Myricitrin

Myricitrin

Myricitrin structure Myricitrin structure
Names
IUPAC name 3′,4′,5,5′,7-Pentahydroxy-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name 5,7-Dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
Other names Myricitroside Myricitrine Myricetrin Myricetol 3-rhamnoside Myricetin 3-O-rhamnoside Myricetin 3-rhamnoside
Identifiers
CAS Number	17912-87-7 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70082 ☒N
ChEMBL	ChEMBL454576 ☒N
ChemSpider	4444992 ☒N
ECHA InfoCard
EC Number	241-856-7
E number
KEGG	C10108 checkY
PubChem CID	5281673
UNII	5Z0ZO61WPJ checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3/t6-,14-,17+,18+,21-/m0/s1 Key: DCYOADKBABEMIQ-OWMUPTOHSA-N
SMILES CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
Properties
Chemical formula	C21H20O12
Molar mass	464.37 g/mol
Density	1.882 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 checkY☒N ?) Infobox references

Myricitrin is a plant compound, the 3-O-α-L-rhamnopyranoside of myricetin.

Occurrences

It can be isolated from the root bark of Myrica cerifera (bayberry, a small tree native to North America), in Myrica esculenta, in Nymphaea lotus and N. odorata, in Chrysobalanus icaco and in Polygonum aviculare.

Myricitrin is used by several beetle species in their communication system. These include Plagioderma versicolora, Agelastica coerulea, Atrachya menetrisi, Altica nipponica, Altica oleracea, Gastrolina depressa.

Pharmacology

Myricitrin is a nitric oxide and protein kinase C inhibitor and exhibits antipsychotic-like and anxiolytic-like effects in animal models of psychosis and anxiety respectively.