D-Gluconic acid, delta-lactone
Glucono-δ-lactone USP26 FCCIV
CAS: 90-80-2
Molecular Formula: C6H10O6
D-Gluconic acid, delta-lactone - Names and Identifiers
D-Gluconic acid, delta-lactone - Physico-chemical Properties
| Molecular Formula | C6H10O6 |
| Molar Mass | 178.14 |
| Density | 0.6 |
| Melting Point | 160°C (dec.)(lit.) |
| Boling Point | 230.35°C (rough estimate) |
| Specific Rotation(α) | 65 º (c=1,H2O) |
| Flash Point | 192.3°C |
| Water Solubility | 500 g/L (20 ºC) |
| Solubility | Easily soluble in water, and slowly hydrolyzed, the solubility in water is 59g/100ml, slightly soluble in ethanol, 1g/100ml in ethanol, insoluble in ether. The pH of the newly prepared 1% solution is 2.5. |
| Vapor Presure | 7.6E-10mmHg at 25°C |
| Appearance | Crystallization |
| Color | White to off-white |
| Merck | 14,4457 |
| BRN | 83286 |
| pKa | 12.06±0.60(Predicted) |
| PH | 3.6 (10g/l, H2O, 20℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 63.5 ° (C=10, H2O) |
| MDL | MFCD00006647 |
| Physical and Chemical Properties | White crystal or crystalline powder, odorless, sweet first and then bitter, sour. Melting point 150~152 ℃ (decomposition). Soluble in water (room temperature, 60g/100mL), slightly soluble in ethanol (1g/100mL), insoluble in ether. Hydrolysis in aqueous solution into an equilibrium solution of gluconic acid and lactone, the newly prepared 1% aqueous solution has a Ph value of 3.5 and becomes 2.5 after 2 hours. Mouse oral LD5017.8 g/kg,ADI does not make special regulations (FAO/WHO,1994). |
| Use | Used as protein coagulant, acidulant, leavening agent, preservative and cosmetics, toothpaste production |
D-Gluconic acid, delta-lactone - Risk and Safety
| Risk Codes | R21 - Harmful in contact with skin R36/38 - Irritating to eyes and skin. R46 - May cause heritable genetic damage R62 - Possible risk of impaired fertility R63 - Possible risk of harm to the unborn child |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S53 - Avoid exposure - obtain special instructions before use. S36/37 - Wear suitable protective clothing and gloves. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S25 - Avoid contact with eyes. |
| WGK Germany | 3 |
| RTECS | LZ5184000 |
| FLUKA BRAND F CODES | 21 |
| TSCA | Yes |
| HS Code | 29322090 |
D-Gluconic acid, delta-lactone - Upstream Downstream Industry
| Raw Materials | Sulfuric acid Sulfuric acid Dextrose Anhydrate Gluconic acid Calcium Gluconate Sodium hydroxide Hydrochloric acid Hydrochloric acid |
D-Gluconic acid, delta-lactone - Reference
| Reference Show more | 1. Chen Lina, Wu Qiong, Zhou Xianfeng. Optimization of processing formula and texture analysis (TPA) of black soybean lactone tofu [J]. Food Science and Technology, 2013, 038(003): 106-109. 2. Li Shuai, ailenzhong, Zhang Hui, et al. Effect of passion fruit pectin and its octenyl succinate esterification on the stability of acidified skim milk beverage [J]. Food and Fermentation Industry, 2020, v.46;No.407(11):155-160. 3. Fang, Zheng, et al. "Effect of simultaneous treatment combining ultrasound and pH-shifting on SPI in." Food Hydrocolloids 111 (2021): 106250.https://doi.org/10.1016/j.foodhyd.2020.106250 4. [IF = 9.147] Anqi Li et al."Gelation mechanism and physical properties of glucono-δ-lactone induced alginate sodium/casein composite gels."Food Hydrocolloid. 2021 Sep;118:106775 5. [IF=9.147] Peiyuan Li et al."Preparation and structural characteristics of composite alginate/casein emulsion gels: A microscopy and rheology study."Food Hydrocolloid. 2021 Sep;118:106792 6. [IF=9.147] Xiaofei Li et al."Structural characteristics of gluconic acid δ-lactone induced casein gels as regulated by gellan gum incorporation."Food Hydrocolloid. 2021 Nov;120:106897 7. [IF=7.514] Xiaofei Li et al."Acid-induced mixed methylcellulose and casein gels: Structures, physical properties and formation mechanism."Food Chem. 2022 Jan;366:130561 8. [IF=6.953] Anqi Li et al."Interpenetrating network gels with tunable physical properties: Glucono-δ-lactone induced gelation of mixed Alg/gellan sol systems."Int J Biol Macromol. 2020 May;151:257 9. [IF=6.953] Anqi Li et al."Preparation of thermally stable emulsion gels based on Glucono-δ-lactone induced gelation of gellan gum."Int J Biol Macromol. 2020 Aug;156:565 10. [IF=6.953] Bin Yu et al."The effects of acetylated distarch phosphate from tapioca starch on rheological properties and microstructure of acid-induced casein gel."Int J Biol Macromol. 2020 Sep;159:1132 11. [IF=3.638] Ze Chen et al."Fabrication and characterization of Pickering emulsions stabilized by desalted duck egg white nanogels and sodium alginate."Journal Of The Science Of Food And Agriculture. 2021 Aug 28 12. [IF=3.616] Ya-Ru Wang et al."Effects of thermal aggregation treatment on the structural, gelation properties and microstructure of phosphorylated rice glutelin gel."J Cereal Sci. 2021 Jul;100:103252 13. [IF=7.514] Lu Han et al."Effects of inducer type and concentration on the formation mechanism of W/O/W double emulsion gels."Food Chem. 2022 Jun;379:132166 14. [IF=1.713] Kai Yuan et al."Effect of bacterial cellulose nanofibers incorporation on acid-induced casein gels: microstructures and rheological properties."Int J Food Eng. 2021 Dec ;: |
D-Gluconic acid, delta-lactone - Nature
Open Data Verified Data
White Crystal or crystalline powder, odorless, taste first sweet and then bitter, sour. Melting point 150~152 °c (decomposition). Soluble in water (room temperature, 60g/lOOmL). Slightly soluble in ethanol (1g/lOOmL). Insoluble in ether. Hydrolysis in aqueous solution forms an equilibrium solution of gluconic acid with its lactone.
Last Update：2024-01-02 23:10:35
D-Gluconic acid, delta-lactone - Preparation Method
Open Data Verified Data
calcium gluconate was hydrolyzed with sulfuric acid to obtain gluconic acid solution. The calcium sulfate precipitate was removed by filtration, and then the solution was refined with barium hydroxide and oxalic acid, and separated by sedimentation to remove SO2-and Ca2 + in the solution. The gluconic acid solution is then further purified by ion exchange resin. The solution was concentrated to 80%-85%, and Glucono -8-lactone seed crystals were added. Concentration and crystallization were continued, followed by centrifugal separation, washing with water and drying.
Last Update：2022-01-01 10:10:02
D-Gluconic acid, delta-lactone - Introduction
Hydrolyzed in aqueous solution to form an equilibrium solution of gluconic acid and its lactone.
Last Update：2022-10-16 17:29:41
D-Gluconic acid, delta-lactone - Use
Open Data Verified Data
used as stabilizer, coagulant, acidulant, integral agent. For bean products (tofu and bean flowers), sausage (sausage), surimi products and grape juice, the maximum amount of 3. Og/kg, as a preservative, the maximum dosage for the preservation of fish and shrimp is 0. lg/kg, the residual amount is 0. Olmg/kg; Can also be used as leavening agent, for the preparation of composite fermentation powder, according to the production needs of the appropriate amount of use.
Last Update：2022-01-01 10:10:02
D-Gluconic acid, delta-lactone - Safety
Open Data Verified Data
- This product is non-toxic. In 200433, the United States FDA has been approved as a non-toxic food additives.
- plastic bag. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:39:00
D-Gluconic acid, delta-lactone - Reference Information
| LogP | -2.38 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| gluconic acid derivative | gluconolactone is an ester formed by dehydration between the carboxyl group of gluconic acid and the hydroxyl group in the molecule, an ester dehydrated from the hydroxyl group on the carbon atom at the 5th (δ) position, called Glucono-δ-lactone; And the 4th (γ-position) an ester formed by dehydration of hydroxyl groups on carbon atoms, called Glucono-gamma-lactone. Crystals. There is a sweet taste different from that of gluconic acid. 153 C decomposition, [alpha] D20 61.7 degrees (C = 1). Soluble in water, in aqueous solution hydrolysis into gluconic acid, and Delta and gamma two kinds of lactone into equilibrium mixture: Figure 1 is gluconolactone molecular structure formula. its 6-phosphate is an intermediate in the oxidative decomposition of glucose in vivo (pentose phosphate pathway). In food processing, as soy protein or milk protein coagulant, meat preservatives, cakes of the coagulant and color stabilizer. This information was edited by chemical book Xiaonan (2015-09-04). |
| Glucono-δ-lactone | Glucono-δ-lactone also known as Glucono-lactone, D-glucono-δ-lactone. This line of gluconic acid to remove water after the formation of lactone compounds. White Crystal or crystalline powder. No smell or slight fragrance. It started with a sweet taste and later showed a sour taste. But the taste is completely different from that of gluconic acid. Relative molecular mass 178.14. Melting point 153 °c. Specific optical rotation +61.7 °(c = 1). Soluble in water, 59(20 ° C); Soluble in ethanol, 1g/100g(20 ° C); Insoluble in ether. The aqueous solution is a mixed solution of an equilibrium system of gluconic acid, Glucono-δ-lactone and Glucono-γ-lactone after hydrolysis. The freshly prepared 1% aqueous solution was at pH 3.6 and after 2H at pH 2.5. If 5 to 10% of calcium stearate is used, it is stable even in articles containing the hygroscopic component. Rabbit intravenous injection of LD507630mg/kg. Purposes: 1983 FAD recognized as non-toxic food additives. Used as a food additive as a sour agent, used in fruit juices, beverages and jelly; Used as a coagulant, gluconolactone is China's GB2760-1996 regulations allow the use of food coagulant, used for soy protein, milk protein, as a tofu coagulant, in soybean milk to add 0.25% ~ 0.3%, compared with calcium sulfate, due to the good water solubility of this product, can be dispersed evenly in soybean milk, made of tofu delicate, often combined with calcium sulfate; Used as a leavening agent, compared with other acids, it is not easy to react at low temperature, and it becomes gluconic acid by heating, and then reacts with sodium bicarbonate to produce carbon dioxide bubbles, which are uniform and fine in foaming, and can be used as a leavening agent for biscuits, bread, etc, especially suitable for cake; Used as a chelating agent, adjust the pH value of milk products, and can prevent the production of milk, prevent the production of beer Stone; Can also be used as a toothpaste additive, help to remove tartar, this is because this product can react with the tooth scale; Can also be used as a photographic developing agent, medicine and cosmetics vitamin stabilizer and irritation and mitigation agent; Fabric sizing additives; Detergent additives; Bottle washing agent; metal Surface cleaning agent before plating. Figure 2 is the reference quality standard of Glucono-δ-lactone. |
| method of use | use stabilizing and coagulating agents, Acidulants, chelating agents. 1. Precautions for use (1) the product is hydrolyzed in aqueous solution to produce gluconic acid, which solidifies the protein. The effect is better than calcium sulfate, calcium chloride and brine. The tofu made of gluconolactone has good water retention, fine texture, smooth and delicious, and has antiseptic effect on tofu. (2) as a preservative, it can be used for the preservation of fish, meat, poultry, shrimp and so on, so that the appearance of the product is glossy and not browning, while maintaining the elasticity of the meat. (3) as a coagulant, this product is mixed with sodium bicarbonate and made into baking powder. When heated, gluconic acid reacts with sodium bicarbonate to produce carbon dioxide, which has good leavening effect and no odor. Particularly suitable for cakes, fried foods and so on. 2. Scope of use and the amount of (1) China's "health standards for the use of food additives" (GB 2760-1996): gluconolactone can be used for fish and shrimp preservation, the maximum use of 0.1g/kg, residues less than 0.01mg/kg; For sausage (sausage), surimi products, grape juice, bean products (tofu, bean flower), the maximum amount of 3.0g/kg; For baking powder, can be used according to the production needs. (2) FAO/WHO(1984) regulations: can be used for lunch meat, meat, limited 3G/kg. (3) reference for practical use: ① when making tofu, add 2.5~2.6g per kg of soybean milk. This product can be dissolved in a small amount of water, and then added to the soy milk, or the addition of this product can be filled with soy milk, water heated to 80 degrees Celsius, keep 15min, you can condensed into tofu. (2) gluconolactone and sodium bicarbonate were mixed into baking powder according to 2 ∶ 1, and the dosage of which could account for 50% ~ 70% of the acidifier. Can be used for biscuits, fried noodles and bread, etc., especially for cakes, the dosage of about 0.13% of wheat flour. (3) lunch meat, sausage, red sausage, etc. to add 0.3% of this product, can make the product bright color, good water holding capacity, elastic, and has anti-corrosion effect, can also reduce the production of nitrosamines in products. (4) as a chelating agent, can be used in grape juice or other berry wine, can prevent the formation of tartar. For dairy products, can prevent the formation of milk. (5) This product can be used in juice drinks and jelly as a sour agent, can also be formulated with sodium bicarbonate into a high-grade beverage, not only strong gas production, but also can slowly hydrolyze gluconic acid, with the characteristics of cool and delicious and no stimulation of the stomach. |
| content analysis | accurately weigh the pre-dried sample of about 0.6g, dissolved in 0.1mol/L sodium hydroxide solution 50ml, place for 20min. Phenolphthalein test solution (TS-167) was added 3 drops, and the excess sodium hydroxide was titrated with 0.1mol/L sulfuric acid. At the same time, the blank test was carried out, and the necessary correction was made. Each rnL 0.1mol/L sodium hydroxide equivalent to this product (C6H10O6)17.81mg. |
| toxicity | ADI is not specified (FAO/WHO,2001). Ld507.63 g/kg (rabbit, intravenous injection). GRAS(FDA,§ 184.1318,2000). |
| Use limit | GB 2760-96: lunch meat, sausage (sausage), surimi products, milk, grape juice, bean products (tofu, bean flower, bean brain essence) 3.0g/kg; Fish and shrimp preservation, 0.01g/kg (residue 0.01mg/kg); Compound baking powder, GMP. FAO/WHO(1984): lunch meat, cooked meat, 3g/kg. |
| Use | as stabilizer and coagulant, can be used for bean products (tofu and bean flower), sausage (sausage), surimi products and grape juice, the maximum use of 3.0g/kg; As a preservative, can be used for the preservation of fish and shrimp, the maximum use of 0.1g/kg, residues of 0.01mg/kg; it can also be used as a leavening agent for the preparation of compound baking powder, according to the production needs of the appropriate amount of use. It is used as a raw material of tofu coagulant, flavoring agent, pH-lowering agent and leavening agent. In Japan, tofu coagulant accounted for 50%-70% of the total consumption of Japan, with the product of tofu, pure texture, smooth and delicious, and can extend the preservation time. China's health standards for the use of food additives (GB2760-86), the maximum use of 3.0g/kg. Gluconolactone is used in the milk industry to prevent the formation of milk stone, as a prevention agent for Beer stone in the brewing industry, and is added to toothpaste to help remove tartar. In addition, it is also used for meat and metal surface treatment agents. used as protein coagulant, acidulant, leavening agent, preservative and cosmetics, toothpaste production widely used as acidulant, starter, protein coagulant, PH reducing agent, color retention agent, food preservatives, etc. Made of lactone tofu texture tender, no smell, no protein loss, with antiseptic. It can also be used in cosmetics, textile, paper, medicine and so on. |
| production method | the raw material calcium gluconate is hydrolyzed with sulfuric acid to obtain gluconic acid solution. The calcium sulfate precipitate is removed by filtration, and then the solution is refined by barium hydroxide and oxalic acid, and the SO42-and Ca2 + in the solution are removed by sedimentation and separation. The gluconic acid solution is then further purified by ion exchange resin. The solution was concentrated to a concentration of 80%-85%, and Glucono-δ-lactone seed crystals were added. Concentration and crystallization were continued, followed by centrifugation, washing with water, and drying to obtain a finished product. using glucose as raw material for production of lactone by microbial fermentation in 15% ~ 35% glucose solution, adding nutrients such as magnesium sulfate, potassium dihydrogen phosphate and diammonium hydrogen phosphate, inoculating Aspergillus niger species NRRL3, the cells were incubated for 40H at 30 °c and pH 6.5. The liquid was filtered and post-treated to obtain lactone crystals. Glucose oxidase method glucose oxidase oxidizes glucose to the equilibrium solution of lactone and gluconic acid in aqueous ethanol solution (e. G. 50%) at 35-37 ℃ and pH 6, catalase is also added during the reaction to decompose the generated hydrogen peroxide. The resulting gluconic acid solution was crystallized from The lactone obtained by the above-mentioned post-treatment method, and the yield was 98%. Catalytic Oxidation of 64mg of PdCl. Dissolve in 1ml concentrated hydrochloric acid, add appropriate amount of water and refined activated carbon 3.8g(200 mesh), adjust Ph = 5 with 10% NaOH solution, then, 67mg of NaOH was added to the mixture with stirring at room temperature. The solution (dissolved in 2ml of water) was reduced to metal palladium by ionic palladium, and adsorbed on activated carbon, filtered, washed with water, and dried to obtain 3.838G of Pd-C catalyst. The catalyst was added to 9.0g of an aqueous solution of 8% glucose, and air was introduced at 50 ° C. At the same time, NaOH solution was added dropwise to maintain Ph = 9.5 ~, and the reaction was completed when the Ph value no longer decreased, the catalyst was filtered off and treated with a cation exchange resin to give 310g of gluconic acid solution. Concentrate under reduced pressure at 70 ℃ to a concentration of 80% ~ 85%, cool to below 40 ℃, add seed crystal, after crystallization, filter and dry to obtain 22.6G lactone, and the filtrate is concentrated and crystallized again, another 5.3g of product was obtained with an overall yield of 93.3%. Calcium gluconate is used as raw material to produce lactone. Calcium gluconate is firstly decomposed by inorganic acid or decalcified by ion exchange resin to obtain gluconic acid solution. If 100 parts of concentrated sulfuric acid is added to 500 parts of water, calcium gluconate is added, the temperature is maintained at 60-85 ℃ for 1.5h; After standing for 12h, the filtrate is filtered, oxalic acid is added to the filtrate, and the temperature is maintained at 50 ℃ for 1h; after standing, the gluconic acid solution was obtained by filtration, and the lactone was obtained by post-treatment. There are several methods of post-processing. Non-solvent crystallization method the gluconic acid solution is concentrated to a slurry under reduced pressure, and a non-solvent for lower ketones is added, slowly stirred and cooled to precipitate crystals, and then separated, washed and dried to obtain a finished product. This method is simple, high yield. Fractional crystallization The gluconic acid solution was concentrated to 78% ~ 85% at 52~54 ℃, cooled to 47~48 ℃, added with seeds of gluconolactone and continued concentration, the first lactone crystals were isolated after the seed crystals were grown. The concentration of the mother liquor by evaporation was continued in the same manner. The crystals were washed and dried to obtain a finished product with a total yield of 75% to 78%. The advantage of this method is that no organic solvent is used, but the viscosity of the concentrated solution is high, and the crystallization separation operation is difficult. Azeotropic dehydration crystallization method C3 to C4 alkanols are added to the gluconic acid solution, and azeotropic dehydration is carried out at 50 ° C. And 16kPa. Then, seed crystal is added to the concentrated liquid, and the crystal is cooled and crystallized, and then separated, washed and dried to obtain a finished product. The advantages of this method are that the viscosity of the system is low, the separation operation is easy, and the single-pass yield can reach more than 91%. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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Raw Materials for D-Gluconic acid, delta-lactone