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5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside

3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-benzopyran-4-one

CAS: 17912-87-7

Molecular Formula: C21H20O12

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5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Names and Identifiers

Name 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-benzopyran-4-one
Synonyms MYRICITRIN
myricitrin
17912-87-7
Myricetrin
CANNABISCITRIN
MYRICETIN-3-RHAMNOSIDE
MYRICETIN-3-O-RHAMNOSIDE
MYRICETIN-3-O-RHAVINOSIDE
5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside
5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxy-a-L-mannopyranoside
5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl-6-deoxy-alpha-L-mannopyranoside
5,7-Dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxy-alpha-L-mannopyranoside
3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-benzopyran-4-one
6-Désoxy-alpha-L-mannopyranoside de 5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphényl)-4H-chromén-3-yle
3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-benzopyran-4-one
4H-1-benzopyran-4-one, 3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
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-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-on
5,7-Dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphényl)-4H-chromén-4-one
5,7-Dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
CAS 17912-87-7
EINECS 241-856-7
InChI InChI=1/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

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Physico-chemical Properties

Molecular FormulaC21H20O12
Molar Mass464.38
Density1.88±0.1 g/cm3(Predicted)
Melting Point197°C(lit.)
Boling Point896.6±65.0 °C(Predicted)
Specific Rotation(α)-138.6 (c, 0.5 in MeOH)
Flash Point315.6°C
JECFA Number2207
Solubility Soluble in DMSO, hot methanol, slightly soluble in water and absolute ethanol.
Vapor Presure1.44E-34mmHg at 25°C
Appearancepale yellow flake crystal
ColorLight yellow to Yellow to Orange
pKa6.16±0.40(Predicted)
Storage Condition-20°C
Refractive Index1.805
MDLMFCD00016930
Physical and Chemical PropertiesYellow crystalline powder, soluble in water, soluble in methanol, ethanol, glacial acetic acid, from storage, Bayberry Bark, bayberry leaves.
In vitro studyMyricitrin, a compound isolated from the bark of the waxberry Myrica rubra, exerts analgesic effects. In rodent models of chemical and mechanical pain, Myricitrin produces significant analgesia by preventing activation of protein kinase C (PKC) α and PKC ε by phorbol ester (PMA). Another study demonstrated that the opening of voltage and small conductance calcium-gated K (+) channels and the reduction of calcium influx are responsible for the analgesic effect of myricitrin. Myricitrin also activates caspase-3 and MAPK signaling pathways by inhibiting p53 gene expression, and change the expression pattern of pro-apoptotic and anti-apoptotic genes and reduce the apoptosis induced by H 2 O 2 in vascular endothelial cells.
In vivo studyIn mice, myricitrin (I. p. 10 mg/kg or 30 mg/kg) blocked apomorphine-induced stereotyped behavior and climbing and increased hindlimb withdrawal time (HRT).

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Risk and Safety

Safety Description24/25 - Avoid contact with skin and eyes.
WGK Germany3
HS Code29389090

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Reference

Reference
Show more
1. Guo Shuangshuang Zheng Fangfang Ke Cong Xue et al. Analysis of Enzymatic Properties of α-L-rhamnosidase from Pediococcus lactis AS1.2696 [J]. Food Science 2019 040(004):160-169.
2. [IF = 4.098] Chunlin Li et al."Rapid and non-destructive discrimination of special-grade flat green tea using Near-infrared spectroscopy." Spectrochim Acta A. 2019 Jan;206:254
3. [IF = 3.738] Selma Houchi et al."Investigation of common chemical components and inhibitory effect on GES-type β-lactamase (GES22) in methanolic extracts of Algerian seaweeds." Microb Pathogenesis. 2019 Jan;126:56
4. [IF = 5.81] Mu Jianfei et al."Determination of Polyphenols in Ilex kudingcha and Insect Tea (Leaves Altered by Animals) by Ultra-high-performance Liquid Chromatography-Triple Quadrupole Mass Spectrometry (UHPLC-QqQ-MS) and Comparison of Their Anti-Aging Effects." Fro
5. [IF = 4.879] Yang Liu et al."UV-B Radiation Largely Promoted transformation of Primary Metabolites to Phenols in Astragalus mongholicus Seedlings." Biomolecules. 2020 Apr;10(4):504
6. [IF = 4.411] Min Yang et al."Comparative Transcriptome Analysis of Ampelopsis megalophylla for Identifying Genes Involved in Flavonoid Biosynthesis and Accumulation during Different Seasons." Molecules. 2019 Jan;24(7):1267
7. [IF = 4.36] Zhao-Yi Wang et al."Integrated strategy of LC-MS and network pharmacology for predicting active constituents and pharmacological mechanisms of Ranunculus japonicus Thunb. for treating rheumatoid arthritis." J Ethnopharmacol. 2021 May;271:113818
8. [IF = 6.576] Junkun Pan et al."Inhibition of Dipeptidyl Peptidase-4 by Flavonoids: Structure-Activity Relationship, kinetics and Interaction Mechanism." Frontiers in Nutrition. 2022; 9: 892426

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Nature

Open Data Verified Data

The melting point of myricetin containing one crystal of water of crystallization is 194 to 197 °c.

Last Update:2024-01-02 23:10:35

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Preparation Method

Open Data Verified Data

The fruits, bark and leaves of Myrica rubra were extracted with water, ethanol or methanol and refined.

Last Update:2022-01-01 11:13:50

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Use

Open Data Verified Data

can be used as an antioxidant. Added to cosmetics, has the effect of whitening the skin.

Last Update:2022-01-01 11:13:50

5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside - Reference Information

FEMA4491 | MYRICITRIN
Biological activity Myricitrin (Myricitrine) is a chemical compound that can be isolated from the root bark of Myrica cerifera (Bayberry genus, small tree, native to North America).
TargetValue
use used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: It has the effects of constricting blood vessels, raising blood pressure, exciting the heart, choleretic, anti-inflammatory, mutagenic, etc.
product name myricin; myricin; pentahydroxyflavone-3-rhamnoside
Last Update:2024-04-09 21:32:04
5,7-dihydroxy-4-oxo-2-(3,4,5-trihydroxyphenyl)-4H-chromen-3-yl 6-deoxyhexopyranoside
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Email: sales@chinaskyrun.com
Mobile: +8618958170122
QQ: 2531159185 Click to send a QQ messageSend QQ message
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Multiple SpecificationsSpot supply
Product Name: Myricitrin Visit Supplier Webpage Request for quotation
CAS: 17912-87-7
Tel: 609-228-6898
Email: sales@medchemexpress.com
     tech@medchemexpress.com
Mobile: 609-228-6898
SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
Spot supply
Product Name: Myricetrin Visit Supplier Webpage Request for quotation
CAS: 17912-87-7
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922 Click to send a QQ message
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Shanghai Macklin Biochemical Co., Ltd
Spot supply
Product Name: Myricitrin Visit Supplier Webpage Request for quotation
CAS: 17912-87-7
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328 Click to send a QQ message
WhatsApp: +86-18821248368
Shanghai Yuanye Bio-Technology Co., Ltd.
Multiple SpecificationsSpot supply
Product Name: Myricetrin Visit Supplier Webpage Request for quotation
CAS: 17912-87-7
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409 Click to send a QQ message
View History
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