Roccellic acid

Roccellic acid
Names
IUPAC name
(2R,3S)-2-Dodecyl-3-methylbutanedioic acid
Other names
Rocellic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C17H32O4/c1-3-4-5-6-7-8-9-10-11-12-13-15(17(20)21)14(2)16(18)19/h14-15H,3-13H2,1-2H3,(H,18,19)(H,20,21)/t14-,15+/m0/s1
    Key: CADNMISJDLVPCK-LSDHHAIUSA-N
  • CCCCCCCCCCCC[C@H]([C@H](C)C(=O)O)C(=O)O
Properties
C17H32O4
Molar mass 300.439 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Roccellic acid is a chemical compound with the molecular formula C17H32O4. It was first described as a chemical constituent of the lichen Roccella tinctoria by Friedrich Heeren, sometime before 1830. He sent a purified sample to Liebig, who analyzed them in the fall of 1830. It has since been identified in a variety of other lichens including Roccella montagnei, Lobodirina cerebriformes, Lobodirina mahuiana, and Dirina lutosa, among others.

Several laboratory syntheses of roccellic acid have been reported.

Toensbergianic acid is a stereoisomer of roccellic acid and angardianic acid has been reported to be closely related, but its exact chemical structure is undetermined.

References

  1. ↑ Liebig, Justus (January 1831). "Ueber einen neuen Apparat zur Analyse organischer Körper, und über die Zusammensetzung einiger organischen Substanzen". Annalen der Physik. 97 (1): 1–43. Bibcode:1831AnP....97....1L. doi:10.1002/andp.18310970102. ISSN 0003-3804.
  2. ↑ Schunck, Edward (1845). "CLXVII. On the substances contained in the Roccella tinctoria". Memoirs and Proceedings of the Chemical Society. 3: 144. doi:10.1039/MP8450300144.
  3. ↑ Usselman, Melvyn; Rocke, Alan; Reinhart, Christina; Foulser, Kelly (January 2005). "Restaging Liebig: A Study in the Replication of Experiments". Annals of Science. 62 (1): 1–55. doi:10.1080/00033790410001711922. ISSN 0003-3790.
  4. ↑ Mishra, Tripti; Shukla, Shipra; Meena, Sanjeev; Singh, Ruchi; Pal, Mahesh; Upreti, Dalip Kumar; Datta, Dipak (2017). "Isolation and identification of cytotoxic compounds from a fruticose lichen Roccella montagnei, and it's in silico docking study against CDK-10". Revista Brasileira de Farmacognosia. 27 (6): 724–728. doi:10.1016/j.bjp.2017.07.006.
  5. ↑ Quilhot, W.; Garbarino, J. A.; Gambaro, V. (1983). "Studies on Chilean Lichens, IV. Additions to the Chemistry of Lobodrina cerebriformes". Journal of Natural Products. 46 (4): 594–595. Bibcode:1983JNAtP..46..594Q. doi:10.1021/np50028a033.
  6. ↑ Quilhot, W.; Redń, J.; Zúñiga, E.; Vidal, S. (1975). "Depsides from Lobodirina mahuiana". Phytochemistry. 14 (8): 1865–1866. Bibcode:1975PChem..14.1865Q. doi:10.1016/0031-9422(75)85312-X.
  7. ↑ Huneck, Siegfried; Follmann, Gerhard (1964). "Lichen constituents. X. Chemistry of Chilean lichens. 3. Occurrence of psoromic acid in Chiodecton stalactinum and rocellic acid in Dirina lutosa". Zeitschrift für Naturforschung. 19b (7): 658–659. doi:10.1515/znb-1964-0726.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ↑ Mangaleswaran, Sivaprakasam; Argade, Narshinha P. (2001). "First efficient synthesis of (±)-erythro-roccellic acid†". Journal of the Chemical Society, Perkin Transactions 1 (15): 1764–1766. doi:10.1039/B104105N.
  9. ↑ Brebion, Franck; Delouvrié, Bénédicte; Nájera, Francisco; Fensterbank, Louis; Malacria, Max; Vaissermann, Jacqueline (2003). "Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)- erythro -Roccellic Acid". Angewandte Chemie. 115 (43): 5500–5503. Bibcode:2003AngCh.115.5500B. doi:10.1002/ange.200352356.
  10. ↑ Bayerová, Štěpánka; Haas, Klaus (2005). "Toensbergianic Acid, a New Aliphatic Diacid from the Genus Lepraria (Ascomycota, Stereocaulaceae)". The Bryologist. 108 (2): 224–227. doi:10.1639/8.
  11. ↑ Slavíková-Bayerová, Štěpánka; Orange, Alan (2006). "Three new species of Lepraria (Ascomycota, Stereocaulaceae) containing fatty acids and atranorin". The Lichenologist. 38 (6): 503–513. Bibcode:2006ThLic..38..503S. doi:10.1017/S0024282906006177.