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Palustric acid

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Palustric acid
Names
IUPAC name (1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,5,6,9,10,10a-octahydrophenanthrene-1-carboxylic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C20H30O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h12-13,17H,5-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1Key: MLBYBBUZURKHAW-MISYRCLQSA-N
SMILES
  • CC(C)C1=CC2=C(CC1)3(CCC(3CC2)(C)C(=O)O)C
Properties
Chemical formula C20H30O2
Molar mass 302.458 g·mol
Appearance colorless solid
Melting point 164.5 °C (328.1 °F; 437.6 K)
Solubility in water 2.41mg/L
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Palustric acid is an organic compound with the formula C20H30O2. It is classified as a diterpenoid (a C20 hydrocarbon with oxygenated groups) and a resin acid. Palustric acid is an isomer of abietic acid: the location of the two C=C bonds differ in these two compounds. It is a colorless solid that is soluble in polar organic solvents. In terms of biological function palustric acid protects its host trees, especially conifers, against insects, an example of plant defense against herbivory. It is biosynthesized from the C20 precursor geranylgeranyl diphosphate.

Safety

Palustric acid is very poorly soluble in water and has low acute toxicity.

References

  1. Fiebach, Klemens; Grimm, Dieter (2000). "Resins, Natural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a23_073. ISBN 3-527-30673-0.
  2. Martin, Diane; Tholl, Dorothea; Gershenzon, Jonathan; Bohlmann, Jörg (2002). "Methyl Jasmonate Induces Traumatic Resin Ducts, Terpenoid Resin Biosynthesis, and Terpenoid Accumulation in Developing Xylem of Norway Spruce Stems". Plant Physiology. 129 (3): 1003–1018. doi:10.1104/pp.011001. PMC 166496. PMID 12114556.
  3. Peng, Guomei; Roberts, John C. (2000). "Solubility and Toxicity of Resin Acids". Water Research. 34 (10): 2779–2785. Bibcode:2000WatRe..34.2779P. doi:10.1016/s0043-1354(99)00406-6.
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