Menadiol

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Menadiol
Skeletal formula of menadiol Menadiol.svg
Skeletal formula of menadiol
Ball-and-stick model of menadiol Menadiol-3D-balls.png
Ball-and-stick model of menadiol
Names
Preferred IUPAC name
2-Methylnaphthalene-1,4-diol
Other names
2-Methyl-1,4-naphthalenediol; 2-Methyl-1,4-dihydroxynaphthalene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.886 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C11H10O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6,12-13H,1H3
  • Oc2c1ccccc1c(O)c(c2)C
Properties
C11H10O2
Molar mass 174.199 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Menadiol is an organic compound with the formula C6H4(COH)2(CH)(CH3). It is formally a derivative of p-hydroquinone. The name vitamin K4 can refer to:

Menadiol sodium diphosphate is approved in the UK for treatment and prevention of haemorrhage, mainly in obstructive jaundice (before and after surgery). [6]

Menadiol is probably naturally produced by reduction of menadione ("vitamin K3"; see Quinone § Reduction) as an intermediate in the conversion from K3 to MK-4. [7] It can be oxidized in experimental conditions back to menadione. [8]

Related Research Articles

<span class="mw-page-title-main">Thiamine</span> Chemical compound

Thiamine, also known as thiamin and vitamin B1, is a vitamin, an essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some metabolic reactions, including the breakdown of glucose and amino acids.

<span class="mw-page-title-main">Vitamin K</span> Fat-soluble vitamers

Vitamin K is a family of structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-synthesis modification of certain proteins that are required for blood coagulation or for controlling binding of calcium in bones and other tissues. The complete synthesis involves final modification of these so-called "Gla proteins" by the enzyme gamma-glutamyl carboxylase that uses vitamin K as a cofactor.

<span class="mw-page-title-main">Pantothenic acid</span> Chemical compound

Pantothenic acid (vitamin B5) is a B vitamin and an essential nutrient. All animals need pantothenic acid in order to synthesize coenzyme A (CoA), which is essential for cellular energy production and for the synthesis and degradation of proteins, carbohydrates, and fats.

Vitamin E is a group of eight fat soluble compounds that include four tocopherols and four tocotrienols. Vitamin E deficiency, which is rare and usually due to an underlying problem with digesting dietary fat rather than from a diet low in vitamin E, can cause nerve problems. Vitamin E is a fat-soluble antioxidant which may help protect cell membranes from reactive oxygen species. Worldwide, government organizations recommend adults consume in the range of 3 to 15 mg per day. As of 2016, consumption was below recommendations according to a worldwide summary of more than one hundred studies that reported a median dietary intake of 6.2 mg per day for alpha-tocopherol. Foods rich in vitamin E include seeds and nuts, seed oils, peanut butter, and vitamin E-fortified foods, such as margarine.

Vitamin B<sub>6</sub> Class of chemically related vitamins

Vitamin B6 is one of the B vitamins, and thus an essential nutrient. The term refers to a group of six chemically similar compounds, i.e., "vitamers", which can be interconverted in biological systems. Its active form, pyridoxal 5′-phosphate, serves as a coenzyme in more than 140 enzyme reactions in amino acid, glucose, and lipid metabolism.

<span class="mw-page-title-main">Dietary supplement</span> Product providing additional nutrients

A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill, capsule, tablet, powder, or liquid. A supplement can provide nutrients either extracted from food sources, or that are synthetic. The classes of nutrient compounds in supplements include vitamins, minerals, fiber, fatty acids, and amino acids. Dietary supplements can also contain substances that have not been confirmed as being essential to life, and so are not nutrients per se, but are marketed as having a beneficial biological effect, such as plant pigments or polyphenols. Animals can also be a source of supplement ingredients, such as collagen from chickens or fish for example. These are also sold individually and in combination, and may be combined with nutrient ingredients. The European Commission has also established harmonized rules to help insure that food supplements are safe and appropriately labeled.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans.

<span class="mw-page-title-main">Sodium selenite</span> Chemical compound

Sodium selenite is the inorganic compound with the formula Na2SeO3. This salt is a colourless solid. The pentahydrate Na2SeO3(H2O)5 is the most common water-soluble selenium compound.

<span class="mw-page-title-main">Menadione</span> Chemical compound

Menadione is a natural 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 sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.

<span class="mw-page-title-main">Menatetrenone</span> Form of vitamin K

Menatetrenone (INN), also known as menaquinone-4 (MK-4), is one of the nine forms of vitamin K2.

Vitamin B<sub><small>12</small></sub> Vitamin used in animal cells metabolism

Vitamin B12, also known as cobalamin, is a water-soluble vitamin involved in metabolism. It is one of eight B vitamins. It is required by animals, which use it as a cofactor in DNA synthesis, and in both fatty acid and amino acid metabolism. It is important in the normal functioning of the nervous system via its role in the synthesis of myelin, and in the circulatory system in the maturation of red blood cells in the bone marrow. Plants do not need cobalamin and carry out the reactions with enzymes that are not dependent on it.

<span class="mw-page-title-main">Kappadione</span> Chemical compound

Kappadione is a vitamin K derivative used for the treatment of side effects of vitamin K antagonists such as warfarin, prophylaxis and treatment of vitamin K deficiency bleeding, and hypoprothrombinemia due to various causes. It was manufactured by Eli Lilly and Company. Chemically, it is menadiol sodium diphosphate. It was approved by the US Food and Drug Administration prior to 1982 and marketed by Lilly. It has since been discontinued and is not available in North America.

<span class="mw-page-title-main">Vitamin D</span> Group of fat-soluble secosteroids

Vitamin D is a group of fat-soluble secosteroids responsible for increasing intestinal absorption of calcium, magnesium, and phosphate, and for many other biological effects. In humans, the most important compounds in this group are vitamin D3 (cholecalciferol) and vitamin D2 (ergocalciferol).

"Autoschizis" is a term derived from the Greek αὐτο- auto-, meaning "self", and σχίζειν skhizein, "to split". It was introduced in 1998 to describe a novel form of cancer cell death characterized by a reduction in cell size that occurs due to the loss of cytoplasm through self-excision without the loss of cell organelles, morphologic degradation of the cells nucleus and nucleolus without the formation of apoptotic bodies and destruction of the cell membrane. The cell death results from karyorrhexis and karyolysis. Autoschizis can be initiated via in vivo treatment with vitamin C (VC), synthetic vitamin K (VK3) or, better, a combination of both. The treatment has been tested on various types of cancer cells in vitro and in vivo with positive results.

Vitamin K<sub>2</sub> Group of vitamins and bacterial metabolites

Vitamin K2 or menaquinone (MK) is one of three types of vitamin K, the other two being vitamin K1 (phylloquinone) and K3 (menadione). K2 is both a tissue and bacterial product (derived from vitamin K1 in both cases) and is usually found in animal products or fermented foods.

<span class="mw-page-title-main">4-Amino-2-methyl-1-naphthol</span> Chemical compound

4-Amino-2-methyl-1-naphthol is a menadione analog. Its water-soluble hydrochloride (HCl) salt is often called vitamin K5. The HCl salt has been used as a medicine for vitamin K deficiency under tradenames such as Synkamin, which was sold by Parke-Davis, but has since been discontinued.

<span class="mw-page-title-main">4-Amino-3-methyl-1-naphthol</span> Chemical compound

4-amino-3-methyl-1-naphthol is a synthetic menadione analog. It is also known as vitamin K7, and was named as such in 1950 when it was recognized as a compound with vitamin K activity.

<span class="mw-page-title-main">2-Methylnaphthalene-1,4-diamine</span> Chemical compound

2-Methylnaphthalene-1,4-diamine is a synthetic menadione analog with vitamin K activity.

References

  1. Fiore LD, et al. (2001). "Anaphylactoid reactions to vitamin K". Journal of Thrombosis and Thrombolysis. 11 (2): 175–183. doi:10.1023/A:1011237019082. ISSN   0929-5305. PMID   11406734. S2CID   975055.
  2. 1 2 3 Sebrell WH, et al. (1971). The vitamins; chemistry, physiology, pathology, methods (2nd ed.). Academic Press. p. 443. ISBN   9780126337631.
  3. "Vitamin K2 added for nutritional purposes in foods for particular nutritional uses, food supplements and foods intended for the general population and Vitamin K2 as a source of vitamin K added for nutritional purposes to foodstuffs, in the context of Regulation (EC) N° 258/97". EFSA Journal. 6 (11): 822. 2008. doi: 10.2903/j.efsa.2008.822 . ISSN   1831-4732.
  4. 1 2 3 4 Oketch-Rabah HA, Roe AL, Marles RJ (2017). "US Pharmacopeial Convention safety evaluation of menaquinone-7, a form of vitamin K". Nutrition Reviews. 75 (7): 553–578. doi:10.1093/nutrit/nux022. ISSN   0029-6643. PMID   28838081.
  5. "Kappadione". go.drugbank.com.
  6. "Menadiol Diphosphate Tablets 10mg - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk.
  7. Shearer, Martin J.; Newman, Paul (March 2014). "Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis". Journal of Lipid Research. 55 (3): 345–362. doi: 10.1194/jlr.R045559 . ISSN   0022-2275. PMC   3934721 . PMID   24489112.
  8. Weber F, Rüttimann A (2012). "Vitamin K". Ullmann's Encyclopedia Of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.o27_o08. S2CID   86263542.