Velleral

Velleral
Names
Preferred IUPAC name
(3aR,8R,8aR)-2,2,8-Trimethyl-1,2,3,3a,8,8a-hexahydroazulene-5,6-dicarbaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C15H20O2/c1-10-4-12(8-16)13(9-17)5-11-6-15(2,3)7-14(10)11/h4-5,8-11,14H,6-7H2,1-3H3/t10-,11+,14+/m0/s1
    Key: GUAUUIHVMRMGCT-MISXGVKJSA-N
  • InChI=1/C15H20O2/c1-10-4-12(8-16)13(9-17)5-11-6-15(2,3)7-14(10)11/h4-5,8-11,14H,6-7H2,1-3H3/t10-,11+,14+/m0/s1
    Key: GUAUUIHVMRMGCT-MISXGVKJBT
  • O=C/C1=C/[C@@H]2CC(C)(C)C[C@@H]2[C@@H](C)/C=C1/C=O
Properties
C15H20O2
Molar mass 232.323 g·mol−1
Density 1.093 g/cm3
Hazards
Flash point 127.95 °C (262.31 °F; 401.10 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Velleral (2,2,8-trimethyl-3,3a,8,8a-tetrahydro-1H-azulene-5,6-dicarbaldehyde) is a sesquiterpene dialdehyde found in certain mushrooms, like Lactarius torminosus[1] and Lactarius vellereus, after which it was named. The compound is thought to be part of a chemical defense system that protects the mushrooms against predation.[2] First isolated in 1969,[3] and characterized structurally in 1973,[4] velleral has antimicrobial activity.[5] Several syntheses have been devised.[6][7][8]

References

  1. ^ Camazine S, Lupo TL Jr (1984). "Labile toxic compounds of the Lactarii: the role of the laticiferous hyphae as a storage depot for precursors of pungent dialdehydes". Mycologia. 76 (2): 355–8. doi:10.2307/3793113. JSTOR 3793113.
  2. ^ Sterner O, Bergman R, Kihlberg J, Wickberg B (1985). "The sesquiterpenes of Lactarius vellereus and their role in a proposed chemical defense system". Journal of Natural Products. 48 (2): 279–88. doi:10.1021/np50038a013.
  3. ^ List PH, Hackenberg H (1969). "Velleral und iso-Velleral, scharf schmeckende Stoffe aus Lactarius vellereus FRIES" [Velleral and iso-velleral, acrid-tasting compounds from Lactarius vellereus FRIES. 17. Mushroom contents]. Archiv der Pharmazie (in German). 302 (2): 125–43. doi:10.1002/ardp.19693020208. PMID 5260842. S2CID 84852148.
  4. ^ Magnusso G, Thoren S, Drakenbe T (1973). "Fungal extractives .4. Structure of a novel sesquiterpene dialdehyde from Lactarius by spectroscopic methods". Tetrahedron. 29 (11): 1621–4. doi:10.1016/S0040-4020(01)83407-4.
  5. ^ Anke H, Sterner O (1991). "Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms". Planta Medica. 57 (4): 344–6. doi:10.1055/s-2006-960114. PMID 1775575. S2CID 260248281.
  6. ^ Froborg J, Magnusson G, Thoren S (1975). "Fungal extractives .9. Synthesis of velleral skeleton and a total synthesis of pyrovellerolactone". Journal of Organic Chemistry. 40 (11): 1595–601. doi:10.1021/jo00899a017.
  7. ^ Fex T, Froborg J, Magnusson G, Thoren S (1976). "Fungal extractives .10. Alternative synthesis of velleral skeleton". Journal of Organic Chemistry. 41 (22): 3518–20. doi:10.1021/jo00884a005.
  8. ^ Froborg J, Magnusson G (1978). "Fungal extractives .12. Construction of vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone – revised structures". Journal of the American Chemical Society. 100 (21): 6728–33. doi:10.1021/ja00489a030.