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Velleral

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Velleral
Names
Preferred IUPAC name (3aR,8R,8aR)-2,2,8-Trimethyl-1,2,3,3a,8,8a-hexahydroazulene-5,6-dicarbaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: 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/s1Key: GUAUUIHVMRMGCT-MISXGVKJBT
SMILES
  • O=C/C1=C/2CC(C)(C)C2(C)/C=C1/C=O
Properties
Chemical formula C15H20O2
Molar mass 232.323 g·mol
Density 1.093 g/cm
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 , 100 kPa). Infobox references
Chemical compound

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 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. First isolated in 1969, and characterized structurally in 1973, velleral has antimicrobial activity. Several syntheses have been devised.

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.
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