Cacodylic acid
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 558642

CAS#: 75-60-5

Description: Cacodylic acid is an arsenical that has been used as a dermatologic agent and as an herbicide.


Price and Availability

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Cacodylic acid, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 558642
Name: Cacodylic acid
CAS#: 75-60-5
Chemical Formula: C2H7AsO2
Exact Mass: 137.97
Molecular Weight: 138.0
Elemental Analysis: C, 17.41; H, 5.11; As, 54.29; O, 23.19


Synonym: Cacodylic acid; Hydroxydimethylarsine oxide; Kyselina kakodylova;

IUPAC/Chemical Name: Arsine oxide, dimethylhydroxy-

InChi Key: OGGXGZAMXPVRFZ-UHFFFAOYSA-N

InChi Code: InChI=1S/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)

SMILES Code: O[As](C)(C)=O


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Kersten M, Daus B. Silicic acid competes for dimethylarsinic acid (DMA) immobilization by the iron hydroxide plaque mineral goethite. Sci Total Environ. 2015 Mar 1;508:199-205. doi: 10.1016/j.scitotenv.2014.11.093. Epub 2014 Dec 5. PubMed PMID: 25478657.

2: Németi B, Gregus Z. Reduction of dimethylarsinic acid to the highly toxic dimethylarsinous acid by rats and rat liver cytosol. Chem Res Toxicol. 2013 Mar 18;26(3):432-43. doi: 10.1021/tx300505v. Epub 2013 Mar 4. PubMed PMID: 23414340.

3: Banerjee M, Carew MW, Roggenbeck BA, Whitlock BD, Naranmandura H, Le XC, Leslie EM. A novel pathway for arsenic elimination: human multidrug resistance protein 4 (MRP4/ABCC4) mediates cellular export of dimethylarsinic acid (DMAV) and the diglutathione conjugate of monomethylarsonous acid (MMAIII). Mol Pharmacol. 2014 Aug;86(2):168-79. doi: 10.1124/mol.113.091314. Epub 2014 May 28. PubMed PMID: 24870404.

4: Liu S, Zhang L, Sun Q, Wang F, Xi S, Sun G. The distribution in tissues and urine of arsenic metabolites after subchronic exposure to dimethylarsinic acid (DMAV) in rats. Biol Trace Elem Res. 2015 Apr;164(2):219-25. doi: 10.1007/s12011-014-0208-0. Epub 2015 Jan 10. PubMed PMID: 25575662.

5: Rogers EH, Chernoff N, Kavlock RJ. The teratogenic potential of cacodylic acid in the rat and mouse. Drug Chem Toxicol. 1981;4(1):49-61. PubMed PMID: 7261946.

6: Zhang M, Wang WW, Jin HF, Bao LL, Naranmandura H, Qin YJ, Li CH. [The molecular mechanism of interaction of trivalent dimethylarsinous acid (DMA(III)) binding to rat hemoglobin]. Yao Xue Xue Bao. 2014 May;49(5):666-71. Chinese. PubMed PMID: 25151739.

7: Garcia RI, Ibrahim JG, Wambaugh JF, Kenyon EM, Setzer RW. Identifiability of PBPK models with applications to dimethylarsinic acid exposure. J Pharmacokinet Pharmacodyn. 2015 Dec;42(6):591-609. doi: 10.1007/s10928-015-9424-2. Epub 2015 Jul 21. PubMed PMID: 26194069.

8: Yamamoto S, Konishi Y, Matsuda T, Murai T, Shibata MA, Matsui-Yuasa I, Otani S, Kuroda K, Endo G, Fukushima S. Cancer induction by an organic arsenic compound, dimethylarsinic acid (cacodylic acid), in F344/DuCrj rats after pretreatment with five carcinogens. Cancer Res. 1995 Mar 15;55(6):1271-6. PubMed PMID: 7882321.

9: Siewicki TC. Tissue retention of arsenic in rats fed witch founder or cacodylic acid. J Nutr. 1981 Apr;111(4):602-9. PubMed PMID: 7218032.

10: Németi B, Poór M, Gregus Z. Reduction of the Pentavalent Arsenical Dimethylarsinic Acid and the GSTO1 Substrate S-(4-Nitrophenacyl)glutathione by Rat Liver Cytosol: Analyzing the Role of GSTO1 in Arsenic Reduction. Chem Res Toxicol. 2015 Nov 16;28(11):2199-209. doi: 10.1021/acs.chemrestox.5b00368. Epub 2015 Nov 3. PubMed PMID: 26496421.

11: Ebert F, Leffers L, Weber T, Berndt S, Mangerich A, Beneke S, Bürkle A, Schwerdtle T. Toxicological properties of the thiolated inorganic arsenic and arsenosugar metabolite thio-dimethylarsinic acid in human bladder cells. J Trace Elem Med Biol. 2014 Apr;28(2):138-46. doi: 10.1016/j.jtemb.2013.06.004. Epub 2013 Jul 5. PubMed PMID: 23994116.

12: Kim E, Kim M, Sung K, Hyun J, Jang J, Kim K. Effect of topical dimethylarsinic acid on the expression of apoptosis-related proteins in mouse skin. Bull Environ Contam Toxicol. 2012 May;88(5):672-7. doi: 10.1007/s00128-012-0520-3. Epub 2012 Jan 15. PubMed PMID: 22246474.

13: MCALPINE JC. HISTOCHEMICAL DEMONSTRATION OF THE ACTIVATION OF RAT ACETYLCHOLINESTERASE BY SODIUM CACODYLATE AND CACODYLIC ACID USING THE THIOACETIC ACID METHOD. J R Microsc Soc. 1963 Oct;82:95-106. PubMed PMID: 14328462.

14: Dodmane PR, Arnold LL, Pennington KL, Thomas DJ, Cohen SM. Effect of dietary treatment with dimethylarsinous acid (DMA(III)) on the urinary bladder epithelium of arsenic (+3 oxidation state) methyltransferase (As3mt) knockout and C57BL/6 wild type female mice. Toxicology. 2013 Mar 8;305:130-5. doi: 10.1016/j.tox.2013.01.015. Epub 2013 Jan 30. PubMed PMID: 23376817.

15: Leffers L, Unterberg M, Bartel M, Hoppe C, Pieper I, Stertmann J, Ebert F, Humpf HU, Schwerdtle T. In vitro toxicological characterisation of the S-containing arsenic metabolites thio-dimethylarsinic acid and dimethylarsinic glutathione. Toxicology. 2013 Mar 8;305:109-19. doi: 10.1016/j.tox.2013.01.007. Epub 2013 Jan 23. PubMed PMID: 23353027.

16: An J, Kim KH, Kim JA, Jung H, Yoon HO, Seo J. A simplified analysis of dimethylarsinic acid by wavelength dispersive X-ray fluorescence spectrometry combined with a strong cation exchange disk. J Hazard Mater. 2013 Sep 15;260:24-31. doi: 10.1016/j.jhazmat.2013.04.033. Epub 2013 Apr 30. PubMed PMID: 23747461.

17: Stevens JT, Hall LL, Farmer JD, DiPasquale LC, Chernoff N, Durham WF. Disposition of 14C and/or 74As-cacodylic acid in rats after intravenous, intratracheal, or peroral administration. Environ Health Perspect. 1977 Aug;19:151-7. PubMed PMID: 908294; PubMed Central PMCID: PMC1637384.

18: Stevens JT, DiPasquale LC, Farmer JD. The acute inhalation toxicology of the technical grade organoarsenical herbicides, cacodylic acid and disodium methanearsonic acid; a route comparison. Bull Environ Contam Toxicol. 1979 Feb;21(3):304-11. PubMed PMID: 444720.

19: Leffers L, Wehe CA, Hüwel S, Bartel M, Ebert F, Taleshi MS, Galla HJ, Karst U, Francesconi KA, Schwerdtle T. In vitro intestinal bioavailability of arsenosugar metabolites and presystemic metabolism of thio-dimethylarsinic acid in Caco-2 cells. Metallomics. 2013 Aug;5(8):1031-42. doi: 10.1039/c3mt00039g. PubMed PMID: 23752250; PubMed Central PMCID: PMC3744932.

20: Naranmandura H, Chen X, Tanaka M, Wang WW, Rehman K, Xu S, Chen Z, Chen SQ, Suzuki N. Release of apoptotic cytochrome C from mitochondria by dimethylarsinous acid occurs through interaction with voltage-dependent anion channel in vitro. Toxicol Sci. 2012 Jul;128(1):137-46. doi: 10.1093/toxsci/kfs154. Epub 2012 Apr 26. PubMed PMID: 22539622.