Sandaracopimaric acid

Sandaracopimaric acid
Names
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
  • (-)-sandaracopimaric acid
  • Isodextropimaric acid
  • Pimaradienoic acid
  • (ent)-pimara-8(14),15-dien-19-oic acid
  • sandaracopimarate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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-KRFUXDQASA-N
  • CC1(CCC2C(=C1)CCC3C2(CCCC3(C)C(=O)O)C)C=C
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).
Infobox references

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]

Structure

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.

Biological activity

Sandaracopimaric acid demonstrates anti-inflammatory effects, notably by reducing contractions in phenylephrine-induced pulmonary arteries.[9] It acts as an inhibitor of GABA receptors and has been studied for potential therapeutic applications in inflammation-related conditions.[3][10][11]

Research suggests roles in plant-herbivore interactions and possible antimicrobial properties, though human clinical applications remain exploratory.

Uses

The acid is commercially available for research as a reference standard and is used in studies of diterpenoid biosynthesis and bioactivity.[12]

References

  1. ^ Glasby, J. S. (2 July 1991). Directory Of Plants Containing Secondary Metabolites. CRC Press. p. 913. ISBN 978-0-203-48987-1. Retrieved 29 January 2026.
  2. ^ Yang, Kai; Fei, Chenchen; Gao, Xiang (1 March 2024). "Mechanism exploration of SanShi ShengXin Ointment in the treatment of pressure ulcers based on network pharmacology and molecular docking". Medicine. 103 (9) e37390. doi:10.1097/MD.0000000000037390. ISSN 1536-5964. PMC 10906572. PMID 38428859.
  3. ^ a b "Sandaracopimaric acid". MedChemExpress. Retrieved 2026-01-29.
  4. ^ a b Edwards, O.E. (1960). "The Structure of Sandaracopimaric Acid". Canadian Journal of Chemistry. 38 (10): 1928–1935. Bibcode:1960CaJCh..38..663E. doi:10.1139/v60-096.
  5. ^ Afonso, A. (1968). "Synthesis of (-)-sandaracopimaric acid". Journal of the American Chemical Society. 90 (2): 399–405. Bibcode:1968JAChS..90.7375A. doi:10.1021/ja01028a053.
  6. ^ Nakanishi, Koji; Goto, Toshio; Itô, Shô (22 October 2013). Natural Products Chemistry: Volume 1. Academic Press. p. 217. ISBN 978-1-4832-1886-1. Retrieved 29 January 2026.
  7. ^ Kenkyūjo (Japan), Rikagaku (1964). Scientific Papers. Tokyo: Tokyo Institute of Physical and Chemical. p. 21. Retrieved 29 January 2026.
  8. ^ Comte, G.; Allais, D. P.; Simon, A.; Es-Saady, D.; Chulia, A. J.; Delage, C.; Saux, M. (1 February 1995). "Crystal Structure of Sandaracopimaric Acid, a Lipoxygenase Inhibitor from Juniperus phoenicea". Journal of Natural Products. 58 (2): 239–243. Bibcode:1995JNAtP..58..239C. doi:10.1021/np50116a012. ISSN 0163-3864. Retrieved 29 January 2026.
  9. ^ "CAS 471-74-9: (-)-Sandaracopimaric acid | CymitQuimica". cymitquimica.com. Retrieved 29 January 2026.
  10. ^ "Sandaracopimaric acid". TargetMol. Retrieved 2026-01-29.
  11. ^ "Sandaracopimaric acid". GLP Bio. Retrieved 2026-01-29.
  12. ^ "Sandaracopimaric acid". ChemSrc. Retrieved 2026-01-29.
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