// Workers AI · dad joke modeWhat did Roccellic acid say? I'm bonding with you.

Roccellic acid
Names
	IUPAC name (2R,3S)-2-Dodecyl-3-methylbutanedioic acid
	Other names Rocellic acid
Identifiers
CAS Number	29838-46-8;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:144218;
ChEMBL	ChEMBL3138662;
ChemSpider	9624298;
PubChem CID	11449446;
UNII	AEL38V7F67;
CompTox Dashboard (EPA)	DTXSID90952266 ;
	InChI 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;
	SMILES CCCCCCCCCCCC[C@H]([C@H](C)C(=O)O)C(=O)O;
Properties
Chemical formula	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

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.^[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". Annalen der Physik. 97 (1): 1–43. Bibcode:1831AnP....97....1L. doi:10.1002/andp.18310970102. ISSN 0003-3804.
↑ 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". Annals of Science. 62 (1): 1–55. doi:10.1080/00033790410001711922. ISSN 0003-3790.
↑ 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. Bibcode:1983JNAtP..46..594Q. doi:10.1021/np50028a033.
↑ 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.
↑ 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)
↑ 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. Bibcode:2003AngCh.115.5500B. doi:10.1002/ange.200352356.
↑ 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. Bibcode:2006ThLic..38..503S. doi:10.1017/S0024282906006177.

[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.

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