Tropodithietic acid

Tropodithietic acid is a tropolone derivative produced by the marine bacteria Phaeobacter piscinae, Phaeobacter inhibens and Phaeobacter gallaeciensis.[1][2] Its structure is composed by a dithiete moiety fused to tropone-2-carboxylic acid.

Tropodithietic acid
Chemical structure of tropodithietic acid
Names
Preferred IUPAC name
3-Oxo-8,9-dithiabicyclo[5.2.0]nona-1,4,6-triene-2-carboxylic acid
Other names
TDA
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.233.118
EC Number
  • 806-061-7
  • InChI=1S/C8H4O3S2/c9-4-2-1-3-5-7(13-12-5)6(4)8(10)11/h1-3H,(H,10,11)
    Key: BLFCMITWMARUSM-UHFFFAOYSA-N
  • C1=CC(=O)C(=C2C(=C1)SS2)C(=O)O
Properties
C8H4O3S2
Molar mass 212.24 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Rabe, Patrick; Klapschinski, Tim A; Brock, Nelson L; Citron, Christian A; D’Alvise, Paul; Gram, Lone; Dickschat, Jeroen S (6 August 2014). "Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid". Beilstein Journal of Organic Chemistry. 10: 1796–1801. doi:10.3762/bjoc.10.188. PMC 4142847. PMID 25161739.
  2. Beyersmann, Paul G.; Tomasch, Jürgen; Son, Kwangmin; Stocker, Roman; Göker, Markus; Wagner-Döbler, Irene; Simon, Meinhard; Brinkhoff, Thorsten (December 2017). "Dual function of tropodithietic acid as antibiotic and signaling molecule in global gene regulation of the probiotic bacterium Phaeobacter inhibens". Scientific Reports. 7 (1): 730. Bibcode:2017NatSR...7..730B. doi:10.1038/s41598-017-00784-7. PMC 5429656. PMID 28389641.


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