Applications of NMR Spectroscopy

Volume: 4

The Application of NMR Spectroscopy to the Study of Pyranoanthocyanins: Structural Elucidation, Solution Equilibria and Exhibited Color in Foods and Beverages

Author(s): M. Victoria Gomez, Sergio Gómez-Alonso and Isidro Hermosín-Gutiérrez

Pp: 96-187 (92)

DOI: 10.2174/9781681081434116040005

* (Excluding Mailing and Handling)

Abstract

Anthocyanins are an important class of natural pigments widely distributed throughout the Plant Kingdom and foodstuffs. They are rather reactive compounds that are involved in several equilibria in aqueous solution and give rise to new classes of anthocyanin-derived pigments. This reactivity creates changes in the exhibited color that is especially interesting with regards to foods and beverages. Among the anthocyanin-derived pigments, pyranoanthocyanins have gained attention in the last two decades because of their higher stability, mainly the resistance to discoloration by changing pH or after the addition of bisulfite, in comparison to their precursor anthocyanins. One of the first challenges regarding pyranoanthocyanins was their structural elucidation, leading to an increasing difficulty due to the finding of several new subclasses of chemical structures, beginning with one the first discovered, relatively simple, vitisin-type pyrano-anthocyanins and continuing with other more complex structures like those of flavanyl-vinyl-pyranoanthocyanins or pyranoanthocyanin dimers. Multidimensional Mass Spectrometry (MSn) and Nuclear Magnetic Resonance (NMR) spectroscopy have been crucial tools for the structure elucidation of pyranoanthocyanins. In addition, NMR spectroscopy has contributed to the gaining of knowledge about the aqueous solution equilibria in which pyranoanthocyanins are involved, thus helping the interpretation of the molecular basis behind the higher stability of such anthocyanin-derived pigments. This review introduces the pyranoanthocyanins by means of a description of the anthocyanin reactivity and the formation of anthocyanin-derived pigments in foods and beverages. The review continues with an overview of the current knowledge about different structures of pyranoanthocyanins, their main properties related to exhibited color, especially their behavior against changing pH and bisulfite bleaching, their reactivity, and the occurrence of pyranoanthocyanins in foods and beverages. Finally, this review deals with the application of NMR spectroscopy to several interesting issues related to pyranoanthocyanin chemistry, namely the structure elucidation of the different classes of pyrano-anthocyanins, the behavior of these compounds in aqueous equilibria of hydration and proton transfer, and the formation of new pyranoanthocyanin-related compounds.


Keywords: Anthocyanin, Bleaching resistance, Color, Food, Fruit, Hydration, Juice, NMR, Pigment, Pinotin, Portisin, Pyranoanthocyanin, Vitisin, Wine.

Related Journals
Related Books
© 2025 Bentham Science Publishers | Privacy Policy
Request history8.2.27PHP Version163msRequest Duration26MBMemory UsageGET chapter/{id}/{param?}Route
  • warninglog[02:55:22] LOG.warning: Optional parameter $id declared before required parameter $request is implic...
  • Booting (88.8ms)time
  • Application (73.78ms)time
  • 1 x Booting (54.62%)
    88.80ms
    1 x Application (45.38%)
    73.78ms
    12 templates were rendered
    • ebook.chapter_detailschapter_details.blade.php#?blade
    • layouts.chapter_header_sectionchapter_header_section.blade.php#?blade
    • ebook.chapter_top_bannerchapter_top_banner.blade.php#?blade
    • ebook.chapter_bottom_bannerchapter_bottom_banner.blade.php#?blade
    • ebook.ebook_right_bannerebook_right_banner.blade.php#?blade
    • includes.inc_related_journalsinc_related_journals.blade.php#?blade
    • includes.inc_related_ebooksinc_related_ebooks.blade.php#?blade
    • layouts.appapp.blade.php#?blade
    • layouts._login_access_login_access.blade.php#?blade
    • layouts._header_header.blade.php#?blade
    • layouts._main_menu_main_menu.blade.php#?blade
    • layouts._footer_menu_footer_menu.blade.php#?blade
    uri
    GET chapter/{id}/{param?}
    middleware
    web, check_user_access
    controller
    App\Http\Controllers\ChapterController@GetChapterDetails
    namespace
    App\Http\Controllers
    where
    as
    chapter
    file
    app/Http/Controllers/ChapterController.php:1350-1704
    19 statements were executed22.77ms
    • Connection Establishedalphaeurekaselec_live_10_06_2022UserAccessCheck.php#24
      Backtrace
      • 9. middleware::check_user_access:24
      • 10. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 11. vendor/laravel/framework/src/Illuminate/Routing/Middleware/SubstituteBindings.php:50
      • 12. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 13. vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/VerifyCsrfToken.php:88
    • INSERT INTO visitor_ip_address (ip_address,visitor_agent,visitor_count, created_on,updated_on) VALUES ('222027364','',1,1739847322,1739847322) ON DUPLICATE KEY UPDATE visitor_count=visitor_count + 1, updated_on=1739847322
      910μsalphaeurekaselec_live_10_06_2022UserAccessCheck.php#24
      Backtrace
      • 11. middleware::check_user_access:24
      • 12. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 13. vendor/laravel/framework/src/Illuminate/Routing/Middleware/SubstituteBindings.php:50
      • 14. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 15. vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/VerifyCsrfToken.php:88
    • INSERT INTO visitor_ip_address_detail (ip_address,visitor_url,visitor_count, created_on,updated_on) VALUES ('222027364','/chapter/8862',1,1739847322,1739847322)
      140μsalphaeurekaselec_live_10_06_2022UserAccessCheck.php#27
      Backtrace
      • 11. middleware::check_user_access:27
      • 12. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 13. vendor/laravel/framework/src/Illuminate/Routing/Middleware/SubstituteBindings.php:50
      • 14. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 15. vendor/laravel/framework/src/Illuminate/Foundation/Http/Middleware/VerifyCsrfToken.php:88
    • (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_journal_volume_trail WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_journal_volume_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_journal_volume_token WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_ebook_volume_trail WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_ebook_volume_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_ebook_volume_token WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_issue_trail WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_issue_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_issue_token WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_article_trail WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_article_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_article_token WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_chapter_trail WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_chapter_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_chapter_token WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) union (select `user_id`, `to_ip`, `from_ip` from (select user_id, to_ip, from_ip FROM user_access_disease_corporate WHERE to_ip >= 222027364 ORDER BY to_ip ASC LIMIT 1) as `tjv` where `from_ip` <= 222027364) limit 1
      14.36msalphaeurekaselec_live_10_06_2022UserAccess.php#784
      Bindings
      • 0: 222027364
      • 1: 222027364
      • 2: 222027364
      • 3: 222027364
      • 4: 222027364
      • 5: 222027364
      • 6: 222027364
      • 7: 222027364
      • 8: 222027364
      • 9: 222027364
      • 10: 222027364
      • 11: 222027364
      • 12: 222027364
      • 13: 222027364
      • 14: 222027364
      • 15: 222027364
      Backtrace
      • 14. app/Models/UserAccess/UserAccess.php:784
      • 15. middleware::check_user_access:114
      • 16. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Middleware/SubstituteBindings.php:50
      • 18. vendor/laravel/framework/src/Illuminate/Pipeline/Pipeline.php:183
    • select * from `chapter` where `chapter_id` = '8862' limit 1
      260μsalphaeurekaselec_live_10_06_2022ChapterController.php#1406
      Bindings
      • 0: 8862
      Backtrace
      • 16. app/Http/Controllers/ChapterController.php:1406
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 18. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 19. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
      • 20. vendor/laravel/framework/src/Illuminate/Routing/Route.php:206
    • select CONCAT_WS(' ',au.first_name, ' ', ifnull(au.initials,''), ' ', au.last_name) as authors, CONCAT(au.last_name, IFNULL(CONCAT(' ', au.initials), ''), ' ', au.first_name) AS authorsRIS, CONCAT_WS(' ',au.last_name, ' ', ifnull(au.initials,''), ' ', au.first_name) as authorsCiteAs, CONCAT_WS(' ',au.first_name, IFNULL(CONCAT(' ', au.initials), ''), IFNULL(CONCAT(' ', au.last_name), '')) as authorsmodal , `au`.*, `af`.`ror_id`, `af`.`institution`, `af`.`department`, `af`.`country`, `af`.`city`, `af`.`address`, (GROUP_CONCAT(TRIM(BOTH ', ' FROM CONCAT(ifnull(concat(af.institution,','),''), ifnull(concat(af.department,','),''), ifnull(concat(af.address,','),''), ifnull(concat(af.city,','),''), ifnull(concat(af.country,','),''), ifnull(concat(af.postal_code,','),''), ifnull(concat(af.phone,','),''), ifnull(concat(af.fax,','),''))) SEPARATOR '|')) as `author_affiliation`, (GROUP_CONCAT(TRIM(BOTH ', ' FROM CONCAT(ifnull(concat(af.web_view,','),''))) SEPARATOR '|')) as `web_view` from `author` as `au` left join `author_affiliation` as `af` on `au`.`author_id` = `af`.`author_id` where `au`.`chapter_id` = '8862' group by `au`.`author_id` order by `au`.`article_id` asc, `au`.`sequence` asc
      660μsalphaeurekaselec_live_10_06_2022Author.php#86
      Bindings
      • 0: 8862
      Backtrace
      • 13. app/Models/Author.php:86
      • 14. app/Http/Controllers/ChapterController.php:1411
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select * from `keywords` where `chapter_id` = '8862'
      270μsalphaeurekaselec_live_10_06_2022ChapterController.php#1415
      Bindings
      • 0: 8862
      Backtrace
      • 15. app/Http/Controllers/ChapterController.php:1415
      • 16. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 17. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
      • 19. vendor/laravel/framework/src/Illuminate/Routing/Route.php:206
    • select * from `ebook` where `ebook_id` = 444 limit 1
      200μsalphaeurekaselec_live_10_06_2022ChapterController.php#1430
      Bindings
      • 0: 444
      Backtrace
      • 16. app/Http/Controllers/ChapterController.php:1430
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 18. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 19. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
      • 20. vendor/laravel/framework/src/Illuminate/Routing/Route.php:206
    • select count(*) as aggregate from `subject_ebook` as `se` inner join `ebook` as `e` on `e`.`ebook_id` = `se`.`ebook_id` inner join `ebook_volume` as `v` on `v`.`ebook_id` = `e`.`ebook_id` where subject_id IN (select subject_id FROM subject_ebook WHERE ebook_id=444) and se.ebook_id!=444 and v.ebook_status='1'
      1.02msalphaeurekaselec_live_10_06_2022Subject.php#238
      Backtrace
      • 16. app/Models/Subject.php:238
      • 17. app/Http/Controllers/ChapterController.php:1434
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 19. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 20. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select distinct v.nid as volume_id,e.nid,e.title,v.issn,v.eissn,v.isbn,v.eisbn,e.ebook_id, v.image_file_name,v.file_path,v.flyer_link,v.ebook_volume_id, v.volume_name,v.doi,v.year_id,v.introduction from `subject_ebook` as `se` inner join `ebook` as `e` on `e`.`ebook_id` = `se`.`ebook_id` inner join `ebook_volume` as `v` on `v`.`ebook_id` = `e`.`ebook_id` where subject_id IN (select subject_id FROM subject_ebook WHERE ebook_id=444) and se.ebook_id!=444 and v.ebook_status='1' limit 10 offset 0
      650μsalphaeurekaselec_live_10_06_2022Subject.php#238
      Backtrace
      • 14. app/Models/Subject.php:238
      • 15. app/Http/Controllers/ChapterController.php:1434
      • 16. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 17. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select count(*) as aggregate from `subject_journal` as `sj` inner join `journal` as `j` on `j`.`journal_id` = `sj`.`journal_id` where subject_id IN (select subject_id FROM subject_ebook WHERE ebook_id=444)
      360μsalphaeurekaselec_live_10_06_2022Subject.php#255
      Backtrace
      • 16. app/Models/Subject.php:255
      • 17. app/Http/Controllers/ChapterController.php:1435
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 19. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 20. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select distinct j.nid as journal_nid,j.title,j.subtitle,j.issn,j.eissn,j.keyword,sj.journal_id,j.image_file_name,j.flyer_link from `subject_journal` as `sj` inner join `journal` as `j` on `j`.`journal_id` = `sj`.`journal_id` where subject_id IN (select subject_id FROM subject_ebook WHERE ebook_id=444) limit 10 offset 0
      400μsalphaeurekaselec_live_10_06_2022Subject.php#255
      Backtrace
      • 14. app/Models/Subject.php:255
      • 15. app/Http/Controllers/ChapterController.php:1435
      • 16. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 17. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select `e`.*, `a`.*, `y`.`year`, `e`.`ebook_volume_id` as `ebook_volume_id`, `a`.`ebook_volume_id` as `ebk_vol_id`, `e`.`ebook_id` as `ebk_ebook_id` from `ebook_volume` as `e` left join `author` as `a` on `e`.`ebook_volume_id` = `a`.`ebook_volume_id` left join `year` as `y` on `y`.`id` = `e`.`year_id` where `e`.`ebook_volume_id` = 1929 and `e`.`is_uploaded` = 1
      430μsalphaeurekaselec_live_10_06_2022EbookVolume.php#271
      Bindings
      • 0: 1929
      • 1: 1
      Backtrace
      • 13. app/Models/EbookVolume.php:271
      • 14. app/Http/Controllers/ChapterController.php:1438
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select count(*) rcd from `ebook_volume` where `ebook_id` = 444 and ebook_volume_id <> 1929 limit 1
      230μsalphaeurekaselec_live_10_06_2022EbookVolume.php#999
      Bindings
      • 0: 444
      Backtrace
      • 14. app/Models/EbookVolume.php:999
      • 15. app/Http/Controllers/ChapterController.php:1462
      • 16. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 17. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 18. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select count(*) as total_count, content_type_access_id as access_type from ebook_access where content_type_id = '8862' and content_type = 'c' and ( (from_date <= CURDATE() and to_date >= CURDATE() and perpetual= 0) or (from_date is null and to_date is null and perpetual= 1) )
      280μsalphaeurekaselec_live_10_06_2022ContentAccess.php#647
      Backtrace
      • 11. app/Models/ContentAccess.php:647
      • 12. app/Http/Controllers/ChapterController.php:1465
      • 13. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 14. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select count(*) as total_count, content_type_access_id as access_type from ebook_access where content_type_id = '1929' and content_type = 'v' and ( (from_date <= CURDATE() and to_date >= CURDATE() and perpetual= 0) or (from_date is null and to_date is null and perpetual= 1) )
      240μsalphaeurekaselec_live_10_06_2022ContentAccess.php#647
      Backtrace
      • 11. app/Models/ContentAccess.php:647
      • 12. app/Http/Controllers/ChapterController.php:1478
      • 13. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 14. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Trial Access" as access_base_text, CASE j.type WHEN 111 THEN true ELSE false END as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"ebook_volume" as access_level,"" as chapter_id from `user_access_ebook_volume_trail` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.volume_id = 1929) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Subscribed" as access_base_text, false as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"ebook_volume" as access_level,"" as chapter_id from `user_access_ebook_volume_corporate` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.volume_id = 1929) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Token Based Access" as access_base_text, false as terms_popup, "R" as content_download_type, j.uc_id as restricted_user_access_key, "v" as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"ebook_volume" as access_level,"" as chapter_id from `user_access_ebook_volume_token` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.volume_id = 1929)
      550μsalphaeurekaselec_live_10_06_2022UserAccess.php#1266
      Backtrace
      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1518
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Trial Access" as access_base_text, CASE j.type WHEN 111 THEN true ELSE false END as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_trail` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 8862) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Subscribed" as access_base_text, false as terms_popup, "S" as content_download_type, null as restricted_user_access_key, null as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_corporate` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 8862) union (select j.user_access_id,j.volume_id,j.user_id,j.from_ip,j.to_ip,j.type,j.track,"Token Based Access" as access_base_text, false as terms_popup, "R" as content_download_type, j.uc_id as restricted_user_access_key, "v" as restricted_user_access_type, CASE j.track WHEN 0 THEN false ELSE true END as tracksAccessByVolume,"chapter" as access_level, j.chapter_id from `user_access_chapter_token` as `j` inner join `user_access_info` as `info` on `j`.`user_access_id` = `info`.`user_access_id` where ((j.from_ip <= 222027364 and j.to_ip >=222027364 )) and ((j.from_date <= 1739847322 and j.to_date >= 1739847322 and j.perpetual= 0) or (j.from_date is null and j.to_date is null and j.perpetual= 1)) and j.chapter_id = 8862)
      570μsalphaeurekaselec_live_10_06_2022UserAccess.php#1266
      Backtrace
      • 13. app/Models/UserAccess/UserAccess.php:1266
      • 14. app/Http/Controllers/ChapterController.php:1549
      • 15. vendor/laravel/framework/src/Illuminate/Routing/Controller.php:54
      • 16. vendor/laravel/framework/src/Illuminate/Routing/ControllerDispatcher.php:43
      • 17. vendor/laravel/framework/src/Illuminate/Routing/Route.php:260
    • select b.banner_link, b.banner_name, b.banner_script, b.banner_remarks, b.banner_file_name, b.banner_placement, bd.content_type, bd.content_id from `tbl_banner` as `b` inner join `tbl_banner_detail` as `bd` on `bd`.`banner_id` = `b`.`banner_id` inner join `users` as `u` on `u`.`id` = `b`.`updated_by` where `b`.`banner_ebook` = 1 and `bd`.`content_type` = 'B' and `bd`.`content_id` = 1929 and `b`.`banner_from_date` <= 1739847322 and `b`.`banner_to_date` >= 1739847322 and `b`.`banner_status` = 'A' order by `b`.`banner_id` desc
      1.04msalphaeurekaselec_live_10_06_2022Banner.php#95
      Bindings
      • 0: 1
      • 1: B
      • 2: 1929
      • 3: 1739847322
      • 4: 1739847322
      • 5: A
      Backtrace
      • 13. app/Models/Banner.php:95
      • 14. app/Http/helpers.php:404
      • 17. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 18. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    • select count(*) as aggregate from `uc_cart_products` where cart_id='ba8104211971a6fe8854cfe290ac8fa7'
      200μsalphaeurekaselec_live_10_06_2022Cart.php#271
      Backtrace
      • 15. app/Models/Cart.php:271
      • 16. view::layouts._header:260
      • 18. vendor/laravel/framework/src/Illuminate/Filesystem/Filesystem.php:124
      • 19. vendor/laravel/framework/src/Illuminate/View/Engines/PhpEngine.php:58
      • 20. vendor/laravel/framework/src/Illuminate/View/Engines/CompilerEngine.php:73
    App\Models\Keywords
    14Keywords.php#?
    App\Models\Chapter
    1Chapter.php#?
    App\Models\Ebook
    1Ebook.php#?
        _token
        hR40LBRDgNULxuCrjJ53KsD2R3Uei3pOrGZgR9Tt
        uc_cart_id
        ba8104211971a6fe8854cfe290ac8fa7
        _previous
        array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/8862" ]
        _flash
        array:2 [ "old" => [] "new" => [] ]
        PHPDEBUGBAR_STACK_DATA
        []
        path_info
        /chapter/8862
        status_code
        200
        
        status_text
        OK
        format
        html
        content_type
        text/html; charset=UTF-8
        request_query
        []
        
        request_request
        []
        
        request_headers
        0 of 0
        array:17 [ "x-https" => array:1 [ 0 => "1" ] "host" => array:1 [ 0 => "alpha.eurekaselect.com" ] "priority" => array:1 [ 0 => "u=0, i" ] "cookie" => array:1 [ 0 => "wayfindertarget=eyJpdiI6InUzYXQvaXRxeXkreTI4Nk1Qdzl5bnc9PSIsInZhbHVlIjoiOUl2OUZiRmFHTzU3dGNtQmlMYXBuM2lJVEkrcVJ6L1BCSXNkSEtnR3VuZUR2OFVSQlZrc1M1dlk0OVFDeE1yRCIsIm1hYyI6IjNiZGJjODU5MGQwZDg0NDU2NjQ2MTkxODI0MmNjNzQ2NzliYjZlMzVkMzAxYWFiMTZmM2QyOWFlNzIxYzVkOTIiLCJ0YWciOiIifQ%3D%3D; XSRF-TOKEN=eyJpdiI6Illha2Q4WksrVGcweDBkanIvNXl0TWc9PSIsInZhbHVlIjoiWkdiY2lmcm04Qkk4WTBiclJERDFYOWxpNDVVcElSYkNOWTBIQ01SZXJZTUJ5MGU2WW9FR0xyMlN4SE1LVldwWDhEZEpxL25sZWtOTHhEZnFwRlNJa0Rjc05NNWc5eHQ5YzlKdzNVRkRvU3FhaTRWa1FGOVBSWWdScGkwSnFiREMiLCJtYWMiOiI3ZWY1Y2RhNmE2MjljMTNmODJiOGFjODljODIwZTY0YTY0OThiN2Y1MWMzODczNGU3MzI0NDBmMTM0OTVjYzdiIiwidGFnIjoiIn0%3D; alphaeurekaselectnet_session=eyJpdiI6ImdkOXFpQi9iTkMzMnJvL3NiS0psNEE9PSIsInZhbHVlIjoicktrVlRRUDhhczJiWFh6b0RLMW5oNC9tNnUxbnE0UTlVYWVFNWhNZXdXU0FNT0NBbndxNjF3a1lpdXVHL2NncFBUWUZUYVg5all6aEZLS0FuTFFMZk1KMHJFclZjT0hOWU80YzZ3WnJkZkpqTzgza01pa0lKMFFjbUc2WFBEbkoiLCJtYWMiOiI3YzU0ZmU2OGYxMjBmZGM1N2M1ZDE4YTc0ZjZmNDQyYzUxYmM2NDFiMzQ1ZGE1Y2ZjMmE3MDk0YTIxNTcwODcwIiwidGFnIjoiIn0%3Dwayfindertarget=eyJpdiI6InUzYXQvaXRxeXkreTI4Nk1Qdzl5bnc9PSIsInZhbHVlIjoiOUl2OUZiRmFHTzU3dGNtQmlMYXBuM2lJVEkrcVJ6L1BCSXNkSEtnR3VuZUR2OFVSQlZrc1M1dlk0OVFDeE1yRCIs" ] "accept-encoding" => array:1 [ 0 => "gzip, deflate, br, zstd" ] "sec-fetch-dest" => array:1 [ 0 => "document" ] "sec-fetch-user" => array:1 [ 0 => "?1" ] "sec-fetch-mode" => array:1 [ 0 => "navigate" ] "sec-fetch-site" => array:1 [ 0 => "none" ] "accept" => array:1 [ 0 => "text/html,application/xhtml+xml,application/xml;q=0.9,image/avif,image/webp,image/apng,*/*;q=0.8,application/signed-exchange;v=b3;q=0.7" ] "user-agent" => array:1 [ 0 => "Mozilla/5.0 AppleWebKit/537.36 (KHTML, like Gecko; compatible; ClaudeBot/1.0; +claudebot@anthropic.com)" ] "upgrade-insecure-requests" => array:1 [ 0 => "1" ] "sec-ch-ua-platform" => array:1 [ 0 => ""Windows"" ] "sec-ch-ua-mobile" => array:1 [ 0 => "?0" ] "sec-ch-ua" => array:1 [ 0 => ""HeadlessChrome";v="129", "Not=A?Brand";v="8", "Chromium";v="129"" ] "cache-control" => array:1 [ 0 => "no-cache" ] "pragma" => array:1 [ 0 => "no-cache" ] ]
        request_cookies
        0 of 0
        array:3 [ "wayfindertarget" => null "XSRF-TOKEN" => "hR40LBRDgNULxuCrjJ53KsD2R3Uei3pOrGZgR9Tt" "alphaeurekaselectnet_session" => "pmY0iDqNv9DzyOVdmaHEW490KN441WZGD3CFzaCu" ]
        response_headers
        0 of 0
        array:5 [ "content-type" => array:1 [ 0 => "text/html; charset=UTF-8" ] "cache-control" => array:1 [ 0 => "no-cache, private" ] "date" => array:1 [ 0 => "Tue, 18 Feb 2025 02:55:22 GMT" ] "set-cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6ImI4SUQxRWR6bkppQkFMWkFWNEJpWmc9PSIsInZhbHVlIjoiQnlrYmlzQW1qVXUxa0xCWS96R0I5dnI2VGRSRmtEckQ1N0krUHFvcU82WU42WEM1YTBWR280aVRQaFFKTlVLM21GUUh2VTFyOG1vakxMWFBoRUpuaVdCUXlaR0xLQ2xRc3lJcDZhMmY1RnBkMGN2d2QxdzhMbzVPYWFiYmtRdWciLCJtYWMiOiI3Yjc0YTY4ODJhYTQ3ODJhMTA0ZTM2ZjE3NTI3YjE0NWZmNjUxMjFhZjg5MGQyNjQ4NzViMDgxMTRmMDVlZGY3IiwidGFnIjoiIn0%3D; expires=Thu, 20 Feb 2025 14:55:22 GMT; Max-Age=216000; path=/; secure; samesite=laxXSRF-TOKEN=eyJpdiI6ImI4SUQxRWR6bkppQkFMWkFWNEJpWmc9PSIsInZhbHVlIjoiQnlrYmlzQW1qVXUxa0xCWS96R0I5dnI2VGRSRmtEckQ1N0krUHFvcU82WU42WEM1YTBWR280aVRQaFFKTlVLM21GUUh2V" 1 => "alphaeurekaselectnet_session=eyJpdiI6Ikp4MjlsSHBpVnVCL21NL2NtUWlDQWc9PSIsInZhbHVlIjoicGRUSkFXbDU0MWZiWDBvYi80L25paTJNUEUxYythTlZXa1M3N0dCVTQrRVlQUktVVUY5VmQyY2M0RmxKUThEdk5KK3pjM1BZRWZrU0RYbXRDV1gvai9RZ2ErdTdKcmlzazkvQXBYd003aUt6Zmt4YXd3czNxUFp4K1diblBDUHoiLCJtYWMiOiJlYmU0ZDhhNTk0ZjY2M2JiZGQzMTcyMzFkNDE4NjM1OTk5NWZiNTYyZWUzOTJkOGQ3MjlhMjgyNzBlNDAyNzNlIiwidGFnIjoiIn0%3D; path=/; secure; httponly; samesite=laxalphaeurekaselectnet_session=eyJpdiI6Ikp4MjlsSHBpVnVCL21NL2NtUWlDQWc9PSIsInZhbHVlIjoicGRUSkFXbDU0MWZiWDBvYi80L25paTJNUEUxYythTlZXa1M3N0dCVTQrRVlQUktVVUY5VmQyY2M" ] "Set-Cookie" => array:2 [ 0 => "XSRF-TOKEN=eyJpdiI6ImI4SUQxRWR6bkppQkFMWkFWNEJpWmc9PSIsInZhbHVlIjoiQnlrYmlzQW1qVXUxa0xCWS96R0I5dnI2VGRSRmtEckQ1N0krUHFvcU82WU42WEM1YTBWR280aVRQaFFKTlVLM21GUUh2VTFyOG1vakxMWFBoRUpuaVdCUXlaR0xLQ2xRc3lJcDZhMmY1RnBkMGN2d2QxdzhMbzVPYWFiYmtRdWciLCJtYWMiOiI3Yjc0YTY4ODJhYTQ3ODJhMTA0ZTM2ZjE3NTI3YjE0NWZmNjUxMjFhZjg5MGQyNjQ4NzViMDgxMTRmMDVlZGY3IiwidGFnIjoiIn0%3D; expires=Thu, 20-Feb-2025 14:55:22 GMT; path=/; secureXSRF-TOKEN=eyJpdiI6ImI4SUQxRWR6bkppQkFMWkFWNEJpWmc9PSIsInZhbHVlIjoiQnlrYmlzQW1qVXUxa0xCWS96R0I5dnI2VGRSRmtEckQ1N0krUHFvcU82WU42WEM1YTBWR280aVRQaFFKTlVLM21GUUh2V" 1 => "alphaeurekaselectnet_session=eyJpdiI6Ikp4MjlsSHBpVnVCL21NL2NtUWlDQWc9PSIsInZhbHVlIjoicGRUSkFXbDU0MWZiWDBvYi80L25paTJNUEUxYythTlZXa1M3N0dCVTQrRVlQUktVVUY5VmQyY2M0RmxKUThEdk5KK3pjM1BZRWZrU0RYbXRDV1gvai9RZ2ErdTdKcmlzazkvQXBYd003aUt6Zmt4YXd3czNxUFp4K1diblBDUHoiLCJtYWMiOiJlYmU0ZDhhNTk0ZjY2M2JiZGQzMTcyMzFkNDE4NjM1OTk5NWZiNTYyZWUzOTJkOGQ3MjlhMjgyNzBlNDAyNzNlIiwidGFnIjoiIn0%3D; path=/; secure; httponlyalphaeurekaselectnet_session=eyJpdiI6Ikp4MjlsSHBpVnVCL21NL2NtUWlDQWc9PSIsInZhbHVlIjoicGRUSkFXbDU0MWZiWDBvYi80L25paTJNUEUxYythTlZXa1M3N0dCVTQrRVlQUktVVUY5VmQyY2M" ] ]
        session_attributes
        0 of 0
        array:5 [ "_token" => "hR40LBRDgNULxuCrjJ53KsD2R3Uei3pOrGZgR9Tt" "uc_cart_id" => "ba8104211971a6fe8854cfe290ac8fa7" "_previous" => array:1 [ "url" => "https://alpha.eurekaselect.com/chapter/8862" ] "_flash" => array:2 [ "old" => [] "new" => [] ] "PHPDEBUGBAR_STACK_DATA" => [] ]
        ClearShow all
        Date ↕MethodURLData
        #12025-02-18 02:55:22GET/chapter/88621121916