bipinnatin j bipinnatin j bipinnatin j is a diterpene isolated from the bipinnate sea plume antillogorgia bipinnata, a sea fan found in the eastern caribbean sea. it is one of the structurally simplest of the furanocembrenolides, and is speculated to be a biosynthetic precursor to a wide array cembrenolides along with the dehydroxylated analog, rubifolide. bipinnatin j names iupac name (2z,5s,11s,12s)-12-hydroxy-11-isopropenyl-3,14-dimethyl-6,16-dioxatricycloheptadeca-1(15),2,8(17),13-tetraen-7-one identifiers cas number 201742-79-2 3d model (jsmol) interactive image chembl chembl401906 chemspider 10213404 pubchem cid 5470115 inchi inchi=1s/c20h24o4/c1-11(2)17-6-5-14-10-16(24-20(14)22)8-12(3)7-15-9-13(4)19(23-15)18(17)21/h7,9-10,16-18,21h,1,5-6,8h2,2-4h3/b12-7-/t16-,17-,18-/m0/s1key: rcfmtojvvoomto-pvuoxgcvsa-n smiles cc1cc/2oc1((ccc3=c(c/c(=c2)/c)oc3=o)c(=c)c)o properties chemical formula c20h24o4 molar mass 328.40216 melting point 140 to 142 °c (284 to 288 °f; 413 to 415 k) except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). infobox references biosynthesis although the exact biosynthesis of bipinnatin j has not been formally studied, the biosynthesis the core cembrane skeleton, neo-cembrene, has been extensively studied. starting from geranylgeranyl pyrophosphate, the pyrophosphate leaves, creating the allyl carbocation. a type a cyclization then yields the 14-membered cembrane ring with the isopropyl cation outside the ring. proton elimination then yields neo-cembrene. from this point, the biosynthesis of bipinnatin j is speculative. oxidation, most likely utilizing p450 monooxygenases, followed by ring closure creates both the furan and butenolide within the 14-membered ring. ∆ double bond isomerization of the c7-c8 olefin then occurs to afford the z conformation, yielding rubifolide. another oxidation of c2 then yields bipinnatin j. proposed biosynthesis of bipinnatin j