(E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method

A technology of hydroxystilbene and dimethoxyphenyl, which is applied in the -3 field, can solve problems such as limited sources, and achieve the effects of less waste residue, mild reaction conditions, and favorable industrialization

Inactive Publication Date: 2006-12-13
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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AI Technical Summary

Problems solved by technology

[0003] At present, red sandalwood stilbene mainly depends on extracting from natural plants, and the sources are limited

Method used

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  • (E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method
  • (E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method
  • (E)-3,5-dimethox-4'-hydroxy diphenyl ethylene synthesis method

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Experimental program
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Effect test

Embodiment 1

[0034] (1) Synthesis of (Z)-2-(4-acetoxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid: 3,5-dimethoxybenzaldehyde (16.6g , 0.1mol), a mixed solution of p-hydroxyphenylacetic acid (15.2g, 0.1mol), acetic anhydride (30g) and triethylamine (25g) was reacted at 120°C for 8 hours. Obtained a light yellow solid, namely (Z)-2-(4-acetoxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid 33.86g, yield 99%;

[0035] MS m / z: 342 (M + ), 300, 255, 240, 225, 134.

[0036] 1 H NMR (400Hz, CDCl 3 )2.280 (s, 3H, 4'-COCH 3); 3.514 (s, 6H, 3, 5-CH 3 ); 6.237-6.242 (d, 2H, J = 2.0Hz, 2, 6-Ar-H); 6.335-6.346 (t, 1H, J = 2.0Hz, 4-Ar-H); 7.079-7.106 (d, 2H, J = 6.8Hz, 3', 5'-Ar-H); 7.255-7.282 (d, 2H, J = 6.8Hz, 2', 6'-Ar-H); 7.864 (s, 1H, =CH ).

[0037] IR (KBr, cm -1 ): 3500-2500, 2941, 2841, 1672, 1591, 1510, 1460, 1206.

[0038] (2) Synthesis of (E)-3,5-dimethoxy-4'-acetoxystilbene: (Z)-2-(4-acetoxyphenyl)-3-(3,5 -Dimethoxyphenyl) acrylic acid (3.42g, 0.01mol), copper powder (3.0g) and quinol...

Embodiment 2

[0047] (1) Synthesis of (Z)-2-(4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid: 3,5-dimethoxybenzaldehyde (16.6g, 0.1 mol), p-hydroxyphenylacetic acid (15.2g, 0.1mol), acetic anhydride (30g) and triethylamine (25g) were reacted at 120°C for 8 hours, and poured into ice water after the reaction was completed, and the solid obtained by suction filtration Pour directly into 150ml of 5% sodium hydroxide solution by mass, stir at 25°C for 3 hours, add 37% hydrochloric acid to acidify to weak acidity (PH5-6), and obtain 29.52g of light yellow solid It is (Z)-2-(4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid, and the yield is 98.4%.

[0048] MS m / z: 300(M + ), 282, 271, 255, 240, 225, 210, 181, 139, 134.

[0049] IR (KBr, cm -1 ): 3431, 3008, 2949, 1705, 1591, 1512, 1462, 1211, 1159, 833.

[0050] (2) Synthesis of pterostylbene: (Z)-2-(4-hydroxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid (3.00g, 0.01mol), copper powder (3.0g ) and quinoline (30.0g) were reacted at 200...

Embodiment 3

[0052] (1) Synthesis of (Z)-2-(4-acetoxyphenyl)-3-(3,5-dimethoxyphenyl)acrylic acid: 3,5-dimethoxybenzaldehyde (16.6g , 0.1mol), a mixed solution of p-hydroxyphenylacetic acid (15.2g, 0.1mol), acetic anhydride (30g) and triethylamine (25g) was reacted at 80°C for 10 hours, and after the reaction was completed, it was directly poured into ice water to obtain a large amount of Light yellow solid 27.65g, yield 80.8%.

[0053] (2) Synthesis of (E)-3,5-dimethoxy-4'-acetoxystilbene: (Z)-2-(4-acetoxyphenyl)-3-(3,5 -dimethoxyphenyl) acrylic acid (3.42g, 0.01mol), copper powder (3.0g) and quinoline (30.0g) were reacted at 150°C for 5 hours, cooled to room temperature, added 50ml ethyl acetate, mass percent Wash with 17% hydrochloric acid until the water layer is nearly colorless, wash with 5% sodium hydroxide solution until neutral, dry the organic layer over anhydrous magnesium sulfate, and concentrate to obtain a solid (E)-3,5 -Dimethoxy-4'-acetoxystilbene, recrystallized to obtain...

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Abstract

The invention discloses the synthesis of pterostilbene. The method comprises the following steps: using p-hydroxyphenyl acetic acid and veratraldehyde as raw material, carryingout Perkin reaction, getting (Z)-2(4-acetoxylation phenyl)-3-(3, 5- dimethoxy benzoic) acroleic acid, deacetylation, decarboxylation, and getting pterostilbene. The invention has the advantages of cheap raw material, simple technology, easy operation and high productivity. The invention has the advantages of low cost, good economy benefit and environment protection.

Description

technical field [0001] The present invention relates to a kind of chemical synthesis method of polyhydroxy stilbene compound, especially a kind of (E)-3,5-dimethoxy-4'-hydroxy stilbene (Pterostilbene, Pterostilbene) resolve resolution. Background technique [0002] (E)-3,5-dimethoxy-4'-hydroxystilbene (Pterostilbene, English name: Pterostilbene) is a homologue of resveratrol, with a trans-stilbene skeleton structure, is grape, The important active ingredients in blue strawberries, dried blood products and Indian anti-diabetic herbal medicine "Bijasar" also exist in Chinese Dracaena saponifera, and its pharmacological effects are not only partially similar to resveratrol, but also have strong Its antifungal activity, cancer chemoprevention activity, MDR cell apoptosis induction activity, PPARα agonist activity, etc. Its blood lipid lowering activity is better than ciprofibrate, and its antidiabetic activity is equivalent to metformin, showing impo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C43/23
Inventor 邹永张学景林慧贞
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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