Fructose

Names

[ Name ]:
Fructose

[Synonym ]:
(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
D(-)-Fructose
D-Fructose
β-d-Fructose
beta-D-fructopyranose
D-(-)-Fructose
Levulose
Fructose [JAN]
UNII:02T79V874P
Fructose, D-
(3S,4R,5R)-1,3,4,5,6-Pentahydroxy-2-hexanon
(3S,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one
Levugen
Fruit sugar
beta-D-fructofuranose
D-(-)-levulose
Fructose (JP15/USP)
b-D-Fructose
DSSTox_CID_3081
fructose powder
arabino-2-Hexulose
1,3,4,5,6-pentahydroxyl-2-hexanone
D-Levulose
(3S,4R,5R)-1,3,4,5,6-Pentahydroxy-2-hexanone
Frutabs
δ-Fructose
Fructooligosaccharides
Fructose
β-δ-fructose
keto-D-fructose
D-fructofuranose
β-Fruit sugar
(2R,3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
D-arabino-Hexulose
Furucton
β-D-arabino-Hexulose
β-Levulose
keto D-fructose
Laevosan
Laevoral
Fructose, furanose form
Fructosteril
(D)-fructose

Biological Activity

[Description]:

Fructose is a simple ketonic monosaccharide found in many plants, where it is often bonded to glucose to form the disaccharide sucrose.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cardiovascular Disease

Research Areas >> Metabolic Disease

Natural Products >> Saccharides and Glycosides

[In Vitro]

Fructose, at low concentrations do not cause any significant increase of Tissue factor (TF)-mRNA levels. On the contrary, higher Fructose concentrations cause increase in TF mRNA levels at 60 min, as compare to unstimulated cells. Increasing Fructose concentrations causes significant decrease of tPA-mRNA levels. SOD significantly prevents Fructose induced NF-κB activation which is associated with the parallel reduction of Fructose-induced TF expression/activity[1].

[In Vivo]

In mice fed 0% Fructose, portal (0.060±0.006 mM, overall mean for all time points) and systemic (0.030±0.003 mM) Fructose concentrations do not vary with time after feeding. In contrast, portal concentrations in wild-type mice consuming 20% Fructose increase by more than twofold from time (t)=0 to t=1 h after feeding (~0.13 mM). Likewise, systemic serum Fructose goes from 0.037 at t=0 to 0.13 mM 1 h after feeding. Fasted (t=0) serum Fructose in the 20% group is similar to postprandial concentrations in the 0% mice for both portal and systemic levels, suggesting that the baseline Fructose concentration during fasting is not affected by diet. Serum Fructose concentrations in KHK-/- mice are 5- to 100-fold greater than those in wild-type mice for the same diet, time, and sample location. Mean (for all time points) portal and systemic glucose concentrations in mice fed 20% Fructose are ~3 (P=0.004) and ~2 (P=0.04) mM greater, respectively, than those in mice fed 0%. Systemic Fructose concentrations are approximately threefold greater in KHK-/- mice fed Fructose compare with those fed glucose, but are similar between glucose- and Fructose-fed wild-type mice[2].

[Cell Assay]

HUVECs are incubated with Fructose (0.25, 1 and 2.5 mM) for 30 min. Then, cells are washed with PBS and then fresh medium is added. Total mRNA is extracted by cell cultures using TRIzol reagent, at baseline and 60 min after Fructose stimulation and Tissue factor (TF) mRNA levels are examined by realtime reverse transcription (RT) and polymerase chain reaction (PCR). In positive control experiments, HUVECs are incubated with LPS (50 μg/mL), for 30 min and then mRNA is extracted at 60 min[1].

[Animal admin]

50 young adult (7-wk-old) male C57BL6 wild-type mice (~18 g) are divided into 10 cages and acclimatized to a reversed light cycle. Mice are fed a nonpurified commercial diet ad libitum for the first 4 days. On the 5th day and then throughout the experiment, diets are removed at 2001 (lights on) and returned at 0801 (lights off). For days 8 to 14, diets are switched to pellets containing either 0% Fructose, 10% sucrose, 20% glucose (termed as "0% Fructose") or 20% Fructose, 10% sucrose, or 0% glucose (20% Fructose). On the 15th day, mice are killed at 0800 before feeding and 0900, 1030, 1200, and 1530 during the dark phase, with n=5 for each time point and diet[2].

[References]

[1]. Cirillo P, et al. Fructose induces prothrombotic phenotype in human endothelial cells : A new role for "added sugar" in cardio-metabolic risk. J Thromb Thrombolysis. 2015 Nov;40(4):444-51.

[2]. Patel C, et al. Effect of dietary fructose on portal and systemic serum fructose levels in rats and in KHK-/- and GLUT5-/- mice. Am J Physiol Gastrointest Liver Physiol. 2015 Nov 1;309(9):G779-90.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
551.7±50.0 °C at 760 mmHg

[ Melting Point ]:
100 - 110ºC

[ Molecular Formula ]:
C₆H₁₂O₆

[ Molecular Weight ]:
180.156

[ Flash Point ]:
301.5±26.6 °C

[ Exact Mass ]:
180.063385

[ PSA ]:
110.38000

[ LogP ]:
-1.63

[ Vapour Pressure ]:
0.0±3.4 mmHg at 25°C

[ Index of Refraction ]:
1.574

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LS7000000

CHEMICAL NAME :: Fructopyranose, beta-D-

CAS REGISTRY NUMBER :: 7660-25-5

BEILSTEIN REFERENCE NO. :: 1423189

LAST UPDATED :: 199706

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C6-H12-O6

MOLECULAR WEIGHT :: 180.18

WISWESSER LINE NOTATION :: T6OTJ BQ B1Q CQ DQ EQ FRUCTO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,254,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,254,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12750 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,254,1990

TYPE OF TEST :: LD30 - Lethal Dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AGACBH Agents and Actions, A Swiss Journal of Pharmacology. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1969/70- Volume(issue)/page/year: 16,580,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 8,72,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 13350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,254,1990 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5000 mg/kg

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

REFERENCE :: GANNA2 Gann. Japanese Journal of Cancer Research. (Tokyo, Japan) V.1-75, 1907-84. For publisher information, see JJCREP. Volume(issue)/page/year: 46,371,1955

Safety Information

[ HS Code ]:
1702600000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 1702600000