(2R,3S)-butane-1,2,3,4-tetrol
meso-Erythritol
CAS: 149-32-6
Molecular Formula: C4H10O4
(2R,3S)-butane-1,2,3,4-tetrol - Names and Identifiers
| Name | meso-Erythritol |
| Synonyms | Erythrit Erythritol Butanetetrol Antierythrite meso-Erythritol erythritol,meso- Erythritol, meso- butane-1,2,3,4-tetrol 1,2,3,4-Butanetetrol 3,4-butanetetrol,(theta,s)-2 2,3,4-Butanetetrol,(R*,S*)-1 (2R,3R)-butane-1,2,3,4-tetrol (2R,3S)-butane-1,2,3,4-tetrol (2S,3S)-butane-1,2,3,4-tetrol 1,2,3,4-Butanetetrol, (R*,S*)- meso-1,2,3,4-Tetrahydroxybutane |
| CAS | 149-32-6 |
| EINECS | 205-737-3 |
| InChI | InChI=1/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2 |
| InChIKey | UNXHWFMMPAWVPI-ZXZARUISSA-N |
(2R,3S)-butane-1,2,3,4-tetrol - Physico-chemical Properties
| Molecular Formula | C4H10O4 |
| Molar Mass | 122.12 |
| Density | 1,451 g/cm3 |
| Melting Point | 118-120 °C (lit.) |
| Boling Point | 329-331 °C (lit.) |
| Flash Point | 329-331°C |
| Water Solubility | soluble |
| Solubility | Easily soluble in water (saturated solution about 61 grams soluble in 100 grams), soluble in pyridine (saturated solution 2.5%), slightly soluble in alcohol, almost insoluble in ether |
| Vapor Presure | 1.26E-05mmHg at 25°C |
| Appearance | White crystal |
| Color | White to off-white |
| Merck | 14,3675 |
| BRN | 1719753 |
| pKa | 13.9(at 25℃) |
| Storage Condition | -20°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.4502 (estimate) |
| MDL | MFCD00004710 |
| Physical and Chemical Properties | Melting Point 117-121°C boiling point 329-331°C water-soluble solution |
| Use | This product is for scientific research only and shall not be used for other purposes. |
(2R,3S)-butane-1,2,3,4-tetrol - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | KF2000000 |
| FLUKA BRAND F CODES | 3-10 |
| TSCA | Yes |
| HS Code | 29054910 |
| Toxicity | LD50 in male, female rats (g/kg): 6.6, 9.6 i.v.; >16, >16 s.c.; 13.1, 13.5 orally (Munro) |
(2R,3S)-butane-1,2,3,4-tetrol - Reference
| Reference Show more | 1. Wang Xiaodan, Bai Xiaoyan, Zhu Guojun, et al. Simultaneous Determination of Polyols in Yeast Fermentation Broth by HPLC-ELSD Method [J]. China Brewing 2018 v.37;No.313(03):167-170. 2. Liu Jinlong, Sun Xiyou, Zhao Guoqun, Wang Yong, Bai Jing, Sun Xu. Two-stage Regulation of Glucose Concentration to Enhance Erythritol Fermentation [J]. Chinese Brewing 2020 39(06):88-92. 3. Wang Ke, Ye Zhang, Liu Shisheng, et al. Effects of Several Polyols on Thermal Stability of β-Glucosidase in Rubber Seeds [J]. Food Industry 2017(4):14-17. 4. Gu Lina, Li Liangzhi, Guo Weiqiang, etc. Two-stage pH Regulation of Erythritol Production by Sporospora trispora [J]. Journal of Suzhou University of Science and Technology: Natural Science Edition, 2019, 036(001):53-57. 5. Yang Qingling, Lu Wei, Pei Pengfei, et al. Effects of Erythritol on Growth and Acid Production of Major Cariogenic Streptococcus and Fluoride-tolerant Strains [J]. Chinese Journal of Microecology, 2012, 24(002):139-141. 6. Kang Pei, Hu Cuiying, Ju Xin, et al. Effects of Copper Ions and Glucose Synergistic Supplements on Erythritol Production by Sporospora trispora [J]. Chemical Progress, 2018, 37(12):313-319. 7. Hui Heping, Jin Hui, Yang Xiaoyan, Li Xiuzhuang, Xin Ai-Qin Bo. Chemical Structure and Morphology Analysis of Polysaccharide BHP-1 from Lanzhou Lily [J]. 2020 26(08):170-175. 8. Jianbo Pan, Rongzong Zheng, Yi Wang, Xingke Ye, Zhongquan Wan, Chunyang Jia, Xiaolong Weng, Jianliang Xie, Longjiang Deng,A high-performance electrochromic device assembled with hexagonal WO3 and NiO/PB composite nanosheet electrodes towards energy storag 9. Ling Hu, Chenbo Jiang, Qilin Huang, fengyuan Sun, A comb-like branched β-d-glucan produced by a Cordyceps sinensis fungus and its protective effect against cyclophosphamide-induced immunosuppression in mice, Carbohydrate Polymers, Volume 142, 2016, Pages 2 10. [IF = 9.381] Ting Hu et al."A comb-like branched β-d-glucan produced by a Cordyceps sinensis fungus and its protective effect against cyclophosphamide-induced immunosuppression in mice." Carbohyd Polym. 2016 May;142:259 11. [IF = 7.514] ting Hu et al."A hyperbranched β-d-glucan with compact coil conformation from Lignosus rhinocerotis sclerotia." Food Chem. 2017 Jun;225:267 12. [IF = 6.953] ting Hu et al."Structure, molecular conformation, and immunomodulatory activity of four polysaccharide fractions from Lignosus rhinocerotis sclerotia." Int J Biol Macromol. 2017 Jan;94:423 13. [IF = 9.381] Qianwen Xiong et al."Structural characterization and evaluation the elicitors activity of polysaccharides from Chrysanthemum indicum." Carbohyd Polym. 2021 Jul;263:117994 14. [IF = 7.267] Jianbo Pan et al."A high-performance electrochromic device assembled with hexagonal WO3 and NiO/PB composite nanosheet electrodes towards energy storage smart window." Sol Energ Mat Sol C.2020 Apr;207:110337 15. [IF = 7.053] Y.T. Xu et al."Ultraefficient stabilization of high internal phase emulsions by globular proteins in the presence of polyols: Importance of a core-shell nanostructure." Food Hydrocolloid. 2020 Oct;107:105968 16. [IF = 6.953] Huihui Ke et al."Polysaccharide from Rubus chingii Hu affords protection against palmitic acid-induced lipotoxicity in human hepatocytes." Int J Biol Macromol. 2019 Jul;133:1063 17. [IF = 5.279] Meiyu Jin et al."Erythritol Improves Nonalcoholic Fatty Living Disease by Activating Nrf2 Antioxidant Capacity." J Agr Food Chem. 2021;69(44):13080-13092 18. [IF = 3.605] Fei Sheng et al."Pure Hydrogen Production from Polyol Electrolysis Using Polyoxometalates as Both a Liquid Catalyst and a Charge Carrier." Energ Fuel. 2020;34(8):10282-10289 |
(2R,3S)-butane-1,2,3,4-tetrol - Introduction
Pathological virus studies.
Last Update：2022-10-16 17:14:04
(2R,3S)-butane-1,2,3,4-tetrol - Reference Information
| FEMA | 4819 | ?ERYTHRITOL |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| sweetener | erythritol is a zero-calorie, good-tasting filled sweetener suitable for various sugar-free and calorie-reducing foods and beverages. Erythritol has been part of the human diet for thousands of years. Erythritol is contained in fruits and other foods. Erythritol has a high digestive tolerance and does not cause a glycemic response, so it is suitable for diabetic patients, and it does not promote tooth decay formation. Erythritol is a polyol (sugar alcohol), which is naturally found in fruits such as pears, melons and grapes. Erythritol can also be found in other foods such as mushrooms and wine, soy sauce and cheese. Erythritol is a white crystalline powder, its sweet taste is pure and refreshing, and its taste is close to sucrose. The sweetness of erythritol is about the 70% of sucrose; it has good fluidity because it is not hygroscopic. The calorific value of erythritol is 0 calories/g, and the high digestive tolerance distinguishes it from other polyols. Erythritol can be quickly absorbed by the small intestine and quickly digested by the body within 24 hours. Therefore, when eating foods containing erythritol, it is unlikely that the laxative side effects that may occur when excessive intake of polyols may occur. |
| Discovery history | Erythritol was discovered by a Scottish chemist-John. Steenhouse (John Stenhouse). John mainly studied organic chemistry throughout his life. In addition to discovering erythritol, he also discovered dimethylresorcinol and has a number of originality and practicality in dyeing, waterproofing, sugar making, leather making, etc. Patent. John accidentally discovered erythritol while studying the extraction of dyes from several lichens that can be used in the textile industry. When John was studying a lichen named Roccellamontagnei Litmus brought back from Angola, he accidentally discovered this substance. He first named it pseudo-lichenol (Pseudo-Orcin) and published it in 1848. Published in the "Royal Journal of Chemistry. "It is very sweet, and few lichenol are so sweet. When it is heated on aluminum foil, it emits a blue light and emits a caramel-like taste... it looks very much like a substance between lichenol and mannitol." In February 1849, when John continued to publish his previous research results in the "Royal Journal of Chemistry", he changed the name of the "pseudo-lichenol" he discovered and named "erythritol." |
| advantages of erythritol | zero calories: in the United States, Europe and Japan, erythritol calories on food labels are all 0 calories/g. The reason why the calorific value is zero is that erythritol will not be metabolized during its unique absorption and excretion. Therefore, erythritol is the only qualified zero-calorie filled sweetener for "reduced caloric" and "light" products that require caloric values at least 25% lower than the standard formula. High digestive tolerance: Erythritol can be quickly absorbed by the small intestine, and studies have shown that it will not ferment in the human body. Therefore, the side effects of flatulence and laxity after eating foods containing a large amount of erythritol are minimal. Adults can well tolerate daily intake of 1g/kg of erythritol through various food and beverage sources. Suitable for patients with diabetes: Single-dose and 14-day clinical studies have demonstrated that erythritol does not affect blood glucose or insulin levels. Clinical studies in diabetic patients have concluded that it may be safe to replace sucrose with erythritol in foods tailored for diabetic patients. Of course, diabetics should consider the effects of other ingredients in erythritol-containing foods on their diet. Does not promote tooth decay: Unlike other polyols, erythritol is safe and harmless to teeth and will not be metabolized by oral bacteria. Oral bacteria will break down sugar and starch to produce enamel loss or tooth decay. Acid formation. Erythritol is therefore non-cariogenic. The replacement of sugars with polyols such as erythritol and their utility in a comprehensive plan that includes good oral hygiene has been recognized by scientists and regulators. |
| application in the field of candy | erythritol has the characteristics of good thermal stability and low hygroscopicity. it can be operated in an environment above 80 ℃ to shorten the processing time. at the same time, the heating temperature in the chocolate production process using erythritol is higher than the traditional one, which is conducive to promoting the generation of flavor. Erythritol can easily replace sucrose in the product, reduce the energy of chocolate by 34%, and endow the product with cool taste and non-cariogenic characteristics. Due to the low hygroscopicity of erythritol, it also helps to overcome the frosting phenomenon when making chocolate from other sugars. Erythritol can produce all kinds of candies with good quality. The texture and shelf life of the products are exactly the same as those of traditional products. Because erythritol is easy to crush and does not absorb moisture, the prepared candies still have good storage stability even under high humidity storage conditions. At the same time, it is very beneficial to the health of the teeth and will not cause dental caries. |
| Safety | Through a number of safety studies on humans and animals, including short-term and long-term animal feeding, multi-generation reproduction and teratogenicity studies, erythritol The safety of food ingredients under established uses has been confirmed. In 1999, the WHO/FAO Joint Expert Committee on Food Additives (JECFA) reviewed the safety of erythritol and determined that its ADI (allowable daily intake) was "no requirement" and belonged to the highest safety category. Erythritol has been used in Japan since 1990 in candy, chocolate, soft drinks, chewing gum, yogurt, fillings, biscuit coatings, jelly, jam and sugar substitutes. Other government agencies around the world have also received petitions requesting the expansion of the use of erythritol. It has been approved for food use by more than 50 countries, including Canada, the United States, Brazil, Mexico, Australia and the European Union. |
| content analysis | determined by liquid chromatography. The mobile phase is deionized water. The standard solution is prepared in a vacuum dryer with about 2g of standard erythritol dried at 70 ℃ for 6h, accurately weighed about 0.1mg(W), transferred into a 50ml volumetric flask, dissolved with deionized water, and mixed evenly after constant volume. Before the determination, the solution was filtered through an applicable 0.45 μm filter (standard erythritol can be obtained from "Cerestar,EBS Vilvoorde R & D Centre,Centre of fermentation Expertise,84 Havenstraat,1800 Vilvoorde,Belgium", etc.). Determine 0.1g(ω) of 2g of pre-dried sample as "standard solution. HPLC is equipped with a constant speed non-pulsation pump and a sensitive differential refractive index detector, such as RID-6A or similar models. The column is filled with strong cation exchange resin in hydrogen, such as MCl Gel-CK 08 EH, Shodex KC-811 or similar models, and filled with micro-network sulfonated polystyrene-divinylbenzene copolymer, 8% crosslinking, particle size 9 μm. Column temperature 60 ℃. The sampler should be of fixed line type (manual or automatic), which can accurately sample 30 μ1. The integrator can be used in any kind of modern data acquisition system with recorder and operation capability. The operating flow rate is about 0.5ml/min. The maximum pressure of the whole system is about 50kgf/cm2(5000kPa). Before the measurement, the outlet of the sampler is connected with the column inlet, and the column outlet is directly connected with the sewage outlet. When the pump is started, the flow rate of the outflow system is maintained at 0.1 ml/min. The pressure is maintained at a low limit of about 1500kPa below normal operating pressure. The flow rate was gradually increased from 0.1 ml/min to 0.5 ml/min, and the elution of the column was maintained for 2 hours. Connect the column outlet with the detector tube, flush the reference cell and the sample cell for 30min each, then adjust the refractometer to zero and adjust the sensitivity. Then a systematic adaptation test was carried out: the relative standard deviation (100 × standard deviation/average peak area) of the response area after three samples of 30 μ1 standard solution was not more than 1.0%. The average peak area of erythritol was recorded as A. The average peak area of erythritol was recorded as α in three parts of 30 μ1 sample solution. The content of erythritol in the sample is calculated according to the following formula: erythritol (%)= 100(W/ω)(α/A). |
| toxicity | ADI does not make special regulations (FAO/WHO),2001). |
| use limit | GB 276-2001: drinks, candy, cakes, 3%. |
| use | low calorie sweetener; Diluent of high sweetness sweetener. It can be used for chocolate, baked goods, candy, table sugar, soft drinks, etc., with a maximum usage of 3%. sweetener; humectant; fragrance enhancer; tissue improver; forming aid. Used in organic synthesis and biochemical research. Allelic transformation of the Tas1r3 gene affected the taste response of sucrose alcohol. It is a T1R3 receptor ligand. |
| production method | starch from wheat, corn and other starch are subjected to safe and appropriate food-grade hypertonic yeasts such as clonosporin yeast (Moniliella pllinis), Candida lipoides (Candida lipolytica) or Tricho sporonoides megachilensis at high concentrations (>450g/L), fermented mash is heated and sterilized and filtered, then purified by ion exchange resin, activated carbon and ultrafiltration, crystallized, washed and dried. The general yield is about 50%. Erythritol can be extracted from seaweed, moss and some grasses. The artificial synthesis can be made by the reaction of butene glycol and hydrogen peroxide. Among them, butene glycol is made from acetylene and formaldehyde into 2-butyne-1, 4-diol, then its aqueous solution is mixed with Raney nickel and added with inhibitor ammonia water, and hydrogenated at about 0.5MPa. Starch milk is hydrolyzed into glucose, which is concentrated, crystallized, separated and dried by hypertonic yeast after fermentation at high concentration. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:45:29
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