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Basic Description
| Synonyms | 97-67-6 | L-Malic acid | L-(-)-Malic acid | (S)-2-hydroxysuccinic acid | (2S)-2-Hydroxybutanedioic acid | (S)-Malic acid | L(-)-Malic acid | (-)-Malic acid | L-Apple acid | Apple acid | (-)-Hydroxysuccinic acid | L-malate | S-(-)-Malic acid | L-Hydroxybutanedioic acid | S-2-Hydroxyb |
|---|---|
| Specifications & Purity | 10mM in DMSO |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Product Description |
L-(-)-Malic acid is an organic acid that is commonly found in wine. It plays an important role in wine microbiological stability. |
Taxonomic Classification
Taxonomy Tree
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Kingdom
Organic compounds
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Superclass
Organic acids and derivatives
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Class
Hydroxy acids and derivatives
- Subclass Beta hydroxy acids and derivatives
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Class
Hydroxy acids and derivatives
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Superclass
Organic acids and derivatives
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Hydroxy acids and derivatives |
| Subclass | Beta hydroxy acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Beta hydroxy acids and derivatives |
| Alternative Parents | Short-chain hydroxy acids and derivatives Fatty acids and conjugates Dicarboxylic acids and derivatives Alpha hydroxy acids and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Short-chain hydroxy acid - Beta-hydroxy acid - Fatty acid - Dicarboxylic acid or derivatives - Alpha-hydroxy acid - Secondary alcohol - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Alcohol - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
| External Descriptors | malic acid |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Names and Identifiers
| IUPAC Name | (2S)-2-hydroxybutanedioic acid |
|---|---|
| INCHI | InChI=1S/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 |
| Smiles | C(C(C(=O)O)O)C(=O)O |
| Isomeric SMILES | C([C@@H](C(=O)O)O)C(=O)O |
| WGK Germany | 3 |
| Molecular Weight | 134.09 |
| Beilstein | 1723540 |
| Reaxy-Rn | 1723539 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1723539&ln= |
Certificates（CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
| Sensitivity | Light sensitive.Moisture sensitive;Air sensitive |
|---|---|
| Specific Rotation[α] | -6.5° (C=10,Acetone) |
| Flash Point(°C) | 220°C |
| Melt Point(°C) | 101-103°C |
| Molecular Weight | 134.090 g/mol |
| XLogP3 | -1.300 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Exact Mass | 134.022 Da |
| Monoisotopic Mass | 134.022 Da |
| Topological Polar Surface Area | 94.800 Ų |
| Heavy Atom Count | 9 |
| Formal Charge | 0 |
| Complexity | 129.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
Citations of This Product
| 1. Mei Chen, Xu Li, Yinxiang Li, Yanhu Li, Ziyu Qin, Qingji Wang. (2024) MOF-derived Co3O4 nanoparticles over direct grown ZnO nanoflower on ceramic for CO sensor with high selectivity. SENSORS AND ACTUATORS B-CHEMICAL, 401 (134951). |
| 2. Min Wu, Yitao Zhao, Meihan Tao, Meimei Fu, Yue Wang, Qi Liu, Zhihui Lu, Jinshan Guo. (2023) Malate-Based Biodegradable Scaffolds Activate Cellular Energetic Metabolism for Accelerated Wound Healing. ACS Applied Materials & Interfaces, 15 (44): (50836–50853). |
| 3. Jingyi Liang, Hansheng Huang, Hao Zhang, Yanhui Wu, Yongbing Zhuang. (2023) Preparation of Thin Film Composite (TFC) Membrane with DESPs Interlayer and Its Forward Osmosis (FO) Performance for Organic Solvent Recovery. Membranes, 13 (7): (688). |
| 4. Xing Chenyu, Chen Gaoyu, Zhu Xia, An Jiakun, Bao Jianchun, Wang Xuan, Zhou Xiuqing, Du Xiuli, Xu Xiangxing. (2023) Synthesis of carbon dots with predictable photoluminescence by the aid of machine learning. Nano Research, (1-6). |
| 5. Li Yuchen, Xu Guangfu, Chen Jiaquan, Yu Tao, Miao Pandeng, Du Yingxiang. (2023) One-step synthesis of chiral molecularly imprinted polymer TiO2 nanoparticles for enantioseparation of phenylalanine in coated capillary electrochromatography. MICROCHIMICA ACTA, 190 (7): (1-11). |
| 6. Mingjia Bai, Chaoyang Li, Xiaojun Zhao, Qingji Wang, Qinhe Pan. (2023) Controllable Synthesis of Sheet-Flower ZnO for Low Temperature NO2 Sensor. Nanomaterials, 13 (8): (1413). |
| 7. Tao Yan, Jianhua Yang, Jinming Lu, Liang Zhou, Yan Zhang, Gaohong He. (2023) Facile Synthesis of Ultra-microporous Pillar-Layered Metal–Organic Framework Membranes for Highly H2-Selective Separation. ACS Applied Materials & Interfaces, 15 (16): (20571–20582). |
| 8. Yingying Han, Zhicong Su, Jinhua Du. (2023) Effects of apple storage period on the organic acids and volatiles in apple wine. LWT-FOOD SCIENCE AND TECHNOLOGY, 173 (114389). |
| 9. Junjie Wen, Rui Lin, Yibing Wu, Hong Zhang, Hui Zhou, Zheng Liu, Yu Xie, Dapeng Ye, Xinhua Ouyang. (2022) Environmentally friendly cathode interlayer modification on edible bio-acids with enhanced electron extraction and improved power conversion efficiency. EcoMat, 5 (4): (e12318). |
| 10. Yingying Han, Jinhua Du. (2023) A comparative study of the effect of bacteria and yeasts communities on inoculated and spontaneously fermented apple cider. FOOD MICROBIOLOGY, 111 (104195). |
| 11. Haiping Zhao, Ziyi Zhang, Yong Han, Weixia Yang, Wenzhi Tang, Tianli Yue, Zhonghong Li. (2023) Visual detection of vitamin C in fruits and vegetables using UiO-66 loaded Ce-MnO2 mimetic oxidase. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 285 (121900). |
| 12. Feng Y, Gao S, Zhu T, Sun G, Zhang P, Huang Y, Qu S, Du X, Mou D. (2022) Hawthorn fruit acid consumption attenuates hyperlipidemia-associated oxidative damage in rats.. Frontiers in Nutrition, 9 (936229-936229). |
| 13. Tong Wang, Qing Guo, Ping Li, Hua Yang. (2022) Deep-eutectic solvents/ionic liquids/water mixture as a novel type of green thermo-switchable solvent system for selective extraction and separation of natural products from Rosmarinus officinalis leaves. FOOD CHEMISTRY, 390 (133225). |
| 14. Tong Wang, Qing Guo, Hua Yang, Wen Gao, Ping Li. (2022) pH-controlled reversible deep-eutectic solvent based enzyme system for simultaneous extraction and in-situ separation of isoflavones from Pueraria lobata. SEPARATION AND PURIFICATION TECHNOLOGY, 292 (120992). |
| 15. Dandan Cui, Jin Yang, Bosi Lu, Lansheng Deng, Hong Shen. (2022) Extraction and characterization of chitin from Oratosquilla oratoria shell waste and its application in Brassica campestris L.ssp. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 198 (204). |
| 16. Qingping Xin, Meixue Zhao, Jianping Guo, Dandan Huang, Yinan Zeng, Yuhang Zhao, Teng Zhang, Lei Zhang, Shaofei Wang, Yuzhong Zhang. (2021) Light-responsive metal–organic framework sheets constructed smart membranes with tunable transport channels for efficient gas separation. RSC Advances, 12 (1): (517-527). |
| 17. Binbin Zhang, Qi Zhou, Xinwei Zhang, Jiao Ma, Xin Cong, Qin Wang, Yonggui Liao, Yajiang Yang, Hong Wang. (2022) Thermostable fluorescent supramolecular gels constructed from a single gelator and its application in discriminating organic acids. JOURNAL OF MOLECULAR LIQUIDS, 346 (117137). |
| 18. Yingying Han, Jinhua Du, Yan Wang. (2021) Effect of bentonite and calcium chloride on apple wine. JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 102 (1): (425-433). |
| 19. Yaxin Qiu, Dheeman-Roy Munna, Fang Wang, Juqun Xi, Zhifeng Wang, Defeng Wu. (2021) Regulating Asynchronous Deformations of Biopolyester Elastomers via Photoprogramming and Strain-Induced Crystallization. MACROMOLECULES, 54 (12): (5694–5704). |
| 20. Tong Wang, Qing Wang, Qing Guo, Ping Li, Hua Yang. (2021) A hydrophobic deep eutectic solvents-based integrated method for efficient and green extraction and recovery of natural products from Rosmarinus officinalis leaves, Ginkgo biloba leaves and Salvia miltiorrhiza roots. FOOD CHEMISTRY, 363 (130282). |
| 21. Qianru Wanyan, Yaxin Qiu, Wenting Zhang, Hai Yu, Defeng Wu. (2021) Functional biopolyesters based on cross-linked Poly(L-malic acid): Network engineering towards tailoring brittle-ductile transition and shape-memory performance. POLYMER, 221 (123628). |
| 22. Xingyun Huang, Ying Peng, Jing Xu, Feng Wu, Gilles Mailhot. (2021) Iron(III)-induced photooxidation of arsenite in the presence of carboxylic acids and phenols as model compounds of natural organic matter. CHEMOSPHERE, 263 (128142). |
| 23. Shaoping Ma, Fenfang Li, Liangliang Liu, Liping Liao, Li Chang, Zhijian Tan. (2020) Deep-eutectic solvents simultaneously used as the phase-forming components and chiral selectors for enantioselective liquid-liquid extraction of tryptophan enantiomers. JOURNAL OF MOLECULAR LIQUIDS, 319 (114106). |
| 24. Xinyu Wang, Xin Wang, Jian Liu, Ke Wang, Rusong Zhao, Shenghong Yang. (2020) Ingenious aspartic acid-functionalized gold nanoparticles by one-pot protocol for the sensitive detection of chromium (III) ions. MICROCHEMICAL JOURNAL, 159 (105359). |
| 25. Lijie Huang, Hanyu Zhao, Tan Yi, Minghui Qi, Hao Xu, Qi Mo, Chongxing Huang, Shuangfei Wang, Yang Liu. (2020) Preparation and Properties of Cassava Residue Cellulose Nanofibril/Cassava Starch Composite Films. Nanomaterials, 10 (4): (755). |
| 26. Yaxin Qiu, Juqun Xi, Qianru Wanyan, Defeng Wu. (2020) Selectively Sensing Capacities of Biocompatible Shape Memory Materials Based on Cross-Linked Poly(l-malic acid): Visual Discrimination of the Solvents with Similar Structures. ACS Applied Polymer Materials, 2 (4): (1672–1681). |
| 27. Yuchun Qiao, Haifeng Dong, Xueji Zhang. (2020) A Versatile Sunscreen with Minimal ROS Damage and Low Permeability. ACS Applied Materials & Interfaces, 12 (5): (6217–6225). |
| 28. Tong Wang, Qing Wang, Ping Li, Hua Yang. (2020) High-Speed Countercurrent Chromatography-Based Method for Simultaneous Recovery and Separation of Natural Products from Deep Eutectic Solvent Extracts. ACS Sustainable Chemistry & Engineering, 8 (4): (2073–2080). |
| 29. Wanyan Qianru, Qiu Yaxin, Xie Wenyuan, Wu Defeng. (2020) Tuning Degradation and Mechanical Properties of Poly(l-lactic acid) with Biomass-Derived Poly(l-malic acid). JOURNAL OF POLYMERS AND THE ENVIRONMENT, 28 (3): (884-891). |
| 30. Yaxin Qiu, Qianru Wanyan, Wenyuan Xie, Zhifeng Wang, Ming Chen, Defeng Wu. (2019) Green and biomass-derived materials with controllable shape memory transition temperatures based on cross-linked Poly(l-malic acid). POLYMER, 180 (121733). |
| 31. Yingying Han, Jinhua Du, Jie Li, Miaomiao Li. (2019) Quantification of the Organic Acids in Hawthorn Wine: A Comparison of Two HPLC Methods. MOLECULES, 24 (11): (2150). |
| 32. Xiaodong Cao, Xueting Zhu, Shudong He, Xuan Xu, Yongkang Ye, Sundaram Gunasekaran. (2019) Gold nanoparticle-doped three-dimensional reduced graphene hydrogel modified electrodes for amperometric determination of indole-3-acetic acid and salicylic acid. Nanoscale, 11 (21): (10247-10256). |
| 33. Cuimei Liu, Dongmei Li, Jincheng Li, Zhenpeng Guo, Yi Chen. (2019) One-pot sample preparation approach for profiling spatial distribution of gibberellins in a single shoot of germinating cereal seeds. PLANT JOURNAL, 99 (5): (1014-1024). |
| 34. Wei Wang, Tao Liang, Baikai Zhang, Huiyu Bai, Piming Ma, Weifu Dong. (2018) Green functionalization of cellulose nanocrystals for application in reinforced poly(methyl methacrylate) nanocomposites. CARBOHYDRATE POLYMERS, 202 (591). |
| 35. Xueli Luo, Wengang Zhang, Yong Han, Xiumei Chen, Li Zhu, Wenzhi Tang, Jianlong Wang, Tianli Yue, Zhonghong Li. (2018) N,S co-doped carbon dots based fluorescent “on-off-on” sensor for determination of ascorbic acid in common fruits. FOOD CHEMISTRY, 258 (214). |
| 36. Yanan Wu, Rong He, Zhigao Wang, Jian Yuan, Changrui Xing, Lifeng Wang, Xingrong Ju. (2016) A safe, efficient and simple technique for the removal of cadmium from brown rice flour with citric acid and analyzed by inductively coupled plasma mass spectrometry. Analytical Methods, 8 (33): (6313-6322). |
| 37. Ting Su, Xinyu Peng, Jun Cao, Jing Chang, Rong Liu, Zhongwei Gu, Bin He. (2015) Functionalization of biodegradable hyperbranched poly(α,β-malic acid) as a nanocarrier platform for anticancer drug delivery. RSC Advances, 5 (17): (13157-13165). |
| 38. Yang Zhang, Yihong Xia, Yongji Lai, Fang Tang, Zengwei Luo, Yongbo Xue, Guangmin Yao, Yonghui Zhang, Jinwen Zhang. (2014) Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach. MOLECULES, 19 (10): (16950-16958). |
| 39. Wang Panxue, Li Aixia, Dong Mei, Fan Mingtao. (2014) Induction, purification and characterization of malolactic enzyme from Oenococcus oeni SD-2a. EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 239 (5): (827-835). |
| 40. Fangqin Wang, Wenrong Cai, Lilan Tan, Junyao Li, Datong Wu, Yong Kong. (2024) A Liquid–Liquid Interfacial Strategy for Construction of Electroactive Chiral Covalent–Organic Frameworks with the Aim to Enlarge the Testing Scope of Chiral Electroanalysis. ANALYTICAL CHEMISTRY, 96 (7): (3200-3207). |
| 41. Yidan Mo, Jinming Xu, Huangmei Zhou, Yu Zhao, Kai Chen, Jie Zhang, Lunhua Deng, Sanjun Zhang. (2024) A machine learning-assisted fluorescent sensor array utilizing silver nanoclusters for coffee discrimination. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 322 (124760). |
| 42. Tao Wu, Zhiwen Jia, Yufang Meng, Jiamin Ye, Wanyu Li, Yan Sun, Junyu Li, Linghao Li, Zerong Liu, Shiyang Wang, Xiwei Xu. (2024) Biomass-based strong adhesive based on supramolecular deep eutectic solvents pretreatment. CHEMICAL ENGINEERING JOURNAL, (159055). |
| 43. Zhao Jielin, Li Xiaolian, He Ranfeng, Wang Yunshan, Wang Ziqiang. (2024) Construction and Application of a Multienzyme System for Synthesis of l-malate. APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, (1-15). |
| 44. Yiwen Liu, Ruirui Liu, Qingliang Yang, Gensheng Yang. (2024) DES/O microemulsion for solubilizing and delivering curcumin via the nasal administration to treat acute asthma. INTERNATIONAL JOURNAL OF PHARMACEUTICS, 667 (124900). |
| 45. Qianchun Zhang, Jiaxin Liu, Yongxia Ao, Fengling Tian, Xiaofang Tian, Xinyu Luo, Meijie Xie. (2025) Efficient synthesis of red-emissive nitrogen-doped carbon dots for sensitive detection of amaranth in food samples. JOURNAL OF FOOD COMPOSITION AND ANALYSIS, 139 (107113). |
| 46. Yiruo Wang, Hongyu Gan, Qifeng Wei, Shanshan Wang, Xiulian Ren. (2025) Extraction of Chitin from Food Waste Using Recyclable Deep Eutectic Solvents. ACS Food Science & Technology, 5 (2): (780-787). |
| 47. Yanhu Li, Mei Chen, Linghong Xue, Xu Li, Qingji Wang. (2025) High response acetone sensor with ppb detection based on Pd-Pt/ZnO nanoflowers in-situ grown on planar substrates. MATERIALS SCIENCE IN SEMICONDUCTOR PROCESSING, 186 (109100). |
| 48. Wenjuan Shang, Hui Xin, Xiandeng Hou, Li Wu, Lan Wu. (2024) Multifunctional SERS Substrate for Simultaneous Detection of Multiple Contaminants and Photothermal Removal of Pathogenic Bacteria. ACS Applied Materials & Interfaces, 16 (38): (51679-51689). |
| 49. Qianchun Zhang, Yongxia Ao, Jiaxin Liu, Shan Tang, Fengling Tian, Xiaofang Tian, Xinyu Luo, Meijie Xie. (2025) Red-emissive carbon dot as fluorescent probe for the sensitive detection of sunset yellow in foodstuffs. FOOD CHEMISTRY, 463 (141477). |
| 50. Duo Xu, Bowen Du, Yantian Ji, Huimin Sun, Tiecheng Wang, Xianqiang Yin. (2024) Stereoselective transport of 2-aryl propionic acid enantiomers in porous media subjected to chiral organic acids. JOURNAL OF HAZARDOUS MATERIALS, 468 (133824). |
| 51. Duo Xu, Yantian Ji, Bowen Du, Bo He, Hongyang Chen, Huimin Sun, Xianqiang Yin. (2024) The synergistic effect of typical chiral organic acids and solution chemistry conditions on the transport of 2-arylpropionic acid chiral derivatives in porous media. ENVIRONMENTAL POLLUTION, 351 (124059). |
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