Ε. Miscellaneous Benzenoids
115
2. A CHROMANOL
An interesting and so far unique relative of δ-tocopherol (83), which is a
constituent of soybean oil and belongs to the vitamin Ε group of compounds,
has been isolated from the brown alga Taonia atomaria by Gonzalez and
co-workers (1971). It was named taondiol and its structure (84) was deduced
by spectral determinations and several chemical transformations. The unique
feature of taondiol (84) is the cyclized sesquiterpene side chain, which is
acyclic in the tocopherols. Table 3.1 lists the characterized marine benzenoids.
83
84
TABLE 3.1
MARINE BENZENOIDS
0
Text
mp
no.
Name
(in degrees)
Reference
1
5-Bromo-3,4-dihydroxybenzaldehyde 227-228
Saito and Ando (1955)
2
Dipotassium-2,3-dibromobenzyl
—
Hodgkin et al. (1966)
alcohol-4,5-disulfate
5
2,3-Dibromo-4,5-dihydroxy203-205
Katsui et al. (1967)
benzaldehyde
6
2,3-Dibromo-4,5-dihydroxy129-130
Katsui et al. (1967)
benzyl alcohol methyl ether
7
3,5-Dibromo-4-hydroxybenzyl
113-113.5
Craigie and Gruenig
alcohol
(1967)
8
2-Ethyl-3,6-dihydroxy-l,4130-145
Moore et al. (1966a)
benzoquinone
(subl.)
11
6-Ethyl-2,3,7-trihydroxy-naphtha220.5-221
Ball (1936)
zarin (echinochrome A)
14
3-Acetyl-2,6,7-trihydroxy229-230
Kuhn and Wallenfels
naphthazarin (spinone A,
(1941)
spinochrome C)
(continued)
E. Miscellaneous Benzenoids
2. A CHROMANOL
115
An interesting and so far unique relative of S-tocopherol (83), which is a
constituent of soybean oil and belongs to the vitamin E group of compounds,
has been isolated from the brown alga Taonia atomaria by Gonzalez and
co-workers (1971). It was named taondiol and its structure (84) was deduced
by spectral determinations and several chemical transformations. The unique
feature of taondiol (84) is the cyclized sesquiterpene side chain, which is
acyclic in the tocopherols. Table 3.1 lists the characterized marine benzenoids.
o
HO
83
o
HO
OH
84
TABLE 3.1
MARINE BENZENOIDs
a
Text
no.
1
2
5
6
7
8
11
14
Name
5-Bromo-3,4-dihydroxybenzaldehyde
Dipotassium-2,3-dibromobenzyl
alcohol-4,5-disulfate
2,3-Dibromo-4,5-dihydroxybenzaldehyde
2,3-Dibromo-4,5-dihydroxybenzyl alcohol methyl ether
3,5-Dibromo-4-hydroxybenzyl
alcohol
2-Ethyl-3,6-dihydroxy-1,4benzoquinone
6-Ethyl-2,3,7-trihydroxy-naphthazarin (echinochrome A)
3-Acetyl-2,6,7-trihydroxynaphthazarin (spinone A,
spinochrome C)
mp
(in degrees)
227-228
203-205
129-130
113-113.5
130-145
(subI.)
220.5-221
229-230
Reference
Saito and Ando (1955)
Hodgkin et al. (1966)
Katsui et al. (1967)
Katsui et al. (1967)
Craigie and Gruenig
(1967)
Moore et al. (1966a)
Ball (1936)
Kuhn and Wallenfels
(1941)
(continued)
115
2. A CHROMANOL
An interesting and so far unique relative of δ-tocopherol (83), which is a
constituent of soybean oil and belongs to the vitamin Ε group of compounds,
has been isolated from the brown alga Taonia atomaria by Gonzalez and
co-workers (1971). It was named taondiol and its structure (84) was deduced
by spectral determinations and several chemical transformations. The unique
feature of taondiol (84) is the cyclized sesquiterpene side chain, which is
acyclic in the tocopherols. Table 3.1 lists the characterized marine benzenoids.
83
84
TABLE 3.1
MARINE BENZENOIDS
0
Text
mp
no.
Name
(in degrees)
Reference
1
5-Bromo-3,4-dihydroxybenzaldehyde 227-228
Saito and Ando (1955)
2
Dipotassium-2,3-dibromobenzyl
—
Hodgkin et al. (1966)
alcohol-4,5-disulfate
5
2,3-Dibromo-4,5-dihydroxy203-205
Katsui et al. (1967)
benzaldehyde
6
2,3-Dibromo-4,5-dihydroxy129-130
Katsui et al. (1967)
benzyl alcohol methyl ether
7
3,5-Dibromo-4-hydroxybenzyl
113-113.5
Craigie and Gruenig
alcohol
(1967)
8
2-Ethyl-3,6-dihydroxy-l,4130-145
Moore et al. (1966a)
benzoquinone
(subl.)
11
6-Ethyl-2,3,7-trihydroxy-naphtha220.5-221
Ball (1936)
zarin (echinochrome A)
14
3-Acetyl-2,6,7-trihydroxy229-230
Kuhn and Wallenfels
naphthazarin (spinone A,
(1941)
spinochrome C)
(continued)
E. Miscellaneous Benzenoids
2. A CHROMANOL
115
An interesting and so far unique relative of S-tocopherol (83), which is a
constituent of soybean oil and belongs to the vitamin E group of compounds,
has been isolated from the brown alga Taonia atomaria by Gonzalez and
co-workers (1971). It was named taondiol and its structure (84) was deduced
by spectral determinations and several chemical transformations. The unique
feature of taondiol (84) is the cyclized sesquiterpene side chain, which is
acyclic in the tocopherols. Table 3.1 lists the characterized marine benzenoids.
o
HO
83
o
HO
OH
84
TABLE 3.1
MARINE BENZENOIDs
a
Text
no.
1
2
5
6
7
8
11
14
Name
5-Bromo-3,4-dihydroxybenzaldehyde
Dipotassium-2,3-dibromobenzyl
alcohol-4,5-disulfate
2,3-Dibromo-4,5-dihydroxybenzaldehyde
2,3-Dibromo-4,5-dihydroxybenzyl alcohol methyl ether
3,5-Dibromo-4-hydroxybenzyl
alcohol
2-Ethyl-3,6-dihydroxy-1,4benzoquinone
6-Ethyl-2,3,7-trihydroxy-naphthazarin (echinochrome A)
3-Acetyl-2,6,7-trihydroxynaphthazarin (spinone A,
spinochrome C)
mp
(in degrees)
227-228
203-205
129-130
113-113.5
130-145
(subI.)
220.5-221
229-230
Reference
Saito and Ando (1955)
Hodgkin et al. (1966)
Katsui et al. (1967)
Katsui et al. (1967)
Craigie and Gruenig
(1967)
Moore et al. (1966a)
Ball (1936)
Kuhn and Wallenfels
(1941)
(continued)