214 CAROTENOIDS CONTAINING HYDROXYL GROUPS XI 



Zechmeister and von Cholnoky assigned the above formula to lycophyll, 

 but this formula could not be proved because of lack of material. The molecular 

 formula C40H56O2 and the purely hypophasic behaviour of the pigment suggest 

 that it is a dihydroxy-compound. The location of the absorption maxima, which 

 are identical with those of lycopene, indicate the presence of 13 double bonds. 

 For these reasons lycophyll is probably 4 :4'-dihydroxy lycopene. The presence 

 of two hydroxyl groups is confirmed by the preparation of lycophyll dipalmi- 

 tateis. 



Properties 



Lycophyll crystallises from a mixture of benzene and methanol in violet 

 leaflets, or from benzene and petroleum ether in violet-red needles, m.p. 179° 

 (corr.). It is readily soluble in carbon disulphide, less soluble in benzene and 

 ethanol, and only very sparingly soluble in petroleum ether. On partition 

 between methanol and petroleum ether, it is found quantitatively in the lower 

 layer. Lycophyll is adsorbed somewhat more strongly than lycoxanthin on 

 calcium hydroxide from benzene solution. 



Solvent AhsoyptioH ^naxinia 



Carbon disulphide 546 506 472 m/i 



Benzene 521 487 456 m// 



Petrol 504 473 444 m/i 



Ethanol 505 474 444 m/i 



Lycophyll dipalmitate: This compound crystallises from a mixture of benzene 

 and methanol in violet-red needles ,m.p. 76° (corr.). It shows purely epiphasic 

 behaviour and is easily soluble in carbon disulphide and benzene, less easily 

 in petroleum ether and almost insoluble in ethanol. The light absorption pro- 

 perties of the dipalmitate in the visible region are identical with those of 

 lycophyll. 



REFERENCES 



1. L. Zechmeister and L. v. Cholnoky, Ber. 6g (1936) 422. 



2. P. Karrer and co-workers, Helv. chim. Acta 13 (1930) 268, 1084; 14 (1931) 614, 843. 



3. R. KuHN and C. Grundmann, Ber. 67 (1934) 339, 1133. 



4. R. KuHN and C. Grundmann, Ber. 6y (1934) 339, ii33- 



5. R. Yamamoto and S. Tin, Sci. Pap. Inst, physic, chem. Res. 20 (i933) 411; Chem. 

 Centr. 1933, I, 3090. 



6. R. KuHN and C. Grundmann, Ber. 66 (1933) 1746. 



7. P. Karrer and W. Schlientz, Helv. chim. Acta 17 (1934) 55- 



8. R. KuHN and C. Grundmann, Ber. 66 (1933) 1746. 



9. R. KuHN and C. Grundmann, Bey. 66 (1933) ^74^- 



10. R. Yamamoto and Y. Kato, Chem. Ceyitr. 1934, II, 2993. 



11. P. Karrer and W. Schlientz, Helv. chim. Acta 17 (1934) 55- 



12. R. KuHN and C. Grundmann, Ber. 66 (1933) 1746. 



13. P. Karrer and E. Jucker, Helv. chim. Acta 2g (1946) 229. 



14. H. V. Euler, p. Karrer and E. Jucker, Helv. chim. Acta 30 (1947) 1159. 



15. P. Karrer and E. Jucker, Helv. chim. Acta 29 (1946) 229. 



