LACTONES

 AND  QUINONES  
 LACTONES  
 
•  The  gamma  and  delta  hydroacids  easily  lose  
water,  even  when  in  soluAon  at  ordinary  
temperatures,  and  are  converted  into  
intramolecular  esters  called  lactones,  cyclic  
anhydrides  or  inner  anhydrides.      
•  They  are  stable  five  or  six  membered  
heterocycles.    
•  Ascorbic  acid:  Vitamin  C;  It  is  used  in  scurvy  as  
a  propylacAc  and  a  curaAve  agent.  
Vitamin   C   is   the   γ-­‐lactone   of   2,3,4,5,6-­‐
pentahydroxy-­‐2-­‐hexenoic   acid,     and   is   a   five  
membered  heterocycle.  
  HO

HO
O O
H

HO OH
 QUINONES  
 
•    VITAMIN   K   refers   to   a   group   of   substance,  
widespread  in  nature,  having  similar  biological  
acAvity;    
–  one  form  was  isolated  first  from  alfalfa  and  other  
putrefied  fish  meal.      
–  The   primary   acAvity   which   makes   the   vitamin  
essenAal  in  human  metabolism  is  its  involvement  
in   blood   cloTng   system   through   synthesis   of  
prothrombin  and  other  cloTng  factors.  
 VITAMIN  K    
GENERAL  FORMULA    
R
R'

R"
R'"
1.  Ring  A  is  aromaAc  or  hydroaromaAc.  
2.  Ring  A  is  not  subsAtuted.  
3.  Ring  B  is  aromaAc  or  hydroaromaAc.  
4.  R  is  equal  to  OH,  CO,  OR,  OAc  (the  R  in  OR  equals  
methyl  or  ethyl)  
5.  R’  equals  methyl.  
6.  R”  equals  H,  sulfonic  acid,  dimethylamino  or  an  alkyl  
group  containing  ten  or  more  carbon      atoms.  
7.  R”’  equals  H,  OH,  NH2,  CO,  OR,  Ac  (the  R  in  OR  equals  
methyl  or  ethyl)  
Decreased  anAhemorrhagic  acAvity  is  obtained  
when:  
1.  Ring  A  is  subsAtuted.  
2.  R’  is  an  alkyl  group  larger  than  a  methyl  
group.  
3.  R”  is  a  hydroxyl  group.  
4.  R”  contains  a  hydroxyl  group  in  a  side  chain.  
 
 
VITAMIN  K1  PHYLLOQUINONE:    2-­‐methyl-­‐3-­‐phytyl-­‐1,4-­‐naphthoquinone  
2-­‐methyl-­‐3-­‐(3,7,11,15,19,23-­‐hexamethyl-­‐2-­‐tetracontaene)-­‐1,4-­‐
naphthoquinone  
   
VITAMIN  K2  MENAQUINONE:    2-­‐methyl-­‐3-­‐phytyl-­‐1,4-­‐naphthoquinone  
2-­‐methyl-­‐3-­‐(3,7,11,15,19,23-­‐hexamethyl-­‐2,6,10,14,18,22-­‐
tetracontahexaene)-­‐1,4-­‐naphthoquinone  

   
VITAMIN  K3    MENADIONE:  1,4-­‐Naphthalenedione,  2-­‐methyl  
   
     
   
VITAMIN  K4  MENADIOL:  1,4-­‐Naphthalenediol,  2-­‐methyl