| Identification | More | [Name]
Menadione | [CAS]
58-27-5 | [Synonyms]
2-METHYL-1,4-DIHYDRONAPHTHALENE-1,4-DIONE
2-METHYL-1,4-NAPHTHAQUINONE
2-METHYL-1,4-NAPHTHOQUINONE
2-METHYLNAPHTHOQUINONE
MENADIONE
MENAPHTHON
MENAPHTHONE
THYLOQUINONE
VITAMIN K
VITAMIN K2(0)
VITAMIN K3
1,4-Dihydro-1,4-dioxo-2-methylnaphthalene
1,4-Naphthalenedione, 2-methyl-
1,4-Naphthalenedione,2-methyl-
1,4-Naphthoquinone, 2-methyl-
1,4-naphthoquinone,2-methyl-
2-Methyl-1,4-naftochinon
2-Methyl-1,4-naphthalendione
2-Methyl-1,4-Naphthalenedione
2-Methyl-1,4-naphthochinon | [EINECS(EC#)]
200-372-6 | [Molecular Formula]
C11H8O2 | [MDL Number]
MFCD00001681 | [Molecular Weight]
172.18 | [MOL File]
58-27-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Bright yellow crystals | [Melting point ]
105-107 °C(lit.)
| [Boiling point ]
262.49°C (rough estimate) | [density ]
1.1153 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Store at RT. | [solubility ]
oil: soluble
| [form ]
crystalline
| [color ]
yellow
| [Odor]
Slight odor | [Stability:]
Stable. May be light sensitive. Incompatible with strong oxidizing agents. | [Water Solubility ]
INSOLUBLE | [Sensitive ]
Light Sensitive | [Merck ]
14,5831 | [BRN ]
1908453 | [InChIKey]
MJVAVZPDRWSRRC-UHFFFAOYSA-N | [LogP]
2.200 | [Uses]
vitamin K helps promote blood clotting and has been used medically to reduce the possibility of bruising after surgery. It is being incorporated into cosmetic preparations, particularly those used for treating dark circles. It could also be used in acne products, and there are studies underway on its efficacy for the treatment of spider veins. | [CAS DataBase Reference]
58-27-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Menadione(58-27-5) | [EPA Substance Registry System]
58-27-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection .
S24:Avoid contact with skin . | [WGK Germany ]
3
| [RTECS ]
QL9100000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29146900 | [Safety Profile]
Poison by ingestion,
intraperitoneal, and subcutaneous routes.
Experimental teratogenic effects.
Questionable carcinogen with experimental
tumorigenic data. Human mutation data
reported. When heated to decomposition it
emits acrid smoke and irritating fumes. | [Hazardous Substances Data]
58-27-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in mice: ~0.5 g/kg (Molitor, Robinson) |
| Hazard Information | Back Directory | [Hazard]
Irritant to skin and mucous membranes,
especially the alcoholic solution. | [Description]
A general term referring to a group of naphthoquinone derivatives required in the diet for blood clotting.
Vitamin K5 or medadione and its derivatives are synthetic, lipid-soluble compounds. | [Physical properties]
Appearance: phylloquinone is a yellow oil at room temperature, but the other vitamers K are yellow crystals. Solubility: the vitamers K and MK and most forms of menadione are insoluble in water, slightly soluble in ethanol, and readily soluble in ether, chloroform, fats, and oils. Stability: the vitamers K are sensitive to light and alkali, but are relatively stable to heat and oxidizing environments.
Menadione, the formal parent compound of the menaquinone series does not
occur naturally but is a common synthetic form called menadione (2-methyl-1,4-
naphthoquinone). This compound forms a water-soluble sodium bisulfite addition
product, menadione sodium bisulfite, whose practical utility is limited by its instability in complex matrices such as feeds. However, in the presence of excess sodium
bisulfite, it crystallizes as a complex with an additional mole of sodium bisulfite
(i.e., menadione sodium bisulfite complex), which has greater stability, therefore, is
used widely as a supplement to poultry feeds. A third water-soluble compound is
menadione pyridinol bisulfite (MPB). | [Originator]
Kappaxin,Sterling Winthrop | [Definition]
ChEBI: A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. | [Indications]
Vitamin K activity is associated with several quinones,
including phylloquinone (vitamin K1), menadione (vitamin
K3), and a variety of menaquinones (vitamin K2).
These quinones promote the synthesis of proteins that
are involved in the coagulation of blood.These proteins
include prothrombin, factor VII (proconvertin), factor
IX (plasma thromboplastin). The vitamin K quinones are obtained
from three major sources.Vitamin K is present in various
plants, especially green vegetables. The menaquinones
that possess vitamin K2 activity are synthesized
by bacteria, particularly gram-positive organisms;
the bacteria in the gut of animals produce useful quantities
of this vitamin.Vitamin K3 is a chemically synthesized
quinone that possesses the same activity as vitamin
K1. | [Preparation]
Menadione can be prepared by oxidizing 2-methylnaphthalene with chromic acid or hydrogen peroxide. | [Manufacturing Process]
Dissolve 100 g of β-methylnaphthalene in 500 g of carbon tetrachloride. Dissolve 500 g of commercial sodium dichromate in 175 g of hot water. Pour these two solutions into a 3-liter 3-necked flask, equipped with an efficient stirrer, a reflux condenser, and a dropping funnel. The flask should be put into a water bath held at 50°C. The contents of the flask agitated as violently as possible at adding (through the dropping funnel) 896 g of 77% (by weight) sulfuric acid. The rate of dropping depends on the efficiency of the reflux condenser. If the reaction tends to get out of hand due to overheating, cold water should be run into the water bath. After the addition of acid has been completed, keep the water bath at 70°C, for 1% to 2 hours. Then stop the agitation, cool the mixture and decant therefrom as much of the carbon tetrachloride layer as possible. Pour water into the flask; add 100 g more of carbon tetrachloride and stir for an additional ten minutes. The carbon tetrachloride layer will now settle to the bottom. The acid layer can be decanted and discarded, or worked up for those components desired. A complete separation of the acid from the carbon tetrachloride is effected by means of a separatory funnel. All of the carbon tetrachloride solutions are pooled and filtered to clarity through filter paper. The carbon tetrachloride may be distilled off from the quinone in a vacuum, using a water bath heated to 50°C.
The quinone is concentrated to a point where crystallization begins.
Thereupon the concentrated solution is transferred to a beaker and allowed to
crystallize at room temperature. Further crops of crystals are obtained by
allowing the mother liquor to cool in an icebox, or by reducing it still further.
If the β-methylnaphthalene starting material was pure, the 2-methyl-1,4-
naphthoquinone obtained will have a melting point of 100°-104°C, without
further purification. Vacuum sublimation has been found most effective to
produce quinones of a very high purity. There is a rapid method of
oxygenation of β-methylnaphthalene: 3 g of β-methylnaphthalene is dissolved
in 180 grams of carbon tetrachloride. To this is added 15 grams of commercial
sodium dichromate dissolved in 6 grams of hot water. The above solutions are
placed in a 1-liter 3-necked flask equipped with an efficient stirrer, a dropping
funnel, and a distilling condenser of large bore. The mixture is agitated
energetically, and 25 grams of 77% sulfuric acid added through the dropping
funnel. The time of addition need not be over 30 seconds. The flask is not
subjected to exterior cooling, as the distilling carbon tetrachloride should hold
the heat to the proper temperature, which should not exceed 85°C. After five
minutes the reaction may be discontinued and the product handled similarly
to the method outlined in above. The yield of 2-methyl-1,4-naphthoquinone
will be around 80% of theoretical by the use of this rapid method.
| [Brand name]
Kappaxin (Sterling Winthrop); Kayquinone. | [Therapeutic Function]
Prothrombogenic vitamin | [General Description]
Menadione is a prothrombogenic compound and belongs to the Vitamin K class of compounds, which are necessary for the biosynthesis of prothrombin and other blood clotting factors. It is used as a model quinone in cell culture and in vivo investigations. It is obtained as a catabolic product of phylloquinone and circulating precursor of tissue menaquinone-4 in rats. | [Biochem/physiol Actions]
Menadione is an oxidative stress inducer. | [Pharmacology]
The typical role of vitamin K is to maintain normal blood coagulation function. Its role is related to the metabolic processes. | [Clinical Use]
Vitamin K deficiency results in increased bleeding
time. This hypoprothrombinemia may lead to hemorrhage
from the gastrointestinal tract, urinary tract, and
nasal mucosa. In normal, healthy adults, deficiency is
rare. The two groups at greatest risk are newborn infants
and patients receiving anticoagulant therapy; hypoprothrombinemia
preexists in these two groups. Any
disease that causes the malabsorption of fats may lead
to deficiency. Inhibition of the growth of intestinal bacteria
from extended antibiotic therapy will result in decreased
vitamin K synthesis and possible deficiency. | [Side effects]
Toxicity of vitamin K has not been well defined.
Jaundice may occur in a newborn if large dosages of vitamin
K are given to the mother before birth. Although
kernicterus may result, this can be prevented by using
vitamin K. | [Purification Methods]
Recrystallise it from 95% EtOH, or MeOH after filtration. It forms bright yellow crystals which are decomposed by light. Its solubility in EtOH is 1.7% and in *C6H6 it is 10%. It IRRITATES mucous membranes and skin. [Fieser J Biol Chem 133 391 1940, Beilstein 7 IV 2430.] |
| Questions And Answer | Back Directory | [Chemical properties]
It appears as white crystalline or crystalline powder, being almost odorless and hygroscopic. Its color will change in case of light. It is easily soluble in water, slightly soluble in ethanol, but insoluble in ether and benzene. | [Application]
Menadione is a good hemostatic drug, its main function is to participate in the synthesis of thrombin, promote blood coagulation, can effectively prevent bleeding diseases, and also participate in the mineralization of bones. Menadione is also an important component of feed additives, an indispensable nutrient for the growth and development of livestock, and can also be used as plant growth regulators, promoters, herbicides, etc. | [Production]
Menadione is synthesized by oxidizing 2-methylnaphthalene with chromic anhydride and then reacting with sodium bisulfite.
Reaction: Dissolve 2-methylnaphthalene in glacial acetic acid, stir and cool to below 40°C, slowly add a mixture of chromic anhydride and an equal amount of water, and maintain the temperature at 35-40°C. After the addition, the temperature was kept at 40 °C for 0.5 h, then heated to 70 °C for 45 min, and then heated to 85 °C for 15 min. The reactant was poured into a large amount of water, and menadione was precipitated under constant stirring. After filtering, the filter cake was repeatedly washed with water until the aqueous solution had no sour taste, and then filtered to obtain Menadione. Yield 51%. |
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