Lycopene synthesis

4synthesis methods

Product Name:Lycopene
CAS Number:502-65-8
Molecular formula:C40H56
Molecular Weight:536.87

Lycopene extract from tomato is produced from a tomato variety with high lycopene content, within the range of 150 to 250 mg/kg. This particular variety is not generally marketed for direct consumption, but is used primarily in the production of this lycopene extract. The extract is produced by crushing tomatoes into crude tomato juice that is then separated into serum and pulp. The tomato pulp is then extracted with ethyl acetate. The final product is obtained after solvent removal by evaporation under vacuum at 40-60°C.

ψ,ψ-Carotene, 11,11',12,12'-tetrahydro-7,7',15-tris(phenylsulfonyl)-8,8'-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

1116695-25-0
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502-65-8
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$6.00/10mg

Yield:502-65-8 79%

Reaction Conditions:

with potassium methanolate in cyclohexane;benzene at 70 - 80; for 13 h;

Steps:

9.B

Method B: Elimination Reaction from the Compound (M-2); To a stirred suspension of the bis(tetrahydropyranyl)ether (M-2) (0.44 g, 0.38 mmol) in cyclohexane (20 mL) and benzene (10 mL) was added KOMe (0.79 g, 11.3 mmol). The mixture was heated to 7080° C. for 13 h, cooled to room temperature, and 1 M HCl (20 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (40 mL) of hexane and benzene, dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH₃CN (10 mL×3). The combined CH₃CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.20 g, 0.37 mmol) in 97% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.16 g, 0.29 mmol) in 79% yield as a dark red crystal.

References:

US2009/318732,2009,A1 Location in patent:Page/Page column 10