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84-80-0

Basic Information
CAS No.: 84-80-0
Name: 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-
Article Data: 37
Cas Database
Molecular Structure:
Molecular Structure of 84-80-0 (1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]-)
Formula: C31H46O2
Molecular Weight: 450.705
Synonyms: Monodion;Orakay;Phylloquinone K1;Phytonadione;Phytylmenadione;Synthex P;Veda K1;VitaminK1(20);a-Phylloquinone;Natural Vitamine K1;1,4-Naphthalenedione,2-methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-, [R-[R*,R*-(E)]]-;Phylloquinone (8CI);2-Methyl-3-phytyl-1,4-naphthoquinone;AquaMEPHYTON;Kanakion;Kaywan;Mephyton;Mono-Kay;
EINECS: 201-564-2
Density: 0.984 g/mL at 25 °C(lit.)
Melting Point: -20 °C(lit.)
Boiling Point: 546.44 °C at 760 mmHg
Flash Point: 200.441 °C
Solubility: Miscible with dehydrated alcohol, acetone, petroleum ether, hexane, dioxane, chloroform, ether, benzene and vegetable oils. Immiscible with water.
Appearance: clear intense yellow ,viscous,oilyliq
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information: N/A
PSA: 34.14000
LogP: 9.15760
Synthetic route
31599-79-8

2-(chloromethyl)-3-methylnaphthalene-1,4-dione

75-24-1

trimethylaluminum

135011-17-5

(6R,10R)-6,10,14-trimethyl-pentadec-1-yne

84-80-0

phytomenadione

Conditions
ConditionsYield
Stage #1: trimethylaluminum; (6R,10R)-6,10,14-trimethyl-pentadec-1-yne With zirconocene dichloride In 1,2-dichloro-ethane
Stage #2: 2-(chloromethyl)-3-methylnaphthalene-1,4-dione With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Further stages.;
86%
50281-47-5

4-Hydroxy-2-methyl-3-<(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl>naphth-1-yl Acetate

84-80-0

phytomenadione

Conditions
ConditionsYield
With sodium dithionite; potassium hydroxide In methanol; n-heptane; water at 18 - 20℃; for 1h;63.6%
With sodium dithionite; potassium hydroxide In methanol; n-heptane; water at 18 - 20℃; for 1h;63.6%
58-27-5

menadione

150-86-7

phytol

A

84-80-0

phytomenadione

B

74610-11-0

2,3-benzo-5-methyl-5-phytylcyclohexane-1,4-dione

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; tin(II) bromide In N,N-dimethyl-formamide at 50℃; for 24h;A 46%
B 42%
58-27-5

menadione

150-86-7

phytol

A

2,3-benzo-5-methyl-5-phytylcyclohexane-1,4-dione

B

84-80-0

phytomenadione

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; tin(II) bromide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;A 42%
B 46%

2-methyl-3-phytyl-1,4-naphthohydroquinone monopropionate

84-80-0

phytomenadione

Conditions
ConditionsYield
With sodium dithionite; sodium hydroxide In ethanol; water at 25℃; for 4h;22.7%
With sodium dithionite; sodium hydroxide In ethanol; water at 25℃; for 4h;22.7%
481-85-6

2-methyl-1,4-naphthohydroquinone

150-86-7

phytol

84-80-0

phytomenadione

Conditions
ConditionsYield
With boron trifluoride anschliessend Behandeln mit Ag2O;
2211-27-0

4-acetoxy-3-methyl-1-naphthol

150-86-7

phytol

84-80-0

phytomenadione

Conditions
ConditionsYield
Multistep reaction;
5546-13-4

Benzoesaeure-<4-hydroxy-2-methyl-3-((2'E,7'R,11'R)-phytyl)-1-naphthyl>ester

A

84-80-0

phytomenadione

B

(2'Z,7'R,11'R)-Phyllochinon

Conditions
ConditionsYield
With potassium hydroxide In methanol; hexane; water for 2h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
dihydrophylloquinone

dihydrophylloquinone

84-80-0

phytomenadione

Conditions
ConditionsYield
With diethyl ether; silver(l) oxide

1-iodo-2,6,10-trimethyl-undecane

84-80-0

phytomenadione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: Li2CuCl4
1.2: KOH / methanol
2.1: Cp2ZrCl2 / 1,2-dichloro-ethane
2.2: 86 percent / Pd(PPh3)4 / tetrahydrofuran
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  • Casno:

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Chemistry

IUPAC Name: 2-methyl-3-[(E)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione 
Empirical Formula: C31H46O2
Molecular Weight: 450.6957g/mol
EINECS: 201-564-2 
Structure of 1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]- (CAS NO.84-80-0):

Index of Refraction: 1.51
Molar Refractivity: 140.09 cm3
Molar Volume: 467.7 cm3
Polarizability: 55.53×10-24cm3
Surface Tension: 35.5 dyne/cm
Density: 0.963 g/cm3
Flash Point: 200.4 °C
Enthalpy of Vaporization: 82.55 kJ/mol
Boiling Point: 546.4 °C at 760 mmHg
Vapour Pressure: 5.37E-12 mmHg at 25°C 
Product Categories: Biochemistry;Vitamins;Vitamins and derivatives;Drugs & Medication;Vitamin Ingredients 
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)/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+
InChIKey: MBWXNTAXLNYFJB-LKUDQCMESA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intramuscular 11429ug/kg/8D (11.429mg/kg) BLOOD: EOSINOPHILIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Archives of Dermatology. Vol. 121, Pg. 1421, 1985.
mouse LD50 intravenous > 6570mg/kg (6570mg/kg)   Drugs in Japan Vol. 6, Pg. 653, 1982.
mouse LD50 oral 25gm/kg (25000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 1339, 1967.
mouse LDLo subcutaneous 1gm/kg (1000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 25, 1958.
rat LD50 oral > 33487mg/kg (33487mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2808572,

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: QJ5800000
F: 1-8-10
Hazardous Substances Data: 84-80-0(Hazardous Substances Data)

Specification

  1,4-Naphthalenedione,2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethyl-2-hexadecen-1-yl]- , its cas register number is 84-80-0. It also can be called 1,4-Naphthoquinone, 2-methyl-3-phytyl- ; 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione ; 2-Methyl-3-phytyl-1,4-naphthochinon ; 3-Phytylmenadione ; Antihemorrhagic vitamin ; Aqua mephyton ; Combinal K1 ; EINECS 201-564-2 ; Fitomenadiona ; HSDB 3162 ; K-Ject ; Kativ N ; Kephton ; Mephyton ;
 Mono-Kay ; NSC 270681 ; Phyllochinon ; Phyllochinonum ; Phylloquinone ; Phytomenadione ; Phytomenadionum ;
 Phytonadionum ; Phytylmenadione ; Synthex P ; UNII-A034SE7857 ; Vitamin K1 .

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