

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"

