Levopimaric acid

Levopimaric acid
Names
IUPAC name
Abieta-11,13-dien-18-oic acid
Systematic IUPAC name
(1R,4aR,4bS,10aR)-1,4a-Dimethyl-7-(propan-2-yl)-1,2,3,4,4a,4b,5,9,10,10a-decahydrophenanthrene-1-carboxylic acid
Other names
13-isopropylpodocarpa-8(14),12-dien-15-oic acid; D6,8(14)-abietadienoic acid; l-pimaric acid; β-pimaric acid; l-sapietic acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
    Key: RWWVEQKPFPXLGL-ONCXSQPRSA-N
  • InChI=1/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/h6,12-13,16-17H,5,7-11H2,1-4H3,(H,21,22)/t16-,17+,19+,20+/m0/s1
    Key: RWWVEQKPFPXLGL-ONCXSQPRBO
  • O=C(O)[C@]3([C@@H]2CCC\1=C\C(=C/C[C@@H]/1[C@@]2(C)CCC3)C(C)C)C
Properties
C20H30O2
Molar mass 302.458 g·mol−1
Appearance Orthorhombic crystals
Melting point 150 °C (302 °F; 423 K)
Practically insoluble in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. Levopimaric acid accounts for about 18 to 25% of pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.