Enantioseparation of the fungicide imazalil in orange juice by chiral HPLC. Study on degradation rates and extractive/enrichment techniques.
Identifieur interne : 000157 ( PubMed/Curation ); précédent : 000156; suivant : 000158Enantioseparation of the fungicide imazalil in orange juice by chiral HPLC. Study on degradation rates and extractive/enrichment techniques.
Auteurs : L. Ruiz-Rodríguez [Espagne] ; A. Aguilar [Espagne] ; A N Díaz [Espagne] ; F G Sánchez [Espagne]Source :
- Food chemistry [ 0308-8146 ] ; 2015.
English descriptors
- KwdEn :
- MESH :
- chemical , chemistry : Fungicides, Industrial, Imidazoles.
- analysis : Beverages.
- chemistry : Citrus sinensis.
- chemical , isolation & purification : Imidazoles.
- methods : Chromatography, High Pressure Liquid, Liquid Phase Microextraction, Solid Phase Extraction.
- Stereoisomerism.
Abstract
Imazalil ([1-(β-allyloxy-2,4-dichlorophenethyl)imidazole]) is a systemic chiral fungicide used in postharvest protection of citruses against fungi development for during storage and transportation. The chemical structure of imazalil shows an asymmetric carbon in the C7 position. These enantiomers may have different toxicity. A method for both chiral enantiomers extraction and determination in orange juice is developed in order to provide their concentration and to study the degradation rates in orange juice. Spiked imazalil was extracted from orange juice by dispersive liquid-liquid micro extraction and solid phase extraction. Recovery assays of imazalil enantiomers from spiked orange juice samples showed that solid phase extraction is a better choice in order to obtain higher recovery values. Obtained chromatographic data show that within 24h the (-)-imazalil enantiomer decreases from 0.548 to 0.471 (expressed as enantiomer fraction).
DOI: 10.1016/j.foodchem.2015.01.004
PubMed: 25704699
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Aguilar</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga</wicri:regionArea></affiliation></author><author><name sortKey="Diaz, A N" sort="Diaz, A N" uniqKey="Diaz A" first="A N" last="Díaz">A N Díaz</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga</wicri:regionArea></affiliation></author><author><name sortKey="Sanchez, F G" sort="Sanchez, F G" uniqKey="Sanchez F" first="F G" last="Sánchez">F G Sánchez</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain. 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Aguilar</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga</wicri:regionArea></affiliation></author><author><name sortKey="Diaz, A N" sort="Diaz, A N" uniqKey="Diaz A" first="A N" last="Díaz">A N Díaz</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</nlm:affiliation><country xml:lang="fr">Espagne</country><wicri:regionArea>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga</wicri:regionArea></affiliation></author><author><name sortKey="Sanchez, F G" sort="Sanchez, F G" uniqKey="Sanchez F" first="F G" last="Sánchez">F G Sánchez</name><affiliation wicri:level="1"><nlm:affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain. 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The chemical structure of imazalil shows an asymmetric carbon in the C7 position. These enantiomers may have different toxicity. A method for both chiral enantiomers extraction and determination in orange juice is developed in order to provide their concentration and to study the degradation rates in orange juice. Spiked imazalil was extracted from orange juice by dispersive liquid-liquid micro extraction and solid phase extraction. Recovery assays of imazalil enantiomers from spiked orange juice samples showed that solid phase extraction is a better choice in order to obtain higher recovery values. Obtained chromatographic data show that within 24h the (-)-imazalil enantiomer decreases from 0.548 to 0.471 (expressed as enantiomer fraction).</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25704699</PMID><DateCreated><Year>2015</Year><Month>2</Month><Day>23</Day></DateCreated><DateCompleted><Year>2015</Year><Month>09</Month><Day>18</Day></DateCompleted><DateRevised><Year>2015</Year><Month>2</Month><Day>23</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">0308-8146</ISSN><JournalIssue CitedMedium="Internet"><Volume>178</Volume><PubDate><Year>2015</Year><Month>Jul</Month><Day>1</Day></PubDate></JournalIssue><Title>Food chemistry</Title><ISOAbbreviation>Food Chem</ISOAbbreviation></Journal><ArticleTitle>Enantioseparation of the fungicide imazalil in orange juice by chiral HPLC. Study on degradation rates and extractive/enrichment techniques.</ArticleTitle><Pagination><MedlinePgn>179-85</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.foodchem.2015.01.004</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0308-8146(15)00006-0</ELocationID><Abstract><AbstractText>Imazalil ([1-(β-allyloxy-2,4-dichlorophenethyl)imidazole]) is a systemic chiral fungicide used in postharvest protection of citruses against fungi development for during storage and transportation. The chemical structure of imazalil shows an asymmetric carbon in the C7 position. These enantiomers may have different toxicity. A method for both chiral enantiomers extraction and determination in orange juice is developed in order to provide their concentration and to study the degradation rates in orange juice. Spiked imazalil was extracted from orange juice by dispersive liquid-liquid micro extraction and solid phase extraction. Recovery assays of imazalil enantiomers from spiked orange juice samples showed that solid phase extraction is a better choice in order to obtain higher recovery values. Obtained chromatographic data show that within 24h the (-)-imazalil enantiomer decreases from 0.548 to 0.471 (expressed as enantiomer fraction).</AbstractText><CopyrightInformation>Copyright © 2015 The Authors. Published by Elsevier Ltd.. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Ruiz-Rodríguez</LastName><ForeName>L</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Aguilar</LastName><ForeName>A</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Díaz</LastName><ForeName>A N</ForeName><Initials>AN</Initials><AffiliationInfo><Affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sánchez</LastName><ForeName>F G</ForeName><Initials>FG</Initials><AffiliationInfo><Affiliation>Department of Analytical Chemistry, Faculty of Sciences, University of Malaga, Campus de Teatinos s/n, 29071 Malaga, Spain. Electronic address: f_garcia@uma.es.</Affiliation></AffiliationInfo></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2015</Year><Month>Jan</Month><Day>12</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Food Chem</MedlineTA><NlmUniqueID>7702639</NlmUniqueID><ISSNLinking>0308-8146</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D005659">Fungicides, Industrial</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007093">Imidazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>6K0NOF3XQ6</RegistryNumber><NameOfSubstance UI="C017435">enilconazole</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001628" MajorTopicYN="N">Beverages</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="Y">analysis</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D002851" MajorTopicYN="N">Chromatography, High Pressure Liquid</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="Y">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D032084" MajorTopicYN="N">Citrus sinensis</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D005659" MajorTopicYN="N">Fungicides, Industrial</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007093" MajorTopicYN="N">Imidazoles</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D059627" MajorTopicYN="N">Liquid Phase Microextraction</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="N">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D052616" MajorTopicYN="N">Solid Phase Extraction</DescriptorName><QualifierName UI="Q000379" MajorTopicYN="N">methods</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Degradation kinetics</Keyword><Keyword MajorTopicYN="N">Dispersive liquid–liquid microextraction</Keyword><Keyword MajorTopicYN="N">HPLC enantioseparation</Keyword><Keyword MajorTopicYN="N">Imazalil</Keyword><Keyword MajorTopicYN="N">Orange juice</Keyword><Keyword MajorTopicYN="N">Solid phase extraction</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year><Month>2</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2014</Year><Month>7</Month><Day>9</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2015</Year><Month>1</Month><Day>4</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2015</Year><Month>2</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2015</Year><Month>2</Month><Day>24</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2015</Year><Month>9</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">25704699</ArticleId><ArticleId IdType="pii">S0308-8146(15)00006-0</ArticleId><ArticleId IdType="doi">10.1016/j.foodchem.2015.01.004</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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