84-80-0 Usage
Uses
Used in Food Supplements:
Vitamin K1 is used as a food supplement, particularly in infant foods, with a recommended usage amount of 420-475 μg/kg.
Used in Pharmaceutical Industry:
Vitamin K1 is used as a vitamin drug for the prevention and treatment of vitamin K1 deficiency symptoms, low thrombin disease, and natural newborn hemorrhagic disease.
Used in Blood Clotting:
Vitamin K1 is used to promote blood clotting, which is essential for preventing excessive bleeding.
Used in Liver Thrombin Synthesis:
Vitamin K1 is used to promote the synthesis of primary liver thrombin, which is crucial for the blood clotting process.
Used in Gastrointestinal Function:
Vitamin K1 is used to increase intestinal motility and secretion function, contributing to overall digestive health.
Used as an Internal Standard:
Vitamin K1, labeled as Phytonadione, is used as an internal standard for the quantification of Phytonadione by GCor LC-mass spectrometry.
Used in Green Plants and Algae:
Vitamin K1 occurs widely in green plants, algae, and photosynthetic bacteria, where it plays a vital role in their growth and development.
Chemical Properties:
Vitamin K1 appears as a yellow to orange transparent viscous liquid or crystals and is odorless. It has a relative density of 0.967 and a refractive index ranging from 1.525 to 1.528. It is easily soluble in chloroform, ether, and vegetable oil, slightly soluble in ethanol, and insoluble in water. Vitamin K1 is sensitive to light and heat, decomposing when exposed to light and when heated to 120°C.
Vitamin K
In 1929, a famous chemist Dam (Denmark) had first discovered and extracted a yellow crystalline substance from animal liver and linseed oil-vitamin K.
Vitamin K is a the indispensable substance for hepatic synthesis of the four kinds of coagulation factors (active clotting factor Ⅱ (prothrombin), coagulation factor Ⅶ, coagulation factors Ⅺ and coagulation factor Ⅹ). Upon a lack of vitamin K1, the above four coagulation factors synthesized in liver synthesis become abnormal protein molecules while their ability to catalyze clotting effect dropped significantly. It is known that vitamin K is the cofactor for the glutamic acid γ-carboxylation. Lack of vitamin K disables the above γ-carboxylation of coagulation factors; in addition, these types of blood coagulation factors will reduce and will cause blood clotting slowing down and bleeding disorders. In addition, it is generally recognized that vitamin K was dissolved in mitochondrial membrane lipids, playing a role of electron transfer. Vitamin K can increase the intestinal motility and secretion property. Lack of vitamin will cause reduction in the tension and contraction of smooth muscle and can also affect the metabolism of some hormones, such as causing delay of the decomposition of glucocorticoids in the liver. It also has similar effects as hydrocortisone. Long-term injection of vitamin K can increase the thyroid and other endocrine activity.
Vitamin K can be divided into two categories with both of them belonging to 2-methyl-1, 4-naphthoquinone derivatives. One class belongs to fat-soluble vitamins, namely vitamin K1 extracted from green plants (such as alfalfa, spinach and other leafy greens, etc.) and vitamin K2 extracted from microorganisms. Vitamin K2 can also be synthesized by human intestinal bacteria (such as E. coli). Vitamin K1 appears as yellow oil-like liquid while K2 appears pale yellow crystals. Both of them have heat resistance property, but are vulnerable to ultraviolet radiation to be destroyed, and therefore should be stored separately. Another class is water-soluble vitamins, namely artificially synthetic vitamin K3 and K4. The most important vitamins are K1 and K2.
Vitamin K appears as oily liquid or solid and is insoluble in water but soluble in oils and organic solvents such as ether. It is chemically stable with heat and acid resistant, but being susceptible to alkali and UV degradation. The human body has a low demand. However, newborn infants are vulnerable to being lack of vitamin K that is an important vitamin for promoting blood clotting and normal bone growth. Dark green vegetables and yogurt are easily available vitamin K supplements obtained from the daily diet. Human has a very small demand for vitamin K but it is needed to maintain the normal function of blood coagulation, reduce heavy bleeding menstrual period, but also to prevent internal bleeding and hemorrhoids. Patients suffering frequent nosebleeds should be take more vitamin K from natural foods.This information is edited by Xiongfeng Dai from lookchem.
Limited use
Limited GB 14880-94: baby food, 420~475 μg/ku.
Production method
It can be obtained through the following process: o-naphthoquinone is mixed with acetic anhydride to have reduction, acetylation reaction to generate acetylated menadione in the presence of zinc; followed by hydrolysis in ammonia and further condensation reaction with phytol in ether with the catalysis of boron trifluoride to generate dihydro vitamin K1; and finally with hydrolysis, oxidation, purification and refining to derive the products.
Originator
Mephyton ,MSD ,US ,1941
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.
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
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.
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.]
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.
Check Digit Verification of cas no
The CAS Registry Mumber 84-80-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 84-80:
(4*8)+(3*4)+(2*8)+(1*0)=60
60 % 10 = 0
So 84-80-0 is a valid CAS Registry Number.
InChI:InChI=1/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/t23-,24-/m1/s1
84-80-0Relevant articles and documents
Preparation method of vitamin K1 with different cis-trans isomer proportions and intermediate halogenated phytol thereof
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Paragraph 0046; 0048-0049; 0051-0052; 0054-0056; 0058-0060, (2020/06/05)
The invention discloses a preparation method of vitamin K1 with different cis-trans isomer proportions and an intermediate halogenated phytol thereof. The method comprises the following steps: carrying out a halogenation reaction on a raw material phytol and phosphorus trihalide under the catalysis of phosphoric acid to obtain halogenated phytol, reacting the halogenated phytol with cyclopentadienyl menadione, and carrying out high-temperature depolymerization to obtain the vitamin K1. The addition amount of phosphoric acid in the halogenation reaction can be controlled, so that the proportionof the obtained vitamin K1 cis-isomer can be regulated between 1% and 21%.
Method for synthesizing vitamin K1
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Paragraph 0023; 0024; 0026, (2017/02/23)
The invention relates to a method for synthesizing vitamin K1, relating to the technical field of synthesis of organic matters. The method comprises the following steps: reducing 2-methyl1,4-naphthoquinone to 2-methyl-1,4-naphthalenediol in certain solvents by virtue of a reducing agent under certain conditions, then adding phytol, reacting by using an appropriate catalyst under certain conditions to synthesize 2-methyl3-phytyl1,4-naphthalenediol, then oxidizing the 2-methyl3-phytyl1,4-naphthalenediol by using an appropriate oxidizing agent to obtain vitamin K1, and decompressing and concentrating to obtain the vitamin K1. According to the method for synthesizing the vitamin K1, the 2-methyl1,4-naphthoquinone is used as a raw material, and the hydroxyl groups are not required to be protected, so that the method has the characteristics of simple process, moderate reaction conditions, high productivity, high product purity and high yield; moreover, the method is low in production cost and very suitable for industrialized production.
METHOD OF MAKING VITAMIN K1
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, (2016/12/12)
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
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, (2017/03/28)
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.
Ruthenium-catalyzed oxidative dearomatization of phenols to 4-(tert-butylperoxy)cyclohexadienones: Synthesis of 2-substituted quinones from p-substituted phenols
Murahashi, Shun-Ichi,Miyaguchi, Noriko,Noda, Shinji,Naota, Takeshi,Fujii, Akiko,Inubushi, Yasutaka,Komiya, Naruyoshi
, p. 5355 - 5365 (2011/11/14)
The ruthenium-catalyzed oxidation of phenols with tert-butylhydroperoxide efficiently gives the corresponding 4-(tert-butylperoxy)cyclohexadienones. The oxidation proceeds selectively because of ruthenium's ability for rapid single-electron transfer. This biomimetic oxidation reaction is highly useful to obtain the metabolic compounds desired for confirming the safety of medicines and related compounds. Typically, the first metabolic compound of the female hormone estrone is readily obtained by this biomimetic oxidation reaction. The resulting 4-(tert-butylperoxy)cyclohexadienones are versatile synthetic intermediates, which can be transformed into 2-substituted 1,4-benzoquinones by treatment with acid catalysts. Acid-promoted rearrangement followed by a Diels-Alder reaction provides a new strategy for the synthesis of fused cyclic compounds, such as naphthoquinone and anthraquinone derivatives, from readily available phenols. The nonnatural 1,4-diacetoxy steroidal skeleton is obtained by the oxidation of estrone followed by zinc-mediated migration. Vitamin K 3 is synthesized selectively from p-cresol in an overall 79 % yield in 4 steps, and the synthesis includes the ruthenium-catalyzed oxidation.
Synthesis of 2-substituted quinones, vitamin K3, and vitamin K1 from p-cresol. BF3·OEt2-catalyzed methyl migration of 4-tert-butyldioxycyclohexadienones
Murahashi, Shun-Ichi,Fujii, Akiko,Inubushi, Yasutaka,Komiya, Naruyoshi
scheme or table, p. 2339 - 2341 (2010/05/19)
BF3·OEt2-catalyzed methyl group migration of 4-methyl-4-tert-butyldioxycyclohexadienone, which is obtained by ruthenium-catalyzed oxidation of p-cresol with tert-butyl hydroperoxide, in hexafluoro-2-propanol/toluene gave toluquinone efficiently. The reaction can be applied to the regio-selective short-step syntheses of vitamin K3 and vitamin K1 from p-cresol.
NUTRITIONAL FORMULATION
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, (2009/09/08)
The present invention relates to nutritional supplements that provide an adult with essential vitamins and minerals that may be lacking in the adult's diet and prevent chronic diseases, such as osteoporosis. A number of combinations of nutrients in set ratios are provided to increase the body's ability to absorb and use the nutrients. These combinations are important in helping the body reach the proper balance required for maximized function. Because adults over the age of 50 years have different nutritional needs, nutritional supplements specifically designed for them are also provided.
Nutritional supplement
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, (2008/06/13)
A nutritional supplement is provided that is designed to provide nutritional benefits as well as to assist the body with detoxification. By providing a supplement that serves both of these functions, the present invention may enable persons to improve their overall wellness.
Improved synthesis of vitamin K1
Ji, Ya-Fei,Zong, Zhi-Min,Wei, Xian-Yong,Tu, Guang-Zhong,Xu, Li,He, Lin-Tao
, p. 763 - 772 (2007/10/03)
With (E/Z)-isomeric phytyl halides as side-chain materials, vitamin K1 is synthesized via a Diels-Alder reaction to activate the free bridgehead hydrogen of 3 for the alkylation and a retro-Diels-Alder reaction to eliminate cyclopentadiene from 2 in a high yield, in which the configuration of the double bond in the phytyl side-chain is retained.
A convenient and asymmetric protocol for the synthesis of natural products containing chiral alkyl chains via Zr-catalyzed asymmetric carboalumination of alkenes. Synthesis of phytol and vitamins E and K.
Huo,Negishi
, p. 3253 - 3256 (2007/10/03)
[reaction: see text]. A convenient and asymmetric protocol for the synthesis of chiral oligoisoprenoids is described. Typically, a C14 vitamin E side chain 5 was synthesized in 47% yield over four steps. Isomeric purity of 5 was upgraded to >99% R at C-2 and 97% R at C-6 by the statistical formation of stereoisomeric p-phenylenebisurethanes and their diastereomeric separation. In addition, phytol and vitamin K were synthesized in 21% and 28% overall yields, respectively, over five steps from 1.
