Aucubin

Aucubin
Names
	IUPAC name (1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl β-D-glucopyranoside
	Systematic IUPAC name (2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
	Other names Aucubin
Identifiers
CAS Number	479-98-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	50340
ChEMBL	ChEMBL514882 ;
ChemSpider	82585 ;
ECHA InfoCard	100.006.856
EC Number	207-540-8;
KEGG	C09771;
PubChem CID	91458;
UNII	2G52GS8UML ;
CompTox Dashboard (EPA)	DTXSID60963965 ;
	InChI InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1 Key: RJWJHRPNHPHBRN-FKVJWERZSA-N ; InChI=1/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1 Key: RJWJHRPNHPHBRN-FKVJWERZBS;
	SMILES O2\C=C/[C@@H]1[C@@H](C(=C/[C@H]1O)\CO)[C@@H]2O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)CO;
Properties
Chemical formula	C15H22O9
Molar mass	346.332 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Aucubin is an iridoid glycoside.^[1] Iridoids are commonly found in plants and function as defensive compounds.^[1] Iridoids decrease the growth rates of many generalist herbivores.^[2]

^ ^a ^b Nieminen M; Suomi J; Van Nouhuys S (2003). "Effect of iridoid glycoside content on oviposition host plant choice and parasitim in a specialist herbivore". J. Chem. Ecol. 29 (4): 823–843. doi:10.1023/A:1022923514534. PMID 12775146. S2CID 16553547.
^ Puttick G, Bowers M (1998). "Effect of qualitative and quantitative variation in allelochemicals on a generalist insect: Iridoid glycosides and southern armyworm". J. Chem. Ecol. 14 (1): 335–351. doi:10.1007/BF01022550. PMID 24277013. S2CID 28710791.

[pmid12775146-1] Nieminen M; Suomi J; Van Nouhuys S (2003). "Effect of iridoid glycoside content on oviposition host plant choice and parasitim in a specialist herbivore". J. Chem. Ecol. 29 (4): 823–843. doi:10.1023/A:1022923514534. PMID 12775146. S2CID 16553547.

[doi=10.1007/BF01022550-2] Puttick G, Bowers M (1998). "Effect of qualitative and quantitative variation in allelochemicals on a generalist insect: Iridoid glycosides and southern armyworm". J. Chem. Ecol. 14 (1): 335–351. doi:10.1007/BF01022550. PMID 24277013. S2CID 28710791.

[1]

[2]