Agathic acid

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Agathic acid
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
  • InChI=1S/C20H30O4/c1-13(12-17(21)22)6-8-15-14(2)7-9-16-19(15,3)10-5-11-20(16,4)18(23)24/h12,15-16H,2,5-11H2,1,3-4H3,(H,21,22)(H,23,24)/b13-12+/t15-,16+,19+,20-/m0/s1
    Key: QYCOHMYDSOZCQD-GWEOMKHGSA-N
  • C/C(=C\C(=O)O)/CC[C@H]1C(=C)CC[C@@H]2[C@@]1(CCC[C@]2(C)C(=O)O)C
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).

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

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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

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A total synthesis of (–)-agathic acid was first reported in 2016, using andrographolide as starting material in 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

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References

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  1. ^ https://hmdb.ca/metabolites/HMDB0248058 "Showing metabocard for Agathic acid (HMDB0248058)"
  2. ^ 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. 72 (4). Elsevier BV: 555–562. doi:10.1016/j.tet.2015.12.022. ISSN 0040-4020.
  3. ^ acid CID Agathic acid from PubChem
  4. ^ "Agathic Acid". PubChem. Retrieved 2025-10-14.
  5. ^ Frezza, Claudio; Sciubba, Fabio; De Vita, Daniela; Toniolo, Chiara; Foddai, Sebastiano; Tomassini, Lamberto; Petrucci, Rita; Bianco, Armandodoriano; Serafini, Mauro (2022). "Non-volatile compounds from Araucaria columnaris (G.Forst.) Hook leaves". Biochemical Systematics and Ecology. 103 104430. Elsevier BV. Bibcode:2022BioSE.10304430F. doi:10.1016/j.bse.2022.104430. ISSN 0305-1978.
  6. ^ Lee, S. P. (1977). "Distribution of diterpenoid resin acids in the Araucariaceae". Phytochemistry. 16: 1425–1428.
  7. ^ "Agathic acid". Retrieved 15 October 2025.
  8. ^ "Agathic acid, 640-28-8". Retrieved 15 October 2025.
  9. ^ "Agathic acid, 640-28-8". Retrieved 15 October 2025.
  10. ^ 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. 72 (4). Elsevier BV: 555–562. doi:10.1016/j.tet.2015.12.022. ISSN 0040-4020.
  11. ^ 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. ISSN 2511-834X.
  12. ^ Zhang, Yan; Wang, Huannan; Xiao, Jicheng; Xu, Wei; Liu, Wan; Luo, Zhuhua; Wu, Peng; Yang, Xinjia; Zhang, Zhen; Cheng, Zhongbin (2025). "Agathic acid derivatives including a novel ferroptosis inhibitor from the fungus Penicillium thomii". Bioorganic Chemistry. 164 108867. Elsevier BV. doi:10.1016/j.bioorg.2025.108867. ISSN 0045-2068. PMID 40819513.
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