Myricitrin
Basic information
- CAS
17912-87-7- Standard SMILES
C[C@@H]1O[C@@H](Oc2c(-c3cc(O)c(O)c(O)c3)oc3cc(O)cc(O)c3c2=O)[C@H](O)[C@H](O)[C@H]1O- InChIKey
DCYOADKBABEMIQ-OWMUPTOHSA-N- Molecular formula
- C21H20O12
- Average molar mass
- 464.4 g/mol
- Monoisotopic mass
- 464.09547607
Overview
Myricitrin is a glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity. It has a role as an EC 2.7.11.13 (protein kinase C) inhibitor, an anti-allergic agent, an EC 1.14.13.39 (nitric oxide synthase) inhibitor and a plant metabolite. It is a pentahydroxyflavone, an alpha-L-rhamnoside, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to a myricetin. It is a conjugate acid of a myricitrin(1-).
Names & identifiers
- Preferred name
- Myricitrin
- IUPAC
- 5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
- English name
- Myricitrin
- Molecular formula
- C21H20O12
- Molecular weight
- 464.38
Names & synonyms
Myricitrin17912-87-7MyricitrosideMyricitrineMyricetin 3-O-rhamnosideMyricetin 3-O-alpha-L-rhamnopyranoside5Z0ZO61WPJDTXSID401707715,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-oneFEMA NO. 4491CHEBI:70082NSC-19803
Show more names
MYRICETIN-3-O-RHAMNOSIDECANNABISCITRINMYRICETIN-3-RHAMNOSIDEMIRICITRINMetricationMyricitrin>
5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside3,3',4',5,5',7-Hexahydroxyflavone 3-Rhamnoside5,7-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-oneRefChem:160395DTXCID5093262241-856-7MyricetrinMyricetol 3-rhamnoside
Database identifiers
- CAS
17912-87-7- PubChem CID
- 5281673
- DTXSID
DTXSID40170771- ChEMBL
CHEMBL454576、CHEMBL522983- ChEBI
CHEBI:70082- UNII
- 5Z0ZO61WPJ
- EC Number
- 241-856-7
- Nikkaji
- J986E
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 207 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 3
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 760
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Solubility
Practically insoluble to insoluble
Slightly Soluble (in ethanol)
Physical DescriptionLight yellow powder or mass, Slight bayberry aroma
Physicochemical properties
- Melting point
- 197 °C · 197°C(lit.)
- Boiling point
- 896.6 · 896.6±65.0 °C(Predicted)
- Density
- 1.88 · 1.88±0.1 g/cm3(Predicted)
- FEMA
- 4491 · 4491 | MYRICITRIN
- storage temp.
- -20 °C · -20°C
- solubility
- 93 mg/mL · Soluble to 93 mg/mL (200.26 mM) in DMSO
- pka
- 6.16 · 6.16±0.40(Predicted)
- form
- Solid
- color
- Light yellow to Yellow to Orange
- Odor
- bayberry waxy
- JECFA Number
- 2207 · 2207
- Cosmetics Ingredients Functions
- SKIN PROTECTINGANTIOXIDANT
- InChIKey
- DCYOADKBABEMIQ-AOSJLMIMNA-N
- SMILES
- O([C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O)C1C(C2=C(C=C(O)C=C2OC=1C1C=C(O)C(O)=C(O)C=1)O)=O |&1:1,3,5,7,9,r|
- LogP
- 1.98 · 1.98
- CAS DataBase Reference
- 17912 · 17912-87-7(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- MYRICITRIN
- FDA UNII
- 5 Z0ZO61WPJ · 5Z0ZO61WPJ
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 25 · NA.25
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29389090 · 29389090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- hs_code
- 29389090
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Uses & manufacturing
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
UsesIt was isolated from the leaves of Myrtus communis an inhibitory activity against nifuroxazide, aflatoxine B1 and H2O2 induced mutagenicity. Antioxidant
UsesIt was isolated from the leaves of Myrtus communis; shows antimutagenic activity. Myricitrin was a very potent radical scavenger with an IC50 value of 1.4 .mu.g/mL. Moreover, this compound induced an inhibitory activity against nifuroxazide, aflatoxine B1 and H2O2 induced mutagenicity. Antioxidant.
UsesMyricitrin may be used as an analytical reference standard for determination of the analyte in Folium Rhododendri Micranthi extract using high-performance liquid chromatography. It may also be used as an external standard in the validation of both commercial herbal medicines and crude material of Myrcia uniflora extracts using high-performance liquid chromatography technique.
General DescriptionProduced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: A glycosyloxyflavone that consists of myricetin attached to a alpha-L-rhamnopyranosyl residue at position 3 via a glycosidic linkage. Isolated from Myrica cerifera, it exhibits anti-allergic activity.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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