Menaphthone

Vitamin K3 (2-methyl-l,4-naphthoquinone, Menadione, Menaphthone) [58-27-5] M 172.2, m 105-106", 105-107". Recrystd from 95% EtOH, or MeOH after filtration. Bright yellow crystals which are decomposed by light. Solubility in EtOH is 1.7% and in C6H6 it is 10%. It IRRITATES the mucous membranes and skin. [Fieser J Biol Chem 133 391 1940.]... 

This effect was seen only in hypoxia, not normoxia, was dose-dependent within the range 0.2-200 /rM, and provided a simple in vitro model for investigating the mode of action of the vitamin. By examining the structure-activity relationship of the response, compounds with a phytyl side-chain, phytol and vitamin K-l (phytomenadione), of similar length to vitamin E (9) were found to be also active, but compounds that had structures which resembled the chroman ring of the vitamin, vitamin K-3 (menaphthone) and Trolox, were antagonists of the responses to the phytol side-chain effects. 

Common Name Menadione Menaphthone Menaquinone Methylnaphthochinon(um) Vitamin K3... 

Common Name Menachinonum natrium bisulfurosum Menadione sodium bisulfite Menadionnatriumbisulfit Menaphthone sodium bisulphite ... 

Synonyms. Menaphthene Menaphthone Methylnaphthochi-nonum Vitamin K3. 

Fat-soluble analogues of vitamin K which are available in some countries include acetome-naphthone and menaphthone. 

Menadione, U5P. Menadione. 2-methyl-1.4-naphtho-quinone. menaphthone. vitamin K3. can be prepared readily by the oxidation of 2-methylnaphthalene with chromic acid. It is a bright yellow, crystalline powder and is nearly odorless. It is affected by sunlight. Menadione is practically insoluble in water, it is soluble in vegetable oils, and I g of it is soluble in about 60 inL of alcohol. The USP/NF cautions that menadione powder is irritating to the respiratory tract and the skin and that an alcoholic solution has vesicant properties. 

Phylloquinone, menaquinone, and menaphthone have been extracted from serum into supercritical CO2 and separated with SFC, with detection at 250 nm (127). Serum, supported on celite, was transferred to extraction cartridges and extracted with supercritical CO2 at 45°C prior to the analysis of benzodiazepines, anabolic agents, and nonsteroidal anti-inflammatory drugs by HPLC (128). Phenobarbital, butalbital, pentobarbital, and thiopental have been extracted from human serum prior to liquid chromatography-negative-ion electrospray tandem mass spectrometry analysis (129). The sample was extracted with supercritical CO2 at 40°C and 507 bar with static extraction for 5 min followed by dynamic extraction for 30 min. Calibrations graphs were linear for 1-60 pg/mL of each barbiturate and the detection limits were 23, 25, 50, and 225 ng/mL of thiopental, pentobarbital, butalbital, and phenobarbital, respectively. In the determination of the cited analytes in serum spiked at the 10- and 50-pg/mL levels, the recoveries were 94.2-106.9% and the RSDs were 1.14-5.18% (three replicates). 

Schneiderman MA, Sharma AK, Focke DC. Determination of menadione [menaphthone] in an animal feed using supercritical-fluid extraction and HPFC with electrochemical detector. J Chromatogr Sci 1988 26 458-462. 

Indoleacetic acid (4.82), one of the natural growth-regulators of plants, is an example of a substance whose powerful action is abolished by the insertion of a methyl-group in the 2-position. On the other hand, in the K family of vitamins, e.g. menaphthone (2.33), the presence of a methyl-group in the 2-position is absolutely essential for biological activity (see also below). 

CAS 58-27-5 EINECS/ELINCS 200-372-6 Synonyms Menadion Menaphthon 2-Methyl-1,4-naphthalenedione 2-Methyl-1,4-naphthoquinone 1,4-Naphthalenedione, 2-methyl-Vitamin K3... 

Menaphthon. See Menadione Menhaden acid, hydrogenated. See Hydrogenated menhaden acid Menhaden oil... 

SyuoDyms 2-Methyl-l, 4-naphthalenedione menaphthone vitamin menadione menaphthene methylnaphthochinonum Trade names Bilkaby, Kayklot, Kipca, Kappaxin, Aquinone, Kanone, Koaxin, K-Vitan, Synkay, Thyloquinone Use Vitamin... 

The chemical assay of menaphthone was devised by Pinder and Singer, who showed that under suitable conditions the quinone could be quantitatively reduced to hydroquinone with titanous chloride, the end-point of the reduction being shown by the use of an internal oxidation-reduction indicator. 

Menaphthone sodium bisulphite, CnH905SNa,3H20. Mol. Wt. 330 3. Both the B.P, and the U.S.P, extract the menaphthone by the same method and then determine it by their individual methods given above. 

Injection of Menaphthone Sodium Bisulphite, B.P. A sterile solution of menaphthone sodium bisulphite (usually 10 mg per ml) in water for injection containing 0 2 per cent w/v of sodium metabisulphite. The assay... 

Acetomenaphthone is prepared by reducing menaphthone with zinc and acetic acid in the presence of acetic anhydride. No direct method of assay has been applied but hydrolysis to the quinol and oxidation of this to the quinone is the best method. 

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