Pimaric acid

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]

Quick facts Names, Identifiers ...

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
CAS Number	127-27-5 Y
3D model (JSmol)	Interactive image
ChemSpider	191072 N
KEGG	C09159 N
PubChem CID	220338
UNII	88R98Z71NI Y
CompTox Dashboard (EPA)	DTXSID80858728
InChI 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
SMILES 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
Chemical formula	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). N verify (what is YN ?) Infobox references

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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.