Velleral

Velleral

Names
IUPAC name 2,2,8-Trimethyl-1,2,3,3a,8,8a-hexahydro-5,6-azulenedicarbaldehyde
Identifiers
ChemSpider	20036851
Jmol interactive 3D	Image
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/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
SMILES O=C/C1=C/[C@@H]2CC(C)(C)C[C@@H]2[C@@H](C)/C=C1/C=O
Properties
Chemical formula	C15H20O2
Molar mass	232.146332 g/mol
Density	1.093 g/cm^3
Boiling point	341.125 °C (646.025 °F; 614.275 K)
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).
Infobox references

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.
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.
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.