Citraconic anhydride - ≥98% , CAS No.616-02-4

CAS: 616-02-4 Cat. No.: C106959 Formula: C₅H₄O₃ Molecular Weight: 112.08 Beilstein Registry Number: 1835 EC Number: 210-459-0

GRADE & PURITY ≥98%

Synonyms

2-Methylmaleic anhydride | M0365 | Monomethylmaleic anhydride | 105NP7PMXX | 2,5-Furandione, 3-methyl- | EINECS 210-459-0 | 3-methyl-furan-2,5-dione | 3-methylfuran-2,5-dione | 2,5-Furanedione, 3-methyl | WLN: T5VOVJ D1 | AI3-10030 | Anhydrid kyseliny cit

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

Versatile reagent used for the synthesis of maleimides, bicyclic pyrrolidines, and co- and terpolymers, as well as for the protection of N-terminal amino acids.

Specifications

Synonyms

2-Methylmaleic anhydride | M0365 | Monomethylmaleic anhydride | 105NP7PMXX | 2,5-Furandione, 3-methyl- | EINECS 210-459-0 | 3-methyl-furan-2,5-dione | 3-methylfuran-2,5-dione | 2,5-Furanedione, 3-methyl | WLN: T5VOVJ D1 | AI3-10030 | Anhydrid kyseliny cit

Specifications & Purity

≥98%

Storage

Argon charged,Room temperature

Shipped In

Normal

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488181510
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488181510
• Canonical Smiles: CC1=CC(=O)OC1=O
• IUPAC Name: 3-methylfuran-2,5-dione
• InChIKey: AYKYXWQEBUNJCN-UHFFFAOYSA-N
• INCHI: 1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3
• Isomeric SMILES: CC1=CC(=O)OC1=O
• WGK Germany: 3
• RTECS: GE6825000
• UN Number: 2810
• Molecular Weight: 112.08
• Beilstein: 1835
• Reaxy-Rn: 1835
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1835&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Dihydrofurans
      • Subclass Furanones

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Dihydrofurans
• Subclass: Furanones
• Intermediate Tree Nodes: Not available
• Direct Parent: Butenolides
• Alternative Parents: Dicarboxylic acids and derivatives Carboxylic acid anhydrides Oxacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Dicarboxylic acid or derivatives - 2-furanone - Carboxylic acid anhydride - Oxacycle - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Escherichia coli (133304 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Miscible with water, alcohol, acetone and eth
• Sensitivity: Moisture sensitive
• x_freezing_point: 7 °C
• x_refractive_index: 1.47-1.472
• x_flash_point_drop_fahrenheit: 101℃
• x_flash_point_drop_centigrade: 101℃
• x_boil_point_char: 213°C
• x_melt_point_char: 6-7°C
• Molecular Weight: 112.080 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.016 Da
• Monoisotopic Mass: 112.016 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 178.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• 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

References

1. Yuqi Liu, Li Yuan, Guozheng Liang, Aijuan Gu.  (2023)  Synthesis of new biobased benzoxazine through green strategy and its polybenzoxazine resin with high thermal resistance and mechanical strength.  JOURNAL OF POLYMER SCIENCE,  61  (13): (1279-1288).  [PMID:] [10.1002/pol.20220744]

2. Chen Zhongyin, Liao Tao, Wan Lihui, Kuang Ying, Liu Chang, Duan Junlin, Xu Xiangyu, Xu Ziqiang, Jiang Bingbing, Li Cao.  (2021)  Dual-stimuli responsive near-infrared emissive carbon dots/hollow mesoporous silica-based integrated theranostics platform for real-time visualized drug delivery.  Nano Research,  14  (11): (4264-4273).  [PMID:] [10.1007/s12274-021-3624-4]

3. Xiangyu Xu, Junlin Duan, Yun Liu, Ying Kuang, Jingling Duan, Tao Liao, Ziqiang Xu, Bingbing Jiang, Cao Li.  (2021)  Multi-stimuli responsive hollow MnO2-based drug delivery system for magnetic resonance imaging and combined chemo-chemodynamic cancer therapy.  Acta Biomaterialia,      [PMID:33785453] [10.1016/j.actbio.2021.03.048]

4. Jiandong Zuo, Zhao Liu, Chaoyun Luo, Feng Lin.  (2020)  Preparation and properties of high refractive index polythioetherimide film based on thiol-ene click chemistry.  PROGRESS IN ORGANIC COATINGS,      [PMID:] [10.1016/j.porgcoat.2020.106048]

5. Zhongyin Chen, Lihui Wan, Ye Yuan, Ying Kuang, Xiangyu Xu, Tao Liao, Jia Liu, Zi-Qiang Xu, Bingbing Jiang, Cao Li.  (2020)  pH/GSH-Dual-Sensitive Hollow Mesoporous Silica Nanoparticle-Based Drug Delivery System for Targeted Cancer Therapy.  ACS Biomaterials Science & Engineering,      [PMID:33463161] [10.1021/acsbiomaterials.0c00073]

6. Jie Zhou, Shengnan Ma, Yuxin Zhang, Yiyan He, Jun Yang, Hu Zhang, Kui Luo, Zhongwei Gu.  (2020)  Virus-Inspired Mimics: Dual-pH-Responsive Modular Nanoplatforms for Programmable Gene Delivery without DNA Damage with the Assistance of Light.  ACS Applied Materials & Interfaces,      [PMID:32329598] [10.1021/acsami.0c03486]

7. Lihui Wan, Zhongyin Chen, Yan Deng, Tao Liao, Ying Kuang, Jia Liu, Junlin Duan, Ziqiang Xu, Bingbing Jiang, Cao Li.  (2020)  A novel intratumoral pH/redox-dual-responsive nanoplatform for cancer MR imaging and therapy.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:32283415] [10.1016/j.jcis.2020.04.026]

8. Yanan Xue, Lijun Tao, Yang Zhou, Jie Liu, Bo Yu, Sihui Long, Shiwen Huang, Faquan Yu.  (2018)  Enhanced Targeted Delivery of Doxorubicin Based on Acid Induced Charge Reversal and Combinational Stimuli-Responsive Nanocarrier.  ADVANCED ENGINEERING MATERIALS,  20  (7): (1701151).  [PMID:] [10.1002/adem.201701151]

9. Zhang Han, Xue Yanan, Huang Juan, Xia Xiaoyang, Song Meifang, Wen Kaikai, Zhang Xiaoxiao, Luo Xiaogang, Cai Ning, Long Sihui, Yu Faquan.  (2014)  Tailor-made magnetic nanocarriers with pH-induced charge reversal and pH-responsiveness to guide subcellular release of doxorubicin.  JOURNAL OF MATERIALS SCIENCE,  50  (6): (2429-2442).  [PMID:] [10.1007/s10853-014-8798-7]

10. Xiao-Long Chen, Li-Jun Zhang, Fu-Ge Li, Yong-Xian Fan, Wei-Ping Wang, Bao-Ju Li, Yin-Chu Shen.  (2014)  Synthesis and antifungal evaluation of a series of maleimides.  PEST MANAGEMENT SCIENCE,  71  (3): (433-440).  [PMID:24796632] [10.1002/ps.3824]

11. Guo-Feng Luo, Wei-Hai Chen, Yun Liu, Jing Zhang, Si-Xue Cheng, Ren-Xi Zhuo, Xian-Zheng Zhang.  (2013)  Charge-reversal plug gate nanovalves on peptide-functionalized mesoporous silica nanoparticles for targeted drug delivery.  Journal of Materials Chemistry B,  1  (41): (5723-5732).  [PMID:32261195] [10.1039/C3TB20792G]

12. Shuo Liu, Fangxu Li.  (2025)  Unveiling the role of hydrophobicity and foam property in froth flotation of lepidolite with decamine, dodecylamine, tetradecylamine, hexadecylamine and MIBC.  COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS,      [PMID:] [10.1016/j.colsurfa.2025.136701]

13. Xu Han, Fan Feng, Zixu Wang, Shujun Huang, Kaiyan Xi, Zezheng Fang, Jianyu Shen, Mingrui Wang, Yi Zhang, Ben Liu, Junpeng Wang, Jiahao Wang, Xiangjun Liang, Guangpan Sun, Runlu Zhang, Baoteng Han, Fanlin Liu, Mingze Li, Xun Zhang, Jingjing Wang, Huimin Geng, Yanrong Zhang, Wenli Zhang, Zimei Wu, Xingang Li, Yi Li, Lian Cheng, Yulin Zhang, Shilei Ni.  (2025)  Preventing Glioblastoma Relapse by Igniting Innate Immunity through Mitochondrial Stress in the Surgical Cavity.  ADVANCED MATERIALS,      [PMID:40919729] [10.1002/adma.202511351]

14. Ying Li, Yunqiu Miao, Mingshu Chen, Xi Chen, Feifei Li, Xinxin Zhang, Yong Gan.  (2020)  Stepwise targeting and responsive lipid-coated nanoparticles for enhanced tumor cell sensitivity and hepatocellular carcinoma therapy.  Theranostics,      [PMID:32206118] [10.7150/thno.42008]

15. Bo Zeng, Shuiping Ouyang, Zhaoxiang Wang, Shixiu Cui, Guocheng Du, Song Liu.  (2026)  Ancestral bacterial laccase enables efficient biodetoxification of inhibitory wheat straw hydrolysate for sustainable microbial protein production.  GREEN CHEMISTRY,      [PMID:] [10.1039/D5GC05697G]

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 616-02-4, the molecular formula is C5H4O3, and the molecular weight is 112.08 g/mol. InChIKey AYKYXWQEBUNJCN-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.