Potential Exposure
Phylloquinone is a dietary component essential for normal biosynthesis of several factors required for clotting of blood; as a therapeutic drug used to correct bleeding tendency; and as a food supplement.
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Keep victim quiet and maintain normal body temperature.
Shipping
UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
Incompatibilities
Phylloquinone is photosensitive; decomposes in sunlight and is destroyed by alkali hydroxides and reducing agents such as hydrideds and active metals. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
Description
Vitamin K
1 is a fat-soluble, dietary nutrient that is essential for the synthesis of proteins important for blood-clotting, bone metabolism, and cell growth.
1 It is found in the photosynthetic tissues of green, leafy plants, where it acts as an electron acceptor forming part of the electron transport chain of Photosystem I.
2 Vitamin K
1 also serves as a precursor to vitamin K
2 and is reported to exhibit anticancer activity in various cell lines.
3,4
Waste Disposal
It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
Originator
Mephyton ,MSD ,US ,1941
Definition
ChEBI: Phylloquinone is a member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones. It has a role as a cofactor, a plant metabolite and a human metabolite. It is a vitamin K and a member of phylloquinones.
Manufacturing Process
11 parts by weight of 2-methyl-1,4-naphthohydroquinone, 30 parts by volume of water-free dioxane and 1.5 parts by volume of boron trifluoride etherate are heated to 50°C. While agitating and introducing nitrogen, 10 parts by weight of phytol dissolved in 10 parts by volume of dioxane are added in the course of 15 minutes. Thereupon, the dark colored reaction mixture is stirred for 20 additional minutes at 50°C, cooled down and 60 parts by volume of ether are added. The reaction mixture is washed first with water, then with a mixture of 3 parts of N-sodium hydroxide and 2 parts of a 2.5% solution of sodium hydrosulfite and again with water. The aqueous extracts are washed with ether. The ether solutions are collected, dried over sodium sulfate and concentrated, toward the end under reduced pressure.
The waxlike condensation product so obtained is mixed with 60 parts by volume of petroleum ether (boiling limits 30°C to 40°C) and agitated with hydrogen in the presence of a little active palladium lead catalyst (Pd-CaCO3catalyst, the activity of which is reduced by the addition of lead and quinoline). During the operation, the condensation product separates in the form of a voluminous white precipitate. The latter is separated by filtration in the absence of air while adding an inert coarse-grained adsorption agent (for example, aluminum silicate salt for filter purposes), and washed with cooled petroleum ether. Thereupon, the 2-methyl-3-phytyl-1,4-naphthohydroquinone is extracted from the filter cake by means of ether, the ethereal solution is concentrated to 100 parts by volume and the reaction product is oxidized by stirring the solution with 6.6 parts by weight of silver oxide during 30 minutes. The solution is filtered through sodium sulfate, the latter is rinsed with ether and the solvent is evaporated. There are obtained 5.7 parts by weight of 2-methyl-3-phytyl-1,4-naphthoquinone (vitamin K1) in the form of a golden yellow oil.
Therapeutic Function
Prothrombogenic vitamin
General Description
Vitamin K1, also known as phylloquinone, consists of naphthalenoid and phytyl groups. Phylloquinone is present abundantly in photosynthetic plants and is a major dietary source. It is a fat-soluble vitamin.
Biochem/physiol Actions
Vitamin K1 (Phylloquinone) is a lipid soluble polycyclic aromatic ketone used as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX and X; anticoagulant factors protein C and S and as a cell signaling factor. Vitamin K1 is essential for blood coagulation, bone and vascular metabolism. Phylloquinone from green leafy vegetables and vegetable oil is the most important dietary source of vitamin K for humans.
Clinical Use
Vitamin K deficiency
Antidote to oral anticoagulants
Veterinary Drugs and Treatments
The principal uses of exogenously administered phytonadione is in
the treatment of anticoagulant rodenticide toxicity. It is also used
for treating dicumarol toxicity associated with sweet clover ingestion
in ruminants, sulfaquinoxaline toxicity, and in bleeding disorders
associated with faulty formation of vitamin K-dependent
coagulation factors.
Drug interactions
Potentially hazardous interactions with other drugs
Antagonises effect of coumarins and phenindione.
Metabolism
Phytomenadione is rapidly metabolised to more
polar metabolites and is excreted in bile and urine as
glucuronide and sulphate conjugates.
Purification Methods
Vitamin K1 is a yellow viscous oil, which can be distilled at high vacuum practically unchanged. It is insoluble in H2O, but soluble in common organic solvents. Store it in the dark under N2 as it is oxygen sensitive. It has 1cm 328 at 248nm. [Fieser et al. J Am Chem Soc 61 2557 1939, Hirschmann et al. J Am Chem Soc 76 4592 1954, Isler & Doebel Helv Chim Acta 27 225 1954, Beilstein 7 IV 2496.]
