ChemWiki - User contributions [en]

It:Vitamin C

2006-12-07T11:13:55Z

Zgh05: /* Synthesis */

==Introduction==
The earliest story about Vitamin C happened in the seventheenth century. James Lind who was a ships surgeon in the British Royal Navy attempted to give scientific basis for the cause of scurvy. His test was conducted at sea in May 1747 and involved two groups of men. One group was provded with lemon juice in addition to their normal ration while the other was not. The results of the tests conclusively showed that lemons (in fact, the vitamin) prevented the disease.

Vitamin C (ascorbic acid) which is the most famous in all vitamins was the first vitamin to be discovered (1928), the first to be structurally characterized (1933), and the first to be synthesized in the laboratory (1933). It is essential in wound healing and in the formation of collagen, a protein important in the formation of healthy skin, tendos, bones, and supportive tissues. However, humans do not have the ability to make our own vitamin C and therefore the only way by which we can obtain vitamin C is through our diet.
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Ascorbic acid'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:vitamin_C.gif]]
|-
|3D structure
|<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 15.003 13.124 0.024 1.00 0.00
ATOM 2 C2 MOL 1 16.256 12.216 0.048 1.00 0.00
ATOM 3 O3 MOL 1 14.696 13.485 -1.323 1.00 0.00
ATOM 4 C4 MOL 1 13.783 12.404 0.645 1.00 0.00
ATOM 5 O5 MOL 1 17.367 12.914 -0.520 1.00 0.00
ATOM 6 C6 MOL 1 13.369 11.138 -0.081 1.00 0.00
ATOM 7 O7 MOL 1 12.558 13.256 0.647 1.00 0.00
ATOM 8 O8 MOL 1 14.203 10.059 -0.386 1.00 0.00
ATOM 9 C9 MOL 1 12.090 11.182 -0.361 1.00 0.00
ATOM 10 C10 MOL 1 11.563 12.425 0.083 1.00 0.00
ATOM 11 O11 MOL 1 11.368 10.181 -0.999 1.00 0.00
ATOM 12 O12 MOL 1 10.382 12.761 -0.052 1.00 0.00
ATOM 13 H13 MOL 1 14.048 12.129 1.672 1.00 0.00
ATOM 14 H27 MOL 1 15.201 13.943 0.563 1.00 0.00
ATOM 15 H29 MOL 1 16.467 11.966 0.993 1.00 0.00
ATOM 16 H31 MOL 1 16.076 11.388 -0.483 1.00 0.00
ATOM 17 H33 MOL 1 13.887 14.072 -1.336 1.00 0.00
ATOM 18 H35 MOL 1 18.175 12.325 -0.503 1.00 0.00
ATOM 19 H37 MOL 1 13.679 9.357 -0.867 1.00 0.00
ATOM 20 H39 MOL 1 10.413 10.464 -1.090 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>
|-
| [[IUPAC nomenclature|Chemical name]]
| '2-oxo-L-threo-hexono-1,4-lactone-2,3-enediol
or ( R )-3,4-dihydroxy-5-((S)-1,2-dihydoxyethyl)furan-2(5H)-one
'
|-
| [[CAS nummber]]
| 50-81-7
|-
| [[Chemical formula]]
| {{{formula|C<sub>6</sub>H<sub>8</sub>O<sub>6</sub>
|-
| [[Molecular mass]]
| {{{mol_mass|176.13 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|OC1=C(C(O[C@@H]1[C@H](CO)O)=O)O
|-
| [[Simplified molecular input line entry specification|Density]]
| {{{Density| 1.65
|-
| [[Melting point]]
| 190 -192 ºC(decomposes)
|}

==Use of vitamin C==

• Antiscorbutic properties

-It prevents the onset of scurvy, a bleeding disease affecting those with a deficiency of fresh vegetables and citrus fruits in their diet.

• Reductant in photographic developer solutions and as a preservative.
• Ascorbic acid and its sodium, potassium, and calcium salts are commonly used as antioxidant food additives.

Other possible uses of vitamin C (lacking scientific proofs)

• Prevent the common cold

• Prevent the cure infertility

• Inhibit the development of gastric and cancers.

==IR spectrum of Vitamin C==
[[Image:IR_of_Vc.gif]]

==Acidity of Vitamin C==
[[Image:acidity.gif]]

==Tautomerism==

Ascorbic acid can also interchange to two unstable diketone tautomers, 1,2-diketone and 1,3-diketone.

[[Image:interchange.gif]]

==Synthesis==
The Hoffmann-La Roche Company synthesizes ascorbic acid from glucose through the 5-step rout shown below:

[[Image:synthesisvc.gif]]

==Reference==
Orangic Chemistry by John Mcmurry

http://en.wikipedia.org/wiki/Vitamin_C

http://www.beta-glucan-info.com/vitaminchistory.htm

IR diagram from
http://www.chemgapedia.de/vsengine/vlu/vsc/de/ch/3/anc/vitamin_c/strukturaufklaerung.vlu/Page/vsc/de/ch/3/anc/vitamin_c/3_strukturaufkl/aufgabe_ir/aufgstrukir_m87te0102.vscml.html

It:Vitamin C

2006-12-06T12:09:02Z

Zgh05: /* Introduction */

It:Vitamin C

2006-12-06T12:08:39Z

Zgh05: /* Introduction */

==Introduction==
The earliest story about Vitamin C happened in the seventheenth century. James Lind who was a ships surgeon in the British Royal Navy attempted to give scientific basis for the cause of scurvy. His test was conducted at sea in May 1747 and involved two groups of men. One group was provded with lemon juice in addition to their normal ration while the other was not. The results of the tests conclusively showed that lemons (in fact, the vitamin) prevented the disease.

Vitamin C (ascorbic acid) which is the most famous in all vitamins was the first vitamin to be discovered (1928), the first to be structurally characterized (1933), and the first to be synthesized in the laboratory (1933). It is essential in wound healing and in the formation of collagen, a protein important in the formation of healthy skin, tendos, bones, and supportive tissues. However, humans do not have the ability to make our own vitamin C and therefore the only way by which we can obtain vitamin C is through our diet.
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}}| '''Ascorbic acid'''
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:vitamin_C.gif]]
|-
|3D structure
<jmol>
<jmolApplet>
<size>325</size>
<color>white</color>
<script>zoom 100; cpk off;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>HEADER CSD ENTRY XICKAV
ATOM 1 C1 MOL 1 15.003 13.124 0.024 1.00 0.00
ATOM 2 C2 MOL 1 16.256 12.216 0.048 1.00 0.00
ATOM 3 O3 MOL 1 14.696 13.485 -1.323 1.00 0.00
ATOM 4 C4 MOL 1 13.783 12.404 0.645 1.00 0.00
ATOM 5 O5 MOL 1 17.367 12.914 -0.520 1.00 0.00
ATOM 6 C6 MOL 1 13.369 11.138 -0.081 1.00 0.00
ATOM 7 O7 MOL 1 12.558 13.256 0.647 1.00 0.00
ATOM 8 O8 MOL 1 14.203 10.059 -0.386 1.00 0.00
ATOM 9 C9 MOL 1 12.090 11.182 -0.361 1.00 0.00
ATOM 10 C10 MOL 1 11.563 12.425 0.083 1.00 0.00
ATOM 11 O11 MOL 1 11.368 10.181 -0.999 1.00 0.00
ATOM 12 O12 MOL 1 10.382 12.761 -0.052 1.00 0.00
ATOM 13 H13 MOL 1 14.048 12.129 1.672 1.00 0.00
ATOM 14 H27 MOL 1 15.201 13.943 0.563 1.00 0.00
ATOM 15 H29 MOL 1 16.467 11.966 0.993 1.00 0.00
ATOM 16 H31 MOL 1 16.076 11.388 -0.483 1.00 0.00
ATOM 17 H33 MOL 1 13.887 14.072 -1.336 1.00 0.00
ATOM 18 H35 MOL 1 18.175 12.325 -0.503 1.00 0.00
ATOM 19 H37 MOL 1 13.679 9.357 -0.867 1.00 0.00
ATOM 20 H39 MOL 1 10.413 10.464 -1.090 1.00 0.00
END</inlineContents>
</jmolApplet>
</jmol>
| [[IUPAC nomenclature|Chemical name]]
| '2-oxo-L-threo-hexono-1,4-lactone-2,3-enediol
or ( R )-3,4-dihydroxy-5-((S)-1,2-dihydoxyethyl)furan-2(5H)-one
'
|-
| [[CAS nummber]]
| 50-81-7
|-
| [[Chemical formula]]
| {{{formula|C<sub>6</sub>H<sub>8</sub>O<sub>6</sub>
|-
| [[Molecular mass]]
| {{{mol_mass|176.13 g/mol
|-
| [[Simplified molecular input line entry specification|SMILES]]
| {{{SMILES|OC1=C(C(O[C@@H]1[C@H](CO)O)=O)O
|-
| [[Simplified molecular input line entry specification|Density]]
| {{{Density| 1.65
|-
| [[Melting point]]
| 190 -192 ºC(decomposes)
|}

==Use of vitamin C==

• Antiscorbutic properties

-It prevents the onset of scurvy, a bleeding disease affecting those with a deficiency of fresh vegetables and citrus fruits in their diet.

• Reductant in photographic developer solutions and as a preservative.
• Ascorbic acid and its sodium, potassium, and calcium salts are commonly used as antioxidant food additives.

Other possible uses of vitamin C (lacking scientific proofs)

• Prevent the common cold

• Prevent the cure infertility

• Inhibit the development of gastric and cancers.

==IR spectrum of Vitamin C==
[[Image:IR_of_Vc.gif]]

==Acidity of Vitamin C==
[[Image:acidity.gif]]

==Tautomerism==

Ascorbic acid can also interchange to two unstable diketone tautomers, 1,2-diketone and 1,3-diketone.

[[Image:interchange.gif]]

==Synthesis==
The Hoffmann-La Roche Company synthesizes ascorbic acid from glucose through the 5-step rout shown below:

[[Image:synthesisvc.gif]]

It:Vitamin C

2006-12-05T20:33:13Z

Zgh05: /* Synthesis */

File:Synthesisvc.gif

2006-12-05T20:32:41Z

Zgh05:

It:Vitamin C

2006-12-05T20:30:26Z

Zgh05: /* Tautomerism */

It:Vitamin C

2006-12-05T20:29:40Z

Zgh05: /* Acidity of Vitamin C */

File:Interchange.gif

2006-12-05T20:28:34Z

Zgh05:

It:Vitamin C

2006-12-05T20:27:29Z

Zgh05: /* IR spectrum of Vitamin C */

File:Acidity.gif

2006-12-05T20:26:11Z

Zgh05:

It:Vitamin C

2006-12-05T20:24:05Z

Zgh05: /* Use of vitamin C */

It:Vitamin C

2006-12-05T20:20:33Z

Zgh05: /* Introduction */

File:IR of Vc.gif

2006-12-05T20:19:47Z

Zgh05:

It:Vitamin C

2006-12-05T20:19:26Z

Zgh05: /* Introduction */

It:Vitamin C

2006-12-05T20:16:47Z

Zgh05: /* Use of vitamin C */

It:Vitamin C

2006-12-05T20:14:54Z

Zgh05: /* Use of vitamin C */

It:Vitamin C

2006-12-05T20:12:45Z

Zgh05: /* Introduction */

It:Vitamin C

2006-12-05T20:08:23Z

Zgh05: /* Introduction */

File:Vitamin C.gif

2006-12-05T19:52:19Z

Zgh05:

File:Vitamin C.cdx

2006-12-05T19:47:51Z

Zgh05:

It:Vitamin C

2006-12-05T19:39:17Z

Zgh05:

It:projects

2006-12-05T19:34:58Z

Zgh05: /* Supplemental Project Page */

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