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Basic
Information of Menadione
Chemical Name: Menadione
Cas No.: 58-27-5
Molecular Formula: C11H8O2
Chemical Structure:
Menadione is an
organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of
1,4-naphthoquinone with a methyl group in the 2-position.
It is occasionally used as a nutritional
supplement in animal feed because of its vitamin K activity.
It is sometimes called vitamin K3, although
derivatives of naphthoquinone are not naturally occurring chemicals and
therefore do not qualify as vitamins, and without the side chain in the
2-position (which, as the methyl group is retained in vitamine K, in the
structural formula of menadione is the unsubstituted 3-position!) they cannot
exert all the functions of the K vitamins. Menadione is metabolized by the
human body into K2 which uses alkylation to yield menaquinones (MK-n, n=1-13;
K2 vitamers), hence is better classified as a provitamin. It is also known as
"menaphthone".
It is an intermediate in the chemical
synthesis of vitamin K by first reduction to the diol menadiol, which is
suscepible to coupling to the phytol.
Despite the fact that it can serve as a
precursor to various types of vitamin K, menadione is generally not used as a
nutritional supplement in economically developed countries. Menadione for human
use at pharmaceutical strength is available in some countries with large lower
income populations. It is used in the treatment of hypoprothrombinemia outside
of the United States.
Menadione in combination with vitamin C has
been investigated for the treatment for prostate cancer.
It was reported, that menadione topical
lotion reduces epidermal growth factor receptor inhibitor-related side effects
by the prevention of skin toxicities that result from inhibition of protein
kinases by drugs such as erlotinib (Tarceva) and cetuximab (Erbitux), however,
the paper was later retracted.
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If you are interested in Menadione, click here to send an inquiry!
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References:
https://en.wikipedia.org/wiki/Menadione
https://www.ncbi.nlm.nih.gov/pubmed/8048083
https://www.ncbi.nlm.nih.gov/pubmed/15939799
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