Chemistry:Roccellic acid
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| IUPAC name
(2R,3S)-2-Dodecyl-3-methylbutanedioic acid
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| Other names
Rocellic acid
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
| Infobox references | |
Tracking categories (test):
Roccellic acid is a chemical compound with the molecular formula C
17H
32O
4. 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.[1][2][3] It has since been identified in a variety of other lichens including Roccella montagnei,[4] Lobodirina cerebriformes,[5] Lobodirina mahuiana,[6] and Dirina lutosa,[7] among others.
Several laboratory syntheses of roccellic acid have been reported.[8][9]
Related compounds
Toensbergianic acid is a stereoisomer of roccellic acid[10] and angardianic acid has been reported to be closely related, but its exact chemical structure is undetermined.[11]
References
- ↑ Liebig, Justus (January 1831). "Ueber einen neuen Apparat zur Analyse organischer Körper, und über die Zusammensetzung einiger organischen Substanzen" (in en). Annalen der Physik 97 (1): 1–43. doi:10.1002/andp.18310970102. ISSN 0003-3804. Bibcode: 1831AnP....97....1L. https://onlinelibrary.wiley.com/doi/10.1002/andp.18310970102.
- ↑ 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.
- ↑ Usselman, Melvyn; Rocke, Alan; Reinhart, Christina; Foulser, Kelly (January 2005). "Restaging Liebig: A Study in the Replication of Experiments" (in en). Annals of Science 62 (1): 1–55. doi:10.1080/00033790410001711922. ISSN 0003-3790. https://www.tandfonline.com/doi/full/10.1080/00033790410001711922.
- ↑ 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.
- ↑ 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. doi:10.1021/np50028a033. Bibcode: 1983JNAtP..46..594Q.
- ↑ Quilhot, W.; Redń, J.; Zúñiga, E.; Vidal, S. (1975). "Depsides from Lobodirina mahuiana". Phytochemistry 14 (8): 1865–1866. doi:10.1016/0031-9422(75)85312-X. Bibcode: 1975PChem..14.1865Q. https://repositorio.uchile.cl/handle/2250/153495.
- ↑ 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.
- ↑ 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.
- ↑ 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. doi:10.1002/ange.200352356. Bibcode: 2003AngCh.115.5500B.
- ↑ 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.
- ↑ Slavíková-Bayerová, Štěpánka; Orange, Alan (2006). "Three new species of Lepraria (Ascomycota, Stereocaulaceae) containing fatty acids and atranorin". The Lichenologist 38 (6): 503–513. doi:10.1017/S0024282906006177. Bibcode: 2006ThLic..38..503S.
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