Hyperoside

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

Hyperoside

Names
IUPAC name 3-(β-D-Galactopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names Hyperozide Hyperasid Hyperosid Hyperin quercetin galactoside Quercetin-3-galactoside Quercetin-3-O-galactoside
Identifiers
CAS Number	482-36-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:67486 N
ChemSpider	4444962 N
ECHA InfoCard	100.006.892
KEGG	C10073 Y
PubChem CID	5281643
UNII	8O1CR18L82 Y
CompTox Dashboard (EPA)	DTXSID501028789
InChI InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1 N Key: OVSQVDMCBVZWGM-DTGCRPNFSA-N N InChI=1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1 Key: OVSQVDMCBVZWGM-DTGCRPNFBG
SMILES c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O
Properties
Chemical formula	C21H20O12
Molar mass	464.379 g·mol−1
Density	1.879 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Natural occurrences

Hyperoside has been isolated from Drosera rotundifolia, from the Lamiaceae Stachys sp. and Prunella vulgaris, from Rumex acetosella, Cuscuta chinensis seeds, from St John's wort and from Camptotheca acuminata.^[1] It is one of the phenolic compounds in the invasive plant Carpobrotus edulis and contributes to the antibacterial^[2] properties of the plant.

In Rheum nobile and R. rhaponticum, it serves as a UV blocker found in the bracts.

It is also found in Geranium niveum^[3] and Taxillus kaempferi.^[4]

References

1. Li, Shiyou; Zhang, Zhizhen; Cain, Abigail; Wang, Bo; Long, Melissa; Taylor, Josephine (2005). "Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated from Camptotheca acuminata". Journal of Agricultural and Food Chemistry. 53 (1): 32–7. doi:10.1021/jf0484780. PMID 15631505.
2. Van Der Watt, Elmarie; Pretorius, Johan C (2001). "Purification and identification of active antibacterial components in Carpobrotus edulis L". Journal of Ethnopharmacology. 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID 11378287.
3. Calzada, F; Cerda-García-Rojas, CM; Meckes, M; Cedillo-Rivera, R; Bye, R; Mata, R (1999). "Geranins a and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum". Journal of Natural Products. 62 (5): 705–9. doi:10.1021/np980467b. PMID 10346950.
4. The constituents of Taxillus kaempferi and the host, Pinus thunbergii. I. Catechins and flavones of Taxillus kaempferi. Konishi T, Nishio T, Kiyosawa S, Fujiwara Y and Konoshima T, Yakugaku Zasshi., February 1996, volume 116, issue 2, pages 148-157 (article in Japanese)