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Key Documents

91255

Sigma-Aldrich

Myricitrin

≥99.0% (HPLC)

Synonym(s):

3,3′,4′,5,5′,7-Hexahydroxyflavone 3-O-rhamnoside, Myricetin 3-O-α-L-rhamnopyranoside, Myricetin 3-O-rhamnoside, Myricitroside

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About This Item

Empirical Formula (Hill Notation):
C21H20O12
CAS Number:
Molecular Weight:
464.38
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25

assay

≥99.0% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

light yellow

storage temp.

2-8°C

SMILES string

C[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4cc(O)c(O)c(O)c4)[C@H](O)[C@H](O)[C@H]1O

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

InChI key

DCYOADKBABEMIQ-OWMUPTOHSA-N

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Biochem/physiol Actions

The metabolite myricitrin, 3-O-rhamnoside of myricetin, is found in plants, e.g. in the bark of Myrica esculenta (Myricaceae) and in the leaves of Myrica gale and in Chrysobalanus icaco. It is a feeding stimulant for some leaf beetles; and shown to have strong antioxidant activity against DPPH. Myricitrin may be of potential interest in the management of inflammatory conditions, and could constitute an attractive molecule of interest for the development of new analgesic drugs. Myricitrin is a nitric oxide (NO) and protein kinase C (PKC) inhibitor that has central nervous system activity, including anxiolytic-like action.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Feeding stimulation of flavonoids for various leaf beetles (Coleoptera: Chrysomelidae).
Matsuda, K.
Appl. Entomol. Zool, 13, 228-230 (1978)
Lalith Jayasinghe et al.
Natural product research, 26(8), 717-721 (2011-09-20)
Chemical investigation of the leaves of Elaeocarpus serratus yielded myricitrin (1), mearnsetin 3-O-β-D-glucopyranoside (2), mearnsitrin (3), tamarixetin 3-O-α-L-rhamnopyranoside (4) and the fruits of Filicium decipiens yielded three flavonol glycosides, kaempferol 3-O-rutinoside (5), kaempferol 3-O-robinobioside (6) and trifolin (7). Compound 1
Flavia Carla Meotti et al.
The Journal of pharmacology and experimental therapeutics, 316(2), 789-796 (2005-11-02)
The present study investigated the antinociceptive effects of the flavonoid myricitrin in chemical behavioral models of pain in mice and rats. Myricitrin given by i.p. or p.o. routes produced dose-related antinociception when assessed on acetic acid-induced visceral pain in mice.
Simone Quintyne-Walcott et al.
Journal of natural products, 70(8), 1374-1376 (2007-08-07)
A new cyclic nonapeptide, crotogossamide (1), was isolated from the latex of Croton gossypifolius. Its structure was elucidated by use of 1D and 2D NMR and MS and by hydrolysis followed by GC-MS analysis as cyclo(-Gly(1)-Ala(2)-Ser(3)-Gly(4)-Leu(5)-Asn(6)-Gly(7)-Ile(8)-Phe(9)-). This is the first
Wei Chen et al.
Food chemistry, 141(2), 927-933 (2013-06-26)
Peroxynitrite, a potent oxidising and nitrating species, has been implicated in the pathogenesis of neurodegenerative diseases. This study was undertaken to investigate the protective effect of myricitrin on peroxynitrite-mediated toxicity and the underlying mechanism. Our results showed that the presence

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