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CAS No.: | 863-61-6 |
---|---|
Name: | Menatetrenone |
Article Data: | 11 |
Molecular Structure: | |
Formula: | C31H40O2 |
Molecular Weight: | 444.657 |
Synonyms: | Vitamin K2(mk-4);1,4-Naphthalenedione,2-methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-, (E,E,E)-;1,4-Naphthalenedione,2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-(9CI);2-Methyl-3-geranylgeranyl-1,4-naphthoquinone;Glakay;Kaytwo;MK4;Menaquinone4;Menaquinone K4;Vitamin K2(20);Vitamin MK 4; |
Density: | 0.994 g/cm3 |
Melting Point: | 350 °C |
Boiling Point: | 570.6 °C at 760 mmHg |
Flash Point: | 208.3 °C |
Appearance: | yellow crystals |
Safety: | 22-24/25 |
PSA: | 34.14000 |
LogP: | 8.91790 |
(2'E,6'E,10'E,14'E)-2-(3',7',11',15'-tetramethylhexadeca-2',6',10',14'-tetraenyl)-1,4-dimethoxy-3-methylnaphthalene
menatetrenone
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In water; acetonitrile at 10 - 20℃; for 1h; | 90.6% |
With ammonium cerium(IV) nitrate; triisooctyl amine In hexane; water; acetonitrile for 0.5h; | 86% |
With ammonium cerium(IV) nitrate In dichloromethane; acetonitrile at 0℃; for 0.5h; | 72% |
2-<9'-(2-pyridylthio)-tetraprenyl>-3-methyl-1,4-dimethoxynaphthalene
A
menatetrenone
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; ammonium cerium(IV) nitrate; lithium methanolate; copper dichloride 1.) THF, 1 h, reflux; 2.) CH2Cl2, CH3CN, H2O, 0 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
2-(5'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene
A
menatetrenone
Conditions | Yield |
---|---|
With oxygen; lithium; ethylamine 1.) THF, -70 deg C; 2.) THF, MeOH, H2O, Et2O; Yield given. Multistep reaction; |
2-(9'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene
A
menatetrenone
Conditions | Yield |
---|---|
With oxygen; lithium; ethylamine 1.) THF, -70 deg C; 2.) THF, MeOH, H2O, Et2O; Yield given. Multistep reaction; |
4-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene
menatetrenone
Conditions | Yield |
---|---|
With isotonic phosphate buffer; rat liver homogenate at 37℃; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis; |
1-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene
menatetrenone
Conditions | Yield |
---|---|
With isotonic phosphate buffer; rat liver homogenate at 37℃; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis; |
1,4-bis(N,N-dimethylglycyloxy)-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene
A
menatetrenone
B
4-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene
C
1-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene
Conditions | Yield |
---|---|
With isotonic phosphate buffer; rat liver homogenate at 37℃; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis; |
menatetrenone
Conditions | Yield |
---|---|
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction; |
menatetrenone
Conditions | Yield |
---|---|
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction; |
menatetrenone
Conditions | Yield |
---|---|
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction; |
The molecular structure of Menatetrenone (CAS NO.863-61-6):
IUPAC Name: 2-Methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
Molecular Weight: 444.6481 g/mol
Molecular Formula: C31H40O2
Density: 0.994 g/cm3
Melting Point: 350 °C
Boiling Point: 570.6 °C at 760 mmHg
Flash Point: 208.3 °C
Index of Refraction: 1.538
Molar Refractivity: 139.92 cm3
Molar Volume: 446.8 cm3
Surface Tension: 36.7 dyne/cm
Enthalpy of Vaporization: 85.57 kJ/mol
Vapour Pressure: 4.97E-13 mmHg at 25 °C
Storage Temp.: −20 °C
XLogP3: 8.9
H-Bond Acceptor: 2
Rotatable Bond Count: 11
Tautomer Count: 27
Exact Mass: 444.302831
MonoIsotopic Mass: 444.302831
Topological Polar Surface Area: 34.1
Heavy Atom Count: 33
Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C
Isomeric SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
InChI: InChI=1S/C31H40O2/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/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+
InChIKey: DKHGMERMDICWDU-GHDNBGIDSA-N
Product Categories: Vitamins and derivatives; Osteoporosis; Intermediates & Fine Chemicals; Pharmaceuticals
Menatetrenone (CAS NO.863-61-6) is used as Vitamin (prothrombogenic). It is also used as a hemostatic agent and as adjunctive therapy for the pain of osteoporosis.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD | oral | > 1gm/kg (1000mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. | |
dog | LD | unreported | > 3gm/kg (3000mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 37, Pg. 2518, 1995. | |
dog | LD50 | intravenous | > 40mL/kg (40mL/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS | Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 2003, 1991. |
monkey | LD50 | intravenous | > 10mL/kg (10mL/kg) | BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) | Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 2003, 1991. |
mouse | LD | oral | > 5mg/kg (5mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. | |
mouse | LD50 | intravenous | > 40mL/kg (40mL/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 2003, 1991. |
mouse | LDLo | intraperitoneal | 5gm/kg (5000mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. | |
mouse | LDLo | subcutaneous | 5gm/kg (5000mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. | |
rabbit | LD | intravenous | > 100mg/kg (100mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 461, 1971. | |
rabbit | LDLo | subcutaneous | 100mg/kg (100mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 461, 1971. |
rat | LD | oral | > 5gm/kg (5000mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. | |
rat | LD | subcutaneous | > 5gm/kg (5000mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. |
rat | LD50 | intravenous | > 40mL/kg (40mL/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 2003, 1991. |
rat | LDLo | intraperitoneal | 5gm/kg (5000mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 5, Pg. 445, 1971. |
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: QL9279500
An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
Menatetrenone (CAS NO.863-61-6) is also named as 2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthochinon ; 2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinone ; 2-Methyl-3-geranylgeranyl-1,4-naphthoquinone ; 2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinone ; E3100 ; K2(sub 20) ; Kaytwo ; Kephton ; MK4 ; Menaquinone K4 ; Menaquinone-4 ; Menatetrenona ; Menatetrenona [INN-Spanish] ; Menatetrenonum ; Menatetrenonum [INN-Latin] ; UNII-27Y876D139 ; Vitamin K2(sub 20) ; Vitamin MK 4 . Menatetrenone (CAS NO.863-61-6) is yellow crystals.