Sandaracopimaric acid
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
(1R,4aR,4bS,7R,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H30O2 | |
| Molar mass | 302.458 g·mol−1 |
| Appearance | solid |
| Density | 1.05 g/cm3 |
| Melting point | 248 °C |
| Boiling point | 413.2 °C |
| poorly soluble | |
| Hazards | |
| Flash point | 198.7±23.4 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sandaracopimaric acid is a naturally occurring diterpenoid, a class of tricyclic organic compounds derived from plant resins.[1] It is characterized by its role as a plant metabolite and exhibits potential anti-inflammatory properties.[2][3]
Sandaracopimaric acid features a carboxylic acid group at the position 1 and a vinyl group at the position 7 on a phenanthrene backbone. The compound is a member of the pimaric acids group and also the larger group of resin acids.
The acid is an isomer of 4-epi-sandaracopimaric acid, pimaric acid, continentalic acid, and some other acids. The compound is chiral, with the levorotatory form ((-)-sandaracopimaric acid) being the predominant natural enantiomer.
Synthesis
The structure was identified in 1960 by O. E. Edwards.[4] The total synthesis of the natural enantiomer was achieved in 1968 by A. Afonso et al.[5] The process has 13 steps and starts with testosterone acetate.[6]
Natural occurrence
Sandaracopimaric acid was first isolated in the early 20th century by Henry and by Tschirch and Wolff from the resin of the sandarac tree, native to North Africa.[7][4] It has since been identified in various plant species, including: Ramalina hierrensis, Pinus armandii, Juniperus rigida, Wollemia nobilis, and many others, where it serves as a defense against herbivores.[8]
Sandaracopimaric acid is also found in other resins and terrestrial plants, contributing to their chemical defense mechanisms.