Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H4O2 |
Molecular Weight | 72.0627 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1CCO1
InChI
InChIKey=VEZXCJBBBCKRPI-UHFFFAOYSA-N
InChI=1S/C3H4O2/c4-3-1-2-5-3/h1-2H2
Propiolactone (or beta-propiolactone) is a disinfectant used in vapor form to sterilize vaccines, grafts, blood plasma, surgical instruments. It has been used against bacteria, fungi, and virus. Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen. The results have shown the generation of tumors in several tissues and from different administration routes. Propiolactone is a direct-acting alkylating agent that reacts with polynucleotides and DNA, mainly at N7 of guanine and N1 of adenine, to form carboxyethyl derivatives.
Approval Year
PubMed
Title | Date | PubMed |
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Inactivation of hepatitis viruses and HIV in plasma and plasma derivatives by treatment with beta-propiolactone/UV irradiation. | 1989 |
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Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors. | 2002 Mar 8 |
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ß-Propiolactone. | 2004 |
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[Development of purified HFRS bivalent vaccine]. | 2005 Mar |
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Ophiopojaponin D, a new phenylpropanoid glycoside from Ophiopogon japonicus Ker-Gawl. | 2005 Nov |
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Efficiency of Matricaria chamomilla CH12 and number of doses of rabies vaccine on the humoral immune response in cattle. | 2008 Dec |
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Chemical reactivity and biological activity of diketene. | 2008 Oct |
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Inactivated infectious haematopoietic necrosis virus (IHNV) vaccines. | 2008 Oct |
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Chemical addressability of ultraviolet-inactivated viral nanoparticles (VNPs). | 2008 Oct 2 |
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Quantitative determination of the infectivity of the proviral DNA of a retrovirus in vitro: Evaluation of methods for DNA inactivation. | 2009 Aug |
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Pandemic influenza vaccines - the challenges. | 2009 Dec |
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Combined experimental and theoretical study on hydrogen-bonded complexes between cyclic ketones, lactones, and lactams with 3,4-dinitrophenol. | 2009 Dec 31 |
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Poly(lactide-co-glycolide) microspheres: a potent oral delivery system to elicit systemic immune response against inactivated rabies virus. | 2009 Mar 26 |
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Induction of cell-cell fusion by ectromelia virus is not inhibited by its fusion inhibitory complex. | 2009 Sep 29 |
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The influence of the inactivating agent on the antigen content of inactivated Newcastle disease vaccines assessed by the in vitro potency test. | 2010 Jan |
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NCI_THESAURUS |
C45187
Created by
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IARC | beta-Propiolactone | ||
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NCI_THESAURUS |
C606
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BETA-PROPIOLACTONE
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21626
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DTXSID8021197
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3495
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D011420
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1311565
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6RC3ZT4HB0
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49073
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SUB10109MIG
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811
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1749
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m9204
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100000081358
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2365
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DB09348
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200-340-1
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CHEMBL1200627
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57-57-8
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C44339
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ACTIVE MOIETY