Pimaric acid

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Pimaric acid
Pimaric acid structure.svg
Names
IUPAC name
Pimara-8(14),15-dien-18-oic acid
Systematic IUPAC name
(1R,4aR,4bS,7S,10aR)-7-Ethenyl-1,4a,7-trimethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene-1-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1 X mark.svgN
    Key: MHVJRKBZMUDEEV-APQLOABGSA-N X mark.svgN
  • InChI=1/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,13,15-16H,1,6-12H2,2-4H3,(H,21,22)/t15-,16+,18+,19+,20+/m0/s1
    Key: MHVJRKBZMUDEEV-APQLOABGBB
  • C[C@]1(CC[C@H]2C(=C1)CC[C@@H]3[C@@]2(CCC[C@@]3(C)C(=O)O)C)C=C
Properties
C20H30O2
Molar mass 302.458 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pimaric acid is a carboxylic acid that is classified as a resin acid. It is a major component of the rosin obtained from pine trees. [1] [2]

When heated above 100 °C, pimaric acid converts to abietic acid, which it usually accompanies in mixtures like rosin.

It is soluble in alcohols, acetone, and ethers. The compound is colorless, but almost invariably samples are yellow or brown owing to air oxidation. As a mixture with abietic acid, it is often hydrogenated, esterified, or otherwise modified to produce materials of commerce.

Abietic acid is closely related to and more common than pimaric acid, which is an isomer Abietic acid.svg
Abietic acid is closely related to and more common than pimaric acid, which is an isomer

See also

References

  1. "Pimaric acid". Merriam-Webster.
  2. Fiebach, Klemens; Grimm, Dieter (2000). "Resins, Natural". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a23_073. ISBN   978-3-527-30673-2.