573-20-6

Basic information

• Product Name: Menadiol diacetate
• Synonyms: 1,4-Naphthalenediol,2-methyl-,diacetate;4-naphthalenediol,2-methyl-diacetate;Adaprin;Davitamon-K;Davitamon-K-oral;Kapilin;Kapilon;Kativpowder
• CAS NO: 573-20-6
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27
• EINECS: 209-352-1
• Product Categories: Biochemistry;Vitamins;Vitamins and derivatives;Inhibitors
• Mol File: 573-20-6.mol

Chemical Properties

• Melting Point: 113 °C
• Boiling Point: 361.52°C (rough estimate)
• Flash Point: 195.1 °C
• Appearance: /
• Density: 1.2105 (rough estimate)
• Vapor Pressure: 2.96E-06mmHg at 25°C
• Refractive Index: 1.4872 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• CAS DataBase Reference: Menadiol diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Menadiol diacetate(573-20-6)
• EPA Substance Registry System: Menadiol diacetate(573-20-6)

Safety Data

• RTECS: QJ5250000
• Hazardous Substances Data: 573-20-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Menadiol diacetate is used as a pharmaceutical agent for the treatment of various bleeding disorders and conditions related to impaired blood clotting. It is particularly effective in managing hemorrhagic conditions and supports the body's natural clotting mechanisms.
Used in Veterinary Medicine:
In the veterinary field, Menadiol diacetate is utilized as a treatment for bleeding issues in animals, similar to its application in humans. It helps in managing and preventing excessive bleeding in various medical and surgical situations.
Used in Research Applications:
Menadiol diacetate is also employed in scientific research as a tool to study the mechanisms of blood coagulation and the role of Vitamin K-dependent proteins in this process. It aids in understanding the underlying factors that contribute to clot formation and related disorders.
Used in Dietary Supplements:
As a synthetic form of Vitamin K, Menadiol diacetate is sometimes included in dietary supplements to support overall health and well-being. It is particularly beneficial for individuals with dietary restrictions or those who may have difficulty obtaining adequate amounts of Vitamin K from their diet alone.

InChI:InChI=1/C15H14O4/c1-9-8-14(18-10(2)16)12-6-4-5-7-13(12)15(9)19-11(3)17/h4-8H,1-3H3

Upstream product

• 58-27-5 menadione 
• 481-85-6 2-methyl-1,4-naphthohydroquinone 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 108170-78-1 5,8-diacetoxy-6-methyl-1,4-dihydro-naphthalene 
• 110327-29-2 4-acetoxy-2-methyl-1-naphthol 
• 7664-93-9 sulfuric acid 
• 67597-84-6 2-Methyl-1,4-naphthohydroquinone 
• 67-56-1 methanol 
• 17735-17-0 2,3,4,4-tetrachloro-2-methyl-3,4-dihydro-2H-naphthalen-1-one 
• 861331-93-3 4-chloro-2-methylnaphthalen-1-ol 

Downstream Products

• 483-55-6 phthiocol 
• 3129-39-3 2-bromo-3-methyl-[1,4]naphthoquinone 
• 84-80-0 phytomenadione 
• 53772-20-6 1-benzyloxy-3-methylnaphthalen-4-yl acetate 

Relevant articles and documents

Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition of in Situ Oxidation-Generated ortho-Quinone Methides and Aldehydes

An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation-generated β-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.

METHOD OF MAKING VITAMIN K1

This invention discloses a method of making vitamin K1. The mentioned method of making vitamin K1 comprises performing a first one-pot synthesis with base catalyst, performing a first hydrolysis, performing a substitution, and performing a second one-pot synthesis without metal oxidant. The starting material of this invention is stable 2-methyl-1,4-naphthoquinone. Preferably, this invention provides a method of making vitamin K1 efficiently on simplifying the operation and decreasing the side-product. More preferably, without metal residue, the vitamin K1 of this invention is without metal residue and more safety for clinical application.

A METHOD OF MAKING VITAMIN K1

This invention discloses a method of making vitamin K1. The mentioned method of making vitamin K1 comprises performing a first one-pot synthesis with base catalyst, performing a first hydrolysis, performing a substitution, and performing a second one-pot synthesis for oxidation reaction without using metal oxidant. The starting material of this invention is stable 2-methyl-1,4-naphthoquinone. Preferably, this invention provides a method of making vitamin K1 efficiently on simplifying the operation and decreasing the formation of side-product. More preferably, without the usage of metal residue in this invention results that the vitamin K1 is more safety for clinical application.

One-pot hydroacetylation of menadione (vitamin K3) to menadiol diacetate (vitamin K4) by heterogeneous catalysis

Vitamin K4 (menadiol diacetate, MDD) can be easily synthesized through cleaner and more efficient catalytic alternatives following the green chemistry principles. Ionic gold-based hydroxylated fluorides are active bi-functional catalysts for the one-pot hydroacetylation of menadione leading to MDD with 77% selectivity. Unprecedent results were obtained in the presence of oxide-fluoride catalysts by using a microwave-assisted hydrogen-transfer (Meerwein-Ponndorf-Verley reaction) coupled with an acetylation approach, yielding very high selectivities for the target product (95%). Copyright

The regioselective synthesis of monomethoxynaphthylene diacetates

Methods for the conversion of 1,4,5-naphthalenetriols into the corresponding monomethoxy diacetates are described. All utilise the formation of peri-bridged intermediates.

Regioselective hydrolysis of diacetoxynaphthalenes catalyzed by Pseudomonas sp. lipase in an organic solvent

Depending on the relative positions of the acetyl groups in the aromatic rings, the Pseudomonas sp. lipase-catalyzed hydrolysis of diacetoxynaphthalenes in tert-butylmethyl ether proceeds regioselectively to afford the corresponding monoacetates.

Molecular and crystal structure of 1,4-diacetoxynaphthalene: Structural analysis of methyl substituted 1,4-diacetoxynaphthalenes

Methyl substituted 1,4-diacetoxynaphthalenes have been synthesized and analyzed by means of ultraviolet and 1H-nmr.Positional effects of the methyl substitution on the spectroscopic parameters have been rationalized. 6,7-Dimethyl-1,4-diacetoxynaphthalene, V, has been analyzed by X-ray diffraction techniques.Crystals are monoclinic P21, a = 8.816(1), b = 26.676(7), c = 6.189(1) Angstroem, β = 103.9(2) deg and four molecules in the unit cell.

Oxidation of 1-Naphthols by Lead Tetraacetate in Acetic Acid

A detailed study of the lead tetraacetate-acetic acid oxidation of 1-naphthol, 4-acetoxy-1-naphthol, 2-methyl-1-naphthol, 2,3-dimethyl-1-naphthol and 1,2,3,4-tetrahydro-9-anthrol (17) has been carried out.In the case of 1-naphthol the major product was 4-acetoxy-1-naphthol (4), with 2,2-diacetoxynaphthalen-1(2H)-one (2) being the only other product formed in significant yield.Attack at C4 was again the main reaction with 4-acetoxy-1-naphthol, which gave 1,4-naphthoquinone as the major product.Acetoxylation occurred predominantly at C2 with 2-methyl-1-naphthol and 2,3-dimethyl-1-naphthol to give the naphthalen-1(2H)-ones (11) and (12) respectively.In both cases minor amounts of 4-acetoxylated derivatives and quinones were also produced. 1,2,3,4-Tetrahydro-9-anthrol (17) gave an analogous set of products, the yields of which showed as unusual concentration dependence.In dilute solution 10-acetoxy-1,2,3,4-tetrahydro-9-anthrol (19) was produced in high yield, whereas with a high substrate concentration a good yield of 9a-acetoxy-1,2,3,4-tetrahydroanthracen-9(9aH)-one (18) was obtained.