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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
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| E number | Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). |
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 | edit source]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 | edit source]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 | edit source]References
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External links
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