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 Propiolactone was first commercially available in the United States in 1958 but then was withdrawn because it was discovered that compound was a human carcinogen.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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A vanadium/aspirin complex controlled release using a poly(beta-propiolactone) film. Effects on osteosarcoma cells. | 2001 |
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Glycidol degrades scrapie mouse prion protein. | 2001 Sep |
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Long-term follow-up of HIV-1-infected Thai patients immunized with Remune monotherapy. | 2001 Sep-Oct |
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beta-Propiolactone. | 2002 |
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Platelet adhesion onto segmented polyurethane surfaces modified by carboxybetaine. | 2003 |
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Development of a non-immunising, paraspecific vaccine from attenuated pox viruses: a new type of vaccine. | 2003 Jan |
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ß-Propiolactone. | 2004 |
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Vero-cell rabies vaccine produced using serum-free medium. | 2004 Dec 9 |
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SARS vaccine protective in mice. | 2005 Aug |
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Ru-catalyzed alkene-alkyne coupling. Total synthesis of amphidinolide P. | 2005 Dec 21 |
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Anticomplementary activity of equine whole IgG antivenoms: comparison of three fractionation protocols. | 2005 Jan |
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A kinetic approach to the alkylating potential of carcinogenic lactones. | 2005 Jul |
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Profile of animal bite cases in Pune. | 2005 Mar |
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[Development of purified HFRS bivalent vaccine]. | 2005 Mar |
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Modulation of macrophage functions by sheeppox virus provides clues to understand interaction of the virus with host immune system. | 2005 Mar 22 |
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Role of activation function domain-1, DNA binding, and coactivator GRIP1 in the expression of partial agonist activity of glucocorticoid receptor-antagonist complexes. | 2005 Mar 8 |
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Clinical responses of patients with Kawasaki disease to different brands of intravenous immunoglobulin. | 2006 Jan |
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Influenza: the virus and prophylaxis with inactivated influenza vaccine in "at risk" groups, including COPD patients. | 2007 |
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Quantification of growth factors in allogenic bone grafts extracted with three different methods. | 2007 |
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Ab initio study of the reaction of propionyl (C2H5CO) radical with oxygen (O2). | 2007 Aug 7 |
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Intravaginal administration of an inactivated vaccine prevents lesions induced by caprine herpesvirus-1 in goats. | 2007 Feb 19 |
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Frequencies of mutagen-induced coincident mitotic recombination at unlinked loci in Saccharomyces cerevisiae. | 2007 Mar 1 |
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Inactivated infectious haematopoietic necrosis virus (IHNV) vaccines. | 2008 Oct |
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Serological response in cattle immunized with inactivated oil and Algel adjuvant vaccines against infectious bovine rhinotracheitis. | 2009 Apr |
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Matrix photochemistry, photoelectron spectroscopy, solid-phase structure, and ring strain energy of beta-propiothiolactone. | 2009 Apr 16 |
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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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A pilot study of the immune response to whole inactivated avian influenza H7N1 virus vaccine in mice. | 2009 Jan |
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Seroepidemiology of pandemic influenza A (H1N1) 2009 virus infections in Pune, India. | 2010 Aug 25 |
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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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Randomised controlled double-blind non-inferiority trial of two antivenoms for saw-scaled or carpet viper (Echis ocellatus) envenoming in Nigeria. | 2010 Jul 27 |
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Molecular identification of the vaccine strain from the inactivated oil emulsion H9N2 low pathogenic avian influenza vaccine. | 2010 Jun |
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GMP-grade pneumococcal whole-cell vaccine injected subcutaneously protects mice from nasopharyngeal colonization and fatal aspiration-sepsis. | 2010 Nov 3 |
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NCI_THESAURUS |
C45187
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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