myricitrin
flavone,3,3',4',5,5',7-hexahydroxy-,3-rhamnoside
Identification
| Name | myricitrin |
| CAS Number | 17912-87-7 |
| EINECS | 241-856-7 |
| FDA UNII | 5Z0ZO61WPJ |
| Molecular Formula | C21 H20 O12 |
| Molecular Weight | 464.38080000 |
| MDL Number | MFCD00016930 |
Regulatory
| JECFA Food Flavoring | 2207 myricitrin |
| FEMA Number | 4491 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 17912-87-7 ; MYRICITRIN |
Physical Properties
| Appearance | light yellow powder (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 197.00 to 199.00 °C. @ 760.00 mm Hg |
| Boiling Point | 895.00 to 897.00 °C. @ 760.00 mm Hg |
| Flash Point | 600.00 °F. TCC ( 315.56 °C. ) |
| logP (o/w) | -0.832 (est) |
| Soluble in | water, 2195 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antioxidants |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | flavoring agents |
| Recommendation for myricitrin usage levels up to | not for fragrance use. |
| baked goods | 10.00000 |
| beverages(nonalcoholic) | 10.00000 |
| beverages(alcoholic) | 10.00000 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 100.00000 |
| condiments / relishes | - |
| confectionery froastings | 10.00000 |
| egg products | - |
| fats / oils | 10.00000 |
| fish products | - |
| frozen dairy | 10.00000 |
| fruit ices | 10.00000 |
| gelatins / puddings | 10.00000 |
| granulated sugar | - |
| gravies | - |
| hard candy | 10.00000 |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | 10.00000 |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | 10.00000 |
| soft candy | 10.00000 |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
5,7-
dihydro-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxy-alpha-L-rhamnopyranoside
5,7-
dihydro-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxy-alpha-laevo-rhamnopyranoside
5,7-
dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-(3,4,5-trihydroxy-phenyl)-1-benzopyran-4-one
5,7-
dihydroxy-3-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
flavone,3,3',4',5,5',7-hexahydroxy-,3-rhamnoside
3,3',4',5,5',7-
hexahydroxyflavone 3-rhamnoside
myricetin 3-o-alpha-L-rhamnopyranoside
myricetin 3-o-alpha-L-rhamnoside
myricetin 3-O-rhamnoside
myricetin 3-ortho-alpha-L-rhamnopyranoside
myricetin 3-ortho-alpha-L-rhamnoside
myricetin 3-ortho-alpha-laevo-rhamnopyranoside
myricetin 3-ortho-alpha-laevo-rhamnoside
myricetin 3-rhamnoside
myricetol 3-rhamnoside
myricitroside
PubMed:
Protective effects of myricitrin against osteoporosis via reducing reactive oxygen species and bone-resorbing cytokines.
PubMed:
A novel copigment of quercetagetin for stabilization of grape skin anthocyanins.
PubMed:
Chemical components of Ardisia splendens leaves and their activity against coxsackie A16 viruses.
PubMed:
Antioxidative Properties and Ability of Phenolic Compounds of Myrtus communis Leaves to Counteract In Vitro LDL and Phospholipid Aqueous Dispersion Oxidation.
PubMed:
Identification of the metabolites of myricitrin produced by human intestinal bacteria in vitro using ultra-performance liquid chromatography/quadrupole time-of-flight mass spectrometry.
PubMed:
Decorosides A and B, cytotoxic flavonoid glycosides from the leaves of Rhododendron decorum.
PubMed:
Inhibition of catechol-o-methyltransferase (COMT) by myricetin, dihydromyricetin, and myricitrin.
PubMed:
A UHPLC-MS/MS method for simultaneous determination of six flavonoids, gallic acid and 5,8-dihydroxy-1,4-naphthoquinone in rat plasma and its application to a pharmacokinetic study of Cortex Juglandis Mandshuricae extract.
PubMed:
Anti-influenza sesquiterpene from the roots of Reynoutria japonica.
PubMed:
[Protective effect of different solvent extracts from platycladi cacumen carbonisatum on LPS-induced human umbilical vein endothelial cells damage].
PubMed:
Myricitrin Alleviates Methylglyoxal-Induced Mitochondrial Dysfunction and AGEs/RAGE/NF-κB Pathway Activation in SH-SY5Y Cells.
PubMed:
Amphetamine-induced appetitive 50-kHz calls in rats: a marker of affect in mania?
PubMed:
Simultaneous quantification and peroxynitrite-scavenging activities of flavonoids in Polygonum aviculare L. herb.
PubMed:
Myricitrin inhibits acrylamide-mediated cytotoxicity in human Caco-2 cells by preventing oxidative stress.
PubMed:
Antibacterial and anti-inflammatory effects of Syzygium jambos L. (Alston) and isolated compounds on acne vulgaris.
PubMed:
Oral administration of the flavonoid myricitrin prevents dextran sulfate sodium-induced experimental colitis in mice through modulation of PI3K/Akt signaling pathway.
PubMed:
[Protect effects and the underlying mechanisms of myricitrin against vascular endothelial cells apoptosis induced by oxidative stress].
PubMed:
Myricitrin protects against peroxynitrite-mediated DNA damage and cytotoxicity in astrocytes.
PubMed:
[Phenolic constituents of Ampelopsis grossedentata from zhangjiajie].
PubMed:
Flavonoid constituents in the leaves of Myrica rubra sieb. et zucc. with anti-inflammatory activity.
PubMed:
Study of the interaction of salmon sperm DNA with myricitrin-CPB based on the enhanced resonance light scattering signal and its potential application.
PubMed:
Inhibitory effects of myricitrin on oxidative stress-induced endothelial damage and early atherosclerosis in ApoE-/- mice.
PubMed:
Modeling anti-allergic natural compounds by molecular topology.
PubMed:
A new anti-inflammatory triterpene saponin isolated from Anabasis setifera.
PubMed:
Inhibition effects and induction of apoptosis of flavonoids on the prostate cancer cell line PC-3 in vitro.
PubMed:
Anti-inflammatory and antinociceptive activities of Campomanesia adamantium.
PubMed:
Identification of flavonoids and flavonoid rhamnosides from Rhododendron mucronulatum for. albiflorum and their inhibitory activities against aldose reductase.
PubMed:
Diarylheptanoid sulfates and related compounds from Myrica rubra bark.
PubMed:
Inhibitory effect of carob (Ceratonia siliqua) leaves methanolic extract on Listeria monocytogenes.
PubMed:
Chemical constituents of Indonesian plant Protium javanicum Burm. f. and their antifeedant activities against Coptotermes formosanus Shiraki.
PubMed:
Anti-inflammatory activity of Pistacia khinjuk in different experimental models: isolation and characterization of its flavonoids and galloylated sugars.
PubMed:
Inhibitory effects of constituents from Euphorbia lunulata on differentiation of 3T3-L1 cells and nitric oxide production in RAW264.7 cells.
PubMed:
Antioxidant flavonol glycosides from Elaeocarpus serratus and Filicium decipiens.
PubMed:
Triterpene hexahydroxydiphenoyl esters and a quinic acid purpurogallin carbonyl ester from the leaves of Castanopsis fissa.
PubMed:
Myricitrin, a nitric oxide and protein kinase C inhibitor, exerts antipsychotic-like effects in animal models.
PubMed:
Differential phenolic profiles in six African savanna woody species in relation to antiherbivore defense.
PubMed:
Ultrasound-assisted extraction of phenolic antioxidants from Acacia confusa flowers and buds.
PubMed:
Anti-allergic effect of the flavonoid myricitrin from Myrica rubra leaf extracts in vitro and in vivo.
PubMed:
Further antinociceptive effects of myricitrin in chemical models of overt nociception in mice.
PubMed:
The diarylheptanoid (+)-aR,11S-myricanol and two flavones from bayberry (Myrica cerifera) destabilize the microtubule-associated protein tau.
PubMed:
Structure-activity relationship of flavonoids derived from medicinal plants in preventing methylmercury-induced mitochondrial dysfunction.
PubMed:
Isoquercitrin is the most effective antioxidant in the plant Thuja orientalis and able to counteract oxidative-induced damage to a transformed cell line (RGC-5 cells).
PubMed:
Assessment of DNA damage induced by extracts, fractions and isolated compounds of Davilla nitida and Davilla elliptica (Dilleniaceae).
PubMed:
Two new C-glucosyl benzoic acids and flavonoids from Mallotus nanus and their antioxidant activity.
PubMed:
Simultaneous determination of myricitrin, hyperin, quercitroside, and quercetin in Folium Rhododendri Micranthi by RP-HPLC.
PubMed:
The flavonoid glycosides, myricitrin, gossypin and naringin exert anxiolytic action in mice.
PubMed:
Polyphenolic profile and bioactivity study of Oenothera speciosa Nutt. aerial parts.
PubMed:
Free radical scavenging and antielastase activities of flavonoids from the fruits of Thuja orientalis.
PubMed:
Inhibitory effect of Myrica bark on lipase activity in mouse plasma and gastrointestinal tract.
PubMed:
[Studies on chemical constituents of Heliciopsis lobata II].
PubMed:
Cytotoxic chalcones and antioxidants from the fruits of a Syzygium samarangense (Wax Jambu).
PubMed:
In vitro activity of uva-ursi against cytochrome P450 isoenzymes and P-glycoprotein.
PubMed:
Myricitrin as a substrate and inhibitor of myeloperoxidase: implications for the pharmacological effects of flavonoids.
PubMed:
Phytochemical investigation and hepatoprotective activity of Cupressus sempervirens L. leaves growing in Egypt.
PubMed:
Involvement of p38MAPK on the antinociceptive action of myricitrin in mice.
PubMed:
Crotogossamide, a cyclic nonapeptide from the latex of Croton gossypifolius.
PubMed:
Preventive effects of a flavonoid myricitrin on the formation of azoxymethane-induced premalignant lesions in colons of rats.
PubMed:
Antinociceptive action of myricitrin: involvement of the K+ and Ca2+ channels.
PubMed:
Flavonoids from the flower of Rhododendron yedoense var. poukhanense and their antioxidant activities.
PubMed:
Anti-allodynic property of flavonoid myricitrin in models of persistent inflammatory and neuropathic pain in mice.
PubMed:
Antioxidant galloylated flavonol glycosides from Calliandra haematocephala.
PubMed:
Influence of different phenolic copigments on the color of malvidin 3-glucoside.
PubMed:
[Studies on antiviral constituents in stems and leaves of Pithecellibium clypearia].
PubMed:
Potential polyphenol markers of phase change in apple (Malus domestica).
PubMed:
Enzymatic production of highly soluble myricitrin glycosides using beta-galactosidase.
PubMed:
Inhibition of thyroid peroxidase by Myrcia uniflora flavonoids.
PubMed:
Studies on nepalese crude drugs. XXVIII. Chemical constituents of Bhote Khair, the underground parts of Eskemukerjea megacarpum HARA.
PubMed:
Analysis of the antinociceptive effect of the flavonoid myricitrin: evidence for a role of the L-arginine-nitric oxide and protein kinase C pathways.
PubMed:
Transepithelial permeability of myricitrin and its degradation by simulated digestion in human intestinal Caco-2 cell monolayer.
PubMed:
Flavonoids from the leaves of Litsea japonica and their anti-complement activity.
PubMed:
Myricitrin degraded by simulated digestion inhibits oxidation of human low-density lipoprotein.
PubMed:
Complement inhibiting properties of dragon's blood from Croton draco.
PubMed:
[Studies on chemical constituents in herb of Polygonum orientale].
PubMed:
Mitochondrial-dependent, reactive oxygen species-independent apoptosis by myricetin: roles of protein kinase C, cytochrome c, and caspase cascade.
PubMed:
Myricetin inhibits matrix metalloproteinase 2 protein expression and enzyme activity in colorectal carcinoma cells.
PubMed:
PTP1B inhibitors from Ardisia japonica.
PubMed:
Analysis of polyphenolic antioxidants from the fruits of three pouteria species by selected ion monitoring liquid chromatography-mass spectrometry.
PubMed:
Dorycnioside, a new phenylbutanone glucoside from Dorycnium pentaphyllum subsp. herbaceum.
PubMed:
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
PubMed:
Bioactive novel polyphenols from the fruit of Manilkara zapota (Sapodilla).
PubMed:
Anti-complement activity of constituents from the stem-bark of Juglans mandshurica.
PubMed:
Phenolic compounds from Nymphaea odorata.
PubMed:
[Studies on the chemical constituents from Ampelopsis grossedentata].
PubMed:
Polyphenolic antioxidants from the fruits of Chrysophyllum cainito L. (Star Apple).
PubMed:
Phytochemical and pharmacological analysis of Bauhinia microstachya (Raddi) Macbr. (Leguminosae).
PubMed:
[Chemical constituents in aerial part of Ampelopsis grossedentata(Hand.-Mazz.) W.T. Wang].
PubMed:
Three new flavonol malonylrhamnosides from Ribes alpinum.
PubMed:
Oroxylin A inhibition of lipopolysaccharide-induced iNOS and COX-2 gene expression via suppression of nuclear factor-kappaB activation.
PubMed:
[Standardization of hazel leaf].
PubMed:
Japanese intake of flavonoids and isoflavonoids from foods.
PubMed:
Expression of antisense chalcone synthase RNA in transgenic hybrid walnut microcuttings. Effect on flavonoid content and rooting ability.
PubMed:
Flavan-3-ols isolated from some medicinal plants inhibiting COX-1 and COX-2 catalysed prostaglandin biosynthesis.
PubMed:
Antidiabetic principles of natural medicines. II. Aldose reductase and alpha-glucosidase inhibitors from Brazilian natural medicine, the leaves of Myrcia multiflora DC. (Myrtaceae): structures of myrciacitrins I and II and myrciaphenones A and B.
PubMed:
Isolation and characterization of Guiera senegalensis J.F.Gmel. active principles.
PubMed:
Effect of myricetin and other flavonoids on the liver plasma membrane Ca2+ pump. Kinetics and structure-function relationships.
PubMed:
Flavonol Glycosides from Moghania faginea.
PubMed:
[Constituents of Berchemia racemosa Sieb. et Zucc].
PubMed:
Inhibitory effects of flavonol glycosides on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion.
PubMed:
Preliminary pharmacological studies on Eugenia uniflora leaves: xanthine oxidase inhibitory activity.
PubMed:
Fast atom bombardment and tandem mass spectrometry for structure determination of steroid and flavonoid glycosides.
PubMed:
Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids.
PubMed:
Inhibition of human lens aldose reductase by flavonoids, sulindac and indomethacin.
PubMed:
Comparative mutagenesis of plant flavonoids in microbial systems.
PubMed:
Flavonoids as inhibitors of lens aldose reductase.
PubMed:
Isolation of myricadiol, myricitrin, taraxerol, and taraxerone from Myrica cerifera L. root bark.
PubMed:
Metabolism of myricetin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro.
PubMed:
Metabolism of myricitrin and 3,4,5-trihydroxyphenylacetic acid.
PubMed:
[Research on flavone heterosides: kaempferol-3-rhamnoglucoside, myricitrin, linarine, saponarine].
PubMed:
The origins of tannins and flavonoids in black-wattle barks and heartwoods, and their associated "non-tannin" components.
PubMed:
[ON THE FLAVONOIDS OF CAESALPINIA PULCHERRIMA SW: ISOLATION OF A FLAVONOSIDE IDENTIFIED AS MYRICITROSIDE].