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Menatetrenone
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Name

Menatetrenone

 EINECS N/A
CAS No. 863-61-6 Density 0.994 g/cm3
PSA 34.14000 LogP 8.91790
Solubility N/A Melting Point 350 °C
Formula C31H40O2 Boiling Point 570.6 °C at 760 mmHg
Molecular Weight 444.657 Flash Point 208.3 °C
Transport Information N/A Appearance yellow crystals
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 863-61-6 (Menatetrenone) Hazard Symbols N/A
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;

Article Data 11

Menatetrenone Synthetic route

66958-54-1

(2'E,6'E,10'E,14'E)-2-(3',7',11',15'-tetramethylhexadeca-2',6',10',14'-tetraenyl)-1,4-dimethoxy-3-methylnaphthalene

863-61-6

menatetrenone

Conditions
ConditionsYield
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%
94827-99-3

2-<9'-(2-pyridylthio)-tetraprenyl>-3-methyl-1,4-dimethoxynaphthalene

A

863-61-6

menatetrenone

B

2-Methyl-3-((2E,6E,9E)-3,7,11,15-tetramethyl-hexadeca-2,6,9,14-tetraenyl)-2,3-dihydro-[1,4]naphthoquinone

Conditions
ConditionsYield
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;
94828-03-2

2-(5'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene

A

863-61-6

menatetrenone

B

2-Methyl-3-((2E,5E,10E)-3,7,11,15-tetramethyl-hexadeca-2,5,10,14-tetraenyl)-[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen; lithium; ethylamine 1.) THF, -70 deg C; 2.) THF, MeOH, H2O, Et2O; Yield given. Multistep reaction;
94828-02-1

2-(9'-p-tosyl-tetraprenyl)-3-methyl-1,4-dibenzyloxynaphthalene

A

863-61-6

menatetrenone

B

2-Methyl-3-((2E,6E,9E)-3,7,11,15-tetramethyl-hexadeca-2,6,9,14-tetraenyl)-2,3-dihydro-[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen; lithium; ethylamine 1.) THF, -70 deg C; 2.) THF, MeOH, H2O, Et2O; Yield given. Multistep reaction;
197071-04-8

4-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene

863-61-6

menatetrenone

Conditions
ConditionsYield
With isotonic phosphate buffer; rat liver homogenate at 37℃; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis;
197071-03-7

1-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene

863-61-6

menatetrenone

Conditions
ConditionsYield
With isotonic phosphate buffer; rat liver homogenate at 37℃; pH=7.4; Kinetics; Further Variations:; Reagents; Hydrolysis;
197071-05-9

1,4-bis(N,N-dimethylglycyloxy)-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene

A

863-61-6

menatetrenone

B

197071-04-8

4-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene

C

197071-03-7

1-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene

Conditions
ConditionsYield
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 hydrocloride

863-61-6

menatetrenone

Conditions
ConditionsYield
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

4-N,N-dimethylglycyloxy-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene hydrochloride

863-61-6

menatetrenone

Conditions
ConditionsYield
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

1,4-bis(N,N-dimethylglycyloxy)-2-methyl-3-tetraprenyl-4-hydroxy-naphthalene dihydrochloride

863-61-6

menatetrenone

Conditions
ConditionsYield
With male Wistar rat liver microsome preparation In water at 25℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

Menatetrenone Chemical Properties

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 Uses

 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.

Menatetrenone Toxicity Data With Reference

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.

Menatetrenone Safety Profile

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 Specification

 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.

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