149-32-6 Usage
Description
1,2,3,4-Butanetetrol, also known as meso-erythritol or meso-1,2,3,4-tetrahydroxybutan, is a sugar alcohol (polyol) that occurs naturally in various food products, fruits, vegetables, beverages, and dietary supplements. It is identified as the meso-diastereomer of butane-1,2,3,4-tetrol and has a white or almost white powder, granular, or crystalline substance appearance. Erythritol is known for its mild sweetness, approximately 60-70% that of sucrose, and a high negative heat of solution that provides a strong cooling effect. It is noncariogenic, not metabolized in the human body, and has a low caloric value, making it a suitable sweetener for diabetic patients and a sugar replacement in various applications.
Uses
Used in Food Industry:
1,2,3,4-Butanetetrol is used as a sugar replacement in confectioneries, beverages, and desserts due to its excellent heat and acid stability, high digestive tolerance, and low caloric value of 0.2 kcal/g.
Used in Pharmaceutical Industry:
1,2,3,4-Butanetetrol is used as a non-cariogenic, low-calorie (0.4 kcal/g) sweetener, making it a suitable additive for diabetic patients and those seeking sugar-free or low-calorie options.
Used in Beverage Industry:
1,2,3,4-Butanetetrol is used as a non-nutritive sweetener in beverages, providing a pleasant taste with a mild sweetness and a strong cooling effect.
Used in Dental Products:
1,2,3,4-Butanetetrol is used as a sugar substitute in toothpaste and chewing gums, offering a non-cariogenic and low-calorie alternative to traditional sweeteners.
Used in Regulatory Approvals:
In the European Union, erythritol is approved as E 968 for a large number of food applications. It is also Generally Recognized As Safe (GRAS) in the United States and approved in many other countries, making it a versatile and widely accepted sweetener for various applications.
Characteristics
The sweetness of erythritol is low, the sweetness of erythritol is only 60%-70% of sucrose, the entrance has a cool taste, the taste is pure, and there is no post-bitterness. It can be used in combination with high-intensity sweeteners to inhibit its Undesirable flavors of high-intensity sweeteners. Erythritol has high stability, is very stable to acid and heat, and has high acid and alkali resistance. It will not decompose and change at temperatures below 200 °C, and will not undergo Maillard reaction to cause discoloration. The heat of dissolution of erythritol is high: erythritol has an endothermic effect when dissolved in water, and the heat of dissolution is only 97.4kJ/kg, which is higher than the endothermic degree of glucose and sorbitol, and has a cooling feeling when eating. The solubility of erythritol at 25 °C is 37% (W/W). With the increase of temperature, the solubility of erythritol increases, and it is easy to crystallize and separate out crystals. Erythritol is very easy to crystallize, but it will not absorb moisture in a 90% humidity environment. It is easy to be crushed to obtain a powdery product, which can be used on the surface of food to prevent food from absorbing moisture and deteriorating.
Production Methods
Erythritol 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).
Biotechnological Production
The 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.
Flammability and Explosibility
Notclassified
Pharmaceutical Applications
Erythritol 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.
Biochem/physiol Actions
Allelic variation of the Tas1r3 gene affects behavioral taste responses to this sugar alcohol, suggesting that it is a T1R3 receptor ligand.
Safety
Erythritol 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
storage
Erythritol 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 Methods
meso-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.]
Incompatibilities
Erythritol is incompatible with strong oxidizing agents and strong
bases.
Check Digit Verification of cas no
The CAS Registry Mumber 149-32-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 149-32:
(5*1)+(4*4)+(3*9)+(2*3)+(1*2)=56
56 % 10 = 6
So 149-32-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2
149-32-6Relevant articles and documents
Product Control and Insight into Conversion of C6 Aldose Toward C2, C4 and C6 Alditols in One-Pot Retro-Aldol Condensation and Hydrogenation Processes
Gao, Lou,Hou, Wenrong,Hui, Yingshuang,Tang, Yi,Zhan, Yulu,Zhang, Yahong
, p. 560 - 566 (2021/06/25)
Alcohols have a wide range of applicability, and their functions vary with the carbon numbers. C6 and C4 alditols are alternative of sweetener, as well as significant pharmaceutical and chemical intermediates, which are mainly obtained through the fermentation of microorganism currently. Similarly, as a bulk chemical, C2 alditol plays a decisive role in chemical synthesis. However, among them, few works have been focused on the chemical production of C4 alditol yet due to its difficult accumulation. In this paper, under a static and semi-flowing procedure, we have achieved the product control during the conversion of C6 aldose toward C6 alditol, C4 alditol and C2 alditol, respectively. About C4 alditol yield of 20 % and C4 plus C6 alditols yield of 60 % are acquired in the one-pot conversion via a cascade retro-aldol condensation and hydrogenation process. Furthermore, in the semi-flowing condition, the yield of ethylene glycol is up to 73 % thanks to its low instantaneous concentration.
Selective and Scalable Synthesis of Sugar Alcohols by Homogeneous Asymmetric Hydrogenation of Unprotected Ketoses
Tindall, Daniel J.,Mader, Steffen,Kindler, Alois,Rominger, Frank,Hashmi, A. Stephen K.,Schaub, Thomas
supporting information, p. 721 - 725 (2020/10/19)
Sugar alcohols are of great importance for the food industry and are promising building blocks for bio-based polymers. Industrially, they are produced by heterogeneous hydrogenation of sugars with H2, usually with none to low stereoselectivities. Now, we present a homogeneous system based on commercially available components, which not only increases the overall yield, but also allows a wide range of unprotected ketoses to be diastereoselectively hydrogenated. Furthermore, the system is reliable on a multi-gram scale allowing sugar alcohols to be isolated in large quantities at high atom economy.
Domino Hydroalkoxylation-[4+2]-Cycloaddition for Stereoselective Synthesis of 1,4-Heterocycle-Fused Chromenes: Rapid Access to the [6-6-7-6] Tetracyclic Core of Cytorhizhins B–D
Fartade, Dipak J.,Gharpure, Santosh J.,Nanda, Santosh K.,Vishwakarma, Dharmendra S.
supporting information, p. 6892 - 6897 (2020/01/25)
A substrate dependent regio- and stereoselective domino hydroalkoxylation-formal-[4+2] cycloaddition is described for the facile synthesis of linear as well as spirocyclic 1,4-heterocycle-fused chromene ketals. Enantiospecific synthesis of oxazepino chromene derivatives was successfully carried out using chiral pool amino alkynols. The developed hydroalkoxylation cascade offered rapid access to the spirocyclic [6-6-7-6] tetracyclic core of cytorhizhins B–D with correct relative configuration.
Xi:Irritant;
