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Erythritol

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Erythritol Basic information
Erythritol Chemical Properties
  • Melting point:118-120 °C(lit.)
  • Boiling point:329-331 °C(lit.)
  • Density 1,451 g/cm3
  • FEMA 4819 | ?ERYTHRITOL
  • refractive index 1.4502 (estimate)
  • Flash point:329-331°C
  • storage temp. −20°C
  • solubility H2O: 0.1 g/mL, clear to almost clear, colorless
  • pka13.9(at 25℃)
  • form Crystalline Powder or Crystals
  • color White to off-white
  • Water Solubility soluble
  • Merck 14,3675
  • BRN 1719753
  • Stability:Stable. Incompatible with strong oxidizing agents.
  • InChIKeyUNXHWFMMPAWVPI-ZXZARUISSA-N
  • CAS DataBase Reference149-32-6(CAS DataBase Reference)
  • NIST Chemistry Reference2(r),3(s)-1,2,3,4-Butanetetrol(149-32-6)
  • EPA Substance Registry SystemErythrol (149-32-6)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36
  • WGK Germany 3
  • RTECS KF2000000
  • 3-10
  • TSCA Yes
  • HS Code 29054910
  • ToxicityLD50 in male, female rats (g/kg): 6.6, 9.6 i.v.; >16, >16 s.c.; 13.1, 13.5 orally (Munro)
MSDS
Erythritol Usage And Synthesis
  • Chemical Propertieswhite crystals or powder
  • Chemical PropertiesErythritol (meso-erythritol, meso-1,2,3,4-Tetrahydroxybutan) has been known for a long time. Its potential use as a bulk sweetener was, however, recognized rather late.
    Erythritol is a natural constituent of several foods and beverages in levels sometimes exceeding 1 g/kg. Its solubility in water is approximately 370 g/L at room temperature and increases with increasing temperature. Erythritol melts at 121 C and is stable up to more than 160 C and in a pH range from 2 to 10. Depending on the concentration used, erythritol is approximately 60 % as sweet as sucrose. It is noncariogenic and not metabolized in the human body which means that it is more or less calorie-free.
    In the European Union, erythritol is approved as E 968 for a large number of food applications. It is GRAS in the United States and also approved in many other countries.
  • Chemical PropertiesErythritol is a sugar alcohol (polyol) that occurs as a white or almost white powder or granular or crystalline substance. It is pleasant tasting with a mild sweetness approximately 60–70% that of sucrose. It also has a high negative heat of solution that provides a strong cooling effect.
  • Usesnon-cariogenic, low-calorie (0.4 kcal/g) sweetener
  • UsesNon-nutritive sweetener in beverages.
  • UsesErythritol is a sweetener (polyol) manufactured by fermentation of glucose, the glucose-rich substrate being obtained by the enzymatic hydrolysis of starch. it is 60–70% as sweet as sugar, has excellent heat and acid stability, a high digestive tolerance, and a caloric value of 0.2 kcal/g. it is the only polyol produced by fermentation. it can be used as a sugar replacement in confectioneries, beverages, and desserts.
  • Production MethodsErythritol is a starch-derived product. The starch is enzymatically hydrolyzed into glucose which is turned into erythritol via a fermentation process, using osmophilic yeasts or fungi (e.g. Moniliella pollinis, or Trichosporonoides megachiliensis).
  • DefinitionChEBI: The meso-diastereomer of butane-1,2,3,4-tetrol.
  • Biotechnological ProductionThe synthesis of erythritol is rather difficult. One of the possibilities is the catalytic reduction of tartaric acid with Raney nickel, which does, however, also produce threitol, a diastereomere of erythritol that requires separation of both. Threitol may be isomerized which increases the yields of erythritol. Another chemical synthesis starts from butane-2-diol-1.4 which is reacted with chlorine in aqueous alkali to yield erythritol-2-chlorohydrin and can be hydrolyzed with sodium carbonate solution. Synthesis from dialdehyde starch in the presence of a nickel catalyst at high temperatures is also possible.
    Owing to the special physiological properties of erythritol, commercial interest increased with the discovery of an increasing number of microorganisms able to produce this substance. Today, the commercial production of erythritol is apparently only based on fermentation.
    Erythrytitol fermentations mostly use osmophilic yeasts. Based on regulatory submissions for commercial production, T. megachiliensis, M. pollinis, and Y. lipolytica are used. It is also claimed that P. tsukubaensis and Aureobasidium sp. are used for commercial production.
    Erythritol-producing microorganisms often produce other polyols such as ribitol. Nevertheless, some strains had a rather high yield of erythritol. A two-step fermentation of C. magnoliae on 400 g/L glucose resulted in a 41 % conversion rate and a productivity of 2.8 g/Lh. M. pollinis cultivated on glucose and several nitrogen sources yielded erythritol concentrations up to 175 g/L with a conversion rate of 43 %. Oxygen limitation resulted in ethanol formation, and nitrogen limitation in strong foaming. A mutant gave even better yields. Aerobically on glucose cultured P. tsukubaensis KN 75 produced 245 g/L of erythritol with an especially high yield of 61 %. The productivity was 2.86 g/Lh. Scale-up from 7-L laboratory fermenter to 50,000-L industrial scale resulted in productivities similar to the laboratory value.
  • Pharmaceutical ApplicationsErythritol is a naturally occurring noncariogenic excipient used in a variety of pharmaceutical preparations, including in solid dosage forms as a tablet filler, and in coatings. It has also been investigated for use in dry powder inhalers.It is also used in sugar-free lozenges,and medicated chewing gum.
    Erythritol can also be used as a diluent in wet granulation in combination with moisture-sensitive drugs. In buccal applications, such as medicated chewing gums, it is used because of its high negative heat of solution which provides a strong cooling effect.
    Erythritol is also used as a noncaloric sweetener in syrups; it is used to provide sensorial profile-modifying properties with intense sweeteners; and it is also used to mask unwanted aftertastes.
    Erythritol is also used as a noncariogenic sweetener in toothpastes and mouthwash solutions.
  • SafetyErythritol is used in oral pharmaceutical formulations, confectionery, and food products. It is generally regarded as a nontoxic, nonallergenic, and nonirritant material. However, there has been a case report of urticaria caused by erythritol.
    The low molecular weight of erythritol allows more than 90% of the ingested molecules to be rapidly absorbed from the small intestine; it is not metabolized and is excreted unchanged in the urine. Erythritol has a low caloric value (0.8 kJ/g). The WHO has set an acceptable daily intake of ‘not specified’ for erythritol.
    Erythritol is noncariogenic; preliminary studies suggest that it may inhibit the formation of dental plaque.
    In general, erythritol is well-tolerated; furthermore, excessive consumption does not cause laxative effects. There is no significant increase in the blood glucose level after oral intake, and glycemic response is very low, making erythritol suitable for diabetics.
    LD50 (mouse, IP): 8–9 g/kg
    LD50 (rat, IV): 6.6 g/kg
    LD50 (rat, oral): >13 g/kg
  • storageErythritol has very good thermal and chemical stability. It is nonhygroscopic, and at 25°C does not significantly absorb additional water up to a relative humidity (RH) of more than 80%. Erythritol resists decomposition both in acidic and alkaline media and remains stable for prolonged periods at pH 2–10.(10) When stored for up to 4 years in ambient conditions (20°C, 50% RH) erythritol has been shown to be stable.
  • Purification Methodsmeso-Erythritol crystallises from distilled water or absolute EtOH and is dried at 60o in a vacuum oven. It sublimes at 110o in a high vacuum. It is optically inactive. [Jeans & Hudson J Org Chem 20 1565 1955, IR: Kuhn Anal Chem 22 276 1950, Beilstein 1 IV 2807.]
  • IncompatibilitiesErythritol is incompatible with strong oxidizing agents and strong bases.
  • Regulatory StatusGRAS listed. Accepted for use as a food additive in Europe.
Erythritol Preparation Products And Raw materials
Erythritol(149-32-6)Related Product Information
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