D-Isoascorbic acid
D-Isoascorbic acid
CAS: 89-65-6
Molecular Formula: C6H8O6
D-Isoascorbic acid - Names and Identifiers
| Name | D-Isoascorbic acid |
| Synonyms | FEMA 2410 Isovitamin C ISOVITAMIN C Erythorbic Acid ISOASCORBIC ACID araboascorbicacid D-Isoascorbic acid D-Araboascorbic acid d-arabino-ascorbicacid d-erythro-3-ketohexonicacidlactone 3-keto-d-erythro-hexonicacigamma-lactone 2,3-didehydro-d-erythro-hexono-1,4-lactone D-erythro-Hex-2-enonic acid, gamma-lactone (5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-5-methyl-furan-2-one |
| CAS | 89-65-6 |
| EINECS | 201-928-0 |
| InChI | InChI=1/C7H10O6/c1-7(3(9)2-8)5(11)4(10)6(12)13-7/h3,8-11H,2H2,1H3/t3?,7-/m1/s1 |
| InChIKey | CIWBSHSKHKDKBQ-JLAZNSOCSA-N |
D-Isoascorbic acid - Physico-chemical Properties
| Molecular Formula | C6H8O6 |
| Molar Mass | 176.12 |
| Density | 1.3744 (rough estimate) |
| Melting Point | 169-172 °C (dec.) (lit.) |
| Boling Point | 227.71°C (rough estimate) |
| Specific Rotation(α) | -17.25 º (c=10, H2O 25 ºC) |
| Flash Point | 212.9°C |
| Water Solubility | 1g/10mL |
| Solubility | Soluble in water, ethanol and pyridine, soluble in acetone, slightly soluble in glycerin, insoluble in ether and benzene. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | Crystallization |
| Color | White to slightly yellow |
| Merck | 14,5126 |
| BRN | 84271 |
| pKa | 4.09±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Combustible. Incompatible with chemically active metals, aluminium, zinc, copper, magnesium, strong bases, strong oxidizing agents. |
| Sensitive | Sensitive to light |
| Refractive Index | -17.5 ° (C=10, H2O) |
| MDL | MFCD00005378 |
| Physical and Chemical Properties | White to light yellow crystals or crystalline powder. Odorless, sour. Gradually blackened under light. In a dry state, it is quite stable in the air. But it deteriorates rapidly in solution and in the presence of air. Melted and decomposed at 164~172 ℃. This strain is an isomer of ascorbic acid, which is chemically similar to ascorbic acid, but has little physiological activity of ascorbic acid (only about 1/20). The oxidation resistance is better than ascorbic acid, the price is also cheaper, but the heat resistance is poor. It has strong reducibility, and slowly colors and decomposes when exposed to light. Heavy metal ions promote its decomposition. Easily soluble in water (40g/100 m1). Soluble in ethanol (5g/100ml). Insoluble in glycerin. Insoluble in ether and benzene. |
| Use | Used as a food antioxidant, with preservation, the role of quality |
D-Isoascorbic acid - 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. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | KF3015000 |
| TSCA | Yes |
| HS Code | 29329990 |
D-Isoascorbic acid - Upstream Downstream Industry
| Raw Materials | Starch potato |
D-Isoascorbic acid - Reference
| Reference Show more | 1. Li Yi Yuan Ping Chuan Wang Yan Tianchi Zhou Yujie Liu Chunyan Chen backshan. Study on biological activity of polysaccharides from Jerusalem artichoke with different molecular weight [J]. Natural product research and development 2018 30(07):1226-1230. 2. [IF = 2.506] Zhang Han et al. Antioxidate activity of L-Ascorbic Acid and D-Isoascorbic Acid Species warnings Reduction of Hexachloroiridate (IV).J Chem-Ny. 2021;2021:5505741 |
D-Isoascorbic acid - Introduction
Easily soluble in water (soluble range is about 30%) and alcohol. Strong reducibility, gradually discoloration (blackening) when exposed to light or heating. The stability is strong in the dry state, but it will quickly decompose when exposed to air in the aqueous solution. Water soluble 1g/10mL, soluble in water, alcohol and pyridine, quite soluble in propanol, slightly soluble in glycerol, its chemical properties are very similar to ascorbic acid, with the same strong reducing effect.
Last Update：2022-10-16 17:29:38
D-Isoascorbic acid - Reference Information
| FEMA | 2410 | ERYTHROBIC ACID |
| LogP | -1.69 at 25℃ |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Introduction | D-isoascorbic acid is a natural, green, efficient food antioxidant, and extend the storage period, plays a considerable role. As an isomer of Vc, D-isoascorbic acid has many similarities with Vc in chemical properties, but as an antioxidant, it has advantages that Vc does not have. First of all, its oxidation resistance is better than Vc, therefore, when used with Vc, it can effectively protect the medicinal ingredients of Vc, and has a good effect in improving the medicinal properties, at the same time, the color of Vc was protected. Second, the safety is high, no residue in the human body, the body takes part in metabolism, can be partially converted into Vc. In recent years, as a kind of medical auxiliary materials, it has been applied in Vc tablets, Vc Yinqiao tablets and Vc health care products, and achieved good results. |
| Application | the application of isoascorbic acid and its sodium salt is very extensive, used as food antioxidant, used in fish, meat, vegetables, prevention of Browning in fruit juices, etc. It is a new type of food antioxidant, preservative, preservative, can effectively reduce the oxidation of food, prevent its color, flavor, at the same time, it can also inhibit the formation of carcinogens in food. At present, the product has been widely used in meat, vegetables, fruits, alcohol, beverages, canned, tea and other foods. In addition to the use of food antioxidants, color aids and preservatives, it also has important applications in medicine and health, daily chemical industry and so on. In medicine, isoascorbic acid has the function of lowering blood pressure, diuresis, hepatic glycogen production, pigment excretion, detoxification, etc. It can be used for hepatobiliary scintigraphy or bone scintigraphy and the treatment of kidney stones; in the chemical industry, isoascorbic acid can stabilize the chemical reaction, ease the reaction rate, and can be used as a stabilizer for chemical raw materials, as well as electrolyte in electrolysis and electroplating. |
| production method | D-isoascorbic acid is an antioxidant produced by a biological fermentation process. using corn starch as raw material, it was prepared by fermentation into gluconic acid. The technological process adopted by Japan's Fujisawa Pharmaceutical Company is: glucose is prepared from corn starch, then 2-gulolonic acid methyl ester (Methly2-ketogluconate) is prepared, and sodium erythorbate is obtained by treating with sodium methoxide, then desalted by ion exchange resin, I .e., isoascorbic acid was obtained. fermentative fermentation (28 °c, 50h) of glucose or starch by electroflurobacteria (Pseudomonasfluores-cence) or Arthrobacter globifomis to obtain calcium α-ketogluconate, this was followed by formation of the methyl ester with methanol and sulfuric acid. Methanol sodium hydroxide solution was added to perform the enolase reaction. |
| Storage Conditions | D-isoascorbic acid is stored in a ventilated, light-protected, dry and cool room. |
| Use | Antioxidant; Preservative; Color builder. isoascorbic acid is one of the most important isomers of vitamin C. Its physiological role, the role of ascorbic acid in the fight against bad blood only 1/20, but in lowering blood pressure, diuresis, liver glycogen production, pigment excretion, detoxification and other aspects of the role, approximately the same as ascorbic acid. Therefore, the market demand of isoascorbic acid has a competitive relationship with vitamin C. Isoascorbic acid is mainly used in the food industry. It accounts for more than 93% of the total demand in Japan. As a food antioxidant, it is widely used in meat food, fish food, beer, fruit juice, fruit juice Crystal, canned fruit and vegetables, cakes, dairy products, jam, wine, pickle, oil and so on. Toxicity of isoascorbic acid: oral LD50 in mice is 5g/kg. The rats were fed with 1% erythorbic acid-containing bait for 6 months without abnormal growth. Feeding was continued for an additional two years without any abnormalities in body weight, Mortality Rate and histopathological observations. Human intake of isoascorbic acid, in the body can be converted into vitamin C. In practice, its sodium salt, such as sodium erythorbate (C6H7NaO6), is almost always used. Sodium erythorbate is a white crystal. Soluble in water, aqueous solution pH 5-6. Oral LD in mice was 15.3g/kg. used as food antioxidant, with preservation, the role of quality |
| category | toxic substances |
| toxicity grade | low toxicity |
| Acute toxicity | oral-rat LD50 18000 mg/kg; Oral-mouse LD50: 8300 mg/kg |
| flammability hazard characteristics | flammable, spicy and irritating smoke |
| storage and transportation characteristics | warehouse low temperature, ventilation, dry |
| extinguishing agent | water, carbon dioxide, dry powder, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:12
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