2-methyl-3-[(7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione

• ChemBase ID: 895
• Molecular Formular: C31H46O2
• Molecular Mass: 450.69574
• Monoisotopic Mass: 450.34978071
• SMILES: c12C(=O)C(=C(C(=O)c1cccc2)C/C=C(/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\C)C
• Canonical SMILES: C[C@H](CCC[C@@H](CCCC(C)C)C)CCC/C(=C/CC1=C(C)C(=O)c2c(C1=O)cccc2)/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
• InChIKey: MBWXNTAXLNYFJB-NKFFZRIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-methyl-3-[(7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione; 2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
• IUPAC Traditional name: vitamin K; 2-methyl-3-[(7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]naphthalene-1,4-dione; phytonadione
• Brand Name: Aqua-Mephytin; AquaMEPHYTON; Combinal K1; K-Ject; Kativ N; Kephton; Kinadion; Konakion; Mephyton; Mono-Kay; Monodion; Synthex P
• Synonyms: Vitamin K1; Vitamin K₁; phytonadione; Phylloquinone; 2-Methyl-3-phytyl-1,4-naphthoquinone; Vitamin K1(20); 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenedione; Konakion; Mephyton; Phytylmenaquinone; Synthex P; Veda K1; Veta K1; trans-Phylloquinone; α-Phylloquinone; 2',3'-trans-Vitamin K1; Vitamin K1; 2-Methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecenyl]-1,4-naphthalenedione-18O; Konakion-18O; Mephyton-18O; Phytonadione-18O; Phytylmenadione-18O; Phytylmenaquinone-18O; Synthex P-18O; Veda K1-18O; Veta K1-18O; Vitamin K1(20)-18O; trans-Phylloquinone-18O; α-Phylloquinone-18O; 2',3'-trans-Vitamin K1-18O; Vitamin K1-18O(Mixture of 1-18O and 4-18O); Phylloquinone (K1); 2', 3'-trans-Vitamin K1; 2-Methyl-3-phythyl-1,4-naphthochinon; 3-Phytylmenadione; alpha-Phylloquinone; Antihemorrhagic vitamin; Phyllochinon; Phylloquinone; Phythyl-menadion (GERMAN); Phytomenadione; Phytylmenadione; Vitamin K1; Vitamin K; Phytonadione; 2-甲基-3-植基-1,4-萘醌; 叶绿醌; 植物甲萘醌; 维生素 K1(20); 维生素 K1; 维生素 K1; 叶绿醌 (K1)

Database IDs

• CAS Number: 84-80-0
• EC Number: 201-564-2
• MDL Number: MFCD00214063
• Beilstein Number: 2568816
• PubChem SID: 24890112; 24900741; 160964358; 24871410
• PubChem CID: 4812; 5284607
• CHEBI ID: 18067
• ATC CODE: B02BA01
• CHEMBL: 1550
• Chemspider ID: 4447652
• DrugBank ID: DB01022
• Unique Ingredient Identifier: A034SE7857
• Wikipedia Title: Phylloquinone

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 9.696445
• LogD (pH = 7.4): 9.696445
• Log P: 9.696445
• Molar Refractivity: 142.9568 cm^3
• Polarizability: 55.337467 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 8.48
• LOG S: -6.88
• Solubility (Water): 5.92e-05 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Dchloromethane; Ether; Insoluble in water
• Apperance: viscous liquid; Yellow Oil
• Melting Point: -20 °C(lit.)
• Flash Point: >113 °C; >235.4 °F
• Density: 0.984 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.527(lit.)
• Hydrophobicity(logP): 9.3

Safety Information

• Storage Condition: Refrigerator
• RTECS: QJ5800000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of isomers, HPLC); 98%
• Grade: analytical standard
• Packaging: ampule of 100 mg
• Ignition Residue: ≤0.1% (as SO4)
• Impurities: ≤20% cis-isomer
• Cation Traces: Al: ≤5 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤10 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤10 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Feature: standard type fat soluble vitamin
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C31H46O2

DETAILS

DrugBank - DB01022

• Drug Groups: approved
• Description: Phytonadione is often called vitamin K1. It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants. Phylloquinone is also an antidote for coumatetralyl. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation.
• Indication: For the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia
• Pharmacology: Phytonadione is a vitamin, indicated in the treatment of coagulation disorders which are due to faulty formation of factors II, VII, IX and X when caused by vitamin K deficiency or interference with vitamin K activity. Phytonadione aqueous colloidal solution of vitamin K1 for parenteral injection, possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X).
• Toxicity: The intravenous LD₅₀ of phytonadione in the mouse is 41.5 and 52 mL/kg for the 0.2% and 1% concentrations, respectively.
• Affected Organisms: Humans and other mammals
• Absorption: Oral phytonadione is adequately absorbed from the gastrointestinal tract only if bile salts are present. After absorption, phytonadione is initially concentrated in the liver, but the concentration declines rapidly. Very little vitamin K accumulates in tissues.
• Elimination: Almost no free unmetabolized vitamin K appears in bile or urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 95271

Other Notes
Review: Vitamin K and γ-carboxyglutamate biosynthesis1; Metabolic functions and mechanism of action2
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.

Sigma Aldrich - V3501

包装
1, 5, 10 g in glass bottle
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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. V3501.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - V676080

Occurs widely in green plants, algae, photosynthetic bacteria.

Toronto Research Chemicals - V676082

Labelled Vitamin K1. Occurs widely in green plants, algae, photosynthetic bacteria. A representative lot was approximately 90% isotopically pure.

REFERENCES

• Hassan, M.M.A., et al.: Anal. Profiles Drug Subs., 17, 449 (1988)
• Breton, J., et al.: Biochemistry, 33, 12405 (1988)
• Dowd, P., et al.: Science, 269, 1684 (1988)
• Hassan, M.M.A., et al.: Anal. Profiles Drug Subs., 17, 449 (1988)
• Breton, J., et al.: Biochemistry, 33, 12405 (1988)
• Dowd, P., et al.: Science, 269, 1684 (1988)