CAROTENOLS AND OXYCAROTENOLS OF THE C40 SERIES 579 



(g) Capsylaldehyde, C27H38O3. According to Zechmeister and Chol- 

 noky,^^^ capsylaldehyde can be ciystallized only in the form of its oxime. 

 The latter compound forms citron-yellow needles which melt at 172°C. 



HjC CHj 



CHj CH3 CH3 Q 



o^hhIhhhhIhhhIhh /\ 

 hc-c:c'c:c'c:c-c:c-c:c'c:c-c:c- c=0 chz 



CHj C 



/ \ / \ 

 HjC C 



H2 



OH 



Capsylaldehyde 



(h) 4-Oxy-^-carotenone aldehyde, C27H36O4. When capsanthin diacetate is 

 oxidized with chromic acid, 4-oxy-/3-carotenone aldehyde originates, as well 

 as capsylaldehyde and capsanthylal. The new aldehyde has been prepared 

 in crj'stalline fonn only as the oxime, which forms cigar-shaped yellow 

 crystals melting at 189°C. The oxime dissolves readily in benzene, 

 methanol, hot hexane, and hot ligroin; solubility is poor in carbon disulfide. 



HjC CH3 



\ / 

 c 



/ \^H H 



HiC 0— c : c 



H\| 

 ^C 0=0 



hq/ \ / \ 



C CHj 



Hz 



4-Oxy-/3-carotene aldehyde 



(i) Capsanthin Epoxide, C40H58O4. Kuhn and Lederer^^^ were the first to 

 prepare the epoxide by oxidation of capsanthin diacetate with monoper- 

 phthalic acid. The epoxide ciystallizes from a benzene-petroleum ether 

 mixture in leaflets and small needles which melt at 189°C. When an 

 ethereal solution is treated with strong hydrochloric acid, it assumes a deep 

 blue color which is somewhat transitory. When partitioned between 

 methanol and petroleum ether, the pigment is dissolved in the lower layer 

 (methanol). On treatment with hj'-drochloric acid, capsanthin epoxide is 

 converted to the corresponding furanoid compound, which is called capso- 

 chrome. This latter compound can be readily separated from a benzene- 

 petroleum ether mixture in crystals which melt at 195°C. It responds to 

 hydrochloric acid in the same way as capsanthin epoxide does. It is hypo- 

 phasic. 



HO 



