Beta-D-Fructose is a beta-fructose produced by the hydrolysis of sucrose. Beta-D-Fructose could be utilized as a sweetness enhancer. β-D-Fructose can be designed as a unit element of an antiproliferation agent against breast (MCF-7) and colon (MDST8) cancer cell lines.

Physicochemical Properties

Molecular Formula	C6H12O6
Molecular Weight	180.16
Exact Mass	180.063
CAS #	53188-23-1
PubChem CID	439709
Appearance	White to off-white solid powder
Density	1.6±0.1 g/cm3
Boiling Point	551.7±50.0 °C at 760 mmHg
Melting Point	119 - 122 °C
Flash Point	301.5±26.6 °C
Vapour Pressure	0.0±3.4 mmHg at 25°C
Index of Refraction	1.574
LogP	-1.63
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Heavy Atom Count	12
Complexity	162
Defined Atom Stereocenter Count	4
SMILES	OCC(=O)C(O)C(O)C(O)CO
InChi Key	RFSUNEUAIZKAJO-ARQDHWQXSA-N
InChi Code	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
Chemical Name	(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Human Endogenous Metabolite
ADME/Pharmacokinetics	Metabolism / Metabolites 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/Toxicokinetics	Toxicity Summary 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 (A15346). 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 (A15346). Many studies have shown that elevated uric acid levels are associated with several metabolic and cardiovascular conditions, including diabetes and coronary artery disease (A15346). Elevated serum uric acid has also been shown to be the most reliable predictor for the development of hypertension and incident renal disease (A15347) as well as fatty liver disease (A15348). Fructose-induced uric acid generation also causes mitochondrial oxidative stress that stimulates fat accumulation independent of excessive caloric intake (A15349). 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 (A15347). 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. Toxicity Data 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)
References	[1]. Novel hydroxyamides and amides containing D-glucopyranose or D-fructose units: Biological assays in MCF-7 and MDST8 cell lines. Bioorg Med Chem Lett. 2016 Feb 1;26(3):1039-1043.
Additional Infomation	Beta-D-fructofuranose is a D-fructofuranose. It has a role as a mouse metabolite. It is an enantiomer of a beta-L-fructofuranose. beta-D-fructofuranose has been reported in Daphnia pulex, Ruellia patula, and Detarium microcarpum with data available. 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. A monosaccharide in sweet fruits and honey that is soluble in water, alcohol, or ether. It is used as a preservative and an intravenous infusion in parenteral feeding. See also: D-Fructose (annotation moved to).

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	5.5506 mL	27.7531 mL	55.5062 mL
	5 mM	1.1101 mL	5.5506 mL	11.1012 mL
	10 mM	0.5551 mL	2.7753 mL	5.5506 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.