Chemistry:Agathic acid
| File:Agathic acid.svg | |
| Names | |
|---|---|
| IUPAC name
(1S,4aR,5S,8aR)-5-[(E)-4-carboxy-3-methylbut-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
PubChem CID
|
|
| |
| |
| Properties | |
| C20H30O4 | |
| Molar mass | 334.456 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Agathic acid, also known as agathate,[1][2] is a diterpenoid resin acid (a labdane-type diterpene with carboxyl functionality) naturally found in the resins of coniferous trees, particularly in the family Araucariaceae (e.g. Agathis, Araucaria).[3][4][5]
Occurrence and chemical properties
Agathic acid is a component of kauri resin, also known as kauri gum from Agathis species, and is also found in some Araucaria resins. It contributes to the chemical profile and physical properties (e.g. durability) of those resins and is used as a biomarker in studies of fossil or subfossil resins and amber-like materials.[6]
Agathic acid has the following molecular formula, C20H30O4. It is a dicarboxylic or bicyclic carboxylic acid.[7][8] It is sometimes given the synonym labda-8(17),13-diene-15,19-dioic acid.[9]
Synthesis and bioactivity
A total synthesis of (–)-agathic acid was first reported in 2016, using andrographolide as starting material in circa 14 steps.[10]
Agathic acid is primarily known as a structural and chemical constituent of resins rather than as a major pharmacological agent. Some resin acids (including related ones) have mild antimicrobial or defensive roles in plants. In modern studies, synthetic derivatives of agathic acid are being investigated for biological effects.[11]
In 2025, a chemical investigation of the fungus Penicillium thomii yielded 14 agathic acid derivatives.[12]
See also
References
- ↑ https://hmdb.ca/metabolites/HMDB0248058 "Showing metabocard for Agathic acid (HMDB0248058)"
- ↑ 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 (Elsevier BV) 72 (4): 555–562. doi:10.1016/j.tet.2015.12.022. ISSN 0040-4020.
- ↑ acid CID Agathic acid from PubChem
- ↑ "Agathic Acid". https://pubchem.ncbi.nlm.nih.gov/compound/Agathic-acid.
- ↑ Frezza, Claudio; Sciubba, Fabio; De Vita, Daniela; Toniolo, Chiara; Foddai, Sebastiano; Tomassini, Lamberto; Petrucci, Rita; Bianco, Armandodoriano et al. (2022). "Non-volatile compounds from Araucaria columnaris (G.Forst.) Hook leaves". Biochemical Systematics and Ecology (Elsevier BV) 103. doi:10.1016/j.bse.2022.104430. ISSN 0305-1978. Bibcode: 2022BioSE.10304430F.
- ↑ Lee, S. P. (1977). "Distribution of diterpenoid resin acids in the Araucariaceae". Phytochemistry 16: 1425–1428.
- ↑ "Agathic acid". https://plantaedb.com/compounds/agathic-acid.
- ↑ "Agathic acid, 640-28-8". https://www.thegoodscentscompany.com/data/rw1491521.html.
- ↑ "Agathic acid, 640-28-8". https://www.thegoodscentscompany.com/data/rw1491521.html.
- ↑ 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 (Elsevier BV) 72 (4): 555–562. doi:10.1016/j.tet.2015.12.022. ISSN 0040-4020.
- ↑ Kumar, Ajay; Singh, Swati; Singh, Munmun Kumar; Gupta, Atul; Tandon, Sudeep; Verma, Ram Swaroop (2021-12-17). "Chemistry, Biological Activities, and Uses of Araucaria Resin". Reference Series in Phytochemistry. Cham: Springer International Publishing. p. 1–20. doi:10.1007/978-3-030-76523-1_28-1. ISBN 978-3-030-76523-1.
- ↑ Zhang, Yan; Wang, Huannan; Xiao, Jicheng; Xu, Wei; Liu, Wan; Luo, Zhuhua; Wu, Peng; Yang, Xinjia et al. (2025). "Agathic acid derivatives including a novel ferroptosis inhibitor from the fungus Penicillium thomii". Bioorganic Chemistry (Elsevier BV) 164. doi:10.1016/j.bioorg.2025.108867. ISSN 0045-2068. PMID 40819513.
External links
 |  |
