Haematopodin
Names
Preferred IUPAC name
(6aR)-6,6a,9,10-Tetrahydro-2H,8H-[1,3]oxazolo[3,2-a]pyrrolo[4,3,2-de]quinoline-2,3(4H)-dione
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C13H12N2O3/c16-9-5-8-11-7(6-14-12(11)13(9)17)4-10-15(8)2-1-3-18-10/h5-6,10,14H,1-4H2/t10-/m1/s1 checkY
    Key: GTVMGUBGOSWMOJ-SNVBAGLBSA-N checkY
  • O=C3/C=C2/N4CCCO[C@@H]4Cc1c[nH]c(c12)C3=O
Properties
C13H12N2O3
Molar mass 244.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Haematopodin is the more stable breakdown product of Haematopodin B.[1] Both compounds are found in the mushroom Mycena haematopus, although haematopodin only occurs in trace amounts in fresh fruit bodies. Similar pigments (with the 1,3,4,5-tetrahydropyrrolo[4,3,2-de]quinoline structure), known as batzellins and damirones, have been found in sea sponges.[1] A chemical synthesis for haematopodin was reported in 1996. Key steps in the synthesis involved the addition of 3-[(2,4-dimethoxybenzyl)amino]-1-propanol to the indolo-6,7-quinone and cyclization of the resulting adduct with trifluoroacetic acid.[2]

References

  1. 1 2 Baumann, C.; Bröckelmann, M.; Fugmann, B.; Steglich, W.; Sheldrick, W. S. (1993). "Pigments of fungi. 62. Haematopodin, an unusual pyrrologuinone derivative isolated from the fungus Mycena haematopus, Agaricales". Angewandte Chemie International Edition in English. 32 (7): 1087–89. doi:10.1002/anie.199310871.
  2. ↑ Hopmann, C.; Steglish, W. (1996). "Synthesis of haematopodin – A pigment from the mushroom Mycena haematopus (Basidiomycetes)". Liebigs Annalen. 1996 (7): 1117–20. doi:10.1002/jlac.199619960709.
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