% fructose feeding as opposed to 10% glucose feeding was found to increase blood triglyceride levels by 86%, whereas the same amount of glucose had no effect on triglycerides. A 2008 study found a substantial risk of incident gout associated with the consumption of fructose or fructose-rich foods. It is suspected that the fructose found in soft drinks (e.g., carbonated beverages) and other sweetened drinks is the primary reason for this increased incidence.

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000660

FooDB ID

FDB031286

Phenol Explorer ID

Not Available

KNApSAcK ID

BiGG ID

BioCyc ID

METLIN ID

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

ECMDB00660

References

Synthesis Reference

Larry W. Peckous, “Integrated process for producing crystalline fructose and a high-fructose, liquid phase sweetener.” U.S. Patent US5656094, issued 0000.

MSDS

Link

General References

1. 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.

2. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.

3. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)

4. 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.

5. 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.

6. 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.

7. 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.

8. Andrade-Rocha FT: Seminal fructose levels in male infertility: relationship with sperm characteristics. Int Urol Nephrol. 1999;31(1):107-11.

9. 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.

10. 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.

11. 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.

12. 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.

13. 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. doi: 10.1038/nature07762.

14. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.

D-Fructose (CHEM003305)

Structure for CHEM003305: D-Fructose