Photodegradation of methoxy substituted curcuminoids

Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longe...
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Gespeichert in:

Autor*in:	Boris Sket [verfasserIn] Petra Galer [verfasserIn]

Format:	E-Artikel
Sprache:	Englisch

Erschienen:	2015

Schlagwörter:	Dimethoxy curcuminoids photodegradation

Übergeordnetes Werk:	In: Acta Chimica Slovenica - Slovenian Chemical Society, 2003, 62(2015), 2, Seite 346-353
Übergeordnetes Werk:	volume:62 ; year:2015 ; number:2 ; pages:346-353

Links:	Link aufrufen Link aufrufen Link aufrufen Journal toc Journal toc

DOI / URN:	10.17344/acsi.2014.1140

Katalog-ID:	DOAJ075805472

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spelling	10.17344/acsi.2014.1140 doi (DE-627)DOAJ075805472 (DE-599)DOAJ695c8abff01547ca96a0093e23fe4e8c DE-627 ger DE-627 rakwb eng QD1-999 Boris Sket verfasserin aut Photodegradation of methoxy substituted curcuminoids 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid. Dimethoxy curcuminoids photodegradation Chemistry Petra Galer verfasserin aut In Acta Chimica Slovenica Slovenian Chemical Society, 2003 62(2015), 2, Seite 346-353 (DE-627)324658842 (DE-600)2029709-9 15803155 nnns volume:62 year:2015 number:2 pages:346-353 https://doi.org/10.17344/acsi.2014.1140 kostenfrei https://doaj.org/article/695c8abff01547ca96a0093e23fe4e8c kostenfrei https://journals.matheo.si/index.php/ACSi/article/view/1140 kostenfrei https://doaj.org/toc/1318-0207 Journal toc kostenfrei https://doaj.org/toc/1580-3155 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 62 2015 2 346-353
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allfieldsGer	10.17344/acsi.2014.1140 doi (DE-627)DOAJ075805472 (DE-599)DOAJ695c8abff01547ca96a0093e23fe4e8c DE-627 ger DE-627 rakwb eng QD1-999 Boris Sket verfasserin aut Photodegradation of methoxy substituted curcuminoids 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid. Dimethoxy curcuminoids photodegradation Chemistry Petra Galer verfasserin aut In Acta Chimica Slovenica Slovenian Chemical Society, 2003 62(2015), 2, Seite 346-353 (DE-627)324658842 (DE-600)2029709-9 15803155 nnns volume:62 year:2015 number:2 pages:346-353 https://doi.org/10.17344/acsi.2014.1140 kostenfrei https://doaj.org/article/695c8abff01547ca96a0093e23fe4e8c kostenfrei https://journals.matheo.si/index.php/ACSi/article/view/1140 kostenfrei https://doaj.org/toc/1318-0207 Journal toc kostenfrei https://doaj.org/toc/1580-3155 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 62 2015 2 346-353
allfieldsSound	10.17344/acsi.2014.1140 doi (DE-627)DOAJ075805472 (DE-599)DOAJ695c8abff01547ca96a0093e23fe4e8c DE-627 ger DE-627 rakwb eng QD1-999 Boris Sket verfasserin aut Photodegradation of methoxy substituted curcuminoids 2015 Text txt rdacontent Computermedien c rdamedia Online-Ressource cr rdacarrier Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid. Dimethoxy curcuminoids photodegradation Chemistry Petra Galer verfasserin aut In Acta Chimica Slovenica Slovenian Chemical Society, 2003 62(2015), 2, Seite 346-353 (DE-627)324658842 (DE-600)2029709-9 15803155 nnns volume:62 year:2015 number:2 pages:346-353 https://doi.org/10.17344/acsi.2014.1140 kostenfrei https://doaj.org/article/695c8abff01547ca96a0093e23fe4e8c kostenfrei https://journals.matheo.si/index.php/ACSi/article/view/1140 kostenfrei https://doaj.org/toc/1318-0207 Journal toc kostenfrei https://doaj.org/toc/1580-3155 Journal toc kostenfrei GBV_USEFLAG_A SYSFLAG_A GBV_DOAJ GBV_ILN_20 GBV_ILN_22 GBV_ILN_23 GBV_ILN_24 GBV_ILN_39 GBV_ILN_40 GBV_ILN_60 GBV_ILN_62 GBV_ILN_63 GBV_ILN_65 GBV_ILN_69 GBV_ILN_70 GBV_ILN_73 GBV_ILN_95 GBV_ILN_105 GBV_ILN_110 GBV_ILN_151 GBV_ILN_161 GBV_ILN_170 GBV_ILN_206 GBV_ILN_213 GBV_ILN_230 GBV_ILN_285 GBV_ILN_293 GBV_ILN_602 GBV_ILN_2005 GBV_ILN_2009 GBV_ILN_2011 GBV_ILN_2014 GBV_ILN_2055 GBV_ILN_2111 GBV_ILN_4012 GBV_ILN_4037 GBV_ILN_4112 GBV_ILN_4125 GBV_ILN_4126 GBV_ILN_4249 GBV_ILN_4305 GBV_ILN_4306 GBV_ILN_4307 GBV_ILN_4313 GBV_ILN_4322 GBV_ILN_4323 GBV_ILN_4324 GBV_ILN_4325 GBV_ILN_4338 GBV_ILN_4367 GBV_ILN_4700 AR 62 2015 2 346-353
language	English
source	In Acta Chimica Slovenica 62(2015), 2, Seite 346-353 volume:62 year:2015 number:2 pages:346-353
sourceStr	In Acta Chimica Slovenica 62(2015), 2, Seite 346-353 volume:62 year:2015 number:2 pages:346-353
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topic_facet	Dimethoxy curcuminoids photodegradation Chemistry
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authorswithroles_txt_mv	Boris Sket @@aut@@ Petra Galer @@aut@@
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topic_title	QD1-999 Photodegradation of methoxy substituted curcuminoids Dimethoxy curcuminoids photodegradation
topic	misc QD1-999 misc Dimethoxy curcuminoids misc photodegradation misc Chemistry
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title	Photodegradation of methoxy substituted curcuminoids
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title_full	Photodegradation of methoxy substituted curcuminoids
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title_sort	photodegradation of methoxy substituted curcuminoids
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title_auth	Photodegradation of methoxy substituted curcuminoids
abstract	Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid.
abstractGer	Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid.
abstract_unstemmed	Photodegradation of dimethoxy curcuminoids in acetonitrile solution was found to depend on the position of the methoxy group bonded to the phenyl ring. The rate of decomposition was expressed as the lifetime of the decomposing substrate, being the shortest in the case of the 3,5-diOCH3 and the longest for the 2,5-diOCH3 derivative. For the 3,5-diOCH3 curcuminoid, the major degradation products were 3,5-dimethoxy benzaldehyde, 3,5-dimethoxybenzoic acid and the Z and E isomers of dimethoxy cinnamic acid, together forming about 90% of the reaction mixture. Minor products found were 4,5-bis(3,5-dimethoxyphenyl)hex-2-endionic acid, and products with the molecular formula C23H24O6 and C23H22O6 attributed to the reaction of intramolecular 2+2 cycloaddition of the dimethoxy curcuminoid and the dioxygenated bicyclopentadione derivative (C23H24O8) derived from autoxidative transformation of the dimethoxy curcuminoid.
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title_short	Photodegradation of methoxy substituted curcuminoids
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