Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

s, typically derived from

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 Glucose is a sugar with the Chemical formula#Molecular formula, molecul ...

s, containing one hydroxyl group attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple groups, they are classified as polyols. Sugar alcohols are used widely in the food industry as thickeners and sweeteners. In commercial foodstuffs, sugar alcohols are commonly used in place of table sugar (

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 ...

), often in combination with high-intensity artificial sweeteners, in order to offset their low sweetness. Xylitol and

sorbitol Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alco ...

are popular sugar alcohols in commercial foods.

Structure

Sugar alcohols have the general formula . In contrast, sugars have two fewer hydrogen atoms, for example, or . Like their parent sugars, sugar alcohols exist in diverse chain length. Most have five- or six-carbon chains, because they are derived respectively from pentoses (five-carbon sugars) and hexoses (six-carbon sugars), which are the more common sugars. They have one −OH group attached to each carbon. They are further differentiated by the relative orientation (

stereochemistry Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined ...

) of these −OH groups. Unlike sugars, which tend to exist as rings, sugar alcohols do not, although they can be dehydrated to give cyclic ethers (e.g. sorbitan can be dehydrated to isosorbide).

Production

Sugar alcohols can be, and often are, produced from renewable resources. Particular feedstocks are

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 diet ...

cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...

and

hemicellulose A hemicellulose (also known as polyose) is one of a number of heteropolymers (matrix polysaccharides), such as arabinoxylans, present along with cellulose in almost all embryophyte, terrestrial plant cell walls. Cellulose is crystalline, strong, an ...

; the main conversion technologies use as the reagent: '' hydrogenolysis'', ''i.e.'' the cleavage of single bonds, converting polymers to smaller molecules, and ''

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

'' of double bonds, converting sugars to sugar alcohols.

Sorbitol and mannitol

Mannitol is no longer obtained from natural sources; currently, sorbitol and mannitol are obtained by

of sugars, using Raney nickel catalysts. The conversion of glucose and mannose to sorbitol and mannitol is given as :

Erythritol

Erythritol Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a food ad ...

is obtained by the

fermentation Fermentation is a type of anaerobic metabolism which harnesses the redox potential of the reactants to make adenosine triphosphate (ATP) and organic end products. Organic molecules, such as glucose or other sugars, are catabolized and reduce ...

of glucose and

Health effects

Sugar alcohols do not contribute to tooth decay; in fact, xylitol deters tooth decay. Sugar alcohols are absorbed at 50% of the rate of sugars, resulting in less of an effect on

blood sugar The blood sugar level, blood sugar concentration, blood glucose level, or glycemia is the measure of glucose concentrated in the blood. The body tightly regulates blood glucose levels as a part of metabolic homeostasis. For a 70 kg (1 ...

levels as measured by comparing their effect to sucrose using 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 ...

Common sugar alcohols

* Ethylene glycol (2-carbon) *

Glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

(3-carbon) *

(4-carbon) * Threitol (4-carbon) * Arabitol (5-carbon) * Xylitol (5-carbon) * Ribitol (5-carbon) * Mannitol (6-carbon) *

Sorbitol Sorbitol (), less commonly known as glucitol (), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alco ...

(6-carbon) * Galactitol (6-carbon) * Fucitol (6-carbon) * Iditol (6-carbon) * Inositol (6-carbon; a cyclic sugar alcohol) * Volemitol (7-carbon) * Isomalt (12-carbon) * Maltitol (12-carbon) *

Lactitol Lactitol is a disaccharide sugar alcohol produced from lactose. It is used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative. Production Lactitol is p ...

(12-carbon) *Maltotriitol (18-carbon) *Maltotetraitol (24-carbon) *Polyglycitol Both

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, ...

s and

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. Chemically, monosaccharides are polyhy ...

s can form sugar alcohols; however, sugar alcohols derived from disaccharides (e.g. maltitol and lactitol) are not entirely hydrogenated because only one aldehyde group is available for reduction.

Sugar alcohols as food additives

This table presents the relative sweetness and

food energy Food energy is chemical energy that animals and humans derive from food to sustain their metabolism and muscular activity. Most animals derive most of their energy from aerobic respiration, namely combining the carbohydrates, fats, and protein ...

of the most widely used sugar alcohols. Despite the variance in food energy content of sugar alcohols, the

European Union The European Union (EU) is a supranational union, supranational political union, political and economic union of Member state of the European Union, member states that are Geography of the European Union, located primarily in Europe. The u ...

's labeling requirements assign a blanket value of 2.4 kcal/g to all sugar alcohols.

Characteristics

As a group, sugar alcohols are not as sweet as sucrose, and they have slightly less

than sucrose. Their flavor is similar to sucrose, and they can be used to mask the unpleasant

aftertaste Aftertaste is the taste intensity of a food or beverage that is perceived immediately after that food or beverage is removed from the mouth. The aftertastes of different foods and beverages can vary by intensity and over time, but the unifying fea ...

s of some high-intensity sweeteners. Sugar alcohols are not metabolized by oral bacteria, and so they do not contribute to tooth decay. They do not brown or caramelize when heated. In addition to their sweetness, some sugar alcohols can produce a noticeable cooling sensation in the mouth when highly concentrated, for instance in sugar-free hard candy or

chewing gum Chewing gum is a soft, cohesive substance designed to be chewed without being swallowed. Modern chewing gum is composed of gum base, sweeteners, softeners/plasticizers, flavors, colors, and, typically, a hard or powdered polyol coating. Its tex ...

. This happens, for example, with the crystalline phase of sorbitol, erythritol, xylitol, mannitol,

lactitol Lactitol is a disaccharide sugar alcohol produced from lactose. It is used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative. Production Lactitol is p ...

and maltitol. The cooling sensation is due to the dissolution of the sugar alcohol being an endothermic (heat-absorbing) reaction, one with a strong heat of solution.

Absorption from the small intestine

Sugar alcohols are usually incompletely absorbed into the blood stream from the

small intestine The small intestine or small bowel is an organ (anatomy), organ in the human gastrointestinal tract, gastrointestinal tract where most of the #Absorption, absorption of nutrients from food takes place. It lies between the stomach and large intes ...

which generally results in a smaller change in blood glucose than "regular" sugar (sucrose). This property makes them popular sweeteners among diabetics and people on

low-carbohydrate diet Low-carbohydrate diets restrict carbohydrate consumption relative to the average diet (nutrition), diet. Foods high in carbohydrates (e.g., sugar, bread, pasta) are limited, and replaced with foods containing a higher percentage of fat and pro ...

s. As an exception,

erythritol Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L- erythrose and one of the two reduced forms of erythrulose. It is used as a food ad ...

is actually absorbed in the small intestine and excreted unchanged through urine, so it contributes no calories even though it is rather sweet.

Side effects

Like many other incompletely digestible substances, overconsumption of sugar alcohols can lead to

bloating Abdominal bloating (or simply bloating) is a short-term disease that affects the gastrointestinal tract. Bloating is generally characterized by an excess buildup of gas, air or fluids in the stomach. A person may have feelings of tightness, pressu ...

diarrhea Diarrhea (American English), also spelled diarrhoea or diarrhœa (British English), is the condition of having at least three loose, liquid, or watery bowel movements in a day. It often lasts for a few days and can result in dehydration d ...

and

flatulence Flatulence is the expulsion of gas from the Gastrointestinal tract, 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 swal ...

because they are not fully absorbed in the small intestine. Some individuals experience such symptoms even in a single-serving quantity. With continued use, most people develop a degree of tolerance to sugar alcohols and no longer experience these symptoms.

References

{{Alcohols Sugar substitutes fr:Polyol