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Mercusic acid

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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 X markN
    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).
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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]

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