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Menaquinone-7 is a long-chain menaquinone member of Vitamin K2, showing anti-cancer activity.

Synonyms: Vitamin K2-7;Vitamin K2(35);MK-7

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Quality Control of Menaquinone-7 Purity: 98% SDS Specification

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Product Details of Menaquinone-7

CAS No. :	2124-57-4
Formula :	C₄₆H₆₄O₂
M.W :	649.00
SMILES Code :	O=C1C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(C2=C1C=CC=C2)=O
Synonyms :	Vitamin K2-7;Vitamin K2(35);MK-7
English Name :	2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-Heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-dione
MDL No. :	MFCD06200757
InChI Key :	RAKQPZMEYJZGPI-LJWNYQGCSA-N
Pubchem ID :	5287554

Safety of Menaquinone-7

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Application In Synthesis of Menaquinone-7

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2124-57-4 ]

[ 2124-57-4 ] Synthesis Path-Downstream 1~14

1
[ 2124-57-4 ]
[ 108-24-7 ]
[ 122726-03-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyridine; zinc at 25 - 30℃; for 2h;	Step-1: Preparation of acetic acid 4-acetoxy-3-((2E,6E,10E,14E,18E,22E)-3.7.11.15.19.23.27 -heptamethyl-octacosa-2,6, 10,14,18 ,22,26-heptaenyl)-2-methyl- naphthalen-l-yl ester IXa, where n = 7, from 2-((2E,6E,10E,14E,18E,22E)-3.7.11.15.19.23.27 -heptamethyl-octacosa-2,6, 10, 14, 18, 22, 26-heptaenyl)-3-methyl- [l,4]naphthoquinone (MK-7), where n = 7: To a stirring solution of MK-7 (5.0 g, 7.7 mmol) in pyridine (10 mL, 2V) were added acetic anhydride (75 mL, 15V) and Zn dust (3.2 g, 50 mmol) at room temperature (25- 30 °C). The reaction mixture was stirred at RT for 2h. The reaction completion was monitored by TLC (15% ethyl acetate/hexane). The reaction mixture was filtered through celite and washed with ethyl acetate (10 mL), filtrate was diluted with ethyl acetate (250 mL) and washed with water (2X100 mL), separated organic layer was concentrated and crude obtained was purified by column chromatography (3-4% ethyl acetate/hexane) to yield the compound IXa as a pale yellow liquid (4.2 g, 75%). The H1nmr obtained was consistent with the product.
	With sodium acetate; zinc
	With sodium acetate; zinc

75%

With pyridine; zinc at 25 - 30℃;

Step-1: Preparation of acetic acid 4-acetoxy-3-((2E,6E,10E,14E,18E,22E)-3.7.11.15.19.23.27 -heptamethyl-octacosa-2,6, 10,14,18 ,22,26-heptaenyl)-2-methyl- naphthalen-l-yl ester IXa, where n = 7, from 2-((2E,6E,10E,14E,18E,22E)-3.7.11.15.19.23.27 -heptamethyl-octacosa-2,6, 10, 14, 18, 22, 26-heptaenyl)-3-methyl- [l,4]naphthoquinone (MK-7), where n = 7: To a stirring solution of MK-7 (5.0 g, 7.7 mmol) in pyridine (10 mL, 2V) were added acetic anhydride (75 mL, 15V) and Zn dust (3.2 g, 50 mmol) at room temperature (25- 30 °C). The reaction mixture was stirred at RT for 2h. The reaction completion was monitored by TLC (15% ethyl acetate/hexane). The reaction mixture was filtered through celite and washed with ethyl acetate (10 mL), filtrate was diluted with ethyl acetate (250 mL) and washed with water (2X100 mL), separated organic layer was concentrated and crude obtained was purified by column chromatography (3-4% ethyl acetate/hexane) to yield the compound IXa as a pale yellow liquid (4.2 g, 75%). The H1nmr obtained was consistent with the product.

References: [1]Current Patent Assignee: EPIZON PHARMA - WO2022/147047, 2022, A1 Location in patent: Paragraph 0128-0129; 0138-0139.
[2]Binkley et al. [Journal of the American Chemical Society, 1939, vol. 61, p. 1612][Journal of Biological Chemistry, 1939, vol. 130, p. 219,230] McKee et al. [Journal of Biological Chemistry, 1939, vol. 131, p. 327,340].
[3]Current Patent Assignee: PRESIDENT BOARD OF TRUSTEES - US2456686, 1944, A Current Patent Assignee: PRESIDENT AND BOARD - US2373105, 1939, A.
[4]Current Patent Assignee: EPIZON PHARMA - WO2022/147047, 2022, A1 Location in patent: Paragraph 0128-0129; 0138-0139.

Yield	Reaction Conditions	Operation in experiment
	In carbon dioxide at 35℃;
	In chloroform; carbon dioxide at 35℃;
	In ethanol; carbon dioxide at 35℃;

	In carbon dioxide; acetone at 35℃;
	In methanol; carbon dioxide at 25 - 75℃; for 0.0833333 - 0.5h;
	In methanol; carbon dioxide at 35℃;

3
[ 2124-57-4 ]
[ 123-62-6 ]
[ 1453189-07-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium acetate; zinc at 130℃; for 0.5h;	7 Example 7 Example 7 2-((2E,6E, 10E, 14E, 18E,22E)-3 ,7, 11,15,19,23 ,27-heptamethyloctacosa- 2,6,10,14,18,22,26-heptaen-l-yl)-3-methylnaphthalene-l,4-dione (324 mg, 0.50 mmol), propanoic anhydride (7.50 mL, 80 mmol), NaOAc (50 mg, 0.60 mmol) and Zn powder (100 mg, 1.55 mmol) were added together and heated to 130 °C. The reaction mixture was stirred for 30 minutes. After cooling to room temperature, the reaction mixture was poured into water and extracted with CHCI3 (x2) and the combined organic phases were dried (Na2S04), filtrated and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (heptane : EtOAc gradient) to give 250 mg (66%) of 2- ((2E,6E, 10E, 14E, 18E,22E)-3 ,7, 11 , 15 , 19,23 ,27-heptamethyloctacosa- 2,6,10,14,18,22,26-heptaen-l-yl)-3-methylnaphthalene-l,4-diyl dipropionate as a yellow oil. 1H NMR (300 MHz, CDC13) δ 7.76 - 7.55 (m, 2H), 7.55 - 7.33 (m, 2H), 5.09 (dt, J = 5.4, 3.7, 7H), 3.39 (d, J= 4.7, 2H), 2.77 (qd, J= 7.6, 5.3, 4H), 2.22 (s, 3H), 2.15 - 1.82 (m, 24H), 1.76 (s, 3H), 1.67 (s, 3H), 1.58 (d, J= 5.9, 18H), 1.37 (td, J= 7.6, 6.1, 6H). 13C NMR (75 MHz, CDC13) δ 173.06, 172.64, 136.40, 135.38, 135.11, 131.45, 126.44, 126.35, 124.60, 124.44, 124.13, 121.56, 121.38, 77.65, 77.23, 76.81, 39.94, 39.80, 27.74, 27.21, 27.02 - 26.89, 26.80, 25.92, 17.90, 16.59, 16.24, 13.26, 9.63. MS: m/z [M + Na calcd for C52H7404:785.55; found: 785.7
66%	With sodium acetate; zinc at 130℃; for 0.5h;	7 Example 7 Example 7 [0158] 2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-dione (324 mg, 0.50 mmol), propanoic anhydride (7.50 mL, 80 mmol), NaOAc (50 mg, 0.60 mmol) and Zn powder (100 mg, 1.55 mmol) were added together and heated to 130° C. The reaction mixture was stirred for 30 minutes. After cooling to room temperature, the reaction mixture was poured into water and extracted with CHCl3 (×2) and the combined organic phases were dried (Na2SO4), filtrated and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography (heptane:EtOAc gradient) to give 250 mg (66%) of 2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dipropionate as a yellow oil. [0159] 1H NMR (300 MHz, CDCl3) δ 7.76-7.55 (m, 2H), 7.55-7.33 (m, 2H), 5.09 (dt, J=5.4, 3.7, 7H), 3.39 (d, J=4.7, 2H), 2.77 (qd, J=7.6, 5.3, 4H), 2.22 (s, 3H), 2.15-1.82 (m, 24H), 1.76 (s, 3H), 1.67 (s, 3H), 1.58 (d, J=5.9, 18H), 1.37 (td, J=7.6, 6.1, 6H). [0160] 13C NMR (75 MHz, CDCl3) δ 173.06, 172.64, 136.40, 135.38, 135.11, 131.45, 126.44, 126.35, 124.60, 124.44, 124.13, 121.56, 121.38, 77.65, 77.23, 76.81, 39.94, 39.80, 27.74, 27.21, 27.02-26.89, 26.80, 25.92, 17.90, 16.59, 16.24, 13.26, 9.63. [0161] MS: m/z [M+Na]+ calcd for C52H74O4:785.55; found: 785.7

References: [1]Current Patent Assignee: KAPPA BIOSCIENCE - WO2013/128037, 2013, A1 Location in patent: Page/Page column 28-29.
[2]Current Patent Assignee: KAPPA BIOSCIENCE - US2015/31651, 2015, A1 Location in patent: Paragraph 0157; 0158; 0159; 0160; 0161.

4
[ 2124-57-4 ]
[ 1453189-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
	Multi-step reaction with 2 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C
	Multi-step reaction with 2 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C

References: [1]Current Patent Assignee: KAPPA BIOSCIENCE - WO2013/128037, 2013, A1.
[2]Current Patent Assignee: KAPPA BIOSCIENCE - WO2013/128037, 2013, A1.
[3]Current Patent Assignee: KAPPA BIOSCIENCE - US2015/31651, 2015, A1.

5
[ 2124-57-4 ]
[ 1453189-03-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C