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HomeProduct name listMenadione

Menadione

Synonym(s):2-Methyl-1,4-naphthoquinone;Menadione;MN;Vitamin K3

  • CAS NO.:58-27-5
  • Empirical Formula: C11H8O2
  • Molecular Weight: 172.18
  • MDL number: MFCD00001681
  • EINECS: 200-372-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-04-28 16:56:32
Menadione Structural Picture

What is Menadione?

Absorption

Variable and ranges from 10% to 80%

Toxicity

Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.

Description

Vitamin K is a general term referring to a group of naphthoquinone derivatives required in the diet for blood clotting. Menadione is a fat-soluble vitamin that is essential for blood clotting. It is destroyed by irradiation during processing but has no appreciable loss during storage. It occurs in spinach, cabbage, liver, and wheat bran.

The Uses of Menadione

Menadione is precursor to verious types of Vitamin K. It is of industrial importance as an intermediate in the synthesis of phylloquinone, and salts of its bisulfite adduct are used as stabilized forms in the animal feed industry. Commercially significant forms are menadione sodium bisulfite and menadione dimethyl pyrimidinol. Used as a micronutrient for livestock and pet foods.

Background

A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.

Indications

The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.

What are the applications of Application

Vitamin K3 is an apoptotic inducer and Cdc2 (cdk1 inhibitor

Pharmacokinetics

Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.

Metabolism

Hepatic

Properties of Menadione

Melting point: 105-107 °C(lit.)
Boiling point: 262.49°C (rough estimate)
Density  1.1153 (rough estimate)
storage temp.  room temp
solubility  oil: soluble
form  crystalline
color  yellow
Odor Slight odor
Water Solubility  INSOLUBLE
Sensitive  Light Sensitive

Safety information for Menadione

Signal word Danger
Pictogram(s)

Exclamation Mark
Irritant
GHS07

Health Hazard
GHS08

Environment
GHS09
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H334:Sensitisation, respiratory
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P273:Avoid release to the environment.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Menadione

InChIKey MJVAVZPDRWSRRC-UHFFFAOYSA-N

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