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Pimaric acid

From Wikipedia, the free encyclopedia
Pimaric acid
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
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 ☒N
    Key: MHVJRKBZMUDEEV-APQLOABGSA-N ☒N
  • 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 mass302.458 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Pimaric acid is acarboxylic acid that is classified as aresin acid. It is a major component of the rosin obtained from pine trees.[1][2]

When heated above 100 °C, pimaric acid converts toabietic acid, which it usually accompanies in mixtures likerosin.

It is soluble inalcohols,acetone, andethers. The compound is colorless, but almost invariably samples are yellow or brown owing to air oxidation. As a mixture with abietic acid, it is oftenhydrogenated, 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

See also

[edit]

References

[edit]
  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.

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