Mercusic acid

Mercusic acid
Names
IUPAC name
(1S,4aR,5S,8aR)-5-[(3S)-4-carboxy-3-methylbutyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Other names
  • Junicedric acid
  • 13S-Dihydroagathic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C20H32O4/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/h13,15-16H,2,5-12H2,1,3-4H3,(H,21,22)(H,23,24)/t13-,15-,16+,19+,20-/m0/s1 N
    Key: HPQKNJHVWUWAOR-BWCMQUJESA-N
  • C[C@@H](CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O)CC(=O)O
Properties
C20H32O4
Molar mass 336.472 g·mol−1
Density 1.09 g/cm3
Melting point 122–128 °C (252–262 °F; 395–401 K)
Practically insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Mercusic acid is a naturally occurring organic compound classified as a diterpenoid with the molecular formula C20H32O4.[1][2] The acid features a labdane skeleton with exocyclic double bond at C8(17) and carboxylic groups at C15 and C19.

Natural occurrence

Mercusic acid was obtained from rosin of Pinus merkusii, a conifer native to Southeast Asia, hence the name.[3][4] The acid is also found in such taxons as Brickellia glomerata, Cryptomeria japonica, Dicranopteris linearis, Juniperus formosana, Pinus yunnanensis, Cupressus sempervirens, among others.[5]

Pine resin acids generally deter pests and pathogens. As part of oleoresin, mercusic acid acts as a chemical defense against herbivores, fungi, and bacteria via antimicrobial and antioxidative properties.[6]

Uses

Natural resin acids present in rosin of Pinus species, including isopimaric acid, mercusic acid, neoabietic acid, dehydroabietic acid, and podocarpic acid, have been studied for their possible inhibitory effects on Epstein–Barr virus. The acid is also known for its cancer chemopreventive activity.[7][8]

References

  1. ^ "Mercusic acid | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp. Retrieved 23 February 2026.
  2. ^ "Chemical: Detail Information". koreantk.com. Retrieved 23 February 2026.
  3. ^ Glasby, J. S. (2 July 1991). Directory Of Plants Containing Secondary Metabolites. CRC Press. p. 922. ISBN 978-0-203-48987-1. Retrieved 23 February 2026.
  4. ^ Wood Industry Abstracts. Washington State University, Engineering Extension Service. 1974. p. 285. Retrieved 23 February 2026.
  5. ^ Kumar, Manish; Kumar, Praveen; Sharma, Ashita (31 January 2023). Bioactive Phytochemicals from Himalayas: A Phytotherapeutic Approach. Bentham Science Publishers. p. 7. ISBN 978-981-5123-29-6. Retrieved 23 February 2026.
  6. ^ López-Goldar, Xosé; Lundborg, Lina; Borg-Karlson, Anna Karin; Zas, Rafael; Sampedro, Luis (2020). "Resin acids as inducible chemical defences of pine seedlings against chewing insects". PLOS One. 15 (5) e0232692. doi:10.1371/journal.pone.0232692. ISSN 1932-6203. PMC 7194405. PMID 32357193.
  7. ^ Tanaka, Reiko; Tokuda, Harukuni; Ezaki, Yoichiro (November 2008). "Cancer chemopreventive activity of "rosin" constituents of Pinus spez. and their derivatives in two-stage mouse skin carcinogenesis test". Phytomedicine. 15 (11): 985–992. doi:10.1016/j.phymed.2008.02.020. PMID 18424098. Retrieved 23 February 2026.
  8. ^ Kumar, Manish; Kumar, Praveen; Sharma, Ashita (31 January 2023). Bioactive Phytochemicals from Himalayas: A Phytotherapeutic Approach. Bentham Science Publishers. p. 7. ISBN 978-981-5123-29-6. Retrieved 24 February 2026.
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