The structure of the acetoxy group .mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}  blue.
The structure of the acetoxy group   blue.

In organic chemistry, the acetoxy group (abbr. AcO or OAc; IUPAC name: acetyloxy[1]), is a functional group with the formula −OCOCH3 and the structure −O−C(=O)−CH3.[2][3] As the -oxy suffix implies, it differs from the acetyl group (−C(=O)−CH3) by the presence of an additional oxygen atom.[4][5] The name acetoxy is the short form of acetyl-oxy.[6]

Functionality

An acetoxy group may be used as a protection for an alcohol functionality in a synthetic route although the protecting group itself is called an acetyl group.[7]

Alcohol protection

There are several options of introducing an acetoxy functionality in a molecule from an alcohol (in effect protecting the alcohol by acetylation):

An alcohol is not a particularly strong nucleophile and, when present, more powerful nucleophiles like amines will react with the above-mentioned reagents in preference to the alcohol.[12]

Alcohol deprotection

For deprotection (regeneration of the alcohol)

See also

References

  1. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 805. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4. The systematic name 'acetyloxy' is preferred to the contracted name 'acetoxy' that may be used in general nomenclature.
  2. ^ Ueno, H.; Maruyama, A.; Miyake, M.; Nakao, E.; Nakao, K.; Umezu, K.; Nitta, I. (1991). "Synthesis and evaluation of antiinflammatory activities of a series of corticosteroid 17 alpha-esters containing a functional group". Journal of Medicinal Chemistry. 34 (8): 2468–2473. doi:10.1021/jm00112a023. ISSN 0022-2623. PMID 1875343.
  3. ^ "Data from NIST Standard Reference Database 69: NIST Chemistry WebBook". National Institute of Standards and Technology. Retrieved 2022-10-03.
  4. ^ "AID 622471 - Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced hind paw edema at 10 mg/kg, po measured after 3 hrs post dose - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-10-03.
  5. ^ "AID 622470 - Antiinflammatory activity in po dosed rat assessed as inhibition of carrageenan-induced hind paw edema measured after 3 hrs post dose - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-10-03.
  6. ^ Zhuo, Zhen-Jian; Xiao, Min-Jie; Lin, Hui-Ran; Luo, Jing; Wang, Tao (2018). "Novel betulin derivative induces anti-proliferative activity by G2/M phase cell cycle arrest and apoptosis in Huh7 cells". Oncology Letters. 15 (2): 2097–2104. doi:10.3892/ol.2017.7575. ISSN 1792-1074. PMC 5776954. PMID 29434911.
  7. ^ Jiménez-Orozco, Fausto Alejandro; Galicia-Zapatero, Sergio; López-López, Edgar; Medina-Franco, José L.; Cedeño, Fernando León; Flores-García, Mirthala; Mejia-Domínguez, Ana María; de la Peña-Díaz, Aurora (2022). "Monosubstituted Coumarins Inhibit Epinephrine-induced Platelet Aggregation". Cardiovascular & Hematological Agents in Medicinal Chemistry. 20 (1): 43–51. doi:10.2174/1871525719666210427132808. ISSN 1875-6182. PMC 9127734. PMID 33906594.
  8. ^ Stepień, Marcin; Latos-Grazyński, Lechosław (2003-10-06). "Core-modified porphyrin incorporating a phenolate donor. Characterization of Pd(II), Ni(II), Zn(II), Cd(II), and Fe(III) complexes". Inorganic Chemistry. 42 (20): 6183–6193. doi:10.1021/ic0345121. ISSN 0020-1669. PMID 14514294.
  9. ^ Liu, Han; Li, Xuechen (2014-06-20). "A stereoselective ring-closing glycosylation via nonglycosylating pathway". The Journal of Organic Chemistry. 79 (12): 5834–5841. doi:10.1021/jo5006763. ISSN 1520-6904. PMID 24877607.
  10. ^ Flesher, James W.; Lehner, Andreas F. (2016). "Structure, function and carcinogenicity of metabolites of methylated and non-methylated polycyclic aromatic hydrocarbons: a comprehensive review". Toxicology Mechanisms and Methods. 26 (3): 151–179. doi:10.3109/15376516.2015.1135223. ISSN 1537-6524. PMID 26894797. S2CID 25946888.
  11. ^ Horishny, Volodymyr; Lesyk, Roman; Kowiel, Marcin; Gzella, Andrzej K. (2013-03-01). "2-[N-(2,4-Dimeth-oxy-phen-yl)acetamido]-1,3-thia-zol-4-yl acetate". Acta Crystallographica, Section E. 69 (Pt 3): o356–357. doi:10.1107/S1600536813003474. ISSN 1600-5368. PMC 3588517. PMID 23476547.
  12. ^ Fujioka, Hiromichi; Minamitsuji, Yutaka; Moriya, Takahiro; Okamoto, Kazuhisa; Kubo, Ozora; Matsushita, Tomoyo; Murai, Kenichi (2012). "Preparation of THP-ester-derived pyridinium-type salts and their reactions with various nucleophiles". Chemistry: An Asian Journal. 7 (8): 1925–1933. doi:10.1002/asia.201200234. ISSN 1861-471X. PMID 22639340.
  13. ^ Azuma, Hideki; Aizawa, Yui; Higashitani, Nao; Tsumori, Takashi; Kojima-Yuasa, Akiko; Matsui-Yuasa, Isao; Nagasaki, Takeshi (2011-06-15). "Biological activity of water-soluble inclusion complexes of 1'-acetoxychavicol acetate with cyclodextrins". Bioorganic & Medicinal Chemistry. 19 (12): 3855–3863. doi:10.1016/j.bmc.2011.04.038. ISSN 1464-3391. PMID 21596572.
  14. ^ Nandi, Soutick; Reinsch, Helge; Biswas, Shyam (2020-12-22). "An acetoxy functionalized Al(III) based metal-organic framework showing selective "turn on" detection of perborate in environmental samples". Dalton Transactions (Cambridge, England: 2003). 49 (48): 17612–17620. doi:10.1039/d0dt02422h. ISSN 1477-9234. PMID 33241803. S2CID 227176678.
  15. ^ de Costa, B. R.; Iadarola, M. J.; Rothman, R. B.; Berman, K. F.; George, C.; Newman, A. H.; Mahboubi, A.; Jacobson, A. E.; Rice, K. C. (1992-07-24). "Probes for narcotic receptor mediated phenomena. 18. Epimeric 6 alpha- and 6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinans as potential ligands for opioid receptor single photon emission computed tomography: synthesis, evaluation, and radiochemistry of [125I]-6 beta-iodo-3,14-dihydroxy-17-(cyclopropylmethyl)-4,5 alpha-epoxymorphinan". Journal of Medicinal Chemistry. 35 (15): 2826–2835. doi:10.1021/jm00093a016. ISSN 0022-2623. PMID 1322988.
  16. ^ Camus, A. M.; Wiessler, M.; Malaveille, C.; Bartsch, H. (1978). "High mutagenicity of N-(alpha-acyloxy)alkyl-N-alkylnitrosamines in S. typhimurium: model compounds for metabolically activated N,N-dialkylnitrosamines". Mutation Research. 49 (2): 187–194. doi:10.1016/0027-5107(78)90156-2. ISSN 0027-5107. PMID 342933.
  17. ^ Kaur, Jatinder; Bhardwaj, Atul; Huang, Zhangjian; Knaus, Edward E. (2012-01-02). "Aspirin analogues as dual cyclooxygenase-2/5-lipoxygenase inhibitors: synthesis, nitric oxide release, molecular modeling, and biological evaluation as anti-inflammatory agents". ChemMedChem. 7 (1): 144–150. doi:10.1002/cmdc.201100460. ISSN 1860-7187. PMID 22095955. S2CID 38843343.
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