Iodoacetic acid - AR, ≥98% , CAS No.64-69-7

CAS: 64-69-7 Cat. No.: I104613 Molecular Weight: 185.95 Beilstein Registry Number: 1739079 EC Number: 200-590-1

GRADE & PURITY AR, ≥98%

Synonyms

CCRIS 667 | ICH2COOH | Monoiodoacetic acid | NSC 2125 | BRN 1739079 | F8880-2820 | InChI=1/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) | AI3-52119 | BP-13415 | DTXSID5025445 | 4-02-00-00534 (Beilstein Handbook Reference) | ICH2CO2H | WF5188V710 | CHEBI:74571 | STR095

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads,FedEx DG Service

Overview

Iodoacetic acid is a reagent for the modification and alkylation of cysteine residues in proteins. It has also been used in glycopeptide synthesis.
Reagent for the modification of cysteine residues in proteins.

Specifications

Synonyms

CCRIS 667 | ICH2COOH | Monoiodoacetic acid | NSC 2125 | BRN 1739079 | F8880-2820 | InChI=1/C2H3IO2/c3-1-2(4)5/h1H2, (H, 4, 5) | AI3-52119 | BP-13415 | DTXSID5025445 | 4-02-00-00534 (Beilstein Handbook Reference) | ICH2CO2H | WF5188V710 | CHEBI:74571 | STR095

Specifications & Purity

AR, ≥98%

Biochemical and Physiological Mechanisms

Iodoacetic acid (IAA) blocks the thiol group of cysteine. IAA inhibits glyceraldehyde-3-phosphate dehydrogenase (G3PDH) by interacting with sulfhydryl group of the active site cysteine. IAA inhibits the progression of solid Ehrlich carcinoma. IAA is one o

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads, FedEx DG Service

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

AR

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C(C(=O)O)I
• IUPAC Name: 2-iodoacetic acid
• InChIKey: JDNTWHVOXJZDSN-UHFFFAOYSA-N
• INCHI: 1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)
• Isomeric SMILES: C(C(=O)O)I
• WGK Germany: 1
• RTECS: AI3500000
• UN Number: 1759
• Packing Group: I
• Molecular Weight: 185.95
• Beilstein: 1739079
• Reaxy-Rn: 1739079
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1739079&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Alpha-halocarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Alpha-halocarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Alpha-halocarboxylic acids
• Alternative Parents: Monocarboxylic acids and derivatives Carboxylic acids Organoiodides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl iodides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Alpha-halocarboxylic acid - Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organoiodide - Organohalogen compound - Carbonyl group - Alkyl iodide - Alkyl halide - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
• External Descriptors: Halogenated fatty acids

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(Human)

MG-63 (795 Activities)

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

MDA-MB-231 (73002 Activities)

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

Associated Targets(non-human)

Salmonella typhimurium (15756 Activities)

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (600 g/L) at 20 °C, and alcohol.
• Sensitivity: Light sensitive.
• Boil Point(°C): 208℃
• Melt Point(°C): 77-79°C
• Molecular Weight: 185.950 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 185.918 Da
• Monoisotopic Mass: 185.918 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 5
• Formal Charge: 0
• Complexity: 42.900
• 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

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2. Haoliang Cheng, Min Wang, Yaru Li, Guanyu Zhao, Zhong-Sheng Wang.  (2019)  An imidazolium iodide salt as a bifunctional co-adsorbent for quasi-solid-state dye-sensitized solar cells: improvements of electron lifetime and charge collection efficiency.  Journal of Materials Chemistry A,  7  (6): (2702-2708).  [PMID:] [10.1039/C8TA11333E]

3. Lei Wang, Yanan Sun, Baiyang Chen.  (2018)  Rejection of haloacetic acids in water by multi-stage reverse osmosis: Efficiency, mechanisms, and influencing factors.  WATER RESEARCH,      [PMID:30056322] [10.1016/j.watres.2018.07.045]

4. Liang Jianming, Li Ruixiang, He Yuwei, Ling Chengli, Wang Qi, Huang Yongzhuo, Qin Jing, Lu Weigen, Wang Jianxin.  (2018)  A novel tumor-targeting treatment strategy uses energy restriction via co-delivery of albendazole and nanosilver.  Nano Research,  11  (9): (4507-4523).  [PMID:] [10.1007/s12274-018-2032-x]

5. Lei Wang, Ruilan Niu, Baiyang Chen, Liwei Wang, Guan Zhang.  (2017)  A comparison of photodegradation kinetics, mechanisms, and products between chlorinated and brominated/iodinated haloacetic acids in water.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2017.08.086]

6. Xingxing Jin, Yanfang Wang, Jiang Yuan, Jian Shen.  (2016)  Extraction, characterization, and NO release potential of keratin from human hair.  MATERIALS LETTERS,      [PMID:] [10.1016/j.matlet.2016.04.036]

7. Yanfang Wang, Pengfei Li, Ping Xiang, Jueting Lu, Jiang Yuan, Jian Shen.  (2015)  Electrospun polyurethane/keratin/AgNP biocomposite mats for biocompatible and antibacterial wound dressings.  Journal of Materials Chemistry B,  4  (4): (635-648).  [PMID:32262945] [10.1039/C5TB02358K]

8. Luo Kairan, Hu Wenbin.  (2025)  A dual thermo/pH-sensitive hydrogel as 5-Fluorouracil carrier for breast cancer treatment.  ANTI-CANCER DRUGS,      [PMID:39773648] [10.1097/CAD.0000000000001657]

9. Li Wang, Meng Zhang, Yufei Shu, Qi Han, Li Long, Beizhao Chen, Mengxia Wang, Li Li, Siyu Cao, Zhe Yang, Bei Liu, Zhongying Wang, Chuyang Y. Tang.  (2024)  Covalently modified MoS2 for the fabrication of interlayered thin film composite membranes with excellent structural stability against swelling and drying in organic solvent nanofiltration.  JOURNAL OF MEMBRANE SCIENCE,      [PMID:] [10.1016/j.memsci.2024.122985]

10. Ling Guo, Hanyu Yan, Qinqin Gong, Weili Zheng, Liang Zhong, Tao Gong, Xun Sun, Zhirong Zhang, Yuan Ping, Zilan Zhu, Jian Xu, Yongping Zhang.  (2024)  Glomerulus-Targeted ROS-Responsive Polymeric Nanoparticles for Effective Membranous Nephropathy Therapy.  ACS Applied Materials & Interfaces,      [PMID:38940537] [10.1021/acsami.4c04345]

11. Yuke Wu, Xi Wang, Zhengqin Pang, Jinyi Zhang, Chengbin Zheng.  (2024)  Rapid and simultaneous analysis of monoiodoacetic acid and inorganic iodine in drinking water by capillary electrophoresis-inductively coupled plasma mass spectrometry.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.110809]

12. Shuang Chen, Yue Qiao, Youwei Jiang, Wei Qiu, Shuang Zang, Jing Zhang, Xianshi Wang, Jun Ma.  (2024)  Trace analysis of 59 halogenated aromatic disinfection byproducts through the SPE-LC-MS/MS method and their occurrence and transformation during chlorine disinfection.  Journal of Environmental Sciences,      [PMID:] [10.1016/j.jes.2024.06.025]

13. Xiaodan Wu, Weiyong Tao, Ziyang Lan, Yaping Tian, Zhenyu Zhong, Jianwei Wang, Jiaqi Li, Xulong Liu, Xin Zhang, Yifan Wang, Jianglin Wang, Bin Zhang, Yingying Du, Shengmin Zhang.  (2025)  pH-Responsive Engineered Exosomes Enhance Endogenous Hyaluronan Production by Reprogramming Chondrocytes for Cartilage Repair.  Advanced Healthcare Materials,      [PMID:40042438] [10.1002/adhm.202405126]