Iodoacetic acid
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MedKoo CAT#: 558641

CAS#: 64-69-7

Description: Iodoacetic acid is a reagent for the modification of sulfhydryl groups. It reacts with cysteine moiety in proteins to prevent the re-formation of disulfide bonds during protein sequencing.

Chemical Structure

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Iodoacetic acid
CAS# 64-69-7
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 558641
Name: Iodoacetic acid
CAS#: 64-69-7
Chemical Formula: C2H3IO2
Exact Mass: 185.92
Molecular Weight: 185.949
Elemental Analysis: C, 12.92; H, 1.63; I, 68.25; O, 17.21

Price and Availability

Size Price Availability Quantity
10g USD 250 2 Weeks
25g USD 500 2 Weeks
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Synonym: Iodoacetic acid; Iodoacetate; Monoiodine acetate; Monoiodoacetate;

IUPAC/Chemical Name: Acetic acid, 2-iodo-

InChi Key: JDNTWHVOXJZDSN-UHFFFAOYSA-N

InChi Code: InChI=1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5)

SMILES Code: O=C(O)CI

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Iodoacetic acid is a reagent for the modification of sulfhydryl groups.
In vitro activity: Next, comparison between the three groups was made using the Kruskal-Wallis test, and these results showed that the average focus number in 5 μM and 10 μM IAA (iodoacetic acid)-treated oocytes was significantly higher than in control (2.94 ± 1.96 in 5 μM, P < 0.05; 4.16 ± 2.10 in 10 μM, P < 0.01 versus 1.48 ± 1.50 in control) (Fig. 5B). Meanwhile, IAA induced oocyte DNA breaks in a dose-dependent manner and the average foci number in 10 μM IAA-treated oocytes was significantly higher than in the 5 μM group (P < 0.05, Fig. 5B). Reference: Environ Pollut. 2021 Jan 1;268(Pt A):115601. https://pubmed.ncbi.nlm.nih.gov/33126034/
In vivo activity: This study found that oral administration of IAA (iodoacetic acid) (35 mg/kg body weight per day for 28 days) in male mice increased serum LH levels and reduced sperm motility, affecting average path velocity and straight line velocity of sperm. In addition, IAA promoted the expression of γH2AX, a marker for DNA double-strand breaks. Moreover, IAA downregulated the protein expression of the scavenger receptor class B type 1 (SRB1), and decreased lipid droplet transport into Leydig cells, which reduced the storage of testosterone synthesis raw materials and might cause a drop in testosterone production. Reference: Front Pharmacol. 2022 Aug 26;13:958204. https://pubmed.ncbi.nlm.nih.gov/36091762/

Preparing Stock Solutions

The following data is based on the product molecular weight 185.95 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Jiao X, Gonsioroski A, Flaws JA, Qiao H. Iodoacetic acid disrupts mouse oocyte maturation by inducing oxidative stress and spindle abnormalities. Environ Pollut. 2021 Jan 1;268(Pt A):115601. doi: 10.1016/j.envpol.2020.115601. Epub 2020 Oct 10. PMID: 33126034; PMCID: PMC7746578. 2. Gonsioroski A, Meling DD, Gao L, Plewa MJ, Flaws JA. Iodoacetic acid inhibits follicle growth and alters expression of genes that regulate apoptosis, the cell cycle, estrogen receptors, and ovarian steroidogenesis in mouse ovarian follicles. Reprod Toxicol. 2020 Jan;91:101-108. doi: 10.1016/j.reprotox.2019.10.005. Epub 2019 Nov 3. PMID: 31693920; PMCID: PMC6980769. 3. Liang Y, Huang X, Fang L, Wang M, Yu C, Guan Q. Effect of iodoacetic acid on the reproductive system of male mice. Front Pharmacol. 2022 Aug 26;13:958204. doi: 10.3389/fphar.2022.958204. PMID: 36091762; PMCID: PMC9461136. 4. Gonzalez RVL, Weis KE, Gonsioroski AV, Flaws JA, Raetzman LT. Iodoacetic Acid, a Water Disinfection Byproduct, Disrupts Hypothalamic, and Pituitary Reproductive Regulatory Factors and Induces Toxicity in the Female Pituitary. Toxicol Sci. 2021 Oct 27;184(1):46-56. doi: 10.1093/toxsci/kfab106. PMID: 34453833; PMCID: PMC8557421.
In vitro protocol: 1. Jiao X, Gonsioroski A, Flaws JA, Qiao H. Iodoacetic acid disrupts mouse oocyte maturation by inducing oxidative stress and spindle abnormalities. Environ Pollut. 2021 Jan 1;268(Pt A):115601. doi: 10.1016/j.envpol.2020.115601. Epub 2020 Oct 10. PMID: 33126034; PMCID: PMC7746578. 2. Gonsioroski A, Meling DD, Gao L, Plewa MJ, Flaws JA. Iodoacetic acid inhibits follicle growth and alters expression of genes that regulate apoptosis, the cell cycle, estrogen receptors, and ovarian steroidogenesis in mouse ovarian follicles. Reprod Toxicol. 2020 Jan;91:101-108. doi: 10.1016/j.reprotox.2019.10.005. Epub 2019 Nov 3. PMID: 31693920; PMCID: PMC6980769.
In vivo protocol: 1. Liang Y, Huang X, Fang L, Wang M, Yu C, Guan Q. Effect of iodoacetic acid on the reproductive system of male mice. Front Pharmacol. 2022 Aug 26;13:958204. doi: 10.3389/fphar.2022.958204. PMID: 36091762; PMCID: PMC9461136. 2. Gonzalez RVL, Weis KE, Gonsioroski AV, Flaws JA, Raetzman LT. Iodoacetic Acid, a Water Disinfection Byproduct, Disrupts Hypothalamic, and Pituitary Reproductive Regulatory Factors and Induces Toxicity in the Female Pituitary. Toxicol Sci. 2021 Oct 27;184(1):46-56. doi: 10.1093/toxsci/kfab106. PMID: 34453833; PMCID: PMC8557421.

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1: Wang S, Zheng W, Liu X, Xue P, Jiang S, Lu D, Zhang Q, He G, Pi J, Andersen ME, Tan H, Qu W. Iodoacetic acid activates Nrf2-mediated antioxidant response in vitro and in vivo. Environ Sci Technol. 2014 Nov 18;48(22):13478-88. doi: 10.1021/es502855x. Epub 2014 Nov 4. PubMed PMID: 25332096.

2: Rösch S, Johnen S, Mazinani B, Müller F, Pfarrer C, Walter P. The effects of iodoacetic acid on the mouse retina. Graefes Arch Clin Exp Ophthalmol. 2015 Jan;253(1):25-35. doi: 10.1007/s00417-014-2652-0. Epub 2014 May 15. PubMed PMID: 24827634.

3: Nan Y, Zhang Q, Ren C, Huang X, Gao J, Li X, Pu M. Functional evaluation of iodoacetic acid induced photoreceptor degeneration in the cat. Sci China Life Sci. 2013 Jun;56(6):524-30. doi: 10.1007/s11427-013-4483-3. Epub 2013 May 8. PubMed PMID: 23657794.

4: Wei X, Wang S, Zheng W, Wang X, Liu X, Jiang S, Pi J, Zheng Y, He G, Qu W. Drinking water disinfection byproduct iodoacetic acid induces tumorigenic transformation of NIH3T3 cells. Environ Sci Technol. 2013 Jun 4;47(11):5913-20. doi: 10.1021/es304786b. Epub 2013 May 21. PubMed PMID: 23641915.

5: Liu X, Wei X, Zheng W, Jiang S, Templeton MR, He G, Qu W. An optimized analytical method for the simultaneous detection of iodoform, iodoacetic acid, and other trihalomethanes and haloacetic acids in drinking water. PLoS One. 2013 Apr 16;8(4):e60858. doi: 10.1371/journal.pone.0060858. Print 2013. PubMed PMID: 23613747; PubMed Central PMCID: PMC3628783.

6: Noel JM, Fernandez de Castro JP, Demarco PJ Jr, Franco LM, Wang W, Vukmanic EV, Peng X, Sandell JH, Scott PA, Kaplan HJ, McCall MA. Iodoacetic acid, but not sodium iodate, creates an inducible swine model of photoreceptor damage. Exp Eye Res. 2012 Apr;97(1):137-47. doi: 10.1016/j.exer.2011.12.018. Epub 2012 Jan 10. PubMed PMID: 22251455; PubMed Central PMCID: PMC3323738.

7: Shimada T, Kuyama H, Sato TA, Tanaka K. Development of iodoacetic acid-based cysteine mass tags: detection enhancement for cysteine-containing peptide by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal Biochem. 2012 Feb 15;421(2):785-7. doi: 10.1016/j.ab.2011.12.005. Epub 2011 Dec 9. PubMed PMID: 22206935.

8: Wang S, Kaltashov IA. A new strategy of using O18-labeled iodoacetic acid for mass spectrometry-based protein quantitation. J Am Soc Mass Spectrom. 2012 Jul;23(7):1293-7. doi: 10.1007/s13361-012-0396-9. Epub 2012 May 5. PubMed PMID: 22562395; PubMed Central PMCID: PMC5809132.

9: Scott PA, Kaplan HJ, Sandell JH. Anatomical evidence of photoreceptor degeneration induced by iodoacetic acid in the porcine eye. Exp Eye Res. 2011 Oct;93(4):513-27. doi: 10.1016/j.exer.2011.06.017. Epub 2011 Jun 30. PubMed PMID: 21740901.

10: Procházka E, Escher BI, Plewa MJ, Leusch FD. In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts. Chem Res Toxicol. 2015 Oct 19;28(10):2059-68. doi: 10.1021/acs.chemrestox.5b00283. Epub 2015 Sep 18. PubMed PMID: 26327680.

11: Wang W, Fernandez de Castro J, Vukmanic E, Zhou L, Emery D, Demarco PJ, Kaplan HJ, Dean DC. Selective rod degeneration and partial cone inactivation characterize an iodoacetic acid model of Swine retinal degeneration. Invest Ophthalmol Vis Sci. 2011 Oct 7;52(11):7917-23. doi: 10.1167/iovs.11-7849. PubMed PMID: 21896868; PubMed Central PMCID: PMC3207852.

12: Pals J, Attene-Ramos MS, Xia M, Wagner ED, Plewa MJ. Human cell toxicogenomic analysis linking reactive oxygen species to the toxicity of monohaloacetic acid drinking water disinfection byproducts. Environ Sci Technol. 2013;47(21):12514-23. doi: 10.1021/es403171b. Epub 2013 Oct 10. PubMed PMID: 24050308; PubMed Central PMCID: PMC4014314.

13: Xiang T, Chumsae C, Liu H. Localization and quantitation of free sulfhydryl in recombinant monoclonal antibodies by differential labeling with 12C and 13C iodoacetic acid and LC-MS analysis. Anal Chem. 2009 Oct 1;81(19):8101-8. doi: 10.1021/ac901311y. PubMed PMID: 19722496.

14: Yamauchi Y, Agawa T, Tsukahara R, Kimura K, Yamakawa N, Miura M, Goto H. Correlation between high-resolution optical coherence tomography (OCT) images and histopathology in an iodoacetic acid-induced model of retinal degeneration in rabbits. Br J Ophthalmol. 2011 Aug;95(8):1157-60. doi: 10.1136/bjo.2010.186718. Epub 2010 Oct 28. PubMed PMID: 21030415.

15: Syvertsen C, McKinley-McKee JS. Affinity labelling of liver alcohol dehydrogenase. Effects of pH and buffers on affinity labelling with iodoacetic acid and (R, S)-2-bromo-3-(5-imidazolyl)propionic acid. Eur J Biochem. 1981 Jun;117(1):165-70. PubMed PMID: 7021155.

16: Houen G, Jensen OM. Conjugation to preactivated proteins using divinylsulfone and iodoacetic acid. J Immunol Methods. 1995 Apr 26;181(2):187-200. PubMed PMID: 7745248.

17: Sheng L, Liu C, Tong Q, Ma M. Central metabolic pathways of Aureobasidium pullulans CGMCC1234 for pullulan production. Carbohydr Polym. 2015 Dec 10;134:333-6. doi: 10.1016/j.carbpol.2015.08.016. Epub 2015 Aug 13. PubMed PMID: 26428132.

18: Santori G, Domenicotti C, Bellocchio A, Pronzato MA, Marinari UM, Cottalasso D. Different efficacy of iodoacetic acid and N-ethylmaleimide in high-performance liquid chromatographic measurement of liver glutathione. J Chromatogr B Biomed Sci Appl. 1997 Aug 1;695(2):427-33. PubMed PMID: 9300880.

19: Escobar-Hoyos LF, Hoyos-Giraldo LS, Londoño-Velasco E, Reyes-Carvajal I, Saavedra-Trujillo D, Carvajal-Varona S, Sánchez-Gómez A, Wagner ED, Plewa MJ. Genotoxic and clastogenic effects of monohaloacetic acid drinking water disinfection by-products in primary human lymphocytes. Water Res. 2013 Jun 15;47(10):3282-90. doi: 10.1016/j.watres.2013.02.052. Epub 2013 Mar 13. PubMed PMID: 23602619.

20: Lau BP, Becalski A. Determination of iodoacetic acid using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2008 Jun;22(12):1787-91. doi: 10.1002/rcm.3547. PubMed PMID: 18470871.