Determine the necessary mass, volume, or concentration for preparing a solution.
AR, ≥98% AR for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 72 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Dimethylglyoxime(DMG) is a complexing ligand. Dimethylglyoxime forms a number of mixed ligand complexes with N-acetylglycine and various metals such as VO(IV), Ni(II), Zn(II), Pd(II), Cd(II) and Pb(II).
| Canonical Smiles | CC(=NO)C(=NO)C |
|---|---|
| IUPAC Name | (NE)-N-[(3E)-3-hydroxyiminobutan-2-ylidene]hydroxylamine |
| InChIKey | JGUQDUKBUKFFRO-GGWOSOGESA-N |
| INCHI | 1S/C4H8N2O2/c1-3(5-7)4(2)6-8/h7-8H,1-2H3/b5-3+,6-4+ |
| Isomeric SMILES | C/C(=N\O)/C(=N/O)/C |
| WGK Germany | 3 |
| RTECS | EK2975000 |
| UN Number | 1325 |
| Packing Group | III |
| Molecular Weight | 116.12 |
| Beilstein | 506731 |
| Reaxy-Rn | 506731 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=506731&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic nitrogen compounds |
| Class | Organonitrogen compounds |
| Subclass | Oximes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Ketoximes |
| Alternative Parents | Organopnictogen compounds Organic oxygen compounds Hydrocarbon derivatives |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Ketoxime - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as ketoximes. These are organic compounds with the general formula RC(R')=NOH (R,R' = organyl). |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
| Certificate of Analysis | Mar 05, 2026 | D111833 | |
| Certificate of Analysis | Mar 05, 2026 | D111833 | |
| Certificate of Analysis | Mar 05, 2026 | D111833 | |
| Certificate of Analysis | Oct 17, 2025 | D111833 | |
| Certificate of Analysis | Oct 17, 2025 | D111833 | |
| Certificate of Analysis | Oct 17, 2025 | D111833 | |
| Certificate of Analysis | Jun 14, 2025 | D111833 | |
| Certificate of Analysis | Jun 14, 2025 | D111833 | |
| Certificate of Analysis | Jun 14, 2025 | D111833 | |
| Certificate of Analysis | Jan 20, 2025 | D111833 | |
| Certificate of Analysis | Jan 20, 2025 | D111833 | |
| Certificate of Analysis | Jan 20, 2025 | D111833 | |
| Certificate of Analysis | Jan 20, 2025 | D111833 | |
| Certificate of Analysis | Nov 16, 2024 | D111833 | |
| Certificate of Analysis | Nov 16, 2024 | D111833 | |
| Certificate of Analysis | Nov 16, 2024 | D111833 | |
| Certificate of Analysis | Aug 15, 2024 | D111833 | |
| Certificate of Analysis | Aug 15, 2024 | D111833 | |
| Certificate of Analysis | Aug 15, 2024 | D111833 | |
| Certificate of Analysis | Jul 04, 2024 | D111833 | |
| Certificate of Analysis | Jul 04, 2024 | D111833 | |
| Certificate of Analysis | Jul 04, 2024 | D111833 | |
| Certificate of Analysis | Oct 17, 2023 | D111833 | |
| Certificate of Analysis | Oct 17, 2023 | D111833 | |
| Certificate of Analysis | Oct 17, 2023 | D111833 | |
| Certificate of Analysis | Oct 17, 2023 | D111833 | |
| Certificate of Analysis | Mar 30, 2023 | D111833 | |
| Certificate of Analysis | Mar 30, 2023 | D111833 | |
| Certificate of Analysis | Mar 30, 2023 | D111833 | |
| Certificate of Analysis | Sep 24, 2022 | D111833 | |
| Certificate of Analysis | Sep 24, 2022 | D111833 | |
| Certificate of Analysis | Sep 24, 2022 | D111833 | |
| Certificate of Analysis | Feb 26, 2022 | D111833 | |
| Certificate of Analysis | Feb 26, 2022 | D111833 | |
| Certificate of Analysis | Feb 26, 2022 | D111833 | |
| Certificate of Analysis | Feb 26, 2022 | D111833 | |
| Certificate of Analysis | Feb 26, 2022 | D111833 |
| Solubility | Soluble in alcohol, acetone, ether; solubility water: soluble 0.1 g/10 mL, clear, colorless; |
|---|---|
| Sensitivity | Moisture sensitive. |
| Melt Point(°C) | 238-240°C |
| Molecular Weight | 116.120 g/mol |
| XLogP3 | 0.100 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 116.059 Da |
| Monoisotopic Mass | 116.059 Da |
| Topological Polar Surface Area | 65.200 Ų |
| Heavy Atom Count | 8 |
| Formal Charge | 0 |
| Complexity | 112.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 2 |
| Covalently-Bonded Unit Count | 1 |
| 1. Xiaochun Liu, Jianyu Wu, Jianxin Wu, Zhiyi Huang, Wei Shen, Xingshan Yin, Yingjuan Sun, Xiaofeng Lin, Wenjing Lin, Guobin Yi. (2023) Tough, self-healing, and recyclable cross-linked polyurethane elastomers via synergistic effect of dual dynamic covalent bonds. JOURNAL OF APPLIED POLYMER SCIENCE, 141 (5): (e54876). [PMID:] [10.1002/app.54876] |
| 2. Xiaoyu Zhang, Yuqing Zhang, Peiyao Li, Ruotong Wang, Binghao Ma, Fanglei Zeng, Qitu Zhang, Hongyan Dai, Ning Li. (2023) Preparation and properties of UV curable room temperature repair bio-based poly(siloxane-urethane) coating. JOURNAL OF APPLIED POLYMER SCIENCE, 140 (44): (e54628). [PMID:] [10.1002/app.54628] |
| 3. Yuetao Liu, Susu Zhao, Yujie Jiang, Qian Liu, Zhi Liu, Chengxin Song, Cancai Wang. (2023) AgNP Hybrid Organosilicon Antifouling Coating with Spontaneous Self-Healing and Long-Term Antifouling Properties. INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, [PMID:] [10.1021/acs.iecr.3c01569] |
| 4. Jun Zhang, Lin Hao, Zitong Chen, Yongjun Gao, Huan Wang, Yufan Zhang. (2023) Facile synthesis of Co–Fe layered double hydroxide nanosheets wrapped on Ni-doped nanoporous carbon nanorods for oxygen evolution reaction. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:37450970] [10.1016/j.jcis.2023.06.199] |
| 5. Yunlong Nie, Fang Zhou, Chenye Wang. (2023) A 3D sliding-strip microfluidic device for the simultaneous determination of multiple target analytes. TALANTA, [PMID:37354626] [10.1016/j.talanta.2023.124821] |
| 6. Han Zai-Gang, Zhang Lingli, Qi Chao, Shi Qing, Min Jun Zhe. (2023) A novel reagent pre-column derivatization method for UHPLC-MS/MS to determine four α-dicarbonyl compounds in beer. EUROPEAN FOOD RESEARCH AND TECHNOLOGY, 249 (8): (2017-2027). [PMID:] [10.1007/s00217-023-04269-y] |
| 7. Yuying Hu, Xiangjian Liu, Marlene Davis Ekpo, Jiangming Chen, Xiaoxiao Chen, Wenqian Zhang, Rui Zhao, Jingxian Xie, Yongju He, Songwen Tan. (2023) Dimethylglycine Can Enhance the Cryopreservation of Red Blood Cells by Reducing Ice Formation and Oxidative Damage. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (7): (6696). [PMID:37047668] [10.3390/ijms24076696] |
| 8. Junwei He, Qionghai Chen, Jiajun Qu, Sai Li, Zuwei Fu, Yuan Wei, Shikai Hu, Anchao Feng, Liqun Zhang, Jun Liu. (2023) Mechanically Robust and Self-Healing Elastomers Based on Dynamic Oxime–Carbamate Bonds: A Combined Experiment and All-Atom Simulation Study. ACS Applied Polymer Materials, [PMID:] [10.1021/acsapm.3c00339] |
| 9. Shangshu Liu, Feng Li, Taohai Li, Wei Cao. (2023) High-performance ZnIn2S4/Ni(dmgH)2 for photocatalytic hydrogen evolution: Ion exchange construction, photocorrosion mitigation, and efficiency enhancement by photochromic effect. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:37001449] [10.1016/j.jcis.2023.03.123] |
| 10. Nie Fahui, Guan Kun, Zou Chenglong, Xu Zhiwei, Liu Zhanmeng. (2023) Synthesis of magnetic rice husk biochar and its application in the adsorption of Ni(II) from aqueous solutions. Biomass Conversion and Biorefinery, [PMID:] [10.1007/s13399-023-04032-z] |
| 11. Haoxiang Rong, Minhui Wang, Yanan Zhang, Xun Lu. (2023) A high strength, high toughness and transparent room-temperature self-healing elastomer based on the synergy effect of quadruple dynamic bonding structure. REACTIVE & FUNCTIONAL POLYMERS, [PMID:] [10.1016/j.reactfunctpolym.2023.105531] |
| 12. Xu Fan, Lei Zhang, Fuhao Dong, He Liu, Xu Xu. (2023) Room-temperature self-healing polyurethane–cellulose nanocrystal composites with strong strength and toughness based on dynamic bonds. CARBOHYDRATE POLYMERS, [PMID:36813344] [10.1016/j.carbpol.2023.120654] |
| 13. Hao Jiang, Zhikun Wang, Meng Cheng, Wuting Pang, Yizeng Mou, Fanjie Meng, Chunling Li, Shuangqing Sun, Songqing Hu, Zhigang Di, Bingjie Lian. (2022) Smart polymer with rapid self-healing and early corrosion reporting capabilities: Design, performance and mechanism. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2022.141159] |
| 14. Hui Yang, Hao Chen, Wenhua Zhou, Haoan Fan, Chao Chen, Yixuan Sun, Jiaji Zhang, Sifan Wang, Teng Guo, Jie Fu. (2022) Construction of N, O co-doped carbon anchored with Co nanoparticles as efficient catalyst for furfural hydrodeoxygenation in ethanol. Journal of Energy Chemistry, [PMID:] [10.1016/j.jechem.2022.11.037] |
| 15. Xiaolu Xiong, Chengwang Guo, Gengyang Yan, Bingxin Han, Zan Wu, Yueqian Chen, Shiqi Xu, Peng Shao, Hong Song, Xiyan Xu, Junfeng Han. (2022) Simultaneous Cross-type Detection of Water Quality Indexes via a Smartphone-App Integrated Microfluidic Paper-Based Platform. ACS Omega, [PMID:36506192] [10.1021/acsomega.2c05938] |
| 16. Qiyuan Li, Lin Cao, Wei Wang, Xude Qin, Shougang Chen. (2022) Photo-responsive rapid self-healing polyurethane elastomer with anticorrosion and antibacterial functions. COMPOSITES PART A-APPLIED SCIENCE AND MANUFACTURING, [PMID:] [10.1016/j.compositesa.2022.107213] |
| 17. Shiwei Zhao, Anqian Yuan, Hualiang Xu, Zhengkai Wei, Shiyi Zhou, Yao Xiao, Liang Jiang, Jingxin Lei. (2022) Elevating the Photothermal Conversion Efficiency of Phase-Change Materials Simultaneously toward Solar Energy Storage, Self-Healing, and Recyclability. ACS Applied Materials & Interfaces, [PMID:35714067] [10.1021/acsami.2c05302] |
| 18. Zhuoyao Fang, Helan Wang, Kaizhen Zhang, Sikai Cheng, Xiaolin Zhang. (2022) Enhanced removal of nickel(II) from water by utilizing gel-type nanocomposite containing sub-5 nm hydrated manganese(IV) oxides. SEPARATION AND PURIFICATION TECHNOLOGY, [PMID:] [10.1016/j.seppur.2022.121457] |
| 19. Bo-Tao Liu, Xin-Qin Cai, Yu-Hui Luo, Kai Zhu, Qing-Yu Zhang, Tong-Tong Hu, Ting-Ting Sang, Cheng-Yan Zhang, Dong-En Zhang. (2021) Facile synthesis of nickel@carbon nanorod composite for simultaneously electrochemical detection of dopamine and uric acid. MICROCHEMICAL JOURNAL, [PMID:] [10.1016/j.microc.2021.106823] |
| 20. Guyang Ning, Mingxuan Fu, Jiaxian Liu, Yuena Sun, Haijun Lu, Haiyang Wang, Xinyu Fan, Yufan Zhang, Huan Wang. (2021) Carbon nanorod supported metal alloy nanocubes using polydopamine as location reagent for water splitting. INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, [PMID:] [10.1016/j.ijhydene.2021.08.158] |
| 21. Fangyuan Wang, Yu Liu, Zhiling Song, Zhichao Miao, Jinping Zhao. (2021) Ni-N-Doped Carbon-Modified Reduced Graphene Oxide Catalysts for Electrochemical CO2 Reduction Reaction. Catalysts, 11 (5): (561). [PMID:] [10.3390/catal11050561] |
| 22. Xingjiang Liu, Xin Liu, Wenjuan Li, Yi Ru, Yuhan Li, Ailing Sun, Liuhe Wei. (2020) Engineered self-healable elastomer with giant strength and toughness via phase regulation and mechano-responsive self-reinforcing. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2020.128300] |
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| 24. Huixian Jia, Ningzhao Shang, Yue Feng, Huimin Ye, Jianing Zhao, Huan Wang, Chun Wang, Yufan Zhang. (2020) Facile preparation of Ni nanoparticle embedded on mesoporous carbon nanorods for non-enzymatic glucose detection. JOURNAL OF COLLOID AND INTERFACE SCIENCE, [PMID:33007587] [10.1016/j.jcis.2020.09.051] |
| 25. Shuang Luo, Xingyan Liu, Xiangjun Wei, Min Fu, Peng Lu, Xuan Li, Yiming Jia, Qiao Ren, Youzhou He. (2020) Noble-metal-free cobaloxime coupled with metal-organic frameworks NH2-MIL-125: A novel bifunctional photocatalyst for photocatalytic NO removal and H2 evolution under visible light irradiation. JOURNAL OF HAZARDOUS MATERIALS, [PMID:32535515] [10.1016/j.jhazmat.2020.122824] |
| 26. Hongkai Zhao, Xiaoxia Li, Mingyue Zheng, Xian Zhao, Qun Zhang, Yi Luo, Weiliu Fan. (2020) Amorphous TiO2 as a multifunctional interlayer for boosting the efficiency and stability of the CdS/cobaloxime hybrid system for photocatalytic hydrogen production. Nanoscale, 12 (20): (11267-11279). [PMID:32415828] [10.1039/D0NR01453B] |
| 27. Weitian Cai, Dionysios D. Dionysiou, Fenglian Fu, Bing Tang. (2020) CTAB–intercalated molybdenum disulfide nanosheets for enhanced simultaneous removal of Cr(VI) and Ni(II) from aqueous solutions. JOURNAL OF HAZARDOUS MATERIALS, [PMID:32361299] [10.1016/j.jhazmat.2020.122728] |
| 28. Ergang Yao, Siyu Xu, Fengqi Zhao, Taizhong Huang, Haijian Li, Ningning Zhao, Jianhua Yi, Yanjing Yang, Changjian Wang. (2020) Study on Thermal Decomposition Behavior, Gaseous Products, and Kinetic Analysis of Bis-(Dimethylglyoximato) Nickel(II) Complex Using TG-DSC-FTIR-MS Technique. Catalysts, 10 (3): (331). [PMID:] [10.3390/catal10030331] |
| 29. Qinghua Deng, Yun Xu, Ziqun Wang, Tifang Miao, Xianliang Fu, Liancai Xu. (2019) Visible-Light-Driven H2 Evolution with Cobalt Complexes in Aqueous Solution: Theoretical and Experimental Study. Journal of Physical Chemistry C, [PMID:] [10.1021/acs.jpcc.9b08074] |
| 30. Demin Jiang, Yuhan Yang, Chentao Huang, Meiying Huang, Jianjun Chen, Tongde Rao, Xiaoyan Ran. (2019) Removal of the heavy metal ion nickel (II) via an adsorption method using flower globular magnesium hydroxide. JOURNAL OF HAZARDOUS MATERIALS, [PMID:30909138] [10.1016/j.jhazmat.2019.01.096] |
| 31. Wenjin Yang, Jing Li, Xinglai Zhang, Cai Zhang, Xin Jiang, Baodan Liu. (2018) Hydrothermal Approach to Spinel-Type 2D Metal Oxide Nanosheets. INORGANIC CHEMISTRY, [PMID:30532976] [10.1021/acs.inorgchem.8b02742] |
| 32. Hao Sun, Yuan Jia, Hui Dong, Longxiang Fan, Jianping Zheng. (2018) Multiplex quantification of metals in airborne particulate matter via smartphone and paper-based microfluidics. ANALYTICA CHIMICA ACTA, [PMID:30442391] [10.1016/j.aca.2018.07.053] |
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| 37. Shengping Dai, Longhua Zeng, Shuyong Xie, Jiayi Hu, Hao Yan, Wei Huang, Huixian Ye, Ningyi Yuan. (2024) A high mechanical strength, self-healing silicone elastomer for thin film thermal actuator. COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, [PMID:] [10.1016/j.colsurfa.2024.133506] |
| 38. Yanpeng Cao, Rui Yan, Xiaoye Wo, Jinlong Ma, Xiao Yu, Aijun Li, Jian Huang, Fenghua Li, Qixian Zhang. (2024) A self-healing elastomer with outstanding mechanical properties was designed based on urea bonds. Journal of Materials Chemistry C, 12 (26): (9685-9692). [PMID:] [10.1039/D4TC01123F] |
| 39. Feng Tian, Ran Yu, Xiaobiao Zuo, Manwen Zhang, Lingyu Zhao, Xiaojuan Zhao, Xin Yang, Ying Zhang, Wei Huang. (2024) Bioinspired 3D printed elastomer-hydrogel hybrid with robust interfacial bonding for flexible ionotronics. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2024.151164] |
| 40. Longjian Li, Junhui Wang, Qinhua Zhang, Shuai Wang, Hangkai Zhang, Tao Xing, Mingqing Wang, Mingbo Wu, Zhenxing Wang, Wenting Wu. (2024) Carbon Materials Containing Single-Atom Co–N4 Sites Enable Near-Infrared Photooxidation. ACS Catalysis, [PMID:] [10.1021/acscatal.3c05441] |
| 41. Shujun Zhao, Xuebin Lian, Dehuan Kong, Shuangfei Xiang, Feiya Fu, Xiangdong Liu. (2024) Constructing reactive “rod-bead” nanohybrid-driven high-efficient crosslinking network for the preparation of strong and tough plant protein adhesive. INDUSTRIAL CROPS AND PRODUCTS, [PMID:] [10.1016/j.indcrop.2024.118537] |
| 42. Wuting Pang, Hao Jiang, Shuai Wang, Tinglei He, Huang Chen, Tong Yan, Meng Cheng, Shuangqing Sun, Chunling Li. (2024) Graphene oxides enhanced polyurethane based composite coating with long term corrosion resistance and self-healing property. EUROPEAN POLYMER JOURNAL, [PMID:] [10.1016/j.eurpolymj.2024.112825] |
| 43. Xing Gong, Quantao Liu, Wenwei Huang, Jiazhu Wang, Zhilong Cao, Shaopeng Wu. (2024) Green synthesis of polyurethane with reversible oxime-urethane bond to enhance the self-healing properties of asphalt binder at room temperature. CONSTRUCTION AND BUILDING MATERIALS, [PMID:] [10.1016/j.conbuildmat.2023.134766] |
| 44. Hugang Zhang, Guanghui Yang, Xinmiao Li, Yile Wang, Kai Deng, Hongjie Yu, Hongjing Wang, Ziqiang Wang, Liang Wang. (2024) Interstitial Boron-Modulated Porous Pd Nanotubes for Ammonia Electrosynthesis. INORGANIC CHEMISTRY, [PMID:38299496] [10.1021/acs.inorgchem.3c04051] |
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| 54. Wenhe Ding, Hongyan Liu, Yanyan Bo, Siqi Zhan, Zaiqian Yu, Yuting Zhang, Ruize Yuan, Shiwei Wang, Mingyao Zhang. (2024) Study on the effect of chain extenders on aliphatic polyurethane and its application. JOURNAL OF APPLIED POLYMER SCIENCE, [PMID:] [10.1002/app.55445] |
| 55. Ming Chen, Wen-Da Zhang, Qingna Gong, Xiangkun Zhang, Jiangyong Liu, Xiaoping Yang, Jing Wang, Xiaodong Yan. (2025) Sulfhydryl group modified layered double hydroxide accelerates the formation of NiOOH active phase for enhanced urea oxidation reaction. JOURNAL OF POWER SOURCES, [PMID:] [10.1016/j.jpowsour.2025.236834] |
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| 57. Zhang Zeyu, Peng Dejun, Shang Xueyan, Zhao Xin, Ren Shixue, Pang Jiuyin, Li Shujun. (2024) Ultra-tough light-curing ionogels for UV shielding. Communications Materials, 5 (1): (1-12). [PMID:] [10.1038/s43246-024-00702-1] |
| 58. Dai Yang, Qingyong Tian, Jingyang Li, Xiaoqing Sui, Shuiren Liu, Xiaoguang Hu, Qingqing Sun, Linlin Zhang, Mingjun Niu, Xuying Liu, Weijing Yao. (2025) Fluorescent Self-Healing Elastomers with Triple Dynamic Bonds for 2D/3D Printed Information Encryption. Small Science, [PMID:40917399] [10.1002/smsc.202500091] |
| 59. Yichi Zhang, Junsheng Wang, Yuezhu Wang, Yinchun Li, Qiaoyu Feng, Qing Yu. (2025) Micro-Reaction Electrochemical Sensors for Highly Selective Detection of Nickel Ions Using Masking and Complexing Technology. IEEE TRANSACTIONS ON INSTRUMENTATION AND MEASUREMENT, [PMID:] [10.1109/TIM.2025.3586356] |
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Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
View AR grade guide →