Vitamin K1
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| Category | Raw Materials of Healthcare Products |
| Catalog number | BBF-05872 |
| CAS | 84-80-0 |
| Molecular Weight | 450.71 |
| Molecular Formula | C31H46O2 |
| Purity | 97.0-103.0% |
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Description
Vitamin K1 is a fat-soluble vitamin that occurs widely in green plants, algae, photosynthetic bacteria. Vitamin K1 serves as a precursor to vitamin K2 and is essential for the synthesis of proteins required for blood-clotting, bone metabolism, and cell growth. It is commonly used in dietary supplement for the treatment of bleeding disorders.
Vitamin supplement in health care products.
Specification
| Synonyms | Phytonadione; Phytomenadione; Phylloquinone; 3-Phytylmenadione; E-Phytonadione; 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenedione; Konakion; Mephyton; Phytylmenadione; Phytylmenaquinone; Synthex P; Veda K1; Veta K1; trans-Phylloquinone; α-Phylloquinone; 2',3'-trans-Vitamin K1; [R-[R*,R*-(E)]]-2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione; Antihemorrhagic Vitamin; Haemokion; Kativ N; Kaywan; Kenadion; Kephton; Kinadion; Konakion; Mono-Kay; Monodion; NSC 270681; Orakay; Pediatrico; Phylloquinone K1; Reconval |
| Storage | Store at 2-8°C under inert atmosphere |
| IUPAC Name | 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione |
| Canonical SMILES | CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C |
| InChI | InChI=1S/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/b25-20+/t23-,24-/m1/s1 |
| InChI Key | MBWXNTAXLNYFJB-NKFFZRIASA-N |
| Source | The major dietary source of vitamin K found in green plants, algae, and photosynthetic bacteria. |
Properties
| Appearance | Yellow to Dark Yellow Oily Matter |
| Application | Ingredient of health care products. |
| Boiling Point | 546.4±50.0°C at 760 mmHg |
| Melting Point | -20°C |
| Density | 0.984 g/mL at 25°C |
| Solubility | Soluble in chloroform, ether or vegetable oil, slightly soluble in ethanol and insoluble in water. |
| LogP | 9.3 |
Toxicity
| Carcinogenicity | 3, not classifiable as to its carcinogenicity to humans. |
| Mechanism Of Toxicity | Vitamin K is an essential cofactor for the gamma-carboxylase enzymes which catalyze the posttranslational gamma-carboxylation of glutamic acid residues in inactive hepatic precursors of coagulation factors II (prothrombin), VII, IX and X. Gamma-carboxylation converts these inactive precursors into active coagulation factors which are secreted by hepatocytes into the blood. Supplementing with Phylloquinone results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria. |
| Toxicity | LD50: 41.5 mL/kg at 0.2% (Intravenous, Mouse); LD50: 52 mL/kg at 1% (Intravenous, Mouse). |
Reference Reading
1. Effect of vitamin K1 on survival of patients with chronic liver failure: A retrospective cohort study
Yan Leng,Zhuang Xiong,Shaokai Huo,Tianying Chang,Xiaohao Xu,Tiejun Liu,Yangyang Liu,Houbo Deng Medicine (Baltimore) . 2020 Mar;99(13):e19619. doi: 10.1097/MD.0000000000019619.
The effectiveness of vitamin K1 for the treatment of liver failure has been controversial, and no studies have investigated the effect of vitamin K1 on the risk of death and coagulation function in patients with chronic liver failure. This study aimed to explore the effect of vitamin K1 on death risk and international normalized ratio in patients with chronic liver failure.From December 2013 to August 2017, this retrospective cohort study screened patients hospitalized for chronic liver failure (n = 80) who received routine treatment. The patients were categorized into the vitamin K1 and control groups according to whether they had received intramuscular injection of vitamin K1 on the basis of conventional treatment. Baseline data were analyzed with χ test and independent sample t-test; the survival curve of 48 weeks was created with Kaplan-Meier estimator. Correlation between death event and vitamin K1, age, sex, albumin (ALB), total bilirubin (TBIL), and alkaline phosphatase (ALP) was determined with the Cox proportional risk regression model.Fifty-seven Chinese patients were finally included in the analysis. Patients treated with vitamin K1 had a lower risk of death (hazards ratio [HR] 0.37, P = 0.009) than the control group (P = 0.006). Men had a higher risk of death (HR 2.97, P = 0.005). Age, ALB, TBIL, and ALP had a certain correlation with risk of death. Vitamin K1 reduced the international normalized ratio levels [P < 0.01 (95% confidence interval 0.000-0.002)].Vitamin K1 may reduce the risk of death in patients with chronic liver failure. Male sex, age, ALB, TBIL, and ALP are potential risk factors for increased risk of death in these patients. Based on these findings, vitamin k1 can be used in patients with chronic liver failure. Prospective studies are still needed, however, to validate the role of vitamin K1 in the chronic liver failure.
2. In Search of Normality for Vitamin K1: Establishing Age-Dependent Reference Intervals in the Danish Population
Ivan Brandslund,Jonna Skov Madsen,Claus Lohman Brasen,Anne Schmedes,Ida Boegh Andersen J Appl Lab Med . 2020 May 1;5(3):531-543. doi: 10.1093/jalm/jfaa017.
Background:A growing body of evidence suggests that vitamin K has beneficial effects on human health, especially cardiovascular and bone health. Vitamin K1 (phylloquinone), the predominant form of vitamin K in blood, is regarded as an indicator of vitamin K status, but to our knowledge no reference intervals (RIs) have been established for vitamin K1.Methods:In this population-based study, vitamin K1 was measured in serum from 3808 Caucasian individuals without diabetes from 26 to 78 years of age. The need for gender- and age-partitioned vitamin K1 reference intervals was evaluated using Lahti's method, and exclusion criteria were defined to obtain as healthy a study group as possible. The excluded subgroups were tested for differences in mean serum vitamin K1 levels. Serum vitamin K1 levels were quantified using an in-house newly developed, validated, and highly sensitive online SPE-LC-MS/MS method with a limit of quantitation of (LOQ) 0.05 nmol/L.Results:The reference interval for serum vitamin K1 was 0.22 to 3.95 nmol/L for individuals aged 26 to 44 years and 0.35 to 3.70 nmol/L for individuals aged 45 to 78. Similar age-specific reference intervals were established for vitamin K1-triglyceride ratio being 0.20 to 3.16 and 0.31 to 3.44, respectively. No significant difference was found between genders. Serum vitamin K1 was detectable in all serum samples. Individuals with known comorbidity were found to have significantly lower serum vitamin K1 compared to those without comorbidity. Current smokers had lower serum vitamin K1 compared to nonsmokers.Conclusion:Age-dependent reference intervals were established for serum vitamin K1 and vitamin K1-triglyceride ratio in a well-defined, healthy Caucasian population. Lower serum vitamin K1 levels were found in individuals with known comorbidity, suggesting an association between serum vitamin K1 and disease status. Further studies are needed to determine an optimal serum vitamin K1 level.
3. Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions
Scott Latimer,Anna Block,Eric Soubeyrand,Gilles J Basset,Abdelhak Fatihi Mini Rev Med Chem . 2017;17(12):1028-1038. doi: 10.2174/1389557516666160623082714.
Background:Phylloquinone is a prenylated naphthoquinone that is synthesized exclusively by plants, green algae, and some species of cyanobacteria, where it serves as a vital electron carrier in photosystem I and as an electron acceptor for the formation of protein disulfide bonds.Objective:In humans and other vertebrates, phylloquinone plays the role of a vitamin (vitamin K1) that is required for blood coagulation and bone and vascular metabolism. Phylloquinone from green leafy vegetables and vegetable oil represents the major dietary source of vitamin K for humans.Method:In recent years, reverse genetics and biochemical approaches using the model plant Arabidopsis thaliana have shown that phylloquinone biosynthesis in plants involves paralogous and multifunctional enzymes, a compartmentation of the corresponding pathway in plastids and peroxisomes, and trafficking of some biosynthetic intermediates within plastids themselves. Furthermore, phylloquinone biosynthetic intermediates create crucial metabolic branch-points with other plastid-synthesized metabolites such as chlorophylls, tocopherols and salicylate.Results & conclusion:This review presents an update on recent studies of the central role of plastids in the biosynthesis of phylloquinone, in particular on the discovery of novel enzymatic steps that are likely paradigms for phylloquinone and menaquinone (vitamin K2)-synthesizing organisms alike.
4. Vitamin K1 prevents diabetic cataract by inhibiting lens aldose reductase 2 (ALR2) activity
V Srinivasan,K Saraboji,R Ravichandran,R Thiagarajan,M K N Sai Varsha Sci Rep . 2019 Oct 11;9(1):14684. doi: 10.1038/s41598-019-51059-2.
This study investigated the potential of vitamin K1 as a novel lens aldose reductase inhibitor in a streptozotocin-induced diabetic cataract model. A single, intraperitoneal injection of streptozotocin (STZ) (35 mg/kg) resulted in hyperglycemia, activation of lens aldose reductase 2 (ALR2) and accumulation of sorbitol in eye lens which could have contributed to diabetic cataract formation. However, when diabetic rats were treated with vitamin K1 (5 mg/kg, sc, twice a week) it resulted in lowering of blood glucose and inhibition of lens aldose reductase activity because of which there was a corresponding decrease in lens sorbitol accumulation. These results suggest that vitamin K1 is a potent inhibitor of lens aldose reductase enzyme and we made an attempt to understand the nature of this inhibition using crude lens homogenate as well as recombinant human aldose reductase enzyme. Our results from protein docking and spectrofluorimetric analyses clearly show that vitamin K1 is a potent inhibitor of ALR2 and this inhibition is primarily mediated by the blockage of DL-glyceraldehyde binding to ALR2. At the same time docking also suggests that vitamin K1 overlaps at the NADPH binding site of ALR2, which probably shows that vitamin K1 could possibly bind both these sites in the enzyme. Another deduction that we can derive from the experiments performed with pure protein is that ALR2 has three levels of affinity, first for NADPH, second for vitamin K1 and third for the substrate DL-glyceraldehyde. This was evident based on the dose-dependency experiments performed with both NADPH and DL-glyceraldehyde. Overall, our study shows the potential of vitamin K1 as an ALR2 inhibitor which primarily blocks enzyme activity by inhibiting substrate interaction of the enzyme. Further structural studies are needed to fully comprehend the exact nature of binding and inhibition of ALR2 by vitamin K1 that could open up possibilities of its therapeutic application.
Spectrum
GC-MS Spectrum - GC-MS (Non-derivatized)
Experimental Conditions
Instrument Type: GC-MS
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 3391.51
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Chromatography Type: GC
Retention Index Type: based on 9 n-alkanes (C10-C36)
Retention Index: 3391.51
Column Type: 5%-phenyl-95%-dimethylpolysiloxane capillary column
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C31H46O2
Molecular Weight (Monoisotopic Mass): 450.3498 Da
Molecular Weight (Avergae Mass): 450.6957 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C31H46O2
Molecular Weight (Monoisotopic Mass): 450.3498 Da
Molecular Weight (Avergae Mass): 450.6957 Da
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C31H46O2
Molecular Weight (Monoisotopic Mass): 450.3498 Da
Molecular Weight (Avergae Mass): 450.6957 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C31H46O2
Molecular Weight (Monoisotopic Mass): 450.3498 Da
Molecular Weight (Avergae Mass): 450.6957 Da
13C NMR Spectrum
Experimental Conditions
Solvent: H2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
