Communic acid
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| IUPAC name
(1S,4aR,5S,8aR)-1,4a-Dimethyl-6-methylidene-5-(3-methylpenta-2,4-dienyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C20H30O2 | |
| Molar mass | 302.458 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Communic acid is a naturally occurring labdane-type diterpenoid resin acid,[1][2] commonly present in the resins of several coniferous trees, particularly species of Juniperus and other Cupressaceae species.[3]
It has a molecular weight of 302.5 g/mol, and has been studied for its various biological activities, including antimicrobial, antibacterial and antitumor effects, and its use as a synthetic building block for other compounds.[4]
Chemistry and occurrence
[edit]Communic acid belongs to the labdane family of diterpenes and possesses a carboxylic acid functional group. It occurs mainly as two geometric isomers: the trans (E) and cis (Z) forms, which differ in the configuration of the double bond at C-13–C-14. Its molecular formula is C20H32O2, and it features a bicyclic skeleton typical of labdane diterpenes.
Communic acid and its derivatives have been isolated from the resins of Juniperus communis, Austrocedrus chilensis, and other conifers.[5] These resin acids play a defensive role in plants, deterring herbivores and inhibiting microbial growth.[6]
Recently, (+)-communic acid was isolated from the branches of Platycladus orientalis. This acid seems to exhibit protective effects against UVB-induced skin aging.[7]
Biological activity
[edit]Communic acid and its related diterpenes have shown antimicrobial, anti-inflammatory, and antioxidant activities in laboratory studies.[8] In organic synthesis, communic acid serves as a chiral building block (chiron) for constructing complex natural products.
See also
[edit]References
[edit]- ↑ "trans Communic acid". PubChem. Retrieved 2025-10-16.
- ↑ "Communic acid, (E)-". PubChem. Retrieved 2025-10-16.
- ↑ Barrero, Alejandro F.; Herrador, M. Mar; Arteaga, Pilar; Arteaga, Jesús F.; Arteaga, Alejandro F. (2012-02-06). "Communic Acids: Occurrence, Properties and Use as Chirons for the Synthesis of Bioactive Compounds". Molecules. 17 (2). MDPI AG: 1448–1467. doi:10.3390/molecules17021448. ISSN 1420-3049. PMC 6268269.
- ↑ Barrero, Alejandro F.; Arseniyadis, Siméon; Quílez del Moral, José F.; Herrador, M. Mar; Valdivia, M.; Jiménez, D. (2002-04-01). "First Synthesis of the Antifungal Oidiolactone C from trans -Communic Acid: Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds". The Journal of Organic Chemistry. 67 (8): 2501–2508. doi:10.1021/jo0161882. ISSN 0022-3263. Retrieved 2025-10-16.
- ↑ Olate, Verónica Rachel; Usandizaga, Olatz Goikoetxeaundia; Schmeda-Hirschmann, Guillermo (2011-12-20). "Resin Diterpenes from Austrocedrus chilensis". Molecules. 16 (12). MDPI AG: 10653–10667. doi:10.3390/molecules161210653. ISSN 1420-3049. PMC 6264339. PMID 22186953.
- ↑ Keeling, Christopher I.; Bohlmann, Jörg (2006). "Diterpene resin acids in conifers". Phytochemistry. 67 (22). Elsevier BV: 2415–2423. Bibcode:2006PChem..67.2415K. doi:10.1016/j.phytochem.2006.08.019. ISSN 0031-9422. PMID 16996548.
- ↑ "Communic acid ((+)-Communic acid)". MedchemExpress.com. Retrieved 2025-10-16.
- ↑ Jlizi, Salma; Zardi-Bergaoui, Afifa; Znati, Mansour; Flamini, Guido; Ascrizzi, Roberta; Ben Jannet, Hichem (2018). "Chemical composition and biological evaluation of the resin from Tetraclinis articulata (Vahl.) Masters: A promising source of bioactive secondary metabolites". Industrial Crops and Products. 124. Elsevier BV: 74–83. doi:10.1016/j.indcrop.2018.07.055. ISSN 0926-6690.