Erythritol
IUPAC name	(2R,3S)-butane-1,2,3,4-tetraol
Identifiers
CAS number	[10030-58-7],[149-32-6], [188346-77-2]
SMILES	OC[C@@H](O)[C@@H](O)CO
Properties
Molecular formula	C4H10O4
Molar mass	122.12 g mol-1
Density	1.45 g/cm³
Melting point	121 °C, 394 K, 250 °F IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	329-331 °C, 602-604 K, 624-628 °F Italic text This article is about the boiling point of liquids. ...
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Erythritol ((2R,3S)-butane-1,2,3,4-tetraol) is a natural sugar alcohol (a type of sugar substitute) which has been approved for use in the United States^[1] and throughout much of the world. It occurs naturally in fruits and fermented foods ^[2]. At industrial level, it is produced from glucose by fermentation with a yeast, Moniliella pollinis^[3]. It is 60-70% as sweet as table sugar yet it is almost non-caloric, does not affect blood sugar, does not cause tooth decay, and is absorbed by the body, therefore unlikely to cause gastric side effects unlike other sugar alcohols. Under U.S. Food and Drug Administration (FDA) labeling requirements, it has a caloric value of 0.2 calories per gram (95% less than sugar and other carbohydrates), but some countries like Japan label it at 0 calories. European legislation actually considers it at 2.4 kcal/g but pending discussion will certainly achieve a 0 kcal/g caloric value by 2009. The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A sugar alcohol (also known as a polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of carbohydrate, whose carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. ... Typical divisions Ascomycota (sac fungi) Saccharomycotina (true yeasts) Taphrinomycotina Schizosaccharomycetes (fission yeasts) Basidiomycota (club fungi) Urediniomycetes Sporidiales Yeasts are a growth form of eukaryotic microorganisms classified in the kingdom Fungi, with approximately 1,500 species described. ... A sugar alcohol (also known as a polyol, polyhydric alcohol, or polyalcohol) is a hydrogenated form of carbohydrate, whose carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. ... “FDA” redirects here. ... Etymology: French calorie, from Latin calor (heat), from calere (to be warm). ... Etymology: French calorie, from Latin calor (heat), from calere (to be warm). ...

Erythritol and human digestion

In the body, erythritol is absorbed into the bloodstream in the small intestine, and then for the most part excreted unchanged in the urine. Because erythritol is normally absorbed before it enters the large intestine, it does not normally cause laxative effects as are often experienced after over-consumption of other sugar alcohols (such as xylitol and maltitol) and most people will consume erythritol with no side effects. This is a unique characteristic, as other sugar alcohols are not absorbed directly by the body in this manner, and consequently are more prone to causing gastric distress ^[4]. In biology the small intestine is the part of the gastrointestinal tract (gut) between the stomach and the large intestine and includes the duodenum, jejunum, and ileum. ... This article is about the urine of animals generally. ... The large intestine, an organ which is now more commonly referred to by its Greek name, the colon, is the last part of the digestive system: the final stage of the alimentary canal in vertebrate animals. ... Laxatives (or purgatives) are foods, compounds, or drugs taken to induce bowel movements or to loosen the stool, most often taken to treat constipation. ... Xylitol, also called wood sugar or birch sugar, is a five-carbon sugar alcohol that is used as a sugar substitute. ... Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. ...

As a whole, erythritol is generally free of side-effects in regular use, but if consumed in very extreme quantities (sometimes encouraged by its almost non-caloric nature), effectively consuming it faster than one's body can absorb it, a laxative effect may result. The laxative response does not begin until you cross your body's natural absorption threshold, which is the point at which you have ingested more erythritol than is found in reasonable servings of food products and is usually a larger amount than most people will eat in a single sitting. Erythritol, when compared with other sugar alcohols, is also much more difficult for intestinal bacteria to digest, so it is unlikely to cause gas or bloating ^[5], unlike maltitol, sorbitol, or lactitol. Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. ... Sorbitol, also known as glucitol, is a sugar alcohol the body metabolises slowly. ... Lactitol is a sugar alcohol used as a replacement sweetener for low calorie foods with approximately 40% of the sweetness of sugar. ...

Physical properties

Heat of solution

Erythritol has a strong cooling effect (positive heat of solution^[6]) when it dissolves in water, often combined with the cooling effect of mint flavors, but proves distracting with more subtle flavors and textures. The cooling effect is only present when erythritol is not already dissolved in water, a situation that might be experienced in an erythritol-sweetened frosting, chocolate bar, chewing gum, or hard candy. When combined with solid fats, such as coconut oil, cocoa butter or cow's butter, the cooling effect tends to accentuate the waxy characteristics of the fat in a generally undesirable manner. This is particularly pronounced in chocolate bars made with erythritol. The cooling effect of erythritol is very similar to that of xylitol and among the strongest cooling effects of all sugar alcohols. Heat of solution is the quantity of heat evolved or absorbed when one mole of a solute is dissolved in a large volume of a solvent. ... “Mint” redirects here. ... Coconut oil, also known as coconut butter, is a tropical oil extracted from copra (the dried inner flesh of coconuts) with many applications. ... Cocoa butter Cocoa butter, also called theobroma oil, is the pale-yellow, pure edible vegetable fat of the cacao bean. ... For other uses, see Butter (disambiguation). ... Xylitol, also called wood sugar or birch sugar, is a five-carbon sugar alcohol that is used as a sugar substitute. ...

Synergistic sweetening

Erythritol is frequently combined with high intensity sweeteners like sucralose. Sucralose is an artificial sweetener. ...

Blending for sugar-like properties

Beyond high intensity sweeteners, erythritol is often paired with other bulky ingredients that exhibit sugar-like characteristics to better mimic the texture and mouthfeel of sucrose. Often these other ingredients are responsible for the gastric side effects blamed on erythritol. The cooling effect of erythritol is rarely desired, so hence other ingredients are chosen to dilute or even negate that effect. Erythritol also has a propensity to crystallize and is not as soluble as sucrose, so ingredients may also be chosen to help negate this disadvantage. Furthermore, erythritol is non-hygroscopic, meaning it does not attract moisture, which can lead to products, particularly baked goods, drying out if another hygroscopic ingredient is not used in the formulation. Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ...

Very commonly, inulin is combined with erythritol, due to inulin offering a complementary negative heat of solution (warming effect when dissolved that helps cancel erythritol's cooling effect) and non-crystallizing properties. Unfortunately, inulin has a propensity to cause gas and bloating when consumed in moderate to large quantities, particularly in individuals unaccustomed to it. Other sugar alcohols are sometimes utilized with erythritol, particularly isomalt due to its minimally positive heat of solution, and glycerin which has a negative heat of solution, moderate hygroscopicity, and non-crystallizing liquid form. Note: This article title may be easily confused with insulin. ... Heat of solution is the quantity of heat evolved or absorbed when one mole of a solute is dissolved in a large volume of a solvent. ... Note: This article title may be easily confused with insulin. ... Isomalt is the only sugar replacer (sugar alcohol), derived exclusively from sucrose. ... Heat of solution is the quantity of heat evolved or absorbed when one mole of a solute is dissolved in a large volume of a solvent. ... Glycerin, also well known as glycerine and glycerol, and less commonly as 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... Heat of solution is the quantity of heat evolved or absorbed when one mole of a solute is dissolved in a large volume of a solvent. ... A hygroscopic substance is a substance that absorbs water readily from its surroundings. ...

Erythritol and bacteria

Erythritol has been certified as tooth-friendly^[7]. The sugar alcohol cannot be metabolized by oral bacteria, and so does not contribute to tooth decay. Interestingly, erythritol exhibits some, but not all, of the tendencies to "starve" harmful bacteria like xylitol does. Unlike xylitol, erythritol is actually absorbed into the bloodstream after consumption but before excretion. However, it is not clear at present if the effect of starving harmful bacteria occurs systemically. This article is about dental caries in humans. ...

See also

• Threitol, the diastereomer of erythritol

Diastereomers (or diastereoisomers) are stereoisomers that are not enantiomers (mirror images of each other). ...

References

1. ^ FDA/CFSAN: Agency Response Letter: GRAS Notice No. GRN 000076
2. ^ Shindou, T., Sasaki, Y., Miki, H., Eguchi, T., Hagiwara, K., and Ichikawa, T. 1988. Determination of erythritol in fermented foods by high performance liquid chromatography. Shokuhin Eiseigaku Zasshi 29(6):419-422.
3. ^ FDA/CFSAN: Agency Response Letter: GRAS Notice No. GRN 000076
4. ^ Munro, I.C.; Berndt, W.O.; Borzelleca, J.F.; Flamm, G.; Lynch, B.S.; Kennepohl, E.; Bar, E.A.; Modderman, J. 1998. Erythritol: An interpretive summary of biochemical, metabolic, toxicological and clinical data. Food and Chemical Toxicology 36(12):1139-1174. Entrez PubMed 9862657
5. ^ Arrigoni, E.; Brouns, F.; Amadò, R. 2005. Human gut microbiota does not ferment erythritol. British Journal of Nutrition 94(5):643-646. Entrez PubMed 16277764
6. ^ Wohlfarth, Christian. CRC Handbook of Enthalpy Data of Polymer-Solvent Systems. CRC Press, 2006. Google Books result: ISBN 0849393612
7. ^ Kawanabe, J., Hirasawa, M., Takeuchi, T., Oda, T., and Ideda, T. 1992. Noncariogenicity of erythritol as a substrate. Caries Research 26:358-362. Entrez PubMed 1468100

The Entrez logo The Entrez Global Query Cross-Database Search System allows access to databases at the National Center for Biotechnology Information (NCBI) website. ... The Entrez logo The Entrez Global Query Cross-Database Search System allows access to databases at the National Center for Biotechnology Information (NCBI) website. ... The Entrez logo The Entrez Global Query Cross-Database Search System allows access to databases at the National Center for Biotechnology Information (NCBI) website. ...

External links

• Information About Erythritol from Cargill, a US-Producer of Erythritol under the Eridex trade name
• Stoneyfield Farms' Erythritol Information Page