L-malic acid
L(-)-Malic acid
CAS: 97-67-6
Molecular Formula: C4H6O5
L-malic acid - Names and Identifiers
| Name | L(-)-Malic acid |
| Synonyms | pinguosuan L-Mailcacid L-malic acid L(-)-Malic acid l-(ii)-malicacid L-(-)-Malic acid L-(-)-Malic acid, CP L-Hydroxysuccinic acid L-Gydroxybutanedioicacid (2S)-2-hydroxybutanedioate (S)-(-)-Hydroxysuccinic acid hydroxy-,(S)-Butanedioicacid Butanedioicacid,hydroxy-,(S)- (2S)-2-hydroxybutanedioic acid Butanedioic acid, 2-hydroxy-, (2S)- |
| CAS | 97-67-6 |
| EINECS | 202-601-5 |
| InChI | InChI=1/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1 |
| InChIKey | BJEPYKJPYRNKOW-REOHCLBHSA-N |
L-malic acid - Physico-chemical Properties
| Molecular Formula | C4H6O5 |
| Molar Mass | 134.09 |
| Density | 1.60 |
| Melting Point | 101-103 °C (lit.) |
| Boling Point | 167.16°C (rough estimate) |
| Specific Rotation(α) | -2 º (c=8.5, H2O) |
| Flash Point | 220 °C |
| JECFA Number | 619 |
| Water Solubility | soluble |
| Solubility | Soluble in water. 1g of the product can be dissolved in 1.4ml of alcohol, 1.7ml of ether, 0.7ml of methanol, 2.3ml of propanol, almost insoluble in benzene. |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | Crystallization |
| Specific Gravity | 1.595 (20/4℃) |
| Color | White |
| Merck | 14,5707 |
| BRN | 1723541 |
| pKa | (1) 3.46, (2) 5.10(at 25℃) |
| PH | 2.2 (10g/l, H2O, 20℃) |
| Storage Condition | Store below +30°C. |
| Sensitive | Sensitive to light and easy to absorb moisture |
| Refractive Index | -6.5 ° (C=10, Aceton |
| MDL | MFCD00064213 |
| Physical and Chemical Properties | Melting point 101-103°C specific optical rotation -2 ° (c = 8.5, H2O) water-soluble solution |
| Use | Used as food additives, pharmaceutical raw materials |
L-malic 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. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | ON7175000 |
| TSCA | Yes |
| HS Code | 29181980 |
L-malic acid - Reference
| Reference Show more | 1. Duan Zhenzhen, Yuan Min, Chang Rong, etc. Changes of organic acids and volatile aroma in loquat vinegar processing and their effects on quality [J]. Food and Fermentation Industry, 2017, 043(012):114-123. 2. Duan Zhenzhen, Zhou Caiqiong, Yuan Min, etc. Optimization of alcohol fermentation process and analysis of sour taste characteristics in loquat vinegar production [J]. Food and machinery, 2018, 34(003):204-210. 3. Changrong, Yuan Min, Duan Zhenzhen, etc. Optimization of acetic acid fermentation process and quality characteristics of acetic acid flavor of loquat vinegar [J]. Food and Fermentation Industry, 2017, 43(010):102-110. 4. Li Aihua, Wang Xingjie, Liu Hao, et al. Effect of yeast extracellular enzyme treatment on production of ethyl octanoate and phenylethyl acetate during simulated grape juice fermentation [J]. Journal of Food Science and Technology, 37(4). 5. Ren Jiaqi. Study on physicochemical properties and stability of polyphenol/organic acid and apple pectin compound system [D]. Southwest University, 2020. 6. Li, Ning, Zhang, Bo, Niu, mi Ming, et al. Effects of caffeic acid and rosmarinic acid on color and aroma of dry red wine before fermentation [J]. Food and Fermentation Industry, 2020 046(010):132-140. 7. Yang Min, Wang Yuhua, Milan, et al. Effects of sequential inoculation of heat-resistant kluyveri yeast and Saccharomyces cerevisiae on sensory quality of Chardonnay dry white wine [J]. Food and Fermentation Industries, 2019, 45(18). 8. Zhang Nanhai, Liu Rui-yu, Dong Yun-Rui, Guo Yi-san, Yu Qian-hui, Zhao Liang, Zhang Libing, Wang Cheng-Tao, Wu Wei, ji bao-ping, Ge Zhang-chun, Zhou Feng. Study on the acid reduction technology of blackberry juice resin and the preparation of its compound juice [J]. Food Science, 2020,41(10):281-287. 9. Bai Yufeng, Zhang Wenxia, Tian Yanan, Zhang Xiaoyan. Screening of yeast for L-malic acid wine from the east of Helan Mountain in Ningxia [J]. China Brewing, 2021,40(01):49-54. 10. Wang, Min Li, Gao, Mei Zhao, Yang, min. Application potential of heat-resistant kluyveri yeast and Dell spore yeast in ice wine brewing [J]. Food and Fermentation Industry, 2021,47(01):79-87. 11. Yang Xinyue, Yang Yuchi, Zhou Xiujuan, Xue Guixin. Optimization of fermentation conditions and composition analysis of citrus vinegar [J]. Chinese condiment, 2020,45(10):75-79. 12. Ke, W. C., et al. "Influences of malic acid isolers and their application levels on fermentation quality and biochemistry of alfalfa silage." Animal Feed Science and Technology 245 (2018): 1-9.https:// doi.org/10.1016/j. Anifeedsci. [IF = 2.478] Qiang Chang et al."Physicochemical Properties and Antioxidant Capacity of Chinese Olive (Canarium album L.) Cultivars."J Food Sci. 2017 Jun;82(6):1369-1377 14. [IF=6.583] Yani Liang et al."Nickel cobalt bimetallic metal-organic frameworks with a layer-and-channel structure for high-performance supercapacitors."J Energy Storage. 2021 Jan;33:102149 15. [IF=6.429] Limei Wang et al."Changes in cell wall metabolism and flavor qualities of mushrooms (Agaricus bernardii) under EMAP treatments during storage."Food Packaging Shelf. 2021 Sep;29:100732 16. [IF=6.291] Qiao Han et al."Health risk assessment and bioaccessibilities of heavy metals for children in soil and dust from urban parks and schools of Jiaozuo, China."Ecotox Environ Safe. 2020 Mar;191:110157 17. [IF=5.81] Dong Rong et al."An Integrated Strategy for Rapid Discovery and Identification of Quality Markers in Gardenia Fructus Using an Omics Discrimination-Grey Correlation-Biological Verification Method."Front Pharmacol. 2021 Jun;0:1596 18. [IF=5.64] Li Jie et al."Investigation of the Lactic Acid Bacteria in Kazak Cheese and Their Contributions to Cheese Fermentation."Front Microbiol. 2020 Mar;0:228 19. [IF=4.952] Yuting Zheng et al."Antioxidant α-amylase and α-glucosidase inhibitory activities of bound polyphenols extracted from mung bean skin dietary fiber."Lwt Food Sci Technol. 2020 Oct;132:109943 20. [IF=4.556] Dandan Zhao et al."Physico-chemical properties and free amino acids profiles of six wolfberry cultivars in Zhongning."J Food Compos Anal. 2020 May;88:103460 21. [IF=4.466] Yao Tan et al."Multiomics Integrative Analysis for Discovering the Potential Mechanism of Dioscin against Hyperuricemia Mice."J Proteome Res. 2021;20(1):645-660 22. [IF=3.383] Ruizhe Lian et al."Physicochemical, antibacterial properties and cytocompatibility of starch/chitosan films incorporated with zinc oxide nanoparticles."Mater Today Commun. 2021 Jun;27:102265 23. [IF=3.383] Ruizhe Lian et al."Prolonged release of ciprofloxacin hydrochloride from chitosan/gelatin/poly (vinyl alcohol) composite films."Mater Today Commun. 2021 Jun;27:102219 24. [IF=3.251] Jiaran Zhang et al."A Fluorescence Method Based on N, S-Doped Carbon Dots for Detection of Ammonia in Aquaculture Water and Freshness of Fish."Sustainability-Basel. 2021 Jan;13(15):8255 25. [IF=5.154] Ying Jiang et al."Isolation of a novel characterized Issatchenkia terricola from red raspberry fruits on the degradation of citric acid and enrichment of flavonoid and volatile profiles in fermented red raspberry juice."Food Science and Human Wellness. 202 |
L-malic acid - Standard
Authoritative Data Verified Data
This product is L-hydroxysuccinic acid, by enzyme engineering method or fermentation method and separation and purification. The content of C4H6Os shall not be less than 99.0% calculated as anhydrous.
Last Update：2024-01-02 23:10:35
L-malic acid - Trait
Authoritative Data Verified Data
- This product is white crystal or crystalline powder; Odorless, tasteless.
- This product is soluble in water or ethanol, slightly soluble in acetone.
specific rotation
take this product, precision weighing, adding water to dissolve and quantitative dilution to make a solution containing about 85mg per lm l, determined according to law (General rule 0621), the specific rotation is 1. 6 ° to − 2. 6 degrees.
Last Update：2022-01-01 11:23:18
L-malic acid - Differential diagnosis
Authoritative Data Verified Data
- take about 0.5g of this product, Add 10ml of water to dissolve, adjust p H value to Neutral with concentrated ammonia solution, add 1% sulfanilic acid solution lm l, and heat in boiling water bath for 5 minutes, add 5ml of 20% sodium nitrite solution, heat in water bath for 3 minutes, and add 5ml of 4% sodium hydroxide solution. The solution should be red immediately.
- The infrared absorption spectrum of this product should be consistent with that of L-malic acid reference substance (General rule 0402).
Last Update：2022-01-01 11:23:19
L-malic acid - Exam
Authoritative Data Verified Data
clarity and color of solution
take 10.0g of this product, dissolve it in 0901 of water, and check it according to law (General rule 0902 and general rule). The solution should be clear and colorless; If it is turbid, compared with No. 1 turbidity standard solution (General Principles 0902 first method), should not be more concentrated.
easy oxide
take this product 0. 10g, put in a 100ml beaker, add water 25ral and sulfuric acid solution (1-20)25ml to dissolve, shake well, cool in a 20 ° C ± l t water bath, add 0. 02m o l/L potassium permanganate solution 5ml, the color of the solution should not disappear within 3 minutes.
chloride
take l .O g of this product and check it according to law (General rule 0801). Compared with the control solution made of 5. O m l of standard sodium chloride solution, it should not be more concentrated (0. 005%).
sulfate
take this product l.O g, check according to law (General rule 0802), compared with the standard potassium sulfate solution 3. O m l made of the control solution, not more concentrated (0.03%).
insoluble in water
Take 2 5.0g of this product, add 1 0 0 m l of water to dissolve, filter with No. 4 vertical melting crucible with constant weight at 10 0°C, and rinse the filter residue with hot water, dry to constant weight at l00 °C, residual fish shall not pass 0 .1%.
Related substances
take this product, precision weighing, adding mobile phase to dissolve and quantitatively dilute to prepare a solution containing lm g per lm l, as a test solution; Take fumaric acid and maleic acid reference, precision weighing, plus mobile phase dissolution and quantitative dilution made per l m l containing 10mg and 0. 5 tons of mixed solution, as a control solution. Test according to high performance liquid chromatography (General 0512). The mobile phase was 0.1% phosphoric acid solution-methanol (90: 10). The detection wavelength was 214mn. An appropriate amount of fumaric acid, maleic acid and L-malic acid control was taken, and the mobile phase was added to dissolve and dilute to prepare a mixed solution containing 10 meshes, 4f,g and lm g per lm l. Take 10 ^ 1, inject human liquid chromatograph, the peak order of each component is L-malic acid, maleic acid and fumaric acid, the number of theoretical plate L-malic acid peak is not less than 2000, the resolution of L-malic acid peak, maleic acid peak and fumaric acid peak should meet the requirements. The control solution lOfxl was injected into the human liquid chromatograph to adjust the detection sensitivity so that the peak height of the maleic acid peak was about 10% of the full scale. Then the test solution and the reference solution were respectively injected with 1 0 fJ, and the human liquid chromatograph was recorded to 3 times of the retention time of the main peak. If the peaks of impurities are shown in the chromatogram of the test solution, the contents of fumaric acid and maleic acid shall not exceed 1. 0% and 0. 05% based on the peak area by external standard method. The Peak area of other individual impurities shall not be greater than 2 times (0 .1%) The Peak area of maleic acid in the reference solution, and the sum of the peak areas of other impurities shall not be greater than 10 times (0.5%) The Peak area of maleic acid in the reference solution.
moisture
take this product, according to the determination method of moisture (General 0832), the water content shall not be 2 .0%.
ignition residue
The l .O g of this product shall be taken for inspection according to law (General rule 0841), and the remaining residue shall not exceed.
calcium salt
take this product l .O g, add 10ml of water to dissolve, add 20ml of 5% sodium acetate solution, shake well, take 15ml, add 2M o l/L acetic acid solution lm l, shake well, as a test solution; Take the standard calcium solution (precision weighing calcium carbonate 2. 50g, put in 1000ml measuring flask, add 12ml of 5 m d /L acetic acid solution, add appropriate amount of water to dissolve and dilute to the scale, shake well, as a calcium solution stock solution. Immediately before use, accurately measure the stock solution of calcium solution lm l, put it in a 100ml measuring flask, dilute it with water to the scale, and shake it well, with Ca 10 mesh per lm l) 10. 0ml, add 2mol/L acetic acid solution lm l and water 5ml, shake, as a reference solution. Take alcohol to prepare standard calcium solution (before use, take 10ml of calcium solution stock solution, put it in a 100ml measuring flask, dilute it to the scale with ethanol, and shake well. Ca 0. lmg per lm l)
0.2ml, put in Nessler's colorimetric tube, add 4% ammonium oxalate solution lm l,1 min later, add human sample solution, shake, and place for 15 min later, compared with the control solution prepared by the same method, it should not be more concentrated (0.02%).
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
arsenic salt
take 1. 0g of this product, add hydrochloric acid 5m l and water 2 3 m h for inspection according to law (General rule 0822 first law), shall comply with the regulations (0.0002%).
Last Update：2022-01-01 11:23:20
L-malic acid - Content determination
Authoritative Data Verified Data
take this product about l.O g, precision weighing, put in 250ml measuring flask, add water to dissolve and dilute to the scale, shake well, take 25ml, put in Erlenmeyer flask, add 2 drops of phenolphthalein indicator solution, with sodium hydroxide titration solution (0.1 M o l/L) titrated to microscopic red color and held for 30 seconds without fading. Each 1 ml of sodium hydroxide titration solution (0.1 M o l/L) corresponds to 6.704 mg of C4HSO5.
Last Update：2022-01-01 11:23:20
L-malic acid - Category
Authoritative Data Verified Data
pharmaceutical excipients, p H value regulator and antioxidant.
Last Update：2022-01-01 11:23:21
L-malic acid - Storage
Authoritative Data Verified Data
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:23:21
L-malic acid - Reference Information
| FEMA | 2655 | L-MALIC ACID |
| LogP | -1.68 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Background | malic acid there are D-malic acid, DL-malic acid and L-malic acid. L-malic acid, also known as 2-hydroxybutanedioic acid, is a circulating intermediate of organism tricarboxylic acid, which is easily absorbed by human body. Therefore, as a food additive and functional food with excellent performance, L-malic acid is widely used in food, cosmetics, medical and health care products and other fields. Malic acid, also known as 2-hydroxybutanedioic acid, has two stereoisomers due to an asymmetric carbon atom in the molecule. In nature, there are three forms, namely D-malic acid, L-malic acid and mixtures thereof DL-malic acid. Malic acid is white crystal or crystalline powder, has strong hygroscopicity, soluble in water, ethanol. There is a special pleasant sour taste. L-malic acid is mainly used in the food and pharmaceutical industries. |
| Application | L-malic acid contains natural emollient ingredients, which can remove wrinkles on the skin surface, make the skin become tender and white, smooth and elastic, so in the cosmetic formula favored; L-malic acid can be formulated a variety of flavors, spices, for a variety of daily chemical products, such as toothpaste, shampoo, etc; it is used abroad to replace citric acid as a new type of detergent additive for the synthesis of high-grade special detergents. L-malic acid can be used in pharmaceutical preparations, tablets, syrup, can also be mixed into the amino acid solution, can significantly improve the absorption rate of amino acids; L-malic acid can be used for the treatment of liver disease, anemia, low immunity, uremia, hypertension, liver failure and other diseases, and can reduce the toxic effect of anticancer drugs on normal cells; Can also be used for the preparation and synthesis of insect repellents, anti-Tartar agents. In addition, L-malic acid can also be used as industrial cleaning agent, resin curing agent, synthetic material plasticizer, feed additive, etc. |
| preparation | (1) a mixed solution of L-malate and fumarate was prepared according to the cell transformation method of the prior art (DE3310849). The aspergilus wentii strain isolated from soil was treated with sugar 30g/L, diammonium hydrogen phosphate 3G/L, ammonium sulfate 2G/L, potassium chloride 2G/L, magnesium sulfate 1g/L, the cells were cultured in a culture medium containing 5g/L of sodium fumarate for 48 hours and separated by filtration. Prepare 2% carrageenan solution at 60-70 ℃, and add the separated cells at 10%(w/w) when cooling to 50 ℃, stir evenly and then pour into a plate to solidify, 5mm X 5mm X 5mm immobilized cells were prepared. A glass column of 8cm x 60cm was then loaded. A 1.4m sodium fumarate solution was passed through the immobilized cell column at a rate of 1000mL/h to obtain a mixed solution of L-malate and fumarate. (2) take 1000ml of the mixture obtained in step (1), which contains 186g of sodium L-malate and 56g of sodium fumarate. The solution was heated to 60 °c, and G (molar ratio 1.05: 1) of fumaric acid was added with stirring. The reaction was stirred for 3.5 hours, PH = 3.2, cooled to 15~20 °c, filtered, the filter cake was washed with a small amount of water and then neutralized with NaOH to PH = 7-8 for cell transformation. The resulting filtrate was 980ML and contained 40g of monosodium fumarate. Heat to 85 °c, pass through ml 001x7 strong acid cation exchange column (diameter 6cm, height 60cm), collect the eluent and concentrate it under reduced pressure, when L-malic acid concentration is increased to 40%, after cooling to 10-15 °c, fumaric acid was recovered by filtration. The filtrate is further concentrated under reduced pressure to a L-malic acid concentration of 80-82%, cooled to 15 ° C. To crystallize 91gL-malic acid. The mother liquor contains 46gL-malic acid, and the mother liquor can be recycled. The yield of L-malic acid corresponds to 97%. |
| properties | white or colorless powder. Refractory to water. Not fused to ethanol. |
| Use | L-malic acid is used as a cool beverage (such as lactic acid bacteria beverage, milk beverage, soda, Cola), frozen food (such as fruit Dew, ice cream, etc.), processed food (such as fruit wine, mayonnaise) acidulants, fruit drinks and other color retention agents, preservatives and emulsion stabilizers such as egg yolk. Uses also include raw materials for pharmaceutical products, cosmetics, dental solutions, metal detergents, anti-coagulant agents in the textile industry, and fluorescent whitening agents for polyester fibers. for the manufacture of esters; For complexing agents and flavoring agents. According to China's GB 2760-90 regulations, can be used for all kinds of food. As the acidulant, it can be used instead of citric acid (about 80%), and is particularly suitable for foods based on jelly and fruit. The product has the function of maintaining the color of natural fruits, and can also be used as an auxiliary agent for pectin extraction to promote the growth of yeast, and prepare salt-free soy sauce and vinegar to improve the taste of pickled vegetables and margarine, emulsion stabilizer for mayonnaise and the like. Widely used in a variety of anti-corrosion, flavoring and other additives. selective α-amino-protecting agents for amino acid derivatives; Multifunctional synthetic factors for the preparation of factors including κ-opioid receptor agonists, 1 α, chiral compounds including 25-Dihydroxyvitamin D3 analogs and phospholactone B; Substrate for determination of malate dehydrogenase gamma-aminobutyric acid synthase inhibitor. used as food additives, pharmaceutical raw materials |
| production method | malic acid widely exists in nature, is the product of animal and plant metabolism, is the main acid component in Apple. The immature fruit juice of apple, grape and peach is boiled, lime water is added to form calcium salt precipitate, and then it is converted into lead salt, and then treated to form free acid, and L-malic acid can be obtained. Fermentation method is also possible to achieve industrialization, the use of mutant yeast strains for fermentation, can obtain L-malic acid-based special fungi for acid, or use to produce malic acid-based special fungi for fermentation, L-malic acid can be obtained, but the process is more complicated than the synthesis method, and the cost is higher. L-malic acid is produced by biosynthesis in Japan. The Brevibacterium aminophenol cells (breridacterium ammoni-agenes cell) were first fixed with polyacrylamides. A suspension of the cells in physiological saline was mixed with an acrylic acid amide and an appropriate cross-linking agent and a polymerization promoter, and the resulting gel was made into 3mm diameter particles. After washing, the solution was soaked in sodium fumarate containing about 0.3 bovine bile and kept at 37 °c for 20H. The cells treated in this way were used as a filler for the reaction column. 1L of sodium fumarate containing 1mol was passed through a reaction column at 37 ° C. And the malic acid was separated from the effluent in the usual manner to produce a pharmaceutical grade product of L-malic acid from fumaric acid in a yield of about 70%. |
Last Update：2024-04-09 20:52:54
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