FRUCTOSE

Fructose is a naturally occurring simple sugar (monosaccharide) found in many plants. 
It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed directly into the bloodstream during digestion.

CAS Number: 57-48-7
Synonyms 
Fruit sugar,D-Fructose,Levulose,D-arabino-hexulose,β-D-fructofuranose,D-(-)-Fructopyranose
D-fructose, crystalline,Laevulose

Introduction

Fructose is a naturally occurring monosaccharide commonly found in fruits, vegetables, and honey. 
It is one of the three dietary monosaccharides, alongside glucose and galactose, that are absorbed directly into the bloodstream during digestion. 
Fructose has gained significant attention in recent decades due to its increasing prevalence in processed foods and beverages, largely through the use of high-fructose corn syrup (HFCS). 
This sugar, while naturally present in whole foods, has been linked to various health issues when consumed in excess. 
Understanding the chemistry, metabolism, applications, and health effects of fructose is crucial in addressing its role in human nutrition and health.

Historically, fructose was first identified in the 19th century. It was initially isolated from fruits and recognized for its sweetening properties. 
Over time, advances in biotechnology enabled large-scale production from corn starch, making it a key ingredient in the food industry. 
The unique properties of fructose, including its high relative sweetness and ability to retain moisture, have solidified its position as a valuable component in a wide array of consumer products.

Chemical Structure and Properties
Fructose has the molecular formula C6H12O6 and is classified as a ketohexose due to the presence of a ketone group and six carbon atoms. 
It exists in several isomeric forms, including the linear chain and cyclic structures (furanose and pyranose rings). 
The furanose form predominates in aqueous solutions.

Fructose is highly soluble in water, with a solubility of approximately 375 g/L at 25°C, and exhibits a high sweetness index, nearly 1.7 times that of sucrose. 
It is a reducing sugar and participates in Maillard reactions, contributing to browning and flavor development in cooked foods. 
Fructose is optically active, displaying specific rotation depending on its structural form.

Fructose's physical properties include a melting point of 103°C when anhydrous and a refractive index of 1.4818 in aqueous solution. 
It is hygroscopic, which makes it useful in food preservation by inhibiting microbial growth through water activity reduction.

Natural Sources of Fructose
Fructose is abundantly found in many fruits such as apples, grapes, and berries, as well as in vegetables like carrots and sweet onions. 
Honey is another rich source, containing about 38% fructose. 
The content of fructose in natural products varies with factors such as species, cultivar, ripeness, and growing conditions.

Analytical techniques such as high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) are commonly used to quantify fructose levels in food samples. 
Understanding these sources and their compositions is essential for nutritional planning and for individuals with fructose intolerance.

Industrial Production of Fructose
Industrially, fructose is primarily produced from corn starch via enzymatic isomerization of glucose. The process involves the use of glucose isomerase, which converts glucose into fructose, yielding high-fructose corn syrup (HFCS). 
The HFCS can contain varying ratios of fructose to glucose, such as HFCS-42 (42% fructose) and HFCS-55 (55% fructose).

Purification steps involve ion exchange chromatography and crystallization to obtain pure crystalline fructose. 
The production process is economically efficient, contributing to the widespread use of fructose in the food industry. 
Global production statistics indicate that the United States, China, and Brazil are leading producers.

Metabolism and Biochemistry
Unlike glucose, which is metabolized throughout the body, fructose is primarily metabolized in the liver. 
Upon absorption, fructose enters hepatocytes via GLUT5 and GLUT2 transporters. 
It is phosphorylated by fructokinase to fructose-1-phosphate, which is then split by aldolase B into dihydroxyacetone phosphate and glyceraldehyde.

These intermediates can enter glycolysis, gluconeogenesis, or lipogenesis. 
Notably, fructose metabolism bypasses the regulatory step catalyzed by phosphofructokinase, leading to unregulated glycolytic flux. 
This property is central to the hypothesis linking excessive fructose intake to metabolic disorders.

Functional Uses in the Food Industry

Fructose's high sweetness and solubility make it ideal for sweetening beverages, cereals, and baked goods. 
It is used to enhance flavor, improve texture, and increase shelf life. 
Fructose contributes to browning through Maillard reactions, which is desirable in products like cookies and bread.

Its hygroscopic nature helps retain moisture, improving softness and palatability. 
Fructose is also used in sports drinks and nutrition bars due to its rapid energy release. 
The food industry values its versatility and cost-effectiveness, particularly in the form of HFCS.

Technological and Biotechnological Applications

Beyond food, fructose finds use in pharmaceuticals as a stabilizer and excipient. 
It is employed in cough syrups and oral rehydration solutions due to its pleasant taste and osmotic properties.

In biotechnology, fructose is used in microbial fermentation processes. 
Engineered yeast strains utilize fructose to produce ethanol, organic acids, and bioplastics. 
Fructose derivatives are also investigated for use in biodegradable polymers and drug delivery systems.

Health Effects and Nutritional Aspects
Fructose provides 4 kcal/g of energy and has a low glycemic index (GI), which means it causes a slower rise in blood glucose levels. 
However, its metabolism in the liver and potential to promote de novo lipogenesis (fat synthesis) raises concerns.

In moderate amounts, fructose from whole fruits is considered safe and even beneficial due to the presence of fiber, vitamins, and antioxidants. 
Excessive intake from processed foods, however, is associated with increased risk of obesity, insulin resistance, and type 2 diabetes.

Fructose and Metabolic Disorders

Excessive consumption of fructose, especially from HFCS, is linked to metabolic syndrome components, including abdominal obesity, dyslipidemia, and hypertension. 
Fructose increases hepatic triglyceride synthesis, contributing to non-alcoholic fatty liver disease (NAFLD).

It also impacts insulin sensitivity and may exacerbate insulin resistance. 
Epidemiological studies have shown correlations between high fructose intake and increased incidence of cardiovascular disease. 
Mechanistic studies suggest that fructose-induced ATP depletion in the liver triggers oxidative stress and inflammation.

SAFETY INFORMATION ABOUT FRUCTOSE

 
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product