Summary

Vitamin C was discovered in 1928 by the Hungarian Nobel laureate Szent-Gyorgy and synthesized for the first time in 1933 in Switzerland by Tadeusz Reichstein (Polish by origin).

The name “vitamin” was introduced by Kazimierz Funk, also a Pole.

Natural, biologically active, vitamin C has the L configuration. Hence the name L-ascorbic acid. D-ascorbic acid does not occur naturally and has no biological activity. It has nothing to do with left-handedness and right-handedness. These terms refer to optical rotation and not to the spatial configuration of the molecule. Vitamin C turns polarized light in the range of +20.5 to +21.5 degrees. Which means L-Ascorbic Acid C is right-handed!

The industrial method of producing ascorbic acid is partially biological and uses microorganisms that only produce the -L form. The synthesis of “artificial” D-ascorbic acid is much more expensive and difficult so the pharmaceutical industry has no reason to produce the “wrong” one.

So we can safely say that the existence of “left-handed” vitamin C is purely a myth created for marketing purposes only.

First, a bit of history

Vitamin C, at the time still an unknown factor to prevent scurvy, was the subject of a medical experiment considered to be one of the first clinical trials in the history of medicine to be conducted lege artis. This study was carried out in 1747 by Royal Navy surgeon James Lind on board HMS Salisbury. Lind selected 12 crew members with scurvy, divided them into six pairs – and each pair treated them with a different – then considered effective – remedy. The first pair got a quart of cider a day, the second, 25 drops of vitriol (dilute solution of sulfuric acid), the third, half a pint (0.25 liters) of sea water, the fourth, three times a day a paste – a mixture of garlic, mustard seeds, horseradish, peruvian balsam and myrrh, fifth two teaspoons of vinegar three times a day, a sixth, two oranges and one lemon – once a day. After a week of treatment, the condition of the citrus-treated couple improved so significantly that they were able to take care of the rest of the participants in the medical experiment. In this way, he showed that citrus is an effective remedy for scurvy. Today we know that it was the effect of vitamin C presented in citrus.

The pioneer of modern research on vitamin C was the Hungarian Nobel Prize winner Szent-Gyorgy. In 1928 he isolated a substance from the adrenal cortex, peppers, oranges and cabbage, which he called hexauronic acid. The Pole, Kazimierz Funk, called it a vitamin, and in 1933 in Switzerland, Tadeusz Reichstein (a Pole of origin) was the first to synthesize vitamin C. At that time, its chemical structure was thoroughly described.

On the market we have many medicinal products and dietary supplements containing

vitamin C. Therefore, some manufacturers decided to distinguish themselves by introducing “another better product”.It was for marketing reasons and the desire to stand out from other products that the “left-handed vitamin C” appeared on the market, advertised as “Natural and super-powerful vitamin C, easily digestible”. And what is the truth about such products?

L-ascorbic and D-ascorbic acid

L-ascorbic acid

L doesn’t mean left-handedness

Let us first explain what the letter “L” means, which can (rightly!) Be associated with the word “left”. Let’s look at the structural formula of vitamin C. in short, mirror images of the molecule. The existence of enantiomers of a given substance is a necessary condition for optical rotation.

Natural, biologically active, vitamin C has the L configuration. Hence the name L-ascorbic acid.However, it has nothing to do with left-handedness and right-handedness. These terms refer to optical rotation and not to the spatial configuration of the molecule.

Optical rotation is the property of a chemical compound to rotate the plane of polarized light, i.e. with an ordered plane of vibration.

Chemists denote this torsion left as – (minus) and right as + (plus). According to the Encyclopedia of Chemicals, Drugs, and Biologicals, vitamin C turns polarized light in the range of +20.5 to +21.5 degrees. What does it mean?

L-ascorbic acid C is right-handed!

However, there is only one vitamin C occuring in nature. It’s L-ascorbic acid. D-ascorbic acid does not occur naturally in nature and is biologically inactive. There are also no racemates, i.e. mixtures of -L and -D forms.

Thanks to chemists, we are able to recreate the entire process in laboratories (most often D-glucose from corn is synthesized). So it will always be the same substance, equally absorbed by the body.

Moreover, the industrial method for producing ascorbic acid is partially biological and uses microorganisms that only produce the -L form. The synthesis of “artificial” D-ascorbic acid is much more expensive and difficult it means that the pharmaceutical industry has no reason to produce the “wrong” one.

So we can safely say that the existence of “left-handed” vitamin C is purely a myth created for marketing purposes only.

AUTHOR: Dr n. farm. Andrzej Tarasiuk