Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component
Lac dye and cochineal extract contain laccaic acids and carminic acid as the main pigments, respectively. Both laccaic acids and carminic acid are anthraquinone derivatives. 4-Aminocarminic acid (acid-stable carmine), an illegal colorant, has been detected in several processed foods. 4-Aminocarminic...
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| Veröffentlicht in: | Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) 2016/12/25, Vol.57(6), pp.193-200 |
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| container_title | Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi) |
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| creator | NISHIZAKI, Yuzo ISHIZUKI, Kyoko AKIYAMA, Hiroshi TADA, Atsuko SUGIMOTO, Naoki SATO, Kyoko |
| description | Lac dye and cochineal extract contain laccaic acids and carminic acid as the main pigments, respectively. Both laccaic acids and carminic acid are anthraquinone derivatives. 4-Aminocarminic acid (acid-stable carmine), an illegal colorant, has been detected in several processed foods. 4-Aminocarminic acid is obtained by heating cochineal extract (carminic acid) in ammonia solution. We attempted to prepare ammonia-treated lac dye and to identify the structures of the main pigment components. Ammonia-treated lac dye showed acid stability similar to that of 4-aminocarminic acid. The structures of the main pigments in ammonia-treated lac dye were analyzed using LC/MS. One of the main pigments was isolated and identified as 4-aminolaccaic acid C using various NMR techniques, including 2D-INADEQUATE. These results indicated that ammonia-treatment of lac dye results in the generation of 4-aminolaccaic acids. |
| doi_str_mv | 10.3358/shokueishi.57.193 |
| format | Article |
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Both laccaic acids and carminic acid are anthraquinone derivatives. 4-Aminocarminic acid (acid-stable carmine), an illegal colorant, has been detected in several processed foods. 4-Aminocarminic acid is obtained by heating cochineal extract (carminic acid) in ammonia solution. We attempted to prepare ammonia-treated lac dye and to identify the structures of the main pigment components. Ammonia-treated lac dye showed acid stability similar to that of 4-aminocarminic acid. The structures of the main pigments in ammonia-treated lac dye were analyzed using LC/MS. One of the main pigments was isolated and identified as 4-aminolaccaic acid C using various NMR techniques, including 2D-INADEQUATE. These results indicated that ammonia-treatment of lac dye results in the generation of 4-aminolaccaic acids.</description><identifier>ISSN: 0015-6426</identifier><identifier>EISSN: 1882-1006</identifier><identifier>DOI: 10.3358/shokueishi.57.193</identifier><identifier>PMID: 28025453</identifier><language>eng</language><publisher>Japan: Japanese Society for Food Hygiene and Safety</publisher><subject>4-aminolaccaic acid ; acid-stable carmine ; Ammonia ; Azo Compounds - analysis ; Azo Compounds - chemistry ; Azo Compounds - isolation & purification ; Calcium Carbonate ; Carmine - analysis ; Carmine - isolation & purification ; Chromatography, Liquid ; Citrates ; Drug Combinations ; Drug Stability ; Food Analysis ; Food Coloring Agents - analysis ; Food Coloring Agents - chemistry ; Food Coloring Agents - isolation & purification ; Food Contamination - analysis ; lac dye ; Magnesium Oxide ; Magnetic Resonance Spectroscopy - methods ; Mass Spectrometry</subject><ispartof>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi), 2016/12/25, Vol.57(6), pp.193-200</ispartof><rights>2016 Japanese Society for Food Hygiene and Safety</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c529t-f154d4247ca65b3271727e6d9e5d6b17b2205296e32daa93162d8b01347eda4f3</citedby><cites>FETCH-LOGICAL-c529t-f154d4247ca65b3271727e6d9e5d6b17b2205296e32daa93162d8b01347eda4f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28025453$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>NISHIZAKI, Yuzo</creatorcontrib><creatorcontrib>ISHIZUKI, Kyoko</creatorcontrib><creatorcontrib>AKIYAMA, Hiroshi</creatorcontrib><creatorcontrib>TADA, Atsuko</creatorcontrib><creatorcontrib>SUGIMOTO, Naoki</creatorcontrib><creatorcontrib>SATO, Kyoko</creatorcontrib><creatorcontrib>National Institute of Health Sciences</creatorcontrib><title>Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component</title><title>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</title><addtitle>Food Hyg. Saf. Sci.</addtitle><description>Lac dye and cochineal extract contain laccaic acids and carminic acid as the main pigments, respectively. Both laccaic acids and carminic acid are anthraquinone derivatives. 4-Aminocarminic acid (acid-stable carmine), an illegal colorant, has been detected in several processed foods. 4-Aminocarminic acid is obtained by heating cochineal extract (carminic acid) in ammonia solution. We attempted to prepare ammonia-treated lac dye and to identify the structures of the main pigment components. Ammonia-treated lac dye showed acid stability similar to that of 4-aminocarminic acid. The structures of the main pigments in ammonia-treated lac dye were analyzed using LC/MS. One of the main pigments was isolated and identified as 4-aminolaccaic acid C using various NMR techniques, including 2D-INADEQUATE. These results indicated that ammonia-treatment of lac dye results in the generation of 4-aminolaccaic acids.</description><subject>4-aminolaccaic acid</subject><subject>acid-stable carmine</subject><subject>Ammonia</subject><subject>Azo Compounds - analysis</subject><subject>Azo Compounds - chemistry</subject><subject>Azo Compounds - isolation & purification</subject><subject>Calcium Carbonate</subject><subject>Carmine - analysis</subject><subject>Carmine - isolation & purification</subject><subject>Chromatography, Liquid</subject><subject>Citrates</subject><subject>Drug Combinations</subject><subject>Drug Stability</subject><subject>Food Analysis</subject><subject>Food Coloring Agents - analysis</subject><subject>Food Coloring Agents - chemistry</subject><subject>Food Coloring Agents - isolation & purification</subject><subject>Food Contamination - analysis</subject><subject>lac dye</subject><subject>Magnesium Oxide</subject><subject>Magnetic Resonance Spectroscopy - methods</subject><subject>Mass Spectrometry</subject><issn>0015-6426</issn><issn>1882-1006</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1u1DAUhS0EoqPSB2CDvGSTqX9iO1lW09JWGgQSrdSd5dg3jEtiD7az6NvjaoZBYnUX95zP5x4j9JGSNeeiu8y7-GsBn3d-LdSa9vwNWtGuYw0lRL5FK0KoaGTL5Bm6yNkPhJFWMdXL9-iMdYSJVvAVevqeYG-SKT4GHEds8NU8x-BN85DAFHB4ayy-fgFsgsM_SlpsWRLgm2mx3p1s9yXjr8YHvInzPgYI5QN6N5opw8VxnqPHLzcPm7tm--32fnO1baxgfWlGKlrXslZZI8XAmaI1I0jXg3ByoGpgjFShBM6cMT2nkrluIJS3CpxpR36OPh-4-xR_L5CLnn22ME0mQFyypp3sOFU9VVVKD1KbYs4JRr1PfjbpRVOiXzvV_zrVQunaafV8OuKXYQZ3cvxtsApuD4K69dZMMUw-gH6OSwr1bg1RjDG6nWaESk2IUOR1cE0qXtdPoRXFecsq6fpAes7F_ITTUyYVbyf4L5w8Jjyt7c4kDYH_AV7zo8Y</recordid><startdate>20161225</startdate><enddate>20161225</enddate><creator>NISHIZAKI, Yuzo</creator><creator>ISHIZUKI, Kyoko</creator><creator>AKIYAMA, Hiroshi</creator><creator>TADA, Atsuko</creator><creator>SUGIMOTO, Naoki</creator><creator>SATO, Kyoko</creator><general>Japanese Society for Food Hygiene and Safety</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7T2</scope><scope>7U2</scope><scope>C1K</scope><scope>F1W</scope><scope>H95</scope><scope>L.G</scope></search><sort><creationdate>20161225</creationdate><title>Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component</title><author>NISHIZAKI, Yuzo ; ISHIZUKI, Kyoko ; AKIYAMA, Hiroshi ; TADA, Atsuko ; SUGIMOTO, Naoki ; SATO, Kyoko</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c529t-f154d4247ca65b3271727e6d9e5d6b17b2205296e32daa93162d8b01347eda4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>4-aminolaccaic acid</topic><topic>acid-stable carmine</topic><topic>Ammonia</topic><topic>Azo Compounds - analysis</topic><topic>Azo Compounds - chemistry</topic><topic>Azo Compounds - isolation & purification</topic><topic>Calcium Carbonate</topic><topic>Carmine - analysis</topic><topic>Carmine - isolation & purification</topic><topic>Chromatography, Liquid</topic><topic>Citrates</topic><topic>Drug Combinations</topic><topic>Drug Stability</topic><topic>Food Analysis</topic><topic>Food Coloring Agents - analysis</topic><topic>Food Coloring Agents - chemistry</topic><topic>Food Coloring Agents - isolation & purification</topic><topic>Food Contamination - analysis</topic><topic>lac dye</topic><topic>Magnesium Oxide</topic><topic>Magnetic Resonance Spectroscopy - methods</topic><topic>Mass Spectrometry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>NISHIZAKI, Yuzo</creatorcontrib><creatorcontrib>ISHIZUKI, Kyoko</creatorcontrib><creatorcontrib>AKIYAMA, Hiroshi</creatorcontrib><creatorcontrib>TADA, Atsuko</creatorcontrib><creatorcontrib>SUGIMOTO, Naoki</creatorcontrib><creatorcontrib>SATO, Kyoko</creatorcontrib><creatorcontrib>National Institute of Health Sciences</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Health and Safety Science Abstracts (Full archive)</collection><collection>Safety Science and Risk</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ASFA: Aquatic Sciences and Fisheries Abstracts</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) 1: Biological Sciences & Living Resources</collection><collection>Aquatic Science & Fisheries Abstracts (ASFA) Professional</collection><jtitle>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>NISHIZAKI, Yuzo</au><au>ISHIZUKI, Kyoko</au><au>AKIYAMA, Hiroshi</au><au>TADA, Atsuko</au><au>SUGIMOTO, Naoki</au><au>SATO, Kyoko</au><aucorp>National Institute of Health Sciences</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component</atitle><jtitle>Food Hygiene and Safety Science (Shokuhin Eiseigaku Zasshi)</jtitle><addtitle>Food Hyg. 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| subjects | 4-aminolaccaic acid acid-stable carmine Ammonia Azo Compounds - analysis Azo Compounds - chemistry Azo Compounds - isolation & purification Calcium Carbonate Carmine - analysis Carmine - isolation & purification Chromatography, Liquid Citrates Drug Combinations Drug Stability Food Analysis Food Coloring Agents - analysis Food Coloring Agents - chemistry Food Coloring Agents - isolation & purification Food Contamination - analysis lac dye Magnesium Oxide Magnetic Resonance Spectroscopy - methods Mass Spectrometry |
| title | Preparation of a Ammonia-Treated Lac Dye and Structure Elucidation of Its Main Component |
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