Glucoalyssin

Glucoalyssin
Identifiers
CAS Number	499-37-6;
PubChem CID	9589398;
CompTox Dashboard (EPA)	DTXSID40964470 ;
Properties
Chemical formula	C13H25NO10S3
Molar mass	451.5 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Glucoalyssin is an organic compound belonging to the group of glucosinolates, naturally found in cruciferous vegetables. It is structurally similar to glucoberteroin, which contains a thioether unit in the side chain rather than a sulfoxide unit.

Occurrence

Glucoalyssin was first isolated in the 1950s from Alyssum argenteum.^[1] It is also present in other species of the genus stonecrop (Alyssum), such as Alyssum montanum and Alyssum alyssoides. It generally occurs alongside smaller quantities of glucoberteroin, which is likely also the biosynthesis precursor of glucoalyssin. It is not present as a racemate but in a specific angle of rotation, existing as L-(-)-glucoalyssin.^[2] In Degenia velebitica, glucoalyssin coexists with glucoberteroin, primarily concentrated in the stems and leaves, whereas the seeds mainly contain glucoberteroin.^[3] A genetic study examined the formation of mustard oil glycosides with aliphatic side chains and their derivatives in rapeseed and other Brassica species. The study suggests that a specific gene locus determines side-chain length, with methionine chain elongation likely producing glucoiberverine (C₃), glucoerucin (C₄), and glucoberteroin (C₅). These compounds serve as precursors to compounds with sulfoxide or alkene side chains. For C₅ side chains, this includes glucoalyssin and glucobrassicanapin.^[4]

Properties

As a mustard oil glycoside, glucoalyssin can release a corresponding isothiocyanate, alyssin.^[2]

References

^ Otto-Erich Schultz, Werner Wagner (1956-07-01), "Glucoalyssin, ein neues Senfölglucosid aus Alyssum-Arten: XII. Mitt. über Senfölglucoside", Zeitschrift für Naturforschung B, vol. 11, no. 7, pp. 417–419, doi:10.1515/znb-1956-0712
^ ^a ^b Anders Kjær, Rolf Gmelin, S. Lindstedt, A. Norman, B. Thorell (1956), "isoThiocyanates. XIX. L(-)-5-Methylsulphinylpentyl isoThiocyanate, the Aglucone of a New Naturally Occurring Glucoside (Glucoalyssin).", Acta Chemica Scandinavica, vol. 10, pp. 1100–1110, doi:10.3891/acta.chem.scand.10-1100{{citation}}: CS1 maint: multiple names: authors list (link)
^ Gina R. De Nicola, Ivica Blažević, Sabine Montaut, Patrick Rollin, Josip Mastelić, Renato Iori, Arnaud Tatibouët (November 2011), "Glucosinolate Distribution in Aerial Parts of Degenia velebitica", Chemistry & Biodiversity, vol. 8, no. 11, pp. 2090–2096, doi:10.1002/cbdv.201100114{{citation}}: CS1 maint: multiple names: authors list (link)
^ R. Magrath, C. Herron, A. Giamoustaris, R. Mithen (August 1993), "The Inheritance of Aliphatic Glucosinolates in Brassica napus", Plant Breeding, vol. 111, no. 1, pp. 55–72, doi:10.1111/j.1439-0523.1993.tb00607.x{{citation}}: CS1 maint: multiple names: authors list (link)

[1] Otto-Erich Schultz, Werner Wagner (1956-07-01), "Glucoalyssin, ein neues Senfölglucosid aus Alyssum-Arten: XII. Mitt. über Senfölglucoside", Zeitschrift für Naturforschung B, vol. 11, no. 7, pp. 417–419, doi:10.1515/znb-1956-0712

[:0-2] Anders Kjær, Rolf Gmelin, S. Lindstedt, A. Norman, B. Thorell (1956), "isoThiocyanates. XIX. L(-)-5-Methylsulphinylpentyl isoThiocyanate, the Aglucone of a New Naturally Occurring Glucoside (Glucoalyssin).", Acta Chemica Scandinavica, vol. 10, pp. 1100–1110, doi:10.3891/acta.chem.scand.10-1100{{citation}}: CS1 maint: multiple names: authors list (link)

[3] Gina R. De Nicola, Ivica Blažević, Sabine Montaut, Patrick Rollin, Josip Mastelić, Renato Iori, Arnaud Tatibouët (November 2011), "Glucosinolate Distribution in Aerial Parts of Degenia velebitica", Chemistry & Biodiversity, vol. 8, no. 11, pp. 2090–2096, doi:10.1002/cbdv.201100114{{citation}}: CS1 maint: multiple names: authors list (link)

[4] R. Magrath, C. Herron, A. Giamoustaris, R. Mithen (August 1993), "The Inheritance of Aliphatic Glucosinolates in Brassica napus", Plant Breeding, vol. 111, no. 1, pp. 55–72, doi:10.1111/j.1439-0523.1993.tb00607.x{{citation}}: CS1 maint: multiple names: authors list (link)

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