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L-Ascorbic acid
Identifiers
CAS number 50-81-7 Yes check.svgY
PubChem 5785
ChemSpider 17206850
EC number 200-066-2
ATC code A11GA01
SMILES
InChI
InChI key CIWBSHSKHKDKBQ-SZSCBOSDBY
Properties
Molecular formula C6H8O6
Molar mass 176.12 g mol−1
Appearance White or light yellow solid
Density 1.65 g/cm3
Melting point

190-192 °C, 463-465 K, 374-378 °F (decomp.)

Solubility in water 33 g/100 ml
Solubility in ethanol 2 g/100 ml
Solubility in glycerol 1 g/100 ml
Solubility in propylene glycol 5 g/100 ml
Solubility in [[{{{Solvent4}}}]] insoluble in diethyl ether, chloroform, benzene, petroleum ether, oils, fats, fat solvents
Acidity (pKa) 4.17 (first), 11.6 (second)
Hazards
MSDS JT Baker
LD50 11.9 g/kg (oral, rat)[1]
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ascorbic acid is a sugar acid with antioxidant properties. Its appearance is white to light-yellow crystals or powder, and it is water-soluble. One form of ascorbic acid is commonly known as vitamin C. The name is derived from a- (meaning "no") and scorbutus (scurvy), the disease caused by a deficiency of vitamin C. In 1937 the Nobel Prize for chemistry was awarded to Walter Haworth for his work in determining the structure of ascorbic acid (shared with Paul Karrer, who received his award for work on vitamins), and the prize for Physiology or Medicine that year went to Albert Szent-Györgyi for his studies of the biological functions of L-ascorbic acid. At the time of its discovery in the 1920s, it was called hexuronic acid by some researchers.[2]

Contents

Chemistry

Acidity

Ascorbic acid behaves as a vinylogous carboxylic acid where the elections in the double bond ("vinyl"), hydroxyl group lone pair, and the carbonyl double bond form a conjugated system. Because the two major resonance structures stabilize the deprotonated conjugate base of ascorbic acid, the hydroxyl group in ascorbic acid is much more acidic than typical hydroxyl groups. In other words, ascorbic acid can be considered an enol where the deprotonated form is an enolate, which is usually strongly basic.

Electron pushing for major resonance structures in conjugate base of ascorbic acid


Tautomerism

Nucleophilic attack of ascorbic enol on proton to give 1,3-diketone

Ascorbic acid also interconverts into two unstable ketone tautomers by proton transfer, although it is the most stable in the enol form. The proton of the hydroxyl of the enol is removed. Then a pair of electrons from the resulting oxide anion pushes down to form the ketone at the 2 or 3 position and the electrons from the double bond move to the 3 or 2 position, respectively, forming the carbanion, which picks up the proton resulting in two possible forms: 1-carboxyl-2-ketone and 1-carboxyl-3-ketone.

Determination

The concentration of a solution of ascorbic acid can be determined in many ways, the most common ways involving titration with an oxidizing agent.

Iodine

Another method involves using iodine and a starch indicator, wherein iodine reacts with ascorbic acid, and, when all the ascorbic acid has reacted, the iodine is then in excess, forming a blue-black complex with the starch indicator. This indicates the end-point of the titration. As an alternative, ascorbic acid can be reacted with iodine in excess, followed by back titration with sodium thiosulfate while using starch as an indicator.[3]

Iodate and iodine

The above method involving iodine requires making up and standardising the iodine solution. One way around this is to generate the iodine in the presence of the ascorbic acid by the reaction of iodate and iodide ion in acid solution, the ionic equation for this reaction follows;

IO3- + 5I- + 6H+ → 3I2 + 3H2O

N-Bromosuccinimide

A much-less-common oxidising agent is N-bromosuccinimide, (NBS). In this titration, the NBS oxidises the ascorbic acid (in the presence of potassium iodide and starch). When the NBS is in excess (i.e., the reaction is complete), the NBS liberates the iodine from the potassium iodide, which then forms the blue/black complex with starch, indicating the end-point of the titration.

Uses

Ascorbic acid structure.png
Dehydroascorbic acid.png

Ascorbic acid is easily oxidized and so is used as a reductant in photographic developer solutions (among others) and as a preservative.

Exposure to oxygen, metals, light, or heat destroys ascorbic acid, so it must be stored in a dark, cold, and non-metallic container.

The L-enantiomer of ascorbic acid is also known as vitamin C. The name "ascorbic" comes from its property of preventing and curing scurvy. Primates, including humans, and a few other species in all divisions of the animal kingdom, notably the guinea pig, have lost the ability to synthesize ascorbic acid, and must obtain it in their food.

Ascorbic acid and its sodium, potassium, and calcium salts are commonly used as antioxidant food additives. These compounds are water-soluble and thus cannot protect fats from oxidation: For this purpose, the fat-soluble esters of ascorbic acid with long-chain fatty acids (ascorbyl palmitate or ascorbyl stearate) can be used as food antioxidants. Eighty percent of the world's supply of ascorbic acid is produced in China. [4]

The relevant European food additive E numbers are

  1. E300 ascorbic acid,
  2. E301 sodium ascorbate,
  3. E302 calcium ascorbate,
  4. E303 potassium ascorbate,
  5. E304 fatty acid esters of ascorbic acid (i) ascorbyl palmitate (ii) ascorbyl stearate.

In plastic manufacturing, ascorbic acid can be used to assemble molecular chains more quickly and with less waste than traditional synthesis methods.[5]

Antioxidant mechanism

Ascorbate acts as an antioxidant by being available for energetically favourable oxidation. Many oxidants (typically, reactive oxygen species) such as the hydroxyl radical (formed from hydrogen peroxide), contain an unpaired electron, and, thus, are highly reactive and damaging to humans and plants at the molecular level. This is due to their interaction with nucleic acid, proteins, and lipids. Reactive oxygen species oxidize (take electrons from) ascorbate first to monodehydroascorbate and then dehydroascorbate. The reactive oxygen species are reduced to water, while the oxidized forms of ascorbate are relatively stable and unreactive, and do not cause cellular damage.

Ascorbic acid synthesis in non-primates

Ascorbic acid is found in plants, animals, and single-cell organisms. Ascorbic acid is present in a wide range of fruits and vegetables, especially citrus fruits. A guarve contains approximately 183mg of vitamin c per fruit and a valencia orange contains approximately 70mg of vitamin c per fuit (the valencia orange contains the lowest vitamin c of any orange and this is therefore a minimum value). [6] All living animals either make it, eat it, or die from scurvy due to lack of it. Reptiles and older orders of birds make ascorbic acid in their kidneys. Recent orders of birds and most mammals make ascorbic acid in their livers where the enzyme L-gulonolactone oxidase is required to convert glucose to ascorbic acid.[6] Humans, guinea pigs, and some other primates are not able to make L-gulonolactone oxidase because of a genetic mutation and are therefore unable to make ascorbic acid in their livers. This genetic mutation occurred about 63 million years ago [6] This would have had lethal consequences for the mutated primate were it not for the fact that it occurred to an arboreal animal living in a tropical environment where plenty of foodstuffs containing ascorbic acid were available throughout the year. Although ascorbic acid is a vital food nutrient for humans and is therefore termed a vitamin, it is a natural liver metabolite in most other animals. Synthesis and signalling properties are still under investigation[7].

Compendial status

See also

Notes & references

  1. ^ "Safety (MSDS) data for ascorbic acid". Oxford University. 2005-10-09. http://physchem.ox.ac.uk/MSDS/AS/ascorbic_acid.html. Retrieved 2007-02-21. 
  2. ^ Svirbelf, Joseph Louis; Szent-Gyorgyi, Albert (April 25, 1932), The Chemical Nature Of Vitamin C, http://profiles.nlm.nih.gov/WG/B/B/G/W/_/wgbbgw.pdf . Part of the National Library of Medicine collection. Accessed January 2007
  3. ^ A website with an excerpt to using iodine:[1]
  4. ^ "Tainted Chinese Imports Common", Washington Post, May 20, 2007, http://www.washingtonpost.com/wp-dyn/content/article/2007/05/19/AR2007051901273.html .
  5. ^ Vitamin C, water have benefits for plastic manufacturing, Reliable Plant Magazine, 2007, http://reliableplant.com/article.asp?pagetitle=Vitamin%20C,%20water%20have%20benefits%20for%20plastic%20manufacturing&articleid=3133, retrieved 2007-06-25 .
  6. ^ a b c Stone, Irwin (1972), The Natural History of Ascorbic Acid in the Evolution of Mammals and Primates, http://www.seanet.com/~alexs/ascorbate/197x/stone-i-orthomol_psych-1972-v1-n2-3-p82.htm .
  7. ^ Valpuesta, Victoriano; Botella, Miguel (December 2004), "Biosynthesis of L-ascorbic acid in plants: new pathways for an old antioxidant", TRENDS in Plant Science 9 (12), http://www.bmbq.uma.es/lbbv/index_archivos/pdf/Valpuesta%202004.pdf 
  8. ^ British Pharmacopoeia Commission Secretariat (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 4 February 2010. 
  9. ^ "Japanese Pharmacopoeia, Fifteenth Edition". 2006. http://jpdb.nihs.go.jp/jp15e/JP15.pdf. Retrieved 4 Februally 2010. 

Further reading

  • Clayden; Greeves; Warren; Wothers (2001), Organic Chemistry, Oxford University Press, ISBN 0-19-850346-6 .
  • Davies, Michael B.; Austin, John; Partridge, David A., Vitamin C: Its Chemistry and Biochemistry, Royal Society of Chemistry, ISBN 0-85186-333-7 .
  • Coultate, T. P., Food: The Chemistry of Its Components (3rd ed.), Royal Society of Chemistry, ISBN 0-85404-513-9 .
  • Gruenwald, J.; Brendler, T.; Jaenicke, C., eds. (2004), PDR for Herbal Medicines (3rd ed.), Montvale, NJ: Thomson PDR .

External links


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