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HO
OH
O
H
O
OH
+
O
HO
OH
3.11
3.22
DCC
DMAP
HO
OH
O
H
O
O
O
OH
3.23
SCHEME 3.8
H
O
O
OH
O
O
O
O
O
O
HO
3.
24
O
O
O
H
OH
O
OH
O
OH
O
O
O
OH
OH
OH
OH
O
O
HO
O
3.
25
OH
OH
O
O
O
OH
OH
O
HO
O
O
O
O
O
O
HO
HO
O
3.
26
OH
O
O
OH
SH
O
O
N
O
N
H
HO
O
3.
27
NH
2
O
O
SCHEME 3.9
et al. 2005). This conjugate employed a maximum of the i nesse of the synthetic chemistry inherent
in Method 1 of Scheme 3.3, and resulted in a highly hydrophilic ca rotenoid, with orders of magnitude
increased antioxidant capacity compared with astaxanthin itself. In analogy to the antioxidant food
additive ascorbyl palmitate, the corresponding ascorbyl C30-carotenoate,
3.23
, was synthesized.
In many instances the compound barely survived the workup procedure, and the synthesis could
not always be reproduced, Scheme 3.8 (Lerfall 2002). In contrast, retinoyl-ascorbic acid is “con-
veniently prepared” (Yamano and Ito 1998) as well as the ascorbylester of norbixin,
3.8
(Humeau
et al. 2000). The biophysical, biological, and potential human medical applications of several of
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