476 



CHEMISTRY OF PHOSPHATIDES AND CERBBROSIDES 



Phrenosine (also called cerebron by Thierfelder)/^^ which was also dis- 

 covered and named by Thudichum^ in 1874. This contains cerebronic 

 acid as a constituent acid, which has been shown by Ivlenk"^ to be a- 

 hydroxylignoceric acid (CH3(CH2)2iCHOHCOOH). 



Nervone, discovered in 1925 by Klenk,"'^ in which the acid, nervonic acid, 

 was shown to be 15,16-tetracosenic acid (CH3(CH2)7CH : CH(CH2)i3COOH). 



Oxynervone, also discovered by Klenk,^i^ on the basis of separation of 

 oxynervonic acid, which is cc-hydroxynervonic acid (CH3(CH2)7CH: 

 CH(CH2)i2CHOHCOOH). This cerebroside has not been prepared in pure 

 form. 



0=C(CH2)22CH3 



NH 

 H I 

 CH,(CH,),,CH=CHC-C-CH, 



OHH 

 I 

 HC 



HCOH 



I 

 HOCH 



HOCH 

 I 

 HC- 



I 



CHjOH 



OH 



0=C-C-(CH2)e,CH3 

 I H 

 NH 

 H I 



ch,(chJ,,ch=chchc-c-ch, 



3 2 12 III'' 



OHH 



I 

 HC 



HCOH 

 I 

 HOCH 



HOCH 

 I 

 HC 



CHjOH 



Cerasiue 



Phrenosine 



It seems probable that similar cerebrosides of the glycolipid type exist. 

 Of the glycolipids which have been studied, only the cerasine type has been 

 reported. ^^^ It would also appear that isomeric cerebrosides might exist 

 where the galactoside or glucoside attachment to sphingosine occurs 

 through the hydroxyl group on carbon 3 instead of on carbon 1. 



CH3(CH2),,CH = 



H 



= CHC— 0- 

 I 1 

 HO H 



C(CH2),3CH= 

 NH 



= CH(CH2)7CH3 



-GHz 

 I 

 



HC 



HCOH 

 I 

 HOCH 



I 

 HOCH 

 I 

 HC 



CHjOH 



Nervone 



H 



0=C-C-(CH2),2CH=CH(CH2), CH, 



H I 

 CH3(CH2),2CH=CHC-C 



HO H 



NH OH 



CH2 



I 

 



I 

 HC- 



I 



HCOH 

 I 

 HOCH 



HOCH 

 I 

 HC- 

 I 



CHjOH 

 Ox.vnervone 



«« H. Thierfelder, Z. physiol. Chem., 43, 21-31 (1904). 

 "« E. Klenk, Z. physiol. Chem., 179, 312-319 (1928). 

 "T E. Klenk, Z. physiol. Chem., 145, 244-260 (1925). 

 ^18 E. Klenk, Z. physiol. Chem., 174, 214-232 (1928). 



