Copalic acid

Copalic acid
Names
	IUPAC name (E)-5-[(1R,4aR,8aR)-5,5,8a-Trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
	Other names (-)-Copalic acid
Identifiers
CAS Number	20257-75-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:170112;
ChemSpider	9337621;
PubChem CID	11162521;
UNII	6LTQ2LP2NB;
CompTox Dashboard (EPA)	DTXSID701316809 ;
	InChI InChI=1S/C20H32O2/c1-14(13-18(21)22)7-9-16-15(2)8-10-17-19(3,4)11-6-12-20(16,17)5/h13,16-17H,2,6-12H2,1,3-5H3,(H,21,22)/b14-13+/t16-,17-,20+/m1/s1 Key: JFQBNOIJWROZGE-HPMXROJMSA-N;
	SMILES C/C(=C\C(=O)O)/CC[C@@H]1C(=C)CC[C@H]2[C@]1(CCCC2(C)C)C;
Properties
Chemical formula	C20H32O2
Molar mass	304.474 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

Copalic acid is a chemical compound that is a constituent of copaiba oil, an oleoresin extracted from trees in the genus Copaifera.^[1] It is a diterpenoid of the labdane class.^[2]

Because copaiba oil has some uses in traditional herbal medicine, there has been scientific interest in investigating the potential pharmacology of its constituents, including copalic acid.^[2]^[3] In addition, synthetic derivatives of copalic acid have been investigated for their potential pharmacology as well.^[4]

Several laboratory syntheses of copalic acid have been reported.^[5]^[6]

References

^ Souza, Ariana Borges; Moreira, Monique Rodrigues; Borges, Carly Henrique Gambeta; Simão, Marília Rodrigues; Bastos, Jairo Kenupp; Sousa, João Paulo Barreto; Ambrosio, Sérgio Ricardo; Veneziani, Rodrigo Cassio Sola (2012). "Development and validation of a rapid RP-HPLC method for analysis of (−)-copalic acid in copaíba oleoresin". Biomedical Chromatography. 27 (3): 280–283. doi:10.1002/bmc.2788. PMID 22847230.
^ ^a ^b Medeiros, Vanessa Gonçalves; Durán, Fernando Javier; Lang, Karen Luise (2021). "Copalic Acid: Occurrence, Chemistry, and Biological Activities". Revista Brasileira de Farmacognosia. 31 (4): 375–386. doi:10.1007/s43450-021-00173-2. S2CID 258704922.
^ Nakamura, Marcela; Endo, Eliana; De Sousa, João Paulo; Callejon, Daniel; Ueda-Nakamura, Tânia; Dias Filho, Benedito; De Freitas, Osvaldo; Nakamura, Celso; Lopes, Norberto (2016). "Copaiba Oil and Its Constituent Copalic Acid as Chemotherapeutic Agents against Dermatophytes". Journal of the Brazilian Chemical Society. doi:10.21577/0103-5053.20160309.
^ Idippily, Nethrie D.; Zheng, Qiaoyun; Gan, Chunfang; Quamine, Aicha; Ashcraft, Morgan M.; Zhong, Bo; Su, Bin (2017). "Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein". Bioorganic & Medicinal Chemistry Letters. 27 (11): 2292–2295. doi:10.1016/j.bmcl.2017.04.046. PMID 28442254.
^ Fujii, Mikio; Ishii, Sadayuki; Saito, Ryota; Akita, Hiroyuki (2009). "Enzymatic resolution of albicanol and its application to the synthesis of (−)-copalic acid". Journal of Molecular Catalysis B: Enzymatic. 59 (4): 254–260. doi:10.1016/j.molcatb.2008.07.004.
^ Xin, Zhengyuan; Lu, Yunlong; Xing, Xiaolan; Long, Jingjie; Li, Jiabin; Xue, Xiaowen (2016). "Synthesis of (−)-agathic acid and (−)-copalic acid from andrographolide via a regioselective Barton-McCombie reaction". Tetrahedron. 72 (4): 555–562. doi:10.1016/j.tet.2015.12.022.

[1] Souza, Ariana Borges; Moreira, Monique Rodrigues; Borges, Carly Henrique Gambeta; Simão, Marília Rodrigues; Bastos, Jairo Kenupp; Sousa, João Paulo Barreto; Ambrosio, Sérgio Ricardo; Veneziani, Rodrigo Cassio Sola (2012). "Development and validation of a rapid RP-HPLC method for analysis of (−)-copalic acid in copaíba oleoresin". Biomedical Chromatography. 27 (3): 280–283. doi:10.1002/bmc.2788. PMID 22847230.

[Medeiros-2] Medeiros, Vanessa Gonçalves; Durán, Fernando Javier; Lang, Karen Luise (2021). "Copalic Acid: Occurrence, Chemistry, and Biological Activities". Revista Brasileira de Farmacognosia. 31 (4): 375–386. doi:10.1007/s43450-021-00173-2. S2CID 258704922.

[3] Nakamura, Marcela; Endo, Eliana; De Sousa, João Paulo; Callejon, Daniel; Ueda-Nakamura, Tânia; Dias Filho, Benedito; De Freitas, Osvaldo; Nakamura, Celso; Lopes, Norberto (2016). "Copaiba Oil and Its Constituent Copalic Acid as Chemotherapeutic Agents against Dermatophytes". Journal of the Brazilian Chemical Society. doi:10.21577/0103-5053.20160309.

[4] Idippily, Nethrie D.; Zheng, Qiaoyun; Gan, Chunfang; Quamine, Aicha; Ashcraft, Morgan M.; Zhong, Bo; Su, Bin (2017). "Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein". Bioorganic & Medicinal Chemistry Letters. 27 (11): 2292–2295. doi:10.1016/j.bmcl.2017.04.046. PMID 28442254.

[5] Fujii, Mikio; Ishii, Sadayuki; Saito, Ryota; Akita, Hiroyuki (2009). "Enzymatic resolution of albicanol and its application to the synthesis of (−)-copalic acid". Journal of Molecular Catalysis B: Enzymatic. 59 (4): 254–260. doi:10.1016/j.molcatb.2008.07.004.

[6] Xin, Zhengyuan; Lu, Yunlong; Xing, Xiaolan; Long, Jingjie; Li, Jiabin; Xue, Xiaowen (2016). "Synthesis of (−)-agathic acid and (−)-copalic acid from andrographolide via a regioselective Barton-McCombie reaction". Tetrahedron. 72 (4): 555–562. doi:10.1016/j.tet.2015.12.022.

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