{"id":660,"date":"2017-10-26T15:36:29","date_gmt":"2017-10-26T15:36:29","guid":{"rendered":"https:\/\/courses.lumenlearning.com\/sunynutrition\/?post_type=chapter&#038;p=660"},"modified":"2017-11-13T21:08:55","modified_gmt":"2017-11-13T21:08:55","slug":"9-21-alpha-tocopherol-natural-vs-synthetic","status":"publish","type":"chapter","link":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/chapter\/9-21-alpha-tocopherol-natural-vs-synthetic\/","title":{"raw":"9.21 Alpha-Tocopherol: Natural vs. Synthetic","rendered":"9.21 Alpha-Tocopherol: Natural vs. Synthetic"},"content":{"raw":"<div class=\"__UNKNOWN__\">\r\n\r\nIn addition to being found naturally in foods, alpha-tocopherol can also be synthesized. It is important to know whether alpha-tocopherol is natural or synthetic because the stereochemistry differs between these forms. Alpha-tocopherol contains 3 chiral centers (non-superimposable mirror images) designated as R or S. If this is a new topic to you or you would like a refresher, the following link is a fun, animated chirality game.\r\n<table><colgroup> <col \/><\/colgroup>\r\n<tbody>\r\n<tr>\r\n<td><h3>Web Link<\/h3>\r\n\r\n-<a href=\"http:\/\/nobelprize.org\/educational_games\/chemistry\/chiral\/game\/game.html\"><u>Chirality Game<\/u><\/a><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nThe 3 chiral centers in alpha-tocopherol are located at the 2, 4\u2019, and 8\u2019 positions. You can see the full numbering of tocopherols in the link below. In short, the rings are normal numbers and the tail are prime numbers.\r\n<table><colgroup> <col \/><\/colgroup>\r\n<tbody>\r\n<tr>\r\n<td><h3>Web Link<\/h3>\r\n\r\n<a href=\"http:\/\/lpi.oregonstate.edu\/mic\/vitamins\/vitamin-E\"><u>Tocopherol Numbering<\/u><\/a><\/td>\r\n<\/tr>\r\n<\/tbody>\r\n<\/table>\r\nThe figure below shows the 3 chiral centers without the other numbers.\r\n<div>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"1090\"]<img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/2569\/2017\/10\/26153513\/10000000000004420000020E282EA1BE.png\" alt=\"\" width=\"1090\" height=\"526\" \/> Figure 9.211 The 2, 4\u2019, and 8\u2019 positions of alpha-tocopherol are chiral centers[\/caption]\r\n\r\n<\/div>\r\nIn natural alpha-tocopherol, all 3 chiral centers are in the R configuration. Thus, it is designated RRR-alpha-tocopherol. The R\u2019s represent the 2, 4\u2019, and 8\u2019 positions of alpha-tocopherol, respectively, as shown below<sup>1<\/sup>.\r\n<div>\r\n\r\n[caption id=\"\" align=\"aligncenter\" width=\"834\"]<img src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/2569\/2017\/10\/26153515\/1000000000000342000001AEB69BDF8C.png\" alt=\"\" width=\"834\" height=\"430\" \/> Figure 9.212 Natural alpha-tocopherol 2, 4\u2019, and 8\u2019 positions are in the R conformation[\/caption]\r\n\r\n<\/div>\r\nSynthetic alpha-tocopherol is a racemic (equal) mixture of all the different stereochemical possibilities at the three chiral centers. These are:\r\n<ul>\r\n \t<li>RRR<\/li>\r\n \t<li>RRS<\/li>\r\n \t<li>RSS<\/li>\r\n \t<li>RSR<\/li>\r\n \t<li>SRR<\/li>\r\n \t<li>SSR<\/li>\r\n \t<li>SSS<\/li>\r\n \t<li>SRS<\/li>\r\n<\/ul>\r\nThe two forms of alpha-tocopherol are designated (these are placed before alpha-tocopherol to indicate whether it is natural or synthetic) as listed below:\r\n\r\n<h3>1. Natural<\/h3>\r\n\r\nNew designation: RRR-alpha-tocopherol (because all 3 positions are RRR)\r\n\r\nOld designation: d-alpha-tocopherol\r\n\r\n<h3>2. Synthetic<\/h3>\r\n\r\nNew designation: all-rac-alpha-tocopherol (because it is a racemic mixture)\r\n\r\nOld designation: dl-alpha-tocopherol\r\n\r\nThe old d and dl designations were describing the chemical structure that are sometimes still used. Keep in mind the natural and synthetic are describing the stereochemistry of alpha-tocopherol and not whether it is naturally derived. For example, there are natural alpha-tocopherol derivatives where the derivatives are added through synthetic procedures.\r\n\r\n<h3>References &amp; Links<\/h3>\r\n\r\n1. http:\/\/lpi.oregonstate.edu\/mic\/vitamins\/vitamin-E\r\n\r\n<h3>Link<\/h3>\r\n\r\nChirality Game - http:\/\/nobelprize.org\/educational_games\/chemistry\/chiral\/game\/game.html\r\n\r\nTocopherol Numbering - http:\/\/www.chem.qmul.ac.uk\/iupac\/misc\/noGreek\/toc.html\r\n\r\n<\/div>","rendered":"<div class=\"__UNKNOWN__\">\n<p>In addition to being found naturally in foods, alpha-tocopherol can also be synthesized. It is important to know whether alpha-tocopherol is natural or synthetic because the stereochemistry differs between these forms. Alpha-tocopherol contains 3 chiral centers (non-superimposable mirror images) designated as R or S. If this is a new topic to you or you would like a refresher, the following link is a fun, animated chirality game.<\/p>\n<table>\n<colgroup>\n<col \/><\/colgroup>\n<tbody>\n<tr>\n<td>\n<h3>Web Link<\/h3>\n<p>&#8211;<a href=\"http:\/\/nobelprize.org\/educational_games\/chemistry\/chiral\/game\/game.html\"><u>Chirality Game<\/u><\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>The 3 chiral centers in alpha-tocopherol are located at the 2, 4\u2019, and 8\u2019 positions. You can see the full numbering of tocopherols in the link below. In short, the rings are normal numbers and the tail are prime numbers.<\/p>\n<table>\n<colgroup>\n<col \/><\/colgroup>\n<tbody>\n<tr>\n<td>\n<h3>Web Link<\/h3>\n<p><a href=\"http:\/\/lpi.oregonstate.edu\/mic\/vitamins\/vitamin-E\"><u>Tocopherol Numbering<\/u><\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p>The figure below shows the 3 chiral centers without the other numbers.<\/p>\n<div>\n<div style=\"width: 1100px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/2569\/2017\/10\/26153513\/10000000000004420000020E282EA1BE.png\" alt=\"\" width=\"1090\" height=\"526\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 9.211 The 2, 4\u2019, and 8\u2019 positions of alpha-tocopherol are chiral centers<\/p>\n<\/div>\n<\/div>\n<p>In natural alpha-tocopherol, all 3 chiral centers are in the R configuration. Thus, it is designated RRR-alpha-tocopherol. The R\u2019s represent the 2, 4\u2019, and 8\u2019 positions of alpha-tocopherol, respectively, as shown below<sup>1<\/sup>.<\/p>\n<div>\n<div style=\"width: 844px\" class=\"wp-caption aligncenter\"><img loading=\"lazy\" decoding=\"async\" src=\"https:\/\/s3-us-west-2.amazonaws.com\/courses-images\/wp-content\/uploads\/sites\/2569\/2017\/10\/26153515\/1000000000000342000001AEB69BDF8C.png\" alt=\"\" width=\"834\" height=\"430\" \/><\/p>\n<p class=\"wp-caption-text\">Figure 9.212 Natural alpha-tocopherol 2, 4\u2019, and 8\u2019 positions are in the R conformation<\/p>\n<\/div>\n<\/div>\n<p>Synthetic alpha-tocopherol is a racemic (equal) mixture of all the different stereochemical possibilities at the three chiral centers. These are:<\/p>\n<ul>\n<li>RRR<\/li>\n<li>RRS<\/li>\n<li>RSS<\/li>\n<li>RSR<\/li>\n<li>SRR<\/li>\n<li>SSR<\/li>\n<li>SSS<\/li>\n<li>SRS<\/li>\n<\/ul>\n<p>The two forms of alpha-tocopherol are designated (these are placed before alpha-tocopherol to indicate whether it is natural or synthetic) as listed below:<\/p>\n<h3>1. Natural<\/h3>\n<p>New designation: RRR-alpha-tocopherol (because all 3 positions are RRR)<\/p>\n<p>Old designation: d-alpha-tocopherol<\/p>\n<h3>2. Synthetic<\/h3>\n<p>New designation: all-rac-alpha-tocopherol (because it is a racemic mixture)<\/p>\n<p>Old designation: dl-alpha-tocopherol<\/p>\n<p>The old d and dl designations were describing the chemical structure that are sometimes still used. Keep in mind the natural and synthetic are describing the stereochemistry of alpha-tocopherol and not whether it is naturally derived. For example, there are natural alpha-tocopherol derivatives where the derivatives are added through synthetic procedures.<\/p>\n<h3>References &amp; Links<\/h3>\n<p>1. http:\/\/lpi.oregonstate.edu\/mic\/vitamins\/vitamin-E<\/p>\n<h3>Link<\/h3>\n<p>Chirality Game &#8211; http:\/\/nobelprize.org\/educational_games\/chemistry\/chiral\/game\/game.html<\/p>\n<p>Tocopherol Numbering &#8211; http:\/\/www.chem.qmul.ac.uk\/iupac\/misc\/noGreek\/toc.html<\/p>\n<\/div>\n\n\t\t\t <section class=\"citations-section\" role=\"contentinfo\">\n\t\t\t <h3>Candela Citations<\/h3>\n\t\t\t\t\t <div>\n\t\t\t\t\t\t <div id=\"citation-list-660\">\n\t\t\t\t\t\t\t <div class=\"licensing\"><div class=\"license-attribution-dropdown-subheading\">CC licensed content, Shared previously<\/div><ul class=\"citation-list\"><li>Kansas State University Human Nutrition Flexbook. <strong>Authored by<\/strong>: Brian Lindshield. <strong>Provided by<\/strong>: Kansas State University. <strong>Located at<\/strong>: <a target=\"_blank\" href=\"http:\/\/goo.gl\/vOAnR\">http:\/\/goo.gl\/vOAnR<\/a>. <strong>License<\/strong>: <em><a target=\"_blank\" rel=\"license\" href=\"https:\/\/creativecommons.org\/licenses\/by\/4.0\/\">CC BY: Attribution<\/a><\/em><\/li><\/ul><\/div>\n\t\t\t\t\t\t <\/div>\n\t\t\t\t\t <\/div>\n\t\t\t <\/section>","protected":false},"author":44985,"menu_order":8,"template":"","meta":{"_candela_citation":"[{\"type\":\"cc\",\"description\":\"Kansas State University Human Nutrition Flexbook\",\"author\":\"Brian Lindshield\",\"organization\":\"Kansas State University\",\"url\":\"goo.gl\/vOAnR\",\"project\":\"\",\"license\":\"cc-by\",\"license_terms\":\"\"}]","CANDELA_OUTCOMES_GUID":"","pb_show_title":"on","pb_short_title":"","pb_subtitle":"","pb_authors":[],"pb_section_license":""},"chapter-type":[],"contributor":[],"license":[],"class_list":["post-660","chapter","type-chapter","status-publish","hentry"],"part":619,"_links":{"self":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapters\/660","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapters"}],"about":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/wp\/v2\/types\/chapter"}],"author":[{"embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/wp\/v2\/users\/44985"}],"version-history":[{"count":7,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapters\/660\/revisions"}],"predecessor-version":[{"id":1762,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapters\/660\/revisions\/1762"}],"part":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/parts\/619"}],"metadata":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapters\/660\/metadata\/"}],"wp:attachment":[{"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/wp\/v2\/media?parent=660"}],"wp:term":[{"taxonomy":"chapter-type","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/pressbooks\/v2\/chapter-type?post=660"},{"taxonomy":"contributor","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/wp\/v2\/contributor?post=660"},{"taxonomy":"license","embeddable":true,"href":"https:\/\/courses.lumenlearning.com\/suny-nutrition\/wp-json\/wp\/v2\/license?post=660"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}