Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

Communic acid

From Wikipedia, the free encyclopedia
Labdane-type diterpenoid resin acid found in conifers
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 mass302.458 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Communic acid is a naturally occurringlabdane-typediterpenoidresin acid,[1][2] commonly present in theresins of several coniferous trees, particularly species ofJuniperus and otherCupressaceae 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 thelabdane family ofditerpenes 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 ofJuniperus 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 ofPlatycladus 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]
  1. ^"trans Communic acid".PubChem. Retrieved2025-10-16.
  2. ^"Communic acid, (E)-".PubChem. Retrieved2025-10-16.
  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. Retrieved2025-10-16.
  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. Retrieved2025-10-16.
  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.

External links

[edit]
Retrieved from "https://en.wikipedia.org/w/index.php?title=Communic_acid&oldid=1335699032"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2026 Movatter.jp