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D-Psicose (C6H12O6), also known as D-allulose, or simply allulose, is a low-calorie
epimer In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is ...
of the
monosaccharide Monosaccharides (from Greek ''monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-solub ...
sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...
fructose Fructose, or fruit sugar, is a Ketose, ketonic monosaccharide, simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galacto ...
, used by some major commercial food and beverage manufacturers as a low-calorie sweetener. First identified in wheat in the 1940s, allulose is naturally present in small quantities in certain foods. The U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
(FDA) has accepted a petition for Generally Recognized As Safe (GRAS) for allulose as a sugar substitute in various specified food categories. Because it is absorbed and metabolized differently from other sugars, the FDA has exempted allulose from the listing of total and added sugars on the Nutrition and Supplement Facts labels, but requires the labeling of 0.4kcal/g as carbohydrate.


Dietary effect

A
meta-analysis A meta-analysis is a statistical analysis that combines the results of multiple scientific studies. Meta-analyses can be performed when there are multiple scientific studies addressing the same question, with each individual study reporting me ...
was conducted of the effect on
postprandial glucose A postprandial glucose (PPG) test is a blood glucose test that determines the amount of glucose, in the plasma after a meal. The diagnosis is typically restricted to ''postprandial hyperglycemia'' due to lack of strong evidence of co-relation with ...
and insulin responses of adding a median of 5 grams of allulose (range, 2.5-10 g) to a fixed carbohydrate-containing drink or meal, versus the same meal alone. Five studies were included, with a median of 18 largely middle-aged participants, including nondiabetic subjects in three studies and subjects with
pre-diabetes Prediabetes is a component of the metabolic syndrome and is characterized by elevated blood sugar levels that fall below the threshold to diagnose diabetes mellitus. It usually does not cause symptoms but people with prediabetes often have obesit ...
and/or
Type II diabetes Type 2 diabetes, formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, ...
in the other two. Three of the 5 studies used a reference 75 gram
oral glucose tolerance test The glucose tolerance test (GTT, not to be confused with GGT test) is a medical test in which glucose is given and blood samples taken afterward to determine how quickly it is cleared from the blood. The test is usually used to test for diabetes, ...
(OGTT) for at least one comparison; some studies used other glucose-containing foods either as the sole comparison or as an additional arm along with the OGTT, for a total of ten comparisons. To control for sweetness,
aspartame Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names ...
was added to the control preparation in two of the five studies. Overall, compared to the carbohydrate-containing meal alone, the same meal with a small dose of added allulose resulted in a 10% lower integrated
area under the curve In mathematics, an integral assigns numbers to functions in a way that describes displacement, area, volume, and other concepts that arise by combining infinitesimal data. The process of finding integrals is called integration. Along with ...
(iAUC) of postprandial glucose. The quality of the evidence was rated as moderate.


Biochemistry

The
sweetness Sweetness is a Taste#Basic tastes, basic taste most commonly Perception, perceived when eating foods rich in sugars. Sweet tastes are generally regarded as pleasure, pleasurable. In addition to sugars like sucrose, many other chemical compounds ...
of allulose is estimated to be 70% of the sweetness of
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...
. It has some cooling sensation and no bitterness. Its taste is said to be sugar-like, in contrast to certain other sweeteners, like the high-intensity
artificial sweetener A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie () or low-calorie sweetener. Artificial sweeteners may be d ...
s
aspartame Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names ...
and
saccharin Saccharin (''aka'' saccharine, Sodium sacchari) is an artificial sweetener with effectively no nutritional value. It is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is u ...
. The caloric value of allulose in humans is about 0.2 to 0.4 kcal/g, relative to about 4 kcal/g for typical carbohydrates. In rats, the relative energy value of allulose was found to be 0.007 kcal/g, or approximately 0.3% of that of sucrose. Similar to the
sugar alcohol Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (–OH) attached to each carbon atom. They are white, water-soluble solids ...
erythritol Erythritol is an organic compound, a four-carbon sugar alcohol (or polyol) with no optical activity, used as a food additive and sugar substitute. It is naturally occurring. It can be made from corn using enzymes and fermentation. Its formula i ...
, allulose is minimally
metabolized Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
and is
excreted Excretion is a process in which metabolic waste is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after lea ...
largely unchanged. The
glycemic index The glycemic (glycaemic) index (GI; ) is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of ...
of allulose is very low or negligible. Allulose is a weak
inhibitor Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity * Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
of the
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
s
α-glucosidase Glycoside hydrolases (also called glycosidases or glycosyl hydrolases) catalyze the hydrolysis of glycosidic bonds in complex sugars. They are extremely common enzymes with roles in nature including degradation of biomass such as cellulose (cel ...
,
α-amylase α-Amylase is an enzyme (EC 3.2.1.1; systematic name 4-α-D-glucan glucanohydrolase) that hydrolyses α bonds of large, α-linked polysaccharides, such as starch and glycogen, yielding shorter chains thereof, dextrins, and maltose: :Endohydr ...
,
maltase Maltase (, ''alpha-glucosidase'', ''glucoinvertase'', ''glucosidosucrase'', ''maltase-glucoamylase'', ''alpha-glucopyranosidase'', ''glucosidoinvertase'', ''alpha-D-glucosidase'', ''alpha-glucoside hydrolase'', ''alpha-1,4-glucosidase'', ''alp ...
, and
sucrase Sucrase is a digestive enzyme that catalyzes the hydrolysis of sucrose to its subunits fructose and glucose. One form, sucrase-isomaltase, is secreted in the small intestine on the brush border. The sucrase enzyme invertase, which occurs more commo ...
. Because of this, it can inhibit the
metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...
of
starch Starch or amylum is a polymeric carbohydrate consisting of numerous glucose units joined by glycosidic bonds. This polysaccharide is produced by most green plants for energy storage. Worldwide, it is the most common carbohydrate in human diets ...
and
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lact ...
s into
monosaccharide Monosaccharides (from Greek ''monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-solub ...
s in the
gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organ (biology), organs of the digestive syste ...
. Additionally, allulose inhibits the absorption of
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...
via transporters in the
intestine The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans ...
s. For these reasons, allulose has potential
antihyperglycemic Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exceptions of insulin, most GLP receptor agonists (liraglutide, exenatide, and others), and pramlintide, all are administered orally and are thus ...
effects, and has been found to reduce
postprandial Prandial relates to a meal. Postprandial (from post prandium) means after eating a meal, while preprandial is before a meal. Usages of postprandial The term ''postprandial'' is used in many contexts. Gastronomic or social Refers to activities p ...
hyperglycemia Hyperglycemia is a condition in which an excessive amount of glucose circulates in the blood plasma. This is generally a blood sugar level higher than 11.1 mmol/L (200  mg/dL), but symptoms may not start to become noticeable until even ...
in humans. Through modulation of lipogenic
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
s in the
liver The liver is a major Organ (anatomy), organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of proteins and biochemicals necessary for ...
, allulose may also have
antihyperlipidemic Lipid-lowering agents, also sometimes referred to as hypolipidemic agents, cholesterol-lowering drugs, or antihyperlipidemic agents are a diverse group of pharmaceuticals that are used to lower the level of lipids and lipoproteins such as cholester ...
effects. Due to its effect of causing incomplete absorption of carbohydrates from the
gastrointestinal tract The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organ (biology), organs of the digestive syste ...
, and subsequent
fermentation Fermentation is a metabolic process that produces chemical changes in organic substrates through the action of enzymes. In biochemistry, it is narrowly defined as the extraction of energy from carbohydrates in the absence of oxygen. In food ...
of these carbohydrates by intestinal bacteria, allulose can result in unpleasant symptoms such as
flatulence Flatulence, in humans, is the expulsion of gas from the intestines via the anus, commonly referred to as farting. "Flatus" is the medical word for gas generated in the stomach or bowels. A proportion of intestinal gas may be swallowed environm ...
,
abdominal discomfort Abdominal pain, also known as a stomach ache, is a symptom associated with both non-serious and serious medical issues. Common causes of pain in the abdomen include gastroenteritis and irritable bowel syndrome. About 15% of people have a more ...
, and
diarrhea Diarrhea, also spelled diarrhoea, is the condition of having at least three loose, liquid, or watery bowel movements each day. It often lasts for a few days and can result in dehydration due to fluid loss. Signs of dehydration often begin wi ...
. The maximum non-effect dose of allulose in causing diarrhea in humans has been found to be 0.55 g/kg of body weight. This is higher than that of most sugar alcohols (0.17–0.42 g/kg), but is less than that of erythritol (0.66–1.0+ g/kg). D-allulose was found to be more reactive than fructose and glucose in glycation reactions.


Chemistry

Allulose, also known by its
systematic name A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance, out of a specific population or collection. Systematic names are usually part of a nomenclature. A semisystematic name or semitrivial ...
D-ribo-2-hexulose as well as by the name D-psicose, is a
monosaccharide Monosaccharides (from Greek ''monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. They are usually colorless, water-solub ...
and a
ketohexose In chemistry, a hexose is a monosaccharide (simple sugar) with six carbon atoms. The chemical formula for all hexoses is C6H12O6, and their molecular weight is 180.156 g/mol. Hexoses exist in two forms, open-chain or cyclic, that easily convert ...
. It is a C3
epimer In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have opposite configuration at only one stereogenic center out of at least two. All other stereogenic centers in the molecules are the same in each. Epimerization is ...
of
fructose Fructose, or fruit sugar, is a Ketose, ketonic monosaccharide, simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galacto ...
. Fructose can be converted to allulose by the
enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrates, and the enzyme converts the substrates into different molecules known as products. A ...
D-tagatose 3-epimerase, which has allowed for
mass production Mass production, also known as flow production or continuous production, is the production of substantial amounts of standardized products in a constant flow, including and especially on assembly lines. Together with job production and batch ...
of allulose. The compound is found naturally in trace amounts in
wheat Wheat is a grass widely cultivated for its seed, a cereal grain that is a worldwide staple food. The many species of wheat together make up the genus ''Triticum'' ; the most widely grown is common wheat (''T. aestivum''). The archaeologi ...
,
fig The fig is the edible fruit of ''Ficus carica'', a species of small tree in the flowering plant family Moraceae. Native to the Mediterranean and western Asia, it has been cultivated since ancient times and is now widely grown throughout the world ...
s,
raisin A raisin is a dried grape. Raisins are produced in many regions of the world and may be eaten raw or used in cooking, baking, and brewing. In the United Kingdom, Ireland, New Zealand, and Australia, the word ''raisin'' is reserved for the d ...
s,
maple syrup Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple tree ...
, and
molasses Molasses () is a viscous substance resulting from refining sugarcane or sugar beets into sugar. Molasses varies in the amount of sugar, method of extraction and age of the plant. Sugarcane molasses is primarily used to sweeten and flavour foods ...
. Allulose has similar physical properties to those of regular sugar, such as bulk, mouthfeel, browning capability, and freeze point. This makes it favorable for use as a sugar replacement in food products, including ice cream.


History

Allulose was first discovered in the 1940s. The first mass-production method for allulose was established when Ken Izumori at
Kagawa University is a national university in Takamatsu, Kagawa, Japan. The university was established in 1949 as a national university after the consolidation and reorganization of the Kagawa Normal School, the Kagawa Normal School for Youth and the Takamatsu Co ...
in Japan discovered the key enzyme, D-tagatose 3-epimerase, to convert fructose to allulose in 1994. This method of production has a high yield, but suffers from a very high production cost. In June 2012, the U.S.
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a List of United States federal agencies, federal agency of the United States Department of Health and Human Services, Department of Health and Human Services. The FDA is respon ...
(FDA) accepted the assertion of CJ CheilJedang, Inc. that allulose is Generally Recognized As Safe (GRAS) as a sugar substitute in various specified food categories. In June 2014, a similar GRAS letter was issued to Matsutani Chemical Industry Company, Ltd. The first Non-GMO allulose was manufactured by Samyang Corporation. Allulose is not approved for use in the
European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been des ...
. In October 2019, the FDA announced exemption of allulose from total and added sugars on nutritional label but adding 0.4kcal/g as carbohydrate. Studies have shown the commercial product is not absorbed in the human body the way common sugars are and does not raise
insulin Insulin (, from Latin ''insula'', 'island') is a peptide hormone produced by beta cells of the pancreatic islets encoded in humans by the ''INS'' gene. It is considered to be the main anabolic hormone of the body. It regulates the metabolism o ...
levels, but more testing may be needed to evaluate any other potential side effects.


Manufacturing

As of 2018, most commercially available allulose was produced from corn. Allulose is also produced from
beet sugar A sugar beet is a plant whose root contains a high concentration of sucrose and which is grown commercially for sugar production. In plant breeding, it is known as the Altissima cultivar group of the common beet (''Beta vulgaris''). Together wit ...
.


Commercial application

Commercial manufacturers and food laboratories are looking into properties of allulose that may differentiate it from sucrose and fructose sweeteners, including an ability to induce the high foaming property of
egg white Egg white is the clear liquid (also called the albumen or the glair/glaire) contained within an egg. In chickens it is formed from the layers of secretions of the anterior section of the hen's oviduct during the passage of the egg. It forms arou ...
protein and the production of antioxidant substances produced through the
Maillard reaction The Maillard reaction ( ; ) is a chemical reaction between amino acids and reducing sugars that gives browned food its distinctive flavor. Seared steaks, fried dumplings, cookies and other kinds of biscuits, breads, toasted marshmallows, and man ...
. Commercial uses of allulose include
low-calorie Calorie restriction (caloric restriction or energy restriction) is a dietary regimen that reduces intake of energy from caloric foods & beverages without incurring malnutrition. "Reduce" can be defined relative to the subject's previous intake be ...
sweeteners in beverages, yogurt, ice cream, baked goods, and other typically high-calorie items. London-based
Tate & Lyle Tate & Lyle PLC is a British-headquartered, global supplier of food and beverage ingredients to industrial markets. It was originally a sugar refining business, but from the 1970s it began to diversify, eventually divesting its sugar business i ...
released its proprietary variant of allulose, known as Dolcia Prima allulose, and U.S.-based Anderson Global Group released its own proprietary variant into the North American market in 2015. The first major food company to adopt allulose as a sweetener was
Quest Nutrition A quest is a journey toward a specific mission or a goal. The word serves as a plot device in mythology and fiction: a difficult journey towards a goal, often symbolic or allegorical. Tales of quests figure prominently in the folklore of eve ...
in some of their
protein bar Protein bars are nutrition bars that contain a high proportion of protein to carbohydrates/ fats. Dietary purpose Protein bars are targeted to people who primarily want a convenient source of protein that does not require preparation (unless h ...
products. On April 16, 2019, US Food and Drug Administration (FDA) issued a draft guidance, allowing food manufacturers to exclude allulose from total and added sugar counts on Nutrition and Supplement Facts labels. Like sugar alcohols and dietary fiber, allulose will still count towards total carbohydrates on nutrition labels. This, combined with the GRAS designation, has increased interest in including allulose in food products instead of sucrose.


References

{{Carbohydrates Ketohexoses