In addition to the known 3-hydroxydocosa-(4E, 15E)-dien-1-yne [1], 3-hydroxy-16-methyleicos-(4E)-en-1-yne [2], and 3-hydroxy-19-methyleicos-(4E)-en-1-yne [3], the lipophilic extract of the Caribbean sponge Cribrochalina vasculum was shown to contain four new bioactive acetylene metabolites, (3R)-hydroxy-14-methyldocos-(4E)-en-1-yne [4], (3R)-hydroxy-16-methyleicos-1-yne [7], (3R)-hydroxy-19-methyleicos-1-yne [8], and docosa-(3E, 15Z)-dien-1-yne [9], whose structures were elucidated on the basis of chemical and spectral studies. The previously unassigned chirality at C-3 of the known compounds 1-3 has been also established as R.