| Identification | Back Directory | [Name]
SCIADOPITYSIN | [CAS]
521-34-6 | [Synonyms]
Nsc 45108
SCIADOPITYSIN
Einecs 208-311-5
SCIADOPITYSIN(SH)
4',4''',7-Trimethoxyamentoflavone
AMENTOFLAVONE-7,4',4'-TRIMETHYL ETHER
AMENTOFLAVONE-7,4',4''-TRIMETHYL ETHER
AMENTOFLAVONE-7,4',4'''-TRIMETHYL ETHER
Sciadopitysin, 95%, from Ginkgo biloba L.
AMENTOFLAVONE-7,4'',4''-TRIMETHYL ETHER WITH HPLC
5,5'',7''-Trihydroxy-4',4''',7-trimethoxy-3',8''-biflavone
5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl]-2-(4-methoxyphenyl)chromen-4-one
5,7-Dihydroxy-8-(5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl)-2-(4-methoxyphenyl)-4-benzopyrone
5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-methoxyphenyl)-4-benzopyrone
2-(4-Methoxyphenyl)-5,7-dihydroxy-8-[2-methoxy-5-(4-oxo-5-hydroxy-7-methoxy-4H-1-benzopyran-2-yl)phenyl]-4H-1-benzopyran-4-one
2-(4-Methoxyphenyl)-8-[6-methoxy-3-(4-oxo-5-hydroxy-7-methoxy-4H-1-benzopyran-2-yl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one
5,7-Dihydroxy-8-[2-methoxy-5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)phenyl]-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,5,7-dihydroxy-8-[5-(5-hydroxy-7-methoxy-4-oxo-4H-1-benzopyran-2-yl)-2-methoxyphenyl]-2-(4-methoxyphenyl)- | [EINECS(EC#)]
208-311-5 | [Molecular Formula]
C33H24O10 | [MDL Number]
MFCD00017448 | [MOL File]
521-34-6.mol | [Molecular Weight]
580.54 |
| Chemical Properties | Back Directory | [Melting point ]
296-298°C | [Boiling point ]
839.6±65.0 °C(Predicted) | [density ]
1.445±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in ethanol and methan | [form ]
powder | [pka]
6.16±0.40(Predicted) | [color ]
Light yellow | [InChIKey]
YCXRBCHEOFVYEN-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(OC)C=C2)OC2=C(C3=CC(C4OC5=CC(OC)=CC(O)=C5C(=O)C=4)=CC=C3OC)C(O)=CC(O)=C2C(=O)C=1 | [LogP]
5.500 (est) | [CAS DataBase Reference]
521-34-6 |
| Hazard Information | Back Directory | [Description]
Sciadopitysin is a biflavonoid originally isolated from G. biloba and has diverse biological activities.1,2,3,4 It reduces cytotoxicity induced by amyloid-β (1-42) (Aβ42; Item No. 20574) in PC12 cells (EC50 = 9.84 μM).2 Sciadopitysin (0.1-10 μM) decreases methylglyoxal-induced insulin secretion, production of reactive oxygen species (ROS), cardiolipin peroxidation, and cytotoxicity in RIN-m5F pancreatic β-cells.3 It inhibits P-glycoprotein (P-gp; IC50 = 53.42 μM) and increases cellular toxicity of paraquat and paclitaxel (Item No. 10461) in MDR1-MDCKII cells.5 Sciadopitysin inhibits RANKL-induced mRNA expression of the osteoclast-specific genes CTSK, TRAP, and MMP-9, activation of NF-κB, and osteoclastogenesis in a mouse model of LPS-induced bone loss.4 | [Chemical Properties]
White crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from ginkgo leaves and yew branches and leaves. | [Uses]
Sciadopitysin is a type of biflavonoids in leaves from ginkgo biloba[1]. Sciadopitysi inhibits RANKL-induced osteoclastogenesis and bone loss by inhibiting NF-κB activation and reducing the expression of c-Fos and NFATc1[2]. | [Definition]
ChEBI: A biflavonoid that is a 7, 4', 4'''-trimethyl ether derivative of amentoflavone. | [in vivo]
Sciadopitysin (i.p.; 10 mg/kg; every other day for 8 days) can reverse the bone loss in LPS-induced mice model (C57BL/6 mice; 6 weeks old)[2]. | [target]
ROS | MMP(e.g.TIMP) | NO | TNF-α | ATPase | cAMP | Beta Amyloid | [IC 50]
NF-κB | [storage]
4°C, protect from light | [References]
[1] Brian?on-Scheid F, et al. HPLC?Separation?and?Quantitative?Determination?of?Biflavones?in?Leaves?from?Ginkgo biloba. Planta Med.?1983 Dec;49(12):204-7. DOI:10.1055/s-2007-969851
[2] Sciadopitysin?suppresses?RANKL-mediated?osteoclastogenesis?and?prevents?boneloss?in?LPS-treated?mice. Int Immunopharmacol.?2017 Aug;49:109-117. DOI:10.1016/j.intimp.2017.05.029 |
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