velleral

{{chembox

| Verifiedfields =

| Watchedfields =

| verifiedrevid =

| ImageFile = Velleral.svg

| ImageSize = 200px

| PIN = (3aR,8R,8aR)-2,2,8-Trimethyl-1,2,3,3a,8,8a-hexahydroazulene-5,6-dicarbaldehyde

| OtherNames =

|Section1={{Chembox Identifiers

| ChemSpiderID = 20036851

| SMILES = O=C/C1=C/[C@@H]2CC(C)(C)C[C@@H]2[C@@H](C)/C=C1/C=O

| 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

| InChIKey = GUAUUIHVMRMGCT-MISXGVKJBT

| StdInChI = 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

| StdInChIKey = GUAUUIHVMRMGCT-MISXGVKJSA-N

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 479316

| CASNo = 50656-61-6

| CASNo_Ref = {{cascite|changed|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MS9HB5PQ54

| EINECS =

| PubChem = 14412869

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI =

| MeSHName =

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|Section2={{Chembox Properties

| C = 15 | H = 20 | O = 2

| Appearance =

| Density = 1.093 g/cm³

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 127.95

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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

{{Reflist|refs=

{{cite journal |vauthors=Anke H, Sterner O |title=Comparison of the antimicrobial and cytotoxic activities of twenty unsaturated sesquiterpene dialdehydes from plants and mushrooms |journal=Planta Medica |year=1991 |volume=57 |issue=4 |pages=344–6 |pmid=1775575 |doi=10.1055/s-2006-960114|s2cid=260248281 }}

{{cite journal |vauthors=Camazine S, Lupo TL Jr |year=1984 |title=Labile toxic compounds of the Lactarii: the role of the laticiferous hyphae as a storage depot for precursors of pungent dialdehydes |journal=Mycologia |volume=76 |issue=2 |pages=355–8 |jstor=3793113 |url=http://www.cybertruffle.org.uk/cyberliber/59350/0076/002/0355.htm |doi=10.2307/3793113|url-access=subscription }}

{{cite journal |vauthors=Fex T, Froborg J, Magnusson G, Thoren S |title=Fungal extractives .10. Alternative synthesis of velleral skeleton |journal=Journal of Organic Chemistry |year=1976 |volume=41 |issue=22 |pages=3518–20 |doi=10.1021/jo00884a005}}

{{cite journal |vauthors=Froborg J, Magnusson G, Thoren S |title=Fungal extractives .9. Synthesis of velleral skeleton and a total synthesis of pyrovellerolactone |journal=Journal of Organic Chemistry |year=1975 |volume=40 |issue=11 |pages=1595–601 |doi=10.1021/jo00899a017 }}

{{cite journal |vauthors=Froborg J, Magnusson G |title=Fungal extractives .12. Construction of vellerane skeleton with total syntheses of racemic velleral, vellerolactone, and pyrovellerolactone – revised structures |journal=Journal of the American Chemical Society |year=1978 |volume=100 |issue=21 |pages= 6728–33 |doi=10.1021/ja00489a030}}

{{cite journal |vauthors=List PH, Hackenberg H |title=Velleral und iso-Velleral, scharf schmeckende Stoffe aus Lactarius vellereus FRIES |trans-title=Velleral and iso-velleral, acrid-tasting compounds from Lactarius vellereus FRIES. 17. Mushroom contents |journal=Archiv der Pharmazie |year=1969 |volume=302 |issue=2 |pages=125–43 |doi=10.1002/ardp.19693020208 |pmid=5260842 |s2cid=84852148 |language=German}}

{{cite journal |vauthors=Magnusso G, Thoren S, Drakenbe T |title=Fungal extractives .4. Structure of a novel sesquiterpene dialdehyde from Lactarius by spectroscopic methods |journal=Tetrahedron |year=1973 |volume=29 |issue=11 |pages=1621–4 |doi= 10.1016/S0040-4020(01)83407-4}}

{{cite journal |vauthors=Sterner O, Bergman R, Kihlberg J, Wickberg B |title=The sesquiterpenes of Lactarius vellereus and their role in a proposed chemical defense system |journal=Journal of Natural Products |year=1985 |volume=48 |issue=2 |pages=279–88 |doi=10.1021/np50038a013 }}

}}

Category:Sesquiterpenes

Category:Azulenes

Category:Aldehydes