Chemical reactivity of Ascorbic acid with halogen

The halogen derivatives provided by the present invention are derivatives of L-ascorbic acid or its 5-enantiomer, D-araboascorbic acid, in which a halogen atom replaces the hydroxyl group in the 6-position.

Fluorine, chlorine, bromine, and iodine are all examples of halogens.

In accordance with the aforementioned technique, the reaction of L-ascorbic acid or D-araboascorbic acid of formula IIa or IIb with hydrogen chloride or hydrogen bromide is ideally carried out in solution in a lower alkanecarboxylic acid (e.g. formic acid, acetic acid, propionic acid etc). The reaction should be performed in a pressure vessel with a modest over-pressure (e.g. up to about 2 atmospheres). The reaction should be carried out at a temperature that is between room temperature and about 100℃.

Chemical reactivity of ascorbic acid with halogen

Structures of ascorbic acid and 6-halo ascorbates predicted. SVCTs are projected to transport 6-halo ascorbate analogues (f), which are structurally identical to ascorbic acid (a). Ascorbyl (b) and 6-halo ascorbyl (g) free radical intermediates are formed when one electron is lost. When a second electron is lost, DHA (c) is produced, which forms a hydrate (d) and/or cyclizes to the bicyclic hemiketal form (e), which is structurally identical to glucose and is transported by GLUTs. GLUTs can’t transport the oxidised counterparts (h and I) since they can’t cyclize.

Overview of ascorbic acid

Citrus fruits, blackcurrants, red peppers, and leafy green vegetables all contain ascorbic acid, generally known as vitamin C. Because collagen formation requires the presence of ascorbic acid, it works as an antioxidant and also has the ability to stimulate fibroblasts to produce collagen. Vitamin C has been shown to inhibit the production of free radicals caused by UV exposure by interacting with the superoxide anion or the hydroxyl radical; this activity prompted its use in different “after-sun” products in the 1980s. Photoprotective properties of topical vitamin C treatment in animal models were demonstrated clinically by a considerable reduction of erythema and tumour growth, as well as histologically by a decrease in sunburn cells after both UVA and UVB irradiation. When compared to sunscreen alone, topical application of vitamin C mixed with either a UVA or UVB sunscreen improved sun protection in swine skin.

The majority of topical vitamin C solutions now available are unstable and do not penetrate into the dermis, rendering them worthless. When vitamin C formulations are exposed to UV radiation or air, the molecule loses two electrons and transforms into dehydro-l-ascorbic acid, which has an aromatic ring. If this molecule is oxidized, it can be reduced back to ascorbate. any further, the ring irreversibly opens, generating diketogulonic acid, rendering the vitamin C solution inert. As a result, UV-protected airtight containers are required, and the product must be designed at a low pH to enhance absorption. The ascorbyl phosphate form of vitamin C is an exception to this rule, as it can permeate the epidermis even when the pH is not low. Vitamin C products with ascorbyl acid at a low pH will sting the skin of those who are sensitive to it (sensitive skin types that have the stinging subtype). Because of its stimulatory effects on collagen formation, ascorbic acid is the most essential antioxidant for antiaging; nevertheless, only a few companies have succeeded in developing stable vitamin C formulations that are effective. Vitamin C has inhibitory activity on tyrosinase, which makes it a good treatment for pigmentation problems.

Overview of halogen

Halogens are diatomic compounds that react to form reactive elements. All are oxidizers, with fluorine being the most powerful. The components can be found in nature, with salt (NaCl) being the most common chlorine compound. Fluorine can be found in fluorite, calcium fluoride, and other minerals. Bromine and iodine are minor ingredients in chlorides and can be found in seawater. Electrochemically, fluorine and chlorine are created. Interhalogens are halogen compounds that include two distinct halogens and have the formula XX′n, where X is the less electronegative element and n = 1, 3, 5, or 7. Only iodine makes IF7, and not all of the potential compounds are known. The majority of them are highly reactive and act as fluorinating agents. Interhalogen anions and cations are known, and they are normally created by removing or adding X to an interhalogen molecule. Although HF is a mild acid, the hydrogen halides are all acidic. The anhydrides of acids are halogen oxides.

Ascorbic acid and halogen

Ascorbic acid: Vitamin C (also known as ascorbic acid or ascorbate) is a water-soluble vitamin that can be found in citrus fruits and vegetables, as well as being available as a nutritional supplement. This supplement can help to prevent and treat scurvy.  Vitamin C is a necessary nutrient for tissue healing, collagen creation, and the enzymatic manufacture of some neurotransmitters. It is vital for immune system function and is required for the operation of numerous enzymes. It has anti-oxidant qualities as well. The majority of animals can produce vitamin C on their own. Apes (including humans) and monkeys (but not all primates), most bats, some rodents, and a few other creatures, on the other hand, must obtain it through their diet.

Halogen: Fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and astatine (A) are a set of five or six chemically related elements in the periodic table (At). Tennessine (Ts), a man-made element, has the potential to be a halogen. In modern IUPAC nomenclature, this group is known as group 17. “Salt creator” is the direct translation of the word halogen. When halogens react with metals, a variety of salts are generated, including calcium fluoride, sodium chloride (table salt), silver bromide, and potassium iodide.

The halogens are the only periodic table group that comprises elements in all three primary states of matter at ordinary temperatures and pressures. When halogens are combined with hydrogen, acids are produced. Minerals or salts are used to make the bulk of halogens. The middle halogens, chlorine, bromine, and iodine, are extensively used as disinfectants. Organobromides are the most prevalent type of flame retardant, however elemental halogens are harmful and toxic.

Conclusion

Ascorbic acid metabolism and halogenated ascorbic acid analogues Vitamin C (ascorbic acid) is >99% in the form of ascorbate anion under physiological conditions. It can transfer two electrons from the double bond between carbons two and three in a sequential manner. The free radical ascorbate is formed when the first electron is lost (oxidation) (semidehydroascorbic acid). Because of their high reactivity, some reactive free radicals created by biological activities might be hazardous. These can be decreased by ascorbic acid, however ascorbic acid is transformed (oxidised) into ascorbate radical in the process. Depending on the presence of oxygen and metals, the half-life of the ascorbate radical ranges from 10-3 seconds to several minutes. When compared to other free radicals, the ascorbate radical is rather unreactive under physiological settings. The ascorbate radical can be converted to vitamin C again. By losing a second electron, it can also be oxidized to produce dehydroascorbic acid. Because it loses electrons, vitamin C acts as an antioxidant or free radical scavenger.