Sorbitol
Encyclopedia
Sorbitol, also known as glucitol, Sorbogem® and Sorbo®, is a sugar alcohol
that the human body metabolizes slowly. It can be obtained by reduction
of glucose
, changing the aldehyde
group to a hydroxyl
group. Sorbitol is found in apples, pears, peaches, and prunes. It is synthesized by sorbitol-6-phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase
. Succinate dehydrogenase is an enzyme complex that participates in the citric acid
cycle.
. It may be listed under the inactive ingredients listed for some foods and products. Sorbitol is referred to as a nutritive sweetener because it provides dietary energy: 2.6 kilocalories (11 kilojoules) per gram
versus the average 4 kilocalories (17 kilojoules) for carbohydrates. It is often used in diet food
s (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum
.
It also occurs naturally in many stone fruit
s and berries from trees of the genus Sorbus
.
via an oral suspension or enema
. As with other sugar alcohol
s, gastroitestinal distress may result when food products that contain sorbitol are consumed. Sorbitol exerts its laxative effect by drawing water into the large intestine
, thereby stimulating bowel movements. Sorbitol has been determined safe for use by the elderly, although it is not recommended without consultation with a clinician. Sorbitol is found in some dried fruits and may contribute to the laxative effects of prunes.
Sorbitol, combined with kayexalate
, helps the body rid itself of excess potassium
ions in a hyperkalaemic state. The kayexalate exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. The FDA has discouraged this combination when in 2010 it issued a warning of increased risk for GI necrosis.
as a humectant
and thickener. Sorbitol often is used in mouthwash
and toothpaste
. Some transparent gel
s can be made only with sorbitol, as it has a refractive index
sufficiently high for transparent formulations. It is also used frequently in almost all "sugar free" chewing gum.
Sorbitol is used as a cryoprotectant
additive (mixed with sucrose
and sodium polyphosphate
s) in the manufacture of surimi
, a highly refined fish paste most commonly produced from Alaska pollock
(Theragra chalcogramma). It is also used as a humectant
in some cigarette
s.
Sorbitol sometimes is used as a sweetener and humectant in cookies and other foods that are not identified as "dietary" items.
is the first enzyme in the sorbitol-aldose reductase pathway
responsible for the reduction of glucose to sorbitol, as well as the reduction of galactose
to galactitol. Too much sorbitol trapped in retinal cells, the cells of the lens, and the Schwann cells that myelinate
peripheral nerves can damage these cells, leading to retinopathy
, cataract
s and peripheral neuropathy, respectively. Aldose reductase inhibitors, which are substances that prevent or slow the action of aldose reductase, are currently being investigated as a way to prevent or delay these complications, which frequently occur in the setting of long-term hyperglycemia that accompanies poorly-controlled diabetes. It is thought that these agents may help to prevent the accumulation of intracellular sorbitol that leads to cellular damage in diabetics.
, and similar gastrointestinal
conditions, resulting in severe abdominal pain for those affected, even from small amounts ingested.
, and mild to severe diarrhea
. Sorbitol ingestion of 20 gram (0.705479242102239 oz) per day as sugar-free gum has led to severe diarrhea leading to unintended weight loss of 11 kilograms (24.3 lb) in eight months, in a woman originally weighing 52 kilograms (114.6 lb); another patient required hospitalization after habitually consuming 30 grams (1 oz) per day.
has found some success as an amateur solid rocket fuel.
Sorbitol is identified as a potential key chemical intermediate from biomass
resources. Complete reduction of sorbitol opens the way to alkane
s, such as hexane
, which can be used as a biofuel
. Sorbitol itself provides much of the hydrogen required for the transformation.
The above chemical reaction
is exothermic
; 1.5 mole
s of sorbitol generate approximately 1 mole of hexane
. When hydrogen is co-fed, no carbon dioxide
is produced.
Sugar alcohol
A sugar alcohol is a hydrogenated form of carbohydrate, whose carbonyl group has been reduced to a primary or secondary hydroxyl group . Sugar alcohols have the general formula Hn+1H, whereas sugars have HnHCO...
that the human body metabolizes slowly. It can be obtained by reduction
Redox
Redox reactions describe all chemical reactions in which atoms have their oxidation state changed....
of glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...
, changing the aldehyde
Aldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
group to a hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
group. Sorbitol is found in apples, pears, peaches, and prunes. It is synthesized by sorbitol-6-phosphate dehydrogenase, and converted to fructose by succinate dehydrogenase and sorbitol dehydrogenase
Sorbitol dehydrogenase
Sorbitol dehydrogenase is a protein. In humans this protein is encoded by the SORD gene.Sorbitol dehydrogenase is an enzyme in carbohydrate metabolism converting sorbitol, the sugar alcohol form of glucose, into fructose. Together with aldose reductase, it provides a way for the body to produce...
. Succinate dehydrogenase is an enzyme complex that participates in the citric acid
Citric acid
Citric acid is a weak organic acid. It is a natural preservative/conservative and is also used to add an acidic, or sour, taste to foods and soft drinks...
cycle.
Sweetener
Sorbitol is a sugar substituteSugar substitute
A sugar substitute is a food additive that duplicates the effect of sugar in taste, usually with less food energy. Some sugar substitutes are natural and some are synthetic. Those that are not natural are, in general, called artificial sweeteners....
. It may be listed under the inactive ingredients listed for some foods and products. Sorbitol is referred to as a nutritive sweetener because it provides dietary energy: 2.6 kilocalories (11 kilojoules) per gram
Gram
The gram is a metric system unit of mass....
versus the average 4 kilocalories (17 kilojoules) for carbohydrates. It is often used in diet food
Diet food
Diet food refers to any food or drink whose recipe has been altered in some way to make it part of a body modification diet...
s (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum
Chewing gum
Chewing gum is a type of gum traditionally made of chicle, a natural latex product, or synthetic rubber known as polyisobutylene. For economical and quality reasons, many modern chewing gums use rubber instead of chicle...
.
It also occurs naturally in many stone fruit
Drupe
In botany, a drupe is a fruit in which an outer fleshy part surrounds a shell of hardened endocarp with a seed inside. These fruits develop from a single carpel, and mostly from flowers with superior ovaries...
s and berries from trees of the genus Sorbus
Sorbus
Sorbus is a genus of about 100–200 species of trees and shrubs in the subfamily Maloideae of the Rose family Rosaceae. Species of Sorbus are commonly known as whitebeam, rowan, service tree, and mountain ash...
.
Laxative
Sorbitol can be used as a non-stimulant laxativeLaxative
Laxatives are foods, compounds, or drugs taken to induce bowel movements or to loosen the stool, most often taken to treat constipation. Certain stimulant, lubricant, and saline laxatives are used to evacuate the colon for rectal and/or bowel examinations, and may be supplemented by enemas under...
via an oral suspension or enema
Enema
An enema is the procedure of introducing liquids into the rectum and colon via the anus. The increasing volume of the liquid causes rapid expansion of the lower intestinal tract, often resulting in very uncomfortable bloating, cramping, powerful peristalsis, a feeling of extreme urgency and...
. As with other sugar alcohol
Sugar alcohol
A sugar alcohol is a hydrogenated form of carbohydrate, whose carbonyl group has been reduced to a primary or secondary hydroxyl group . Sugar alcohols have the general formula Hn+1H, whereas sugars have HnHCO...
s, gastroitestinal distress may result when food products that contain sorbitol are consumed. Sorbitol exerts its laxative effect by drawing water into the large intestine
Large intestine
The large intestine is the third-to-last part of the digestive system — — in vertebrate animals. Its function is to absorb water from the remaining indigestible food matter, and then to pass useless waste material from the body...
, thereby stimulating bowel movements. Sorbitol has been determined safe for use by the elderly, although it is not recommended without consultation with a clinician. Sorbitol is found in some dried fruits and may contribute to the laxative effects of prunes.
Medical applications
Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, as it is usually incapable of fermenting sorbitol, but 93% of known E. coli strains are capable of doing so.Sorbitol, combined with kayexalate
Sodium polystyrene sulfonate
Sodium polystyrene sulfonate is a type of polymer and ionomer based on polystyrene. It is the sodium salt of polystyrene sulfonic acid.-Chemical properties:...
, helps the body rid itself of excess potassium
Potassium
Potassium is the chemical element with the symbol K and atomic number 19. Elemental potassium is a soft silvery-white alkali metal that oxidizes rapidly in air and is very reactive with water, generating sufficient heat to ignite the hydrogen emitted in the reaction.Potassium and sodium are...
ions in a hyperkalaemic state. The kayexalate exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. The FDA has discouraged this combination when in 2010 it issued a warning of increased risk for GI necrosis.
Health care, food, and cosmetic uses
Sorbitol often is used in modern cosmeticsCosmetics
Cosmetics are substances used to enhance the appearance or odor of the human body. Cosmetics include skin-care creams, lotions, powders, perfumes, lipsticks, fingernail and toe nail polish, eye and facial makeup, towelettes, permanent waves, colored contact lenses, hair colors, hair sprays and...
as a humectant
Humectant
A humectant is a hygroscopic substance. It is often a molecule with several hydrophilic groups, most often hydroxyl groups, but amines and carboxyl groups, sometimes esterified, can be encountered as well; the affinity to form hydrogen bonds with molecules of water is crucial here.Since...
and thickener. Sorbitol often is used in mouthwash
Mouthwash
Mouthwash or mouth rinse is a product used to enhance oral hygiene. Some manufacturers of mouthwash claim that antiseptic and anti-plaque mouth rinse kill the bacterial plaque causing cavities, gingivitis, and bad breath. Anti-cavity mouth rinse uses fluoride to protect against tooth decay...
and toothpaste
Toothpaste
Toothpaste is a paste or gel dentifrice used with a toothbrush as an accessory to clean and maintain the aesthetics and health of teeth. Toothpaste is used to promote oral hygiene: it serves as an abrasive that aids in removing the dental plaque and food from the teeth, assists in suppressing...
. Some transparent gel
Gel
A gel is a solid, jelly-like material that can have properties ranging from soft and weak to hard and tough. Gels are defined as a substantially dilute cross-linked system, which exhibits no flow when in the steady-state...
s can be made only with sorbitol, as it has a refractive index
Refractive index
In optics the refractive index or index of refraction of a substance or medium is a measure of the speed of light in that medium. It is expressed as a ratio of the speed of light in vacuum relative to that in the considered medium....
sufficiently high for transparent formulations. It is also used frequently in almost all "sugar free" chewing gum.
Sorbitol is used as a cryoprotectant
Cryoprotectant
A cryoprotectant is a substance that is used to protect biological tissue from freezing damage . Arctic and Antarctic insects, fish, amphibians and reptiles create cryoprotectants in their bodies to minimize freezing damage during cold winter periods. Insects most often use sugars or polyols as...
additive (mixed with sucrose
Sucrose
Sucrose is the organic compound commonly known as table sugar and sometimes called saccharose. A white, odorless, crystalline powder with a sweet taste, it is best known for its role in human nutrition. The molecule is a disaccharide composed of glucose and fructose with the molecular formula...
and sodium polyphosphate
Phosphate
A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...
s) in the manufacture of surimi
Surimi
Surimi is a Japanese loan word referring to a fish-based food product that has been pulverized to a thick paste and has the property of a dense and rubbery food item when cooked...
, a highly refined fish paste most commonly produced from Alaska pollock
Alaska pollock
Alaska pollock or walleye pollock is a North Pacific species of the cod family Gadidae. While related to the common Atlantic pollock species of the same family, the Alaska pollock is not a member of the same Pollachius genus.The Norwegian pollock , a rare fish of Norwegian waters, may actually be...
(Theragra chalcogramma). It is also used as a humectant
Humectant
A humectant is a hygroscopic substance. It is often a molecule with several hydrophilic groups, most often hydroxyl groups, but amines and carboxyl groups, sometimes esterified, can be encountered as well; the affinity to form hydrogen bonds with molecules of water is crucial here.Since...
in some cigarette
Cigarette
A cigarette is a small roll of finely cut tobacco leaves wrapped in a cylinder of thin paper for smoking. The cigarette is ignited at one end and allowed to smoulder; its smoke is inhaled from the other end, which is held in or to the mouth and in some cases a cigarette holder may be used as well...
s.
Sorbitol sometimes is used as a sweetener and humectant in cookies and other foods that are not identified as "dietary" items.
Medical importance
Aldose reductaseAldose reductase
Aldose reductase is an NADPH-dependent oxidoreductase that catalyzes the reduction of a variety of aldehydes and carbonyls, including monosaccharides...
is the first enzyme in the sorbitol-aldose reductase pathway
Polyol pathway
Also called the sorbitol-aldose reductase pathway, the polyol pathway appears to be implicated in diabetic complications, especially in microvascular damage to the retina, kidney, and nerves....
responsible for the reduction of glucose to sorbitol, as well as the reduction of galactose
Galactose
Galactose , sometimes abbreviated Gal, is a type of sugar that is less sweet than glucose. It is a C-4 epimer of glucose....
to galactitol. Too much sorbitol trapped in retinal cells, the cells of the lens, and the Schwann cells that myelinate
Myelin
Myelin is a dielectric material that forms a layer, the myelin sheath, usually around only the axon of a neuron. It is essential for the proper functioning of the nervous system. Myelin is an outgrowth of a type of glial cell. The production of the myelin sheath is called myelination...
peripheral nerves can damage these cells, leading to retinopathy
Retinopathy
Retinopathy is a general term that refers to some form of non-inflammatory damage to the retina of the eye. Frequently, retinopathy is an ocular manifestation of systemic disease.-Pathophysiology:Causes of retinopathy are varied:...
, cataract
Cataract
A cataract is a clouding that develops in the crystalline lens of the eye or in its envelope, varying in degree from slight to complete opacity and obstructing the passage of light...
s and peripheral neuropathy, respectively. Aldose reductase inhibitors, which are substances that prevent or slow the action of aldose reductase, are currently being investigated as a way to prevent or delay these complications, which frequently occur in the setting of long-term hyperglycemia that accompanies poorly-controlled diabetes. It is thought that these agents may help to prevent the accumulation of intracellular sorbitol that leads to cellular damage in diabetics.
Adverse medical effects
Sorbitol also may aggravate irritable bowel syndromeIrritable bowel syndrome
Irritable bowel syndrome is a diagnosis of exclusion. It is a functional bowel disorder characterized by chronic abdominal pain, discomfort, bloating, and alteration of bowel habits in the absence of any detectable organic cause. In some cases, the symptoms are relieved by bowel movements...
, and similar gastrointestinal
Gastrointestinal tract
The human gastrointestinal tract refers to the stomach and intestine, and sometimes to all the structures from the mouth to the anus. ....
conditions, resulting in severe abdominal pain for those affected, even from small amounts ingested.
Overdose effects
Ingesting large amounts of sorbitol can lead to abdominal pain, flatulenceFlatulence
Flatulence is the expulsion through the rectum of a mixture of gases that are byproducts of the digestion process of mammals and other animals. The medical term for the mixture of gases is flatus, informally known as a fart, or simply gas...
, and mild to severe diarrhea
Diarrhea
Diarrhea , also spelled diarrhoea, is the condition of having three or more loose or liquid bowel movements per day. It is a common cause of death in developing countries and the second most common cause of infant deaths worldwide. The loss of fluids through diarrhea can cause dehydration and...
. Sorbitol ingestion of 20 gram (0.705479242102239 oz) per day as sugar-free gum has led to severe diarrhea leading to unintended weight loss of 11 kilograms (24.3 lb) in eight months, in a woman originally weighing 52 kilograms (114.6 lb); another patient required hospitalization after habitually consuming 30 grams (1 oz) per day.
Compendial status
- Food Chemical Codex
- European PharmacopoeiaEuropean PharmacopoeiaThe European Pharmacopoeia of the Council of Europe is a pharmacopoeia, listing a wide range of active substances and excipients used to prepare pharmaceutical products in Europe...
6.1 - British PharmacopoeiaBritish PharmacopoeiaThe British Pharmacopoeia is an annual published collection of quality standards for UK medicinal substances. It is used by individuals and organizations involved in pharmaceutical research, development, manufacture and testing....
2009 - Japanese Pharmacopoeia 15
Miscellaneous uses
A mixture of sorbitol and potassium nitratePotassium nitrate
Potassium nitrate is a chemical compound with the formula KNO3. It is an ionic salt of potassium ions K+ and nitrate ions NO3−.It occurs as a mineral niter and is a natural solid source of nitrogen. Its common names include saltpetre , from medieval Latin sal petræ: "stone salt" or possibly "Salt...
has found some success as an amateur solid rocket fuel.
Sorbitol is identified as a potential key chemical intermediate from biomass
Biomass
Biomass, as a renewable energy source, is biological material from living, or recently living organisms. As an energy source, biomass can either be used directly, or converted into other energy products such as biofuel....
resources. Complete reduction of sorbitol opens the way to alkane
Alkane
Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...
s, such as hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...
, which can be used as a biofuel
Biofuel
Biofuel is a type of fuel whose energy is derived from biological carbon fixation. Biofuels include fuels derived from biomass conversion, as well as solid biomass, liquid fuels and various biogases...
. Sorbitol itself provides much of the hydrogen required for the transformation.
- 19 C6H14O6 → 13 C6H14 + 36 CO2 + 42 H2O
The above chemical reaction
Chemical reaction
A chemical reaction is a process that leads to the transformation of one set of chemical substances to another. Chemical reactions can be either spontaneous, requiring no input of energy, or non-spontaneous, typically following the input of some type of energy, such as heat, light or electricity...
is exothermic
Exothermic reaction
An exothermic reaction is a chemical reaction that releases energy in the form of light or heat. It is the opposite of an endothermic reaction. Expressed in a chemical equation:-Overview:...
; 1.5 mole
Mole (unit)
The mole is a unit of measurement used in chemistry to express amounts of a chemical substance, defined as an amount of a substance that contains as many elementary entities as there are atoms in 12 grams of pure carbon-12 , the isotope of carbon with atomic weight 12. This corresponds to a value...
s of sorbitol generate approximately 1 mole of hexane
Hexane
Hexane is a hydrocarbon with the chemical formula C6H14; that is, an alkane with six carbon atoms.The term may refer to any of four other structural isomers with that formula, or to a mixture of them. In the IUPAC nomenclature, however, hexane is the unbranched isomer ; the other four structures...
. When hydrogen is co-fed, no carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...
is produced.