Reactions
Ascorbic acerbic resembles the amoroso from which it is
derived, getting a ring absolute abounding oxygen-containing anatomic groups.
The atom exists in calm with two ketone tautomers, which are beneath abiding
than the enol form. In solutions, these forms of ascorbic acerbic rapidly
interconvert.
Nucleophilic advance of ascorbic enol on proton to accord
1,3-diketone Antioxidant mechanismAs a balmy abbreviation agent, ascorbic
acerbic degrades aloft acknowledgment to air, converting the oxygen to water.
The redox acknowledgment is accelerated by the attendance of metal ions and
light. It can be breakable by one electron to a abolitionist accompaniment or
doubly breakable to the abiding anatomy alleged dehydroascorbic acid.
Top: ascorbic acid
(reduced anatomy of Vitamin C)
Bottom: dehydroascorbic acid
(nominal breakable anatomy of Vitamin C)Ascorbate usually
acts as an antioxidant. It about reacts with oxidants of the acknowledging
oxygen species, such as the hydroxyl abolitionist formed from hydrogen
peroxide. Such radicals are damaging to animals and plants at the atomic akin
due to their accessible alternation with nucleic acids, proteins, and lipids.
Sometimes these radicals admit alternation reactions. Ascorbate can abolish
these alternation abolitionist reactions by electron transfer. Ascorbic acerbic
is appropriate because it can alteration a individual electron, attributable to
the adherence of its own abolitionist ion alleged
"semidehydroascorbate", dehydroascorbate.
The breakable forms of ascorbate are almost unreactive,
and do not could cause cellular damage.
However, getting a acceptable electron donor, balance
ascorbate in the attendance of chargeless metal ions can not alone advance but
aswell admit chargeless abolitionist reactions, appropriately authoritative it
a potentially alarming pro-oxidative admixture in assertive metabolic contexts.
Acidity
Ascorbic acid, a reductone, behaves as a
vinylogous carboxylic acerbic wherein the electrons in the bifold bond,
hydroxyl accumulation abandoned pair, and the carbonyl bifold band anatomy a
conjugated system. Because the two above resonance structures balance the
deprotonated conjugate abject of ascorbic acid, the hydroxyl accumulation in
ascorbic acerbic is abundant added acerb than archetypal hydroxyl groups. In
added words, ascorbic acerbic can be advised an enol in which the deprotonated
anatomy is a counterbalanced enolate.
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