1.2 Name: L-Ascorbic Acid 1.3 Common Synonyms: Vitamin C L-threo-2,3,4,5,6-pentahydroxy-1-hexenoic acid-4-lactone 1.4 Empirical Formula: C6H806 1.5 Structural Formula OH OH | | C = C | | 0 = C CH-CHOH-CH2OH 0 .O. OH ,' `. | O==C C--C--CH2OH \ / C===C / \ HO OH From: Ben Norwood Righteo then, since the subject of chemical structures has resurfaced, and it's cold/flu season, I thought I'd have a go at the entire vitamin set, and to spice it up, a bit of biochemical trivia as well :) H3C CH3 CH3 CH3 `.,' | | CH2OH ,'`. ,'\\,'\\,'\\,'\\,' | || `..' `. CH3 mbfh H3C CH3 CH3 CH3 `.,' | | CH2OH ,'`. ,'\\ ,'\\ ,'\\ ,'\\ ,' ,' `, ,' \\,' \\,' \\,' \\,' | :| | :| `. ,' `. `..' `. CH3 mbfh Vitamin A - retinol Amongst other uses in the body, combines with the protein opsin to form rhodopsin (visual purple) in the eye's rod (night-vision) cells. H3C H3C CH3 CH3 CH3 `.,'`, `.,' | | || | ,'`. ,'\\,'\\,'\\,'\\,'\\,'\\,'\\,'\\,'\\,'`.,' mbfh | || | | ,'`, `..' `. CH3 CH3 H3C CH3 CH3 Pro Vitamin A - Beta-carotene Pro-vitamins are precursors of vitamins that can be converted by the body into the 'normal' vitamin. Beta-carotene is one of the most famous of these (yes, eating carrots *can* theoretically improve your night-vision), and is often used as a yellow/orange food colourant. -oOo-oOo-oOo- The B Group Vitamins - also known as 'Vitamin B Complex'. There are currently six numbered vitamins and two unnumbered vitamins in this group. The complex of vitamins was discovered in yeast, and were originally thought to be a single substance. Later, its constituents were seperated and labelled. Further analysis showed that B's 4, 5, 7, 8, 9, 10 and 11 weren't vitamins, hence only 1, 2, 3, 5, 6, 12 remain, plus biotin and folacin. N----. ,----S // \\ +// | H3C--< >--CH2--N | \ / _ \ | mbfh N====' Cl `====+ ,' `.,'`. H3C OH Vitamin B1 - Thiamine Deficiency of which causes beriberi, it's pyrophosphate is also known as Coenzyme A, which plays a vital role in respiration. -oOo- HO `. `. | HO | `. ,' `. `. ,' `. | OH | ,' `. ,' `. HO | H3C | `. ,'`. ,N. ,N. `.,' `.`. ,' `. ,',' `. || ` | | ' | || , | , | | mbfh ,'`. ,',' `. ,',' `. ,N--H ,' `.,' `N' `.,' H3C || O Vitamin B2 - Riboflavin One of the main antioxidant vitamins, a constituent of FAD and FMN co-enzymes, also used as a yellowish colourant in food. -oOo- O || || ,'`, ,'`. ,' `.`. ,' `. || ` | OH || , | `. ,',' `N ' mbfh Vitamin B3 - Nictotinic Acid / Niacin The carboxylic acid of nicotine, American officials called it 'niacin' so as to prevent people thinking that they could fulfil their RDA of this vitamin by smoking... It is readily converted into: O || || ,'`, ,'`. ,' `.`. ,' `. || ` | NH2 || , | `. ,',' mbfh `N ' Nicotinamide, the amine of B3, which itself forms part of NADH (and NADPH in plants), a coenzyme used to extract energy from carbohydrates. Although the vitamin can be produced from nicotine, it is far cheaper to manufacture it from: ,'`, ,'`. ,'`. ,' `.`. ,',' `. ,' `.`. || ` | | ' || ` | || , | | . || , | `. ,',' `.`. ,' `. ,',' `N ' `.,' `N ' mbfh Pyridine or Quinoline -oOo- H3C CH3 OH `.| ,' >---' ,' HO--< H `. ,' >---N OH // `. ,' O `---. ,---< mbfh `. ,' \\ N---' O ,' H Vitamin B5 - Pantothenic Acid Pantothenic acid is another constituent of Coenzyme A, but nowadays perhaps more famous are the numerous derivates collectively labelled as "Pro-Vitamin B5 Complex" or panthenol/panthenate. These were originally developed to help WWII burns victims, but it was somehow discovered at the time that the complex helped to strengthen hair, and the firm Pantene was set up (now owned by Glaxo Smithkline, info from SB's website). -oOo- HOH2C OH `. ,'`, ,' `. ,',' `. ,' | ' || | . || `.`. ,' `. mbfh `N ' `. CH3 Vitamin B6 - Pyridoxine Used in the production of antibodies, manufacture of haemoglobin, and metabolism of proteins. -oOo- Vitamin B12 - Cyanocobalamine Helps make erythrocytes (red blood cells). Structure not asciified due to its complexity. For more info: http://www.chem.ox.ac.uk/mom/vitamins/vitaminb12.html Verbose description: Vitamin B12 consists of: a monovalent cobalt metal at the center, surrounded by a porphyrin-like structure of tetrapyrrole rings, bound to the metal center is a cyano group and a 5',6'-dimethylbenzimidazolyl nucleotide which is linked to the tetrapyrrole rings via a phosphate sugar linkage. (see, I told you it was complicated!) -oOo- H2N `. ,N. ,N. `. ,',' `. ,' `.`. | ' || ` | | . || | `.`. ,' `. ,' `. `.,' `N ' `. | | | | OH NH ,'`. ,' ,' `.`. ,' || ` | O || , | `. ,' `. ,',' `.`.,' `.,' ` | | HN `. ,'||`. `.,' || `. | O OH | ,' ,' | | mbfh ,' `. ,',' `. O ' OH Vitamin Bc - Folacin / Folic Acid Helps synthesise DNA, RNA, erythrocytes, and antibodies, so is essential in foetuses. Found in abundance in green leaves, but easily destroyed by cooking. -oOo- [no pic as altavista can't find it's structure for me to copy] Biotin Used in the metabolism of carbohydrates, maintains healthy skin, hair and nails. -oOo-oOo-oOo- OH | ,O. | O. ,' `. ,' `. `.`.,' `.,' `CH2OH ` \ / \ / mbfh >-----< ,' `, HO' `OH Vitamin C - Ascorbic Acid Since everybody already knows almost everything about this vitamin, I'll give the trivia a miss on this one... -oOo- CH3 | H3C | `. ,'`. ,' `. `. ,' `.`.,' `. | `| CH3 CH3 | | ,'`. | ,'\ CH3 ,' `.|,' \ | | \ H2C | | / ,'`. // `. ,' `. / ,' `.// `.,' `./ | | || | | . || mbfh ,' `. ,' `.`. ,' ,' `.,' `.,' HO Vitamin D2 - Calciferol Essential for the development of teeth and bones, plus the absorption of calcium and phosphorous, vitamin D2 can be formed by the irradiation of 7-dehydrocholesterol (a derivative of cholesterol). -oOo- | mbfh HO | `. ,'`. ,'`. `.,' ., `. ,' `. | | | | | H3C H H3C H | | | | | `.,' `.,' ,' ,' `. `' ,' `. ,'|`. ,'`. ,'`. ,'`. ,'`. ,'`. ,'`. ,' `.,' `O ' | `' `' `' `' `' `' ` | CH3 | Vitamin E - d-alpha tocopherol Helps maintain healthy arteries (it's an anti-coagulant and vaso-dilator), and is an anti-oxidant as well. -oOo- O |"" ""| || | | | | || | | | | ,'`. ,'`. ,'`. ,'`| ,'`. ,'`.| ,' ,. `. ,' `. ,' `.,',' |`.,' `.,' |. | | | | || | | | | | | || | | `. `' ,' `. ,' |__ __|n `.,' `O ' || || O mbfh Vitamin K2 - Menaquinone (side chain length varies) (in K1 - phylloquinone, n=3) Involved in blood clotting, possibly part of prothrombin -oOo- Unless otherwise stated, all diagrams are (manually!) copied from gifs at http://www.geocities.com/CollegePark/Den/5701/ES.htm All asciifications copyright (c) Benjamin Norwood, January 2000 If anyone feels the urge to use any of the asciifications, please attribute with the alias "mbfh"