ChemicalBook CAS DataBase List 32507-66-7

32507-66-7

Name	isorhapontigenin
CAS	32507-66-7
EINECS(EC#)	803-480-7
Molecular Formula	C15H14O4
MDL Number	MFCD12407151
Molecular Weight	258.27
MOL File	32507-66-7.mol

Synonyms

100mg 100MG/1G/100G Isorhapotigenin Isorhapotogenin sorhapontigenin isorhapontigenin isorhapontigenin, Ⅰ Isorhapontigenin&gt 3′-Methoxyresveratrol (E)-3'-Methoxystilbene-3,4',5-triol (E)-3'-Methoxy-3,4',5-stilbenetriol (E)-3-Methoxy-stilbene-4,3',5'-triol (E)-3,4',5-Trihydroxy-3'-methoxystilbene 3,4',5-Trihydroxy-3'-methoxy-trans-stilbene 5-[2-(4-hydroxy-3-methoxyphenyl)ethenyl]benzene-1,3-diol Isorhapontigenin ?(E)-3,4',5-Trihydroxy-3'-methoxystilbene (E)-5-[2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol 5-[(E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol 5-[(1E)-2-(4-Hydroxy-3-methoxyphenyl)ethenyl]-1,3-benzenediol 1,3-Benzenediol, 5-[(1E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]-

Chemical Properties

Melting point	180.0 to 184.0 °C
Boiling point	471.8±35.0 °C(Predicted)
density	1.345
storage temp.	room temp
solubility	DMSO: soluble15mg/mL, clear
form	powder
pka	9.16±0.10(Predicted)
color	white to light brown
InChI	InChI=1S/C15H14O4/c1-19-15-8-10(4-5-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
InChIKey	ANNNBEZJTNCXHY-NSCUHMNNSA-N
SMILES	C1(O)=CC(/C=C/C2=CC=C(O)C(OC)=C2)=CC(O)=C1

Safety Data

Hazard Codes	Xi
Risk Statements	37/38-41-43-51 less more
Safety Statements	26-36/37/39 less more
WGK Germany	3
HS Code	2909.50.5000
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Dam. 1 Skin Irrit. 2 STOT SE 3

Hazard Information

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from Belamcanda chinensis.

Uses

Isorhapontigenin, an orally bioavailable dietary polyphenol isolated from the Chinese herb Gnetum cleistostachyum, displays anti-inflammatory effects. Isorhapontigenin induces autophagy and inhibits invasive bladder cancer formation[1][2].

Definition

ChEBI: Isorhapontigenin is a stilbenoid.

Biochem/physiol Actions

Isorhapontigenin or 4-methoxyresveratrol is a stilbene derivative isolated from a number of plants including Chinese medical herbs Gnetum Cleistostachyum and Iris Domestica (Belamcanda chinensis, leopard lily), and wine grapes. Similarly to resveratrol, isorhapontigenin is a potent antioxidant that attenuates ROS generation. Also, Isorhapontigenin exhibits pro-apoptopic and anti-cancer activities through downregulation of XIAP (X-linked inhibitor of apoptosis protein).

References

[1] Yeo SCM, et al. Isorhapontigenin, a bioavailable dietary polyphenol, suppresses airway epithelial cell inflammation through a corticosteroid-independent mechanism. Br J Pharmacol. 2017 Jul;174(13):2043-2059. DOI:10.1111/bph.13803
[2] Liang Y, et al. SESN2/sestrin 2 induction-mediated autophagy and inhibitory effect of isorhapontigenin (ISO) on human bladder cancers. Autophagy. 2016 Aug 2;12(8):1229-39. DOI:10.1080/15548627.2016.1179403
[3] Jiang G, et al. Isorhapontigenin (ISO) Inhibits Invasive Bladder Cancer Formation In Vivo and Human Bladder Cancer Invasion In Vitro by Targeting STAT1/FOXO1 Axis. Cancer Prev Res (Phila). 2016 Jul;9(7):567-80. DOI:10.1158/1940-6207.CAPR-15-0338

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