Phytonadione

Base Information

• Chemical Name: Phytonadione
• CAS No.: 84-80-0
• Deprecated CAS: 10485-69-5,15973-57-6,50926-17-5,15973-57-6
• Molecular Formula: C31H46O2
• Molecular Weight: 450.705
• Hs Code.: 29362900
• European Community (EC) Number: 201-564-2,234-330-3
• NSC Number: 760373
• UNII: S5Z3U87QHF,MLF3D1712D
• DSSTox Substance ID: DTXSID8023472
• Nikkaji Number: J3.883K
• Wikipedia: Phytomenadione
• Wikidata: Q186093
• NCI Thesaurus Code: C29365
• RXCUI: 8308
• Metabolomics Workbench ID: 29110
• ChEMBL ID: CHEMBL1550
• Mol file: 84-80-0.mol

Synonyms:Aquamephyton;Konakion;Phyllohydroquinone;Phylloquinone;Phytomenadione;Phytonadione;Vitamin K 1;Vitamin K1

Chemical Property of Phytonadione

Chemical Property:

• Appearance/Colour: clear intense yellow ,viscous,oilyliq
• Vapor Pressure: 5.37E-12mmHg at 25°C
• Melting Point: -20 °C(lit.)
• Refractive Index: n20/D 1.527(lit.)
• Boiling Point: 546.44 °C at 760 mmHg
• Flash Point: 200.441 °C
• PSA: 34.14000
• Density: 0.984 g/mL at 25 °C(lit.)
• LogP: 9.15760
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Chloroform (Sparingly), Dioxane (Slightly), Ethyl Acetate (Slightly), Methanol (
• Water Solubility.: Miscible with dehydrated alcohol, acetone, petroleum ether, hexane, dioxane, chloroform, ether, benzene and vegetable oils. Imm
• XLogP3: 10.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 450.349780706
• Heavy Atom Count: 33
• Complexity: 696

Purity/Quality:

5% ^*data from raw suppliers

Vitamin K1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
• Isomeric SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
• Recent ClinicalTrials: Effects of Vitamin K on Lower-extremity Function in Adults With Osteoarthritis:
• Recent EU Clinical Trials: The effect of administering VITamin K preprocedural on the vitamin K dependent coagulation factors and the INR in patients anticoagulated with ACEnocoumarol
• Uses: 1. It can be used as food supplements. It can be used in infant foods with the usage amount being 420~475μg/kg. 2. It belongs to vitamin drugs to be used for the prevention and treatment of vitamin K1 deficiency symptom, low thrombin disease and natural newborn hemorrhagic disease. 3. promote blood clotting. 4. promote the synthesis of primary liver thrombin. 5. increase the intestinal motility and secretion function. vitamin K1 Labeled Phytonadione, intended for use as an internal standard for the quantification of Phytonadione by GC- or LC-mass spectrometry. Occurs widely in green plants, algae, photosynthetic bacteria.
• 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.
• Description: Vitamin K1 is a fat-soluble, dietary nutrient that is essential for the synthesis of proteins important for blood-clotting, bone metabolism, and cell growth. 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. Vitamin K1 also serves as a precursor to vitamin K2 and is reported to exhibit anticancer activity in various cell lines.
• Clinical Use: Vitamin K deficiency Antidote to oral anticoagulants
• Drug interactions: Potentially hazardous interactions with other drugs Antagonises effect of coumarins and phenindione.

Technology Process of Phytonadione

There total 78 articles about Phytonadione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

trans-1,4-Dihydro-vitamin K1(20) (16869-68-4) → vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With dihydrogen peroxide; (Bu₃SnO)2CrO₂ on charcoal; In ethanol; at 40 ℃; for 1.5h;

DOI:10.1246/cl.1986.2075

Reference yield: 56.0%

→ vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With magnesium sulfate; silver(l) oxide; In diethyl ether;

Reference yield:

2-Bromo-3-Methyl-1,1,4,4-tetramethoxy-1,4-dihydronaphthalene (64648-85-7) + (7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide (943232-38-0) → menadione (58-27-5,34524-96-4) + vitamin K1 (84-80-0,16033-41-3,27696-10-2,79082-95-4,79082-96-5,79082-97-6,79083-00-4,81818-54-4,105017-37-6,132487-93-5,132487-94-6,132487-95-7)

Guidance literature:

With hydrogenchloride; n-butyllithium; copper (I) iodide; dimethylsulfide; water; Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo01291a002

upstream raw materials:

menadione

C₁₃H₂₆Sn

2-Bromo-3-Methyl-1,1,4,4-tetramethoxy-1,4-dihydronaphthalene

(7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl bromide

Downstream raw materials:

vitamin K₁ 2,3 epoxide

di-O-acetyl-dihydrophylloquinone

6,10,14-Trimethyl-2-pentadecanon

2-methyl-3-phytyl-1,4-naphthalenediol

Refernces

• 1、 Golubkina, N. A.,Sarycheva, I. K.,Evstigneeva, R. P.,Mikhal'chenko, O. L.,Uzakova, D. U.,Askarov, K. A.. "PREPARATION OF OPTICALLY ACTIVE VITAMIN K1". . p. 126 - 128. Retrieved 1986.
• 2、 -. "Preparation method of vitamin K1 with different cis-trans isomer proportions and intermediate halogenated phytol thereof". Paragraph 0046; 0048-0049; 0051-0052; 0054-0056; 0058-0060. . Retrieved 2020/06/05.
• 3、 -. "METHOD OF MAKING VITAMIN K1". . . Retrieved 2016/12/12.