Communic acid

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Communic acid
Names
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)
ChemSpider
  • InChI=1S/C20H30O2/c1-6-14(2)8-10-16-15(3)9-11-17-19(16,4)12-7-13-20(17,5)18(21)22/h6,8,16-17H,1,3,7,9-13H2,2,4-5H3,(H,21,22)/t16-,17+,19+,20-/m0/s1
    Key: YGBZFOQXPOGACY-CUDHKJQZSA-N
  • CC(=CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C)C=C
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).

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

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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

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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

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References

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  1. ^ "trans Communic acid". PubChem. Retrieved 2025-10-16.
  2. ^ "Communic acid, (E)-". PubChem. Retrieved 2025-10-16.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ "Communic acid ((+)-Communic acid)". MedchemExpress.com. Retrieved 2025-10-16.
  8. ^ 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.
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