Menaquinone 5

Base Information

• Chemical Name: Menaquinone 5
• CAS No.: 1182-68-9
• Molecular Formula: C₃₆H₄₈O₂
• Molecular Weight: 512.776
• UNII: 12V8PA4WCH
• ChEMBL ID: CHEMBL4297659
• NCI Thesaurus Code: C68319
• Nikkaji Number: J1.591.793H,J39.473D
• Wikidata: Q27251438
• Mol file: 1182-68-9.mol

Synonyms:Menaquinone 5;1182-68-9;Menaguinone;Vitamin MK 5;Vitamin K2(25);UNII-12V8PA4WCH;12V8PA4WCH;2-methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]naphthalene-1,4-dione;J39.473D;1,4-Naphthalenedione, 2-methly-3-(3,7,11,15,19-pentamethyl-2,6,10,14,18-eicosapentaenyl)-, (all-E)-;2-Methyl-3-[(2E,6E,10E,14E)-3,7,11,15,19-pentamethyl-2,6,10,14,18-icosapentenyl]-1,4-naphthalenedione;menaquinone-5;menaquinone(5);MENAQUINONE [WHO-DD];MK-5;CHEMBL4297659;SCHEMBL10054543;EX-A5474;DB15381;Q27251438;1,4-NAPHTHALENEDIONE, 2-METHYL-3-((2E,6E,10E,14E)-3,7,11,15,19-PENTAMETHYL-2,6,10,14,18-EICOSAPENTAEN-1-YL)-;2-Methyl-3-((2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaen-1-yl)naphthalene-1,4-dione

Chemical Property of Menaquinone 5

Chemical Property:

• Vapor Pressure: 3.41E-13mmHg at 25°C
• Boiling Point: 574.3°C at 760 mmHg
• Flash Point: 209.5°C
• PSA: 34.14000
• Density: 1.003g/cm³
• LogP: 8.69390
• XLogP3: 10.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 512.365430770
• Heavy Atom Count: 38
• Complexity: 1000

Purity/Quality:

99%, ^*data from raw suppliers

Menaquinone5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCC=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)/CC/C=C(\C)/CCC=C(C)C
• Uses: Vitamin (prothrombogenic). Menaquinones are isoprenoid quinones of the naphthalene series and belongs to the K2 Vitamin homologs. Menaquinones were originally discovered as the anti-hemorrhagic factor and now encompasses a variety of physiological processes.

Technology Process of Menaquinone 5

There total 9 articles about Menaquinone 5 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(+/-)-nerolidol (7212-44-4) → 2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4) (1182-68-9,43086-19-7)

Guidance literature:

Multi-step reaction with 7 steps

1: Al(OiPr)3

2: (i) KOH, (ii) /BRN= 906677/

3: H₂, quinoline / Lindlar catalyst / cyclohexane

4: Al(OiPr)3

5: (i) KOH, (ii) /BRN= 906677/

6: H₂, quinoline / Lindlar catalyst / cyclohexane

7: AlCl₃ / diethyl ether

With quinoline; aluminium trichloride; hydrogen; aluminum isopropoxide; Lindlar's catalyst; In diethyl ether; cyclohexane;

Reference yield:

3,7,11,15-tetramethyl-hexadeca-6,10,14-trien-1-yn-3-ol (2387-69-1,27873-19-4) → 2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4) (1182-68-9,43086-19-7)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂, quinoline / Lindlar catalyst / cyclohexane

2: Al(OiPr)3

3: (i) KOH, (ii) /BRN= 906677/

4: H₂, quinoline / Lindlar catalyst / cyclohexane

5: AlCl₃ / diethyl ether

With quinoline; aluminium trichloride; hydrogen; aluminum isopropoxide; Lindlar's catalyst; In diethyl ether; cyclohexane;

Reference yield:

1,6,10,14-hexadecatetraen-3-ol, 3,7,11,15-tetramethyl- (68931-30-6) → 2-Methyl-3-<3,7,11,15,19-pentamethyl-eicosapentaen-(2,6,10,14,18)-yl-(1)>-naphthochinon-(1,4) (1182-68-9,43086-19-7)

Guidance literature:

Multi-step reaction with 4 steps

1: Al(OiPr)3

2: (i) KOH, (ii) /BRN= 906677/

3: H₂, quinoline / Lindlar catalyst / cyclohexane

4: AlCl₃ / diethyl ether

With quinoline; aluminium trichloride; hydrogen; aluminum isopropoxide; Lindlar's catalyst; In diethyl ether; cyclohexane;

upstream raw materials:

2-methyl-1,4-naphthohydroquinone

4-acetoxy-3-methyl-1-naphthol

3,7,11,15,19-pentamethyl-eicosa-1,6,10,14,18-pentaen-3-ol

3,7,11,15-tetramethyl-hexadeca-6,10,14-trien-1-yn-3-ol

Refernces

Synthesis and redox potentials of methylated vitamin K derivatives

10.1039/a900190e

Ralf Schmid, Friederike Goebel, André Warnecke, and Andreas Labahn study on the synthesis and redox potential measurements of various methylated vitamin K derivatives. The study aims to systematically vary the redox potentials of vitamin K derivatives by introducing different numbers of methyl groups in various positions to investigate their role in electron transfer reactions and structure-function relationships in vitamin K-dependent enzymes. The authors synthesized a range of vitamin K3, K1, and K2 derivatives with varying methyl substitutions and measured their redox potentials using cyclic voltammetry in DMF. They found that increasing the number of methyl substituents generally decreased the reduction potentials due to the electron-donating effect of alkyl groups. The study provides a wide range of reduction potentials for these derivatives, which are relevant for understanding electron transfer in photosynthetic reaction centers and for studying the binding affinity and steric properties of these compounds in biological systems.

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