Bourgeanic acid

Last updated
Bourgeanic acid
Bourgeanic acid.svg
Names
IUPAC name
(2S,3S,4R,6R)-3-[(2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoyl]oxy-2,4,6-trimethyloctanoic acid [1]
Other names
(+)-bourgeanic acid
Identifiers
3D model (JSmol)
ChEBI
PubChem CID
  • InChI=1S/C22H42O5/c1-9-13(3)11-15(5)19(23)17(7)22(26)27-20(18(8)21(24)25)16(6)12-14(4)10-2/h13-20,23H,9-12H2,1-8H3,(H,24,25)/t13-,14-,15-,16-,17+,18+,19+,20+/m1/s1
    Key: ZQEUMOKDJCSNHB-IHRHECOVSA-N
  • CC[C@@H](C)C[C@@H](C)[C@@H]([C@H](C)C(=O)O[C@@H]([C@H](C)C[C@H](C)CC)[C@H](C)C(=O)O)O
Properties
C22H42O5
Molar mass 386.573 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bourgeanic acid is a fatty acid with the molecular formula C22H42O5. [2] [3] [1] Bourgeanic acid is a lichen metabolite. [3] [2]

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A bryophilous lichen is one that grows on a bryophyte – that is, on a moss or liverwort. Those which grow on mosses are known as muscicolous lichens, while those grow on liverworts are called hepaticolous lichens. Muscicolous derives from the Latin muscus meaning moss, while the suffix colous means "living or growing in or on". Lichens are slow-growing organisms, and so are far more likely to be overgrown by a bryophyte than to overgrow one. However, they are better able to compete if the bryophyte is sickly or decaying and they can be parasitic upon them. Some, rather than overgrowing the bryophyte, instead live among its branches. Bryophilous lichens are particularly common in heathland and arctic or alpine tundra. Because many are small and inconspicuous, they are easy to overlook.

References

  1. 1 2 "Bourgeanic acid". Pubchem.ncbi.NLM.nih.gov.
  2. 1 2 Brodo, Irwin M.; Sharnoff, Sylvia Duran; Sharnoff, Stephen; Nature, Canadian Museum of (1 January 2001). Lichens of North America. Yale University Press. p. 247. ISBN   978-0-300-08249-4.
  3. 1 2 Majumdar, Krishna C.; Chattopadhyay, Shital K. (15 June 2011). Heterocycles in Natural Product Synthesis. John Wiley & Sons. p. 32. ISBN   978-3-527-63489-7.

Further reading