Erogorgiaene

Erogorgiaene
2D model of erogorgiaene
Names
IUPAC name
(1S,4R)-1,6-Dimethyl-4-[(2S)-6-methylhept-5-en-2-yl]-1,2,3,4-tetrahydronaphthalene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H30/c1-14(2)7-6-8-16(4)19-12-10-17(5)18-11-9-15(3)13-20(18)19/h7,9,11,13,16-17,19H,6,8,10,12H2,1-5H3/t16-,17-,19+/m0/s1
    Key: JWQVCYABIGUFIY-JENIJYKNSA-N
  • C[C@H]1CC[C@@H](C2=C1C=CC(=C2)C)[C@@H](C)CCC=C(C)C
Properties
C20H30
Molar mass 270.460 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Erogorgiaene is a bicyclic compound found in marine octocoral Psuedoptergorgia elisabethae. It is used as an intermediate to synthesize pseudopterosin and is made by dehydrogenizing elisabethatriene so that a benzene ring is formed.

Research

Erogorgiaene was found to have potential as an antibiotic against mycobacterium tuberculosis. However, limited natural supply and expensive chemical synthesis keeps the usage of the antiboitic very low.

References

  1. ↑ Kohl, Amber C.; Kerr, Russell G. (2003-11-26). "Pseudopterosin Biosynthesis: Aromatization of the Diterpene Cyclase Product, Elisabethatriene". Marine Drugs. 1 (1): 54–65. doi:10.3390/md101054. ISSN 1660-3397. PMC 3783875.
  2. ↑ Incerti-Pradillos, Celia A.; Kabeshov, Mikhail A.; O'Hora, Paul S.; Shipilovskikh, Sergei A.; Rubtsov, Aleksandr E.; Drobkova, Vera A.; Balandina, Svetlana Yu.; Malkov, Andrei V. (2016). "Asymmetric Total Synthesis of (−)-Erogorgiaene and Its C-11 Epimer and Investigation of Their Antimycobacterial Activity". Chemistry – A European Journal. 22 (40): 14390–14396. doi:10.1002/chem.201602440. ISSN 1521-3765. PMID 27529822.
  3. ↑ Munich, Technical University of. "Designed Bacteria Produce Coral Antibiotic". Lab Manager. Retrieved 2025-12-04.