Myricetin

Names

[ CAS No. ]:
529-44-2

[ Name ]:
Myricetin

[Synonym ]:
Delphidenolon 1575
EINECS 208-463-2
MFCD00006827
3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
3,5,7,3',4',5'-hexahydroxyflavonol
2-(3,4,5-TRIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-1-BENZOPYRAN-4-ONE
Myricitin
Myricetin
Cannabiscetin
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
Myricetol
3 3' 4' 5 5' 7-hexahydroxyflavone
4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-
3,5,7,3',4',5'-Hexahydroxyflavone
3,3',4',5,5',7-hexahydroxyflavone

Biological Activity

[Description]:

Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Natural Products >> Flavonoids

Research Areas >> Cancer

[In Vitro]

Myricetin exhibits the scavenging activity towards a number of radicals and ions. It displays poor activity (IC50 value=1.4 mg/mL) in a superoxide dismutase (SOD)-like activity assay[1]. It prevents cancer cell death via apoptosis via regulation of PI3K/Akt and MAPK signalling pathways[2]. Myricetin exhibits antiphotoaging effects by quenching causative free radicals in the skin. Myricetin is able to suppress UVB-induced COX-2 expression in mouse skin epidermal JB6 P+ cells. It inhibits UVB-induced initiation of activator protein-1 and NF-κβ, as well as Fyn kinase activity[1]. Myricetin inhibits viability of SKOV3 ovarian cancer cells in a dose-dependent manner. It induces DNA DSBs and ER stress, which leads to apoptosis in SKOV3 cells[3]. Myricetin inhibits human Hsp70 by more than 80% with IC50 values of 83, 11 and 12 μM, respectively[4].

[In Vivo]

Treatment of orthotopic pancreatic tumors with myricetin results in tumor regression and decreases metastatic spread[2]. Exposure to 150 μM myricetin causes 14%, 26%, 5% and 49% inhibition of rabbit platelet aggregation, induced by ADP, arachidonic acid, collagen and PAF, respectively[5].

[Cell Assay]

Pancreatic cancer cells (MIA PaCa-2, Panc-1 or S2-013) or normal pancreatic ductal cells (PDCs) are treated with myricetin (12.5–200 μM). Cell viability is determined using the Dojindo Cell Counting Kit-8. Cells are seeded onto a 96-well plate at 1×104 cells per well and allowed to adhere overnight. After treatment with myricetin at various concentrations for 24 hours, 10 μL of the tetrazolium substrate is added to each well of the plate. Plates are incubated at 37°C for 1 hour, after which the absorbance at 450 nm is measured[2].

[Animal admin]

Mice: Mice are given daily intraperitoneal injections of myricetin (30mg/kg in the MIA PaCa-2 model and 50mg/kg in the S2-013 model) or vehicle (DMSO) for 35 days (MIA PaCa-2 model) or 18 days (S2-013 model). Ultrasound measurements are performed at regular intervals to monitor tumor growth. At the end of the in vivo experiment, tumor size is measured using calipers and tumor volume is calculated[2].

[References]

[1]. Semwal DK, et al. Myricetin: A Dietary Molecule with Diverse Biological Activities. Nutrients. 2016 Feb 16;8(2):90.

[2]. Phillips PA, et al. Myricetin induces pancreatic cancer cell death via the induction of apoptosis and inhibition of thephosphatidylinositol 3-kinase (PI3K) signaling pathway. Cancer Lett. 2011 Sep 28;308(2):181-8.

[3]. Xu Y, et al. Myricetin induces apoptosis via endoplasmic reticulum stress and DNA double-strand breaks in human ovarian cancer cells. Mol Med Rep. 2016 Mar;13(3):2094-100.

[4]. Jinwal UK, et al. Chemical Manipulation of Hsp70 ATPase Activity Regulates Tau Stability. J Neurosci. 2009 Sep 30;29(39):12079-88.

[5]. Tzeng SH, et al. Inhibition of platelet aggregation by some flavonoids. Thromb Res. 1991 Oct 1;64(1):91-100.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
747.6±60.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₁₅H₁₀O₈

[ Molecular Weight ]:
318.235

[ Flash Point ]:
285.9±26.4 °C

[ Exact Mass ]:
318.037567

[ PSA ]:
151.59000

[ LogP ]:
2.11

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.864

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK8646000

CHEMICAL NAME :: Flavone, 3,3',4',5,5',7-hexahydroxy-

CAS REGISTRY NUMBER :: 529-44-2

BEILSTEIN REFERENCE NO. :: 0332331

LAST UPDATED :: 199709

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C15-H10-O8

MOLECULAR WEIGHT :: 318.25

WISWESSER LINE NOTATION :: T66 BO EVJ CR CQ DQ EQ& DQ GQ IQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Mammal - cattle Cells - not otherwise specified

DOSE/DURATION :: 4 umol/L

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 44,882,1988

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LK8646000

[ HS Code ]:
2914501900

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

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