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Copalic acid

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Copalic acid
Names
IUPAC name (E)-5--3-methylpent-2-enoic acid
Other names (-)-Copalic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: JFQBNOIJWROZGE-HPMXROJMSA-N
SMILES
  • C/C(=C\C(=O)O)/CC1C(=C)CC21(CCCC2(C)C)C
Properties
Chemical formula C20H32O2
Molar mass 304.474 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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

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. In addition, synthetic derivatives of copalic acid have been investigated for their potential pharmacology as well.

Several laboratory syntheses of copalic acid have been reported.

References

  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.
  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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