D(-)-Fructose CAS 57-48-7
Introduction：Basic information about D(-)-Fructose CAS 57-48-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
D(-)-Fructose Basic informationGeneral Description History of fructose consumption Rise of fructose consumption Source of fructose Biomedical importance of fructose Fructose metabolism Fructose and diseases References
| Product Name: | D(-)-Fructose |
| Synonyms: | D-(-)-Fructose 〔Levulose〕;Fructose Standard, 1800ppm;Fructose Standard, 200ppm;Fructose Standard, 18000ppm;Fructose Standard, 100000ppm;Fructose Standard, 20000ppm;Fructose Standard, 1500ppm;Fructose Standard, 3000ppm |
| CAS: | 57-48-7 |
| MF: | C6H12O6 |
| MW: | 180.16 |
| EINECS: | 200-333-3 |
| Product Categories: | API;Food additive and Sweetener;Food additives;Indolines ,Indoles;Dextrins、Sugar & Carbohydrates;Carbohydrates & Derivatives;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Fructose;Sugars;Elisa Kit-plant ELISA Kit |
| Mol File: | 57-48-7.mol |
D(-)-Fructose Chemical Properties
| Melting point | 119-122 °C (dec.)(lit.) |
| alpha | -92.25 º (c=10,H2O,on dry sub.) |
| Boiling point | 232.96°C (rough estimate) |
| bulk density | 700-800kg/m3 |
| density | 1.59 |
| refractive index | -92 ° (C=4, H2O) |
| storage temp. | room temp |
| solubility | H2O: 1 M at 20 °C, clear, colorless |
| pka | pKa (18°): 12.06 |
| form | Crystals or Crystalline Powder |
| color | White |
| PH | 5.0-7.0 (25℃, 0.1M in H2O) |
| Odor | at 100.00 %. odorless |
| Odor Type | odorless |
| Optical Rotation | [α]20/D 93.5 to 91.0°, c = 10% in H2O |
| biological source | natural (organic) |
| Water Solubility | 3750 g/L (20 ºC) |
| λmax | λ: 260 nm Amax: 0.04 λ: 280 nm Amax: 0.04 |
| Merck | 14,4273 |
| BRN | 1239004 |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | pharmaceutical (small molecule) |
| Cosmetics Ingredients Functions | HUMECTANT |
| Cosmetic Ingredient Review (CIR) | D(-)-Fructose (57-48-7) |
| InChI | 1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6-/m1/s1 |
| InChIKey | LKDRXBCSQODPBY-GWVKGMJFSA-N |
| SMILES | OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO |
| LogP | -1.029 (est) |
| CAS DataBase Reference | 57-48-7(CAS DataBase Reference) |
| NIST Chemistry Reference | «beta»-D-Fructose(57-48-7) |
| EPA Substance Registry System | D-Fructose (57-48-7) |
Safety Information
| Hazard Codes | C |
| Risk Statements | 34 |
| Safety Statements | 24/25-45-36/37/39-27-26 |
| WGK Germany | 3 |
| RTECS | LS7120000 |
| F | 3 |
| Autoignition Temperature | 360 °C |
| TSCA | TSCA listed |
| HS Code | 17025000 |
| Storage Class | 11 - Combustible Solids |
| General Description | D-Fructose is present as a monosaccharide in fruits and vegetables[1], as a disaccharide in sucrose (with D-glucose), and as oligoand polysaccharides (fructans) in many plants. It is also used as an added sweetener for food and drink, and as an excipient in pharmaceutical preparations, syrups, and solutions[2]. In equal amounts, it is sweeter than glucose or sucrose and is therefore commonly used as a bulk sweetener. An increase in high fructose corn syrup, as well as total fructose, consumption over the past 10 to 20 years has been linked to a rise in obesity and metabolic disorders[3]. This raises concerns regarding the short and long-term effects of fructose in humans. Fructose is present more or less frequently than glucose in the juices of plants, fruits, and especially the honey, which is about half the solid matters[4]. It leads to an equal amount of glucose by the hydrolysis of sugar cane and a smaller proportion than some other less common sugars. It is used, such as glucose, in the production of glycogen. It enters the body through either be eaten as such or as the result of digestion of sugar cane. It is mainly changed into glycogen or triglycerides after reaching the liver, so do not enter largely in the blood circulation. Glucose and fructose are partially inter-convertible under the influence of very dilute alkali. It is not surprising; therefore, that fructose must be converted to glycogen in the liver, which on hydrolysis yields of glucose[5]. Dubois et al. reported that regular consumption of sugary drinks between meals increases risk of overweight among preschool children[6]. Fructose has been claimed to be of concern due to several factors: First, in the 1980’s, sucrose was replaced to a large extent, particularly in North America, by high fructose corn syrup (HFCS) in carbonated beverages. The intake of soft drinks containing HFCS has risen in parallel with the epidemic of obesity[7]. Second, dietary fructose has been implicated in risk factors for cardiovascular disease (CVD): 1. Plasma triglycerides (TG) and VLDL-TG increased following the ingestion of large quantities of fructose; 2. Fructose intake has been found to predict LDL particle size in overweight schoolchildren[8]. 3. A positive relationship has been demonstrated between fructose intake and uric acid levels[9]. Third, the use of fructose as a sweetener has increased. The third National Health Examination Survey (NHANES) demonstrated that over 10% of Americans’ daily calories were from fructose[10]. These studies suggest that the relationship between fructose and health needs re-evaluation. |
| History of fructose consumption | Before the development of the sugar industry, free fructose was found in relatively few foods.[11] Relatively few unprocessed foods contain any significant amounts of free fructose monosaccharide. Historically, these foods have been relatively hard to obtain and they typically contain fructose in conjunction with glucose and/or fibre, which has significant implications for the absorption and metabolism of the former[12, 13]. As a consequence, humans have historically had low dietary fructose intakes[11] |
| Rise of fructose consumption | Fructose consumption has been escalating over the past several decades and is believed to play a role in the rising epidemic of metabolic disorders[14]. Fructose is a simple monosaccharide that occurs naturally in fruit, though the two main sources of dietary fructose in the Western diet are sucrose (table sugar) and high-fructose corn syrup (HFCS)[14]. Sucrose is cleaved enzymatically during digestion to produce one fructose molecule and one glucose molecule. HFCS, on the contrary, contains free fructose and glucose in varying ratios. A popular type of HFCS that is used to sweeten beverages in the United States – HFCS-55 – contains 55% fructose, 42% glucose and 3% oligosaccharides[15]. The 1999–2004 data from the National Health and Nutrition Examination Survey (NHANES) show that the average daily intake of fructose in the United States is now approximately 49 g, which equates to 9.1% of total energy intake[16]. In comparison, the average daily intake of fructose during 1977–1978 was 37 g[16]. The highest consumers of fructose are 19–22-year-olds, largely due to excess consumption of sugar-sweetened beverages. Fructose consumption as a percentage of total energy intakes amongst male and female 19–22-year-olds in the 95th percentile is 17.5 and 17.9%, respectively[16]. |
| Source of fructose | It is located in fruits and honey. Main source is sucrose; the sucrose is hydrolyzed by sucrase into fructose and glucose. It is absorbed through facilitated diffusion and can be obtained from the portal blood to the liver where it is converted to glucose[17]. |
| Biomedical importance of fructose | This disease occurs due to deficiency of aldolase B. It has been observed in children, when children receive fructose in the diet. The vomiting and hypoglycemia is an important feature of this disease. Fructose 1 phosphate accumulates in the liver. Accumulation exhausts inorganic phosphate thereby inhibiting both glycogen phosphorylase and the synthesis of ATP. Inhibition of these reactions leads to hypoglycaemia. AMP also accumulates and metabolism leads to increased production of uric acid leading to hyperuricemia and gout[18]. Treatment of this disease includes avoiding substances containing fructose[19]. |
| Fructose metabolism | Sugar is present in fruits. Sucrose is hydrolyzed by sucrase to glucose and fructose. Dietary fructose is transferred from the intestine to the liver for metabolism. Fructose is converted to fructose 1 phosphate that further converted to acetone and glyceraldehyde dihydroxy, which is further converted to glyceraldehyde 3 phosphate to enter glycolysis. In the well-fed state, fructose is converted to glycogen[20] or triglycerides[21]. Hyperlipidemia, diabetes mellitus and obesity are interlinked. Consumption of fructose is increasing and is considered responsible for overweight. Several studies show that fructose increases incidence of obesity, dyslipidemia, insulin resistance, and hypertension. Metabolism of fructose takes place mainly in the liver and high fructose stream leads to accumulation of triglycerides in the liver (hepatic steatosis). This results in impairment of lipid metabolism and enhancement of expression of proinflammatory cytokine. Fructose alters glucose-induced expression of activated acetyl CoA carboxylase (ACC), pSer hormone sensitive lipase (pSerHSL) and adipose triglyceride lipase (ATGL) in HepG2 liver or primary liver cell cultures in vitro. This relates to the increased de novo synthesis of triglycerides in vitro and in vivo hepatic steatosis in fructose-fed versus glucose-and standard-diet mice fed. These studies provide new understanding of the mechanisms involved in fructose-mediated hepatic hypertriglyceridemia[22]. Rate of metabolism of fructose is more rapid than glucose, because triose formed from fructose 1-phosphate by pass phosphofructokinase, the primary rate-limiting step in glycolysis. Elevated levels of dietary fructose significantly elevate the rate of lipogenesis in the liver, because of the rapid production of acetyl-coenzyme A[23]. |
| Fructose and diseases | Fructose and hyperuricemia Increased intake of fructose is associated with hyperuricemia. Various studies indicate that that increased intake of sugar sweetened soft drinks and fructose is associated with risk of hyperuricemia in men[24]. Fructose and metabolic syndrome It is hypothesized that fructose induces metabolic syndrome in health individuals. Study was carried out to investigate the role of uric acid in the hypertensive response. In this study, allopurinol was given to patients to lower the serum uric acid level. Ultimately it was found that excessive intake of fructose can increase the blood pressure and is responsible of metabolic syndrome but the lowering of serum uric acid level by allopurinol prevents the increase in mean arterial blood pressure[25]. Fructose and obesity Fructose is almost similar to glucose because they are isomers to each other. Difference is in their metabolic pathway due to its almost complete hepatic extraction and rapid hepatic conversion into glucose, glycogen, lactate, and fat. In initial period when science was not so progressed, the diabetics patients were using fructose due to its low glycemic index. It has been observed now that obesity, diabetes mellitus, insulin resistance and hypertension are associated with chronic consumption of fructose. Dyslipidemia and impairment in hepatic insulin resistance are also due to increase intake of fructose in the diet. Adverse metabolic effects of fructose are responsible for hepatic de novo lipogenesis, hyperuricemia, oxidative stress and lipotoxicity. Epidemiological studies show that obesity, metabolic and cardiovascular disorders are also due to consumption of sweetened beverages (containing either sucrose or a mixture of glucose and fructose). Adverse metabolic effects of fructose are usually on high consumption and there is lack of evidence of adverse effect on moderate consumption of fructose. Study shows that free fructose is more dangerous than consumption of fructose consumed with sucrose[26]. Fructose and hypertension The rise in fructose intake has been paralleled by a rise in hypertension. A study of the US population during 2007–2008 found that 29% of adults were hypertensive, compared to 11–13% in 1939 and 24% during 1988–1994[27,28]. Epidemiological studies have hinted at a link between fructose consumption and hypertension. Jalal et al.[29] reported that excess dietary fructose (>74 g/day) in the form of added sugar was associated with higher blood pressure (BP) values in US adults who did not have a history of hypertension. Similarly, a study of 4867 adolescents found that SBP rose by 2mmHg from the lowest to the highest category of sugar-sweetened beverage intake[30]. In a prospective study of US adults, Chen et al.[31] found that drinking one less sugar-sweetened beverage per day was associated with a 1.8mmHg reduction in SBP and a 1.1mmHg reduction in DBP over 18 months. |
| References |
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| Chemical Properties | White Cyrstalline Solid |
| Chemical Properties | Fructose occurs as odorless, colorless crystals or a white crystallinepowder with a very sweet taste. |
| Originator | Levugen,Baxter,US,1953 |
| History | Despite this ubiquity, fructose remained a noncommercial product until the 1980s because of the expense involved in its isolation and the care required for its handling. The development of technologies for preparing fructose from glucose in the isomerized mixture led to a greater availability of pure, crystalline fructose in the 1970s. However, the price for pure fructose was high enough in 1981 that the product was not competitive with sucrose and corn syrups as a commercial sweetener. With the entry of corn wet-milling companies into the crystalline fructose market in the late 1980s, raw material economies and enlarged manufacturing scale led to a nearly 10-fold production increase within a five-year period, making fructose prices competitive with other sweeteners for specific applications. |
| Uses | D-Fructose occurs in a large number of fruits, honey, and as the sole sugar in bull and human semen |
| Uses | fructose is a naturally occurring sugar in fruits and honey. It has moisture-binding and skin-softening properties. |
| Uses | Fructose is a sweetener that is a monosaccharide found naturally in fresh fruit and honey. It is obtained by the inversion of sucrose by means of the enzyme invertase and by the isomerization of corn syrup. It is 130–180 in sweetness range as compared to sucrose at 100 and is very water soluble. It is used in baked goods because it reacts with amino acids to produce a browning reaction. It is used as a nutritive sweetener in low-calorie beverages. It is also termed levulose and fruit sugar. |
| Production Methods | Fructose, a monosaccharide sugar, occurs naturally in honey and alarge number of fruits. It may be prepared from inulin, dextrose, orsucrose by a number of methods. Commercially, fructose is mainlymanufactured by crystallization from high-fructose syrup derivedfrom hydrolyzed and isomerized cereal starch or cane and beetsugar. |
| Definition | A sugar found in fruit juices,honey, and cane sugar. It is a ketohexose,existing in a pyranose form when free. Incombination (e.g. in sucrose) it exists in thefuranose form. |
| Manufacturing Process | 200 gal of medium containing 2% sucrose, 2% corn steep liquor solids, 0.1%potassium dihydrogen phosphate, and traces of mineral salts, was inoculatedwith Leuconostoc mesenteroides NRRL B-512 and incubated at 25°C. Duringgrowth, alkali was added automatically as needed to maintain the pH between6.6 and 7.0. Fermentation was completed in 11 hours and the culture wasimmediately adjusted to pH 5 to maintain enzyme stability. Bacterial cellswere removed by filtration and yielded a culture filtrate containing 40dextransucrase units per ml, where one unit is the amount of dextransucrasewhich will convert 1 mg of sucrose to dextran, as determined by the amountof fructose liberated, measured as reducing power in 1 hour. 10 gal of the above culture filtrate was diluted to 40 gal with water, 33.3 lb ofsucrose was added to give a 10% solution, and toluene was added as apreservative. Dextran synthesis was complete before 22 hours, and dextranwas harvested at 24 hours by the addition of alcohol to be 40% on a volumebasis. The alcoholic supernatant liquor obtained was evaporated to recover thealcohol and yielded a thick syrup, rich in fructose. Analysis showed the syrupto contain 50.1% of reducing sugar, calculated as monosaccharide and to havean optical rotation equivalent to 35.1% fructose. The percentages areexpressed on a weight/volume basis, and reducing power was determined bythe method of Somogyi, Jour. Biol. Chem. 160, 61 (1945). A portion (4.3liters) of the syrup was cooled to 3°C. One-tenth of this volume was treatedby slow regular addition, with rapid stirring, of a 6-fold volume of cold 20%calcium oxide suspension. A second portion was treated in the same manner,and this process was continued until the entire volume of crude fructose syruphad been utilized. The reaction mixture became thick with a white sedimentcontaining a profusion of microscopic needlelike crystals of calcium levulate.Stirring was continued for 2 hours. The calcium levulate precipitate was separated from the reaction mixture byfiltration and washed with cold water. The precipitate was suspended in waterto give a thick slurry, and solid carbon dioxide added until the solution wascolorless to phenolphthalein. A heavy precipitate of calcium carbonate wasnow present and free fructose remained in the solution. The calciumcarbonate precipitate was removed by filtration, and the filtered solution wasfound to contain 1,436 g of fructose as determined by optical rotation. A smallamount of calcium bicarbonate was present as an impurity in solution and wasremoved by the addition of oxalic acid solution until a test for both calciumand oxalic acid was negative. The insoluble calcium oxalate precipitate wasremoved by filtration. The fructose solution was decolorized by treatment with activated charcoaland concentrated under vacuum to a thick syrup. Two volumes of hot 95%ethyl alcohol were added, and the solution was heated to a boil and filtered to remove a small amount of insoluble material. After cooling, three volumes ofethyl ether were added, and the solution was allowed to stand overnight inthe refrigerator. Fructose separated from the solution as a thick syrup and wasseparated from the supernatant liquid by decantation. The syrup was seededwith fructose crystals and after standing in the cold for 4 days, became acrystalline mass of fructose. The yield of dry fructose was 928 g. Additionalrecoverable quantities of fructose are present in the crystallization motherliquor. In continuous operation this mother liquor may be recycled for additionto subsequent quantities of fructose syrup and the combined liquorscrystallized as in the foregoing example. |
| Therapeutic Function | Fluid replenisher, Pharmaceutic aid |
| General Description | Fructose is a monosaccharide. It is present in fruits and vegetables. Fructose is the major carbohydrate in the diet. It binds with glucose to form sucrose. Excessive intake of fructose is associated with obesity, type 2 diabetes and cardiovascular disease. |
| Pharmaceutical Applications | Fructose is used in tablets, syrups, and solutions as a flavoring andsweetening agent. The sweetness-response profile of fructose is perceived in themouth more rapidly than that of sucrose and dextrose, which mayaccount for the ability of fructose to enhance syrup or tablet fruitflavors and mask certain unpleasant vitamin or mineral ‘off-flavors’. The increased solubility of fructose in comparison to sucrose isadvantageous in syrup or solution formulations that must berefrigerated, since settling or crystallization of ingredients isretarded. Similarly, the greater solubility and hygroscopicity offructose over sucrose and dextrose helps to avoid ‘cap-locking’(sugar crystallization around the bottle cap) in elixir preparations.Fructose also has greater solubility in ethanol (95%) and istherefore used to sweeten alcoholic formulations. The water activity of a sweetener influences product microbialstability and freshness. Fructose has a lower water activity and ahigher osmotic pressure than sucrose. Syrup formulations may bemade at lower dry-substance levels than sugar syrups withoutcompromising shelf-life stability. It may be necessary to include athickener or gelling agent to match the texture or viscosity of thesugar-equivalent formulation. Fructose is sweeter than the sugar alcohols mannitol andsorbitol, which are commonly used as tableting excipients.Although fructose is effective at masking unpleasant flavors intablet formulations, tablets of satisfactory hardness and friabilitycan only be produced by direct compression if tablet presses areoperated at relatively slow speeds. However, by the combination ofcrystalline fructose with tablet-grade sorbitol in a 3 : 1 ratio,satisfactory direct-compression characteristics can be achieved. Adirectly compressible grade of fructose, containing a small amountof starch (Advantose FS 95, SPI Pharma) is also commerciallyavailable. Pregranulation of fructose with 3.5% povidone alsoproduces a satisfactory tablet excipient.(1) The added sweetness offructose may also be used to advantage by coating the surface ofchewable tablets, lozenges, or medicinal gums with powderedfructose. The coprecipitation of fructose with hydrophobic drugs such asdigoxin has been shown to enhance the dissolution profile of suchdrugs. Fructose apparently acts as a water-soluble carrier uponcoprecipitation, thereby allowing hydrophobic drugs to be morereadily wetted. |
| Biochem/physiol Actions | D-(?)-Fructose can enhance mood and gastrointestinal disturbances in fructose malabsorbers. It also possess metabolic and endocrine impact that shows that increased consumption of fructose is a contributing factor in the development of obesity and the accompanying metabolic abnormalities observed in the insulin resistance syndrome. |
| Safety | Although it is absorbed more slowly than dextrose from thegastrointestinal tract, fructose is metabolized more rapidly. Metabolismof fructose occurs mainly in the liver, where it is convertedpartially to dextrose and the metabolites lactic acid and pyruvicacid. Entry into the liver and subsequent phosphorylation is insulinindependent.Further metabolism occurs by way of a variety ofmetabolic pathways. In healthy and well regulated diabetics,glycogenesis (glucose stored as glycogen) predominates. Excessive oral fructose consumption (>75 g daily) in the absenceof dietary dextrose in any form (e.g. sucrose, starch, dextrin, etc.)may cause malabsorption in susceptible individuals, which mayresult in flatulence, abdominal pain, and diarrhea. Except inpatients with hereditary fructose intolerance, there is noevidence to indicate that oral fructose intake at current levels is arisk factor in any particular disease, other than dental caries. |
| storage | Fructose is hygroscopic and absorbs significant amounts ofmoisture at relative humidities greater than 60%. Goods stored inthe original sealed packaging at temperatures below 25°C and arelative humidity of less than 60% can be expected to retain stabilityfor at least 12 months. Aqueous solutions are most stable at pH 3–4 and temperaturesof 4–70°C; they may be sterilized by autoclaving. |
| Purification Methods | Dissolve D(-)-fructose in an equal weight of water (charcoal, previously washed with water to remove any soluble material), filter and evaporate under reduced pressure at 45-50o to give a syrup containing 90% of fructose. After cooling to 40o, the syrup is seeded and kept at this temperature for 20-30hours with occasional stirring. The crystals are removed by centrifugation, washed with a small quantity of water and dried to constant weight under a vacuum over conc H2SO4. For higher purity, this material is recrystallised from 50% aqueous ethanol [Tsuzuki et al. J Am Chem Soc 72 1071 1950]. [Beilstein 31 H 321, 1 IV 4401.] |
| Incompatibilities | Incompatible with strong acids or alkalis, forming a browncoloration. In the aldehyde form, fructose can react with amines,amino acids, peptides, and proteins. Fructose may cause browningof tablets containing amines. |
| Regulatory Status | Included in the FDA Inactive Ingredients Database (oral solutions,syrup, and suspensions; rectal preparations; intravenous infusions).Included in the Canadian List of Acceptable Non-medicinalIngredients. |
D(-)-Fructose Preparation Products And Raw materials
| Raw materials | Carbon dioxide-->Sucrose-->Molasses-->beta-D-Fructopyranose-->High Fructose Syrups-->AROMA-->INVERTOSE-->IRISH MOSS-->DEXTROSE-->Invertase，from yeast-->Immobilized glucose isomerase preparation-->GLUCOSE ISOMERASE FROM STREPTOMYCES-->Honey-->INULIN, 14C-CARBOXYLATED-->CORN STEEP LIQUOR-->(2S,3R)-3-Hydroxyasparagine-->3-Phenyl-L-serine |
| Preparation Products | 1H-Imidazole-4-carbaldehyde-->4-Imidazolemethanol hydrochloride-->Urocanic acid-->N-OMEGA-ACETYLHISTAMINE-->4-IMIDAZOLEACETIC ACID HYDROCHLORIDE-->4(5)-CYANOMETHYLIMIDAZOLE |
