Isofraxidin

Names

[ CAS No. ]:
486-21-5

[ Name ]:
Isofraxidin

[Synonym ]:
isoferaxidin
7-Hydroxy-6,8-dimethoxy-2H-chromen-2-one
iso-Fraxidin
Phytodolor
6,8-dimethoxy-7-hydroxycoumarin
MFCD00221757
7-Hydroxy-6,8-dimethoxy-2H-1-benzopyran-2-one
7-Hydroxy-6,8-dimethoxy coumarin
2H-1- Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-
Coumarin,7-hydroxy-6,8-dimethoxy
Isofraxidin
7-hydroxy-6,8-dimethoxy-chromen-2-one
2H-1-Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-
6,8-Dimethoxyumbelliferone,7-Hydroxy-6,8-dimethoxychromen-2-one,7-Hydroxy-6,8-dimethoxycoumarin
Umbelliferone,6,8-dimethoxy
7-Hydroxy-6,8-dimethoxy-cumarin

Biological Activity

[Description]:

Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits MMP-7 expression and cell invasion of human hepatoma cells. Isofraxidin inhibits the phosphorylation of ERK1/2 in hepatoma cells[1]. Isofraxidin attenuates the expression of iNOS and COX-2, Isofraxidinalso inhibits TLR4/myeloid differentiation protein-2 (MD-2) complex formation[2].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Toll-like Receptor (TLR)

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

Signaling Pathways >> Metabolic Enzyme/Protease >> MMP

[Target]

COX-2

TLR4

MMP-7

[In Vitro]

Isofraxidin inhibits expression of MMP-7 and in vitro cell invasion at a non-toxic level through inhibiting ERK1/2 phosphorylation in hepatoma cell lines[1]. Isofraxidin competitively inhibits TLR4/MD-2 complex formation, and thus TLR4/NF-κB signalling cascades.Isofraxidin has potential in the treatment of Osteoarthritis (OA)[2].

[References]

[1]. Yamazaki T, et al. Isofraxidin, a coumarin component from Acanthopanax senticosus, inhibits matrix metalloproteinase-7 expression and cell invasion of human hepatoma cells.Biol Pharm Bull. 2010;33(10):1716-22.

[2]. Jin J , et al. Isofraxidin targets the TLR4/MD-2 axis to prevent osteoarthritis development.Food Funct. 2018 Nov 14;9(11):5641-5652.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
452.1±45.0 °C at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₁₁H₁₀O₅

[ Molecular Weight ]:
222.194

[ Flash Point ]:
183.2±22.2 °C

[ Exact Mass ]:
222.052826

[ PSA ]:
68.90000

[ LogP ]:
1.31

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.588

[ Storage condition ]:
?20°C

[ Water Solubility ]:
slightly soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ3100020

CHEMICAL NAME :: 2H-1-Benzopyran-2-one, 7-hydroxy-6,8-dimethoxy-

CAS REGISTRY NUMBER :: 486-21-5

BEILSTEIN REFERENCE NO. :: 0202652

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H10-O5

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,1330,1968

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

[ Safety Phrases ]:
S23-S28-S28A-S25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
OY2300000

Precursor & DownStream

Precursor

DownStream

Articles

Determination of isofraxidin and astilbin by HPLC in rat plasma and its application after orally administration the extract of Sarcandra glabra.

Pak. J. Pharm. Sci. 26(1) , 1-6, (2013)

Sarcandra glaber is a common traditional Chinese medicine used to treat psoriasis and other infectious diseases, isofraxidin and astilbin are the main components of it. In order to study the pharmacok...

Active components from Siberian ginseng (Eleutherococcus senticosus) for protection of amyloid β(25-35)-induced neuritic atrophy in cultured rat cortical neurons.

J. Nat. Med. 65(3-4) , 417-23, (2011)

Not only neuronal death but also neuritic atrophy and synaptic loss underlie the pathogenesis of Alzheimer's disease as direct causes of the memory deficit. Extracts of Siberian ginseng (the rhizome o...

Simultaneous determination of protocatechuic acid, syringin, chlorogenic acid, caffeic acid, liriodendrin and isofraxidin in Acanthopanax senticosus Harms by HPLC-DAD.

Biol. Pharm. Bull. 29(3) , 532-4, (2006)

A high performance liquid chromatography (HPLC) method was developed for the first time to quantify simultaneously the six major active ingredients in Acanthopanax senticosus (Rupr. et Maxim.) Harms, ...