13-CIS-LYCOPENE synthesis
- Product Name:13-CIS-LYCOPENE
- CAS Number:13018-46-7
- Molecular formula:C40H56
- Molecular Weight:536.87
Yield:64727-64-6 90 mg ，13018-46-7 18.4 mg
Reaction Conditions:
in benzene at 75; for 14.5 h;Darkness;Inert atmosphere;Solvent;Temperature;
Steps:
2.4. Isolation and identification of (9Z)- and (13Z)-lycopene
(All-E)-lycopene was dissolved in benzene at a concentrationof 0.7 mg ml1, and the solution was heated at 75 C for 14.5 hin the dark. After heating, the solvent was evaporated on a rotaryevaporator, and the residue was dissolved in hexane at aconcentration of 14.8 mg ml1. After filtering through a 0.2-lmPTFE membrane filter, the solution was injected into the normal-phase HPLC instrument at room temperature as describedabove, except for the mobile phase (hexane/DIPEA (400:1 v/v))and flow rate (2.0 ml min1). Under these conditions, fractionsof crude (9Z)-lycopene at a retention time of 48.8-54.2 min andcrude (13Z)-lycopene at 39.5-43.2 min were isolated and appliedto a second normal-phase chromatographic separation using ahexane/DIPEA mobile phase at 700:1 (v/v) for the 9Z-isomer or2000:1 (v/v) for the 13Z-isomer. Finally, the third normal-phasechromatographic separation was conducted with hexane/DIPEA(500:1 v/v) to further purify (13Z)-lycopene. 3.2. Purification and characterisation of (9Z)- and (13Z)-lycopeneIn order to obtain accurate estimations of the concentrations of(9Z)- and (13Z)-lycopene, these isomers were purified from the Z-isomer mixture obtained by heating in benzene at 75 C. From a starting material weight of 2 g of (all-E)-lycopene, 90 mg of the 9Z-isomer (reversed-phase HPLC, 98.8% purity; normal-phaseHPLC, P 99.9%) and 18.4 mg of the 13Z-isomer (reversed-phase HPLC, 97.0%; normal-phase HPLC, P99.9%) were obtained, bothas red fine crystalline powders.
References:
Honda, Masaki;Takahashi, Naoto;Kuwa, Takahiro;Takehara, Munenori;Inoue, Yoshinori;Kumagai, Tsutomu [Food Chemistry,2015,vol. 171,p. 323 - 329]
502-65-8
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502-65-8
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