174
5. Nonaromatic Compounds
19
C. Miscellaneous Functions
1. SULFUR COMPOUNDS
Moore and his group, in addition to examining the essential oil constituents of two species of brown algae of the genus Dictyopteris (Moore et al,
1968; Pettus and Moore, 1970; 1971a,b), have investigated the nonvolatile
lipids of these algae. Solvent extraction, followed by column chromatography
and gel filtration resulted in the isolation of a series of interesting sulfurcontaining compounds, obviously biogenetically related to the dictyopterenes
(Roller et al, 1971). The structures of these compounds were determined
largely by unambiguous spectral analysis and proved to be 5-(3-oxoundecyl)thioacetate (13), bis(3-oxoundecyl)disulfide (14), 5'-(^«5
, -3-oxoundec-4-enyl)thioacetate (15), and 3-hexyl-4,5-dithiacycloheptanone (16).
CH 3 —(CH 2 ) 7 —CO—(CH 2 ) 2 —SCOCH 3
[CH 3 —(CH 2 ) 7 —CO—(CH 2 ) 2 —S—] 2
13
14
Ο
CH 3 —(CH 2 ) 5 —CH=CH—CO—(CH 2 ) 2 —SCOCH 3
/
S —
S
15
\
16
Compound 14, bis(3-oxoundecyl)disulfide, was accompanied by a small
amount of another sulfur compound, which Moore and co-workers (1972)
have now identified as (-)bis(3-acetoxyundec-5-enyl) disulfide (17) by spectral
means. The mixture of 14 and 17 could be separated only after reductive
acetylation to a mixture of .S-(3-oxoundecyl)thioaceatate (18) and S(-)(3acetoxyundec-5-enyl) thioacetate (19), which was separable by gel filtration
(
-J^J.
17
18
^^^^^
5. Nonaromatic Compounds
19
C. Miscellaneous Functions
1. SULFUR COMPOUNDS
Moore and his group, in addition to examining the essential oil constituents of two species of brown algae of the genus Dictyopteris (Moore et al,
1968; Pettus and Moore, 1970; 1971a,b), have investigated the nonvolatile
lipids of these algae. Solvent extraction, followed by column chromatography
and gel filtration resulted in the isolation of a series of interesting sulfurcontaining compounds, obviously biogenetically related to the dictyopterenes
(Roller et al, 1971). The structures of these compounds were determined
largely by unambiguous spectral analysis and proved to be 5-(3-oxoundecyl)thioacetate (13), bis(3-oxoundecyl)disulfide (14), 5'-(^«5
, -3-oxoundec-4-enyl)thioacetate (15), and 3-hexyl-4,5-dithiacycloheptanone (16).
CH 3 —(CH 2 ) 7 —CO—(CH 2 ) 2 —SCOCH 3
[CH 3 —(CH 2 ) 7 —CO—(CH 2 ) 2 —S—] 2
13
14
Ο
CH 3 —(CH 2 ) 5 —CH=CH—CO—(CH 2 ) 2 —SCOCH 3
/
S —
S
15
\
16
Compound 14, bis(3-oxoundecyl)disulfide, was accompanied by a small
amount of another sulfur compound, which Moore and co-workers (1972)
have now identified as (-)bis(3-acetoxyundec-5-enyl) disulfide (17) by spectral
means. The mixture of 14 and 17 could be separated only after reductive
acetylation to a mixture of .S-(3-oxoundecyl)thioaceatate (18) and S(-)(3acetoxyundec-5-enyl) thioacetate (19), which was separable by gel filtration
(
-J^J.
17
18
^^^^^