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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 Code

11 - Combustible Solids

WGK

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
M Pereira et al.
Progress in neuro-psychopharmacology & biological psychiatry, 35(7), 1636-1644 (2011-06-22)
Myricitrin is a nitric oxide (NO) and protein kinase C (PKC) inhibitor that has central nervous system activity, including anxiolytic-like action. Nitric oxide inhibitors blocked the behavioral effects of apomorphine, suggesting an antipsychotic-like effect. Furthermore, PKC inhibition reduced psychotic symptoms
Jeffrey R Jones et al.
Journal of natural products, 74(1), 38-44 (2010-12-15)
Target-based drug discovery for Alzheimer's disease (AD) centered on modulation of the amyloid β peptide has met with limited success. Therefore, recent efforts have focused on targeting the microtubule-associated protein tau. Tau pathologically accumulates in more than 15 neurodegenerative diseases
Shunsuke Shimosaki et al.
Natural product research, 25(4), 374-380 (2011-02-18)
Flavonoids are ingested by the general population as anti-oxidant and anti-inflammatory agents. In this study, we investigated the effects of myricitrin, a flavonoid rich in Myrica rubra leaf, upon anti-inflammatory action. Myrica rubra leaf extracts inhibited pro-inflammatory TNFα production in

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