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SMB00354

Sigma-Aldrich

Fraxinellone

≥98% (HPLC)

Synonym(s):

3-(3-Furyl)-3a,4,5,6-tetrahydro-3a,7-dimethylphthalide

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About This Item

Empirical Formula (Hill Notation):
C14H16O3
CAS Number:
28808-62-0
Molecular Weight:
232.28
MDL number:
MFCD11101451
UNSPSC Code:
41116107
PubChem Substance ID:
329824971

assay

≥98% (HPLC)

form

powder

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

CC1=C(C(O[C@H]2C3=COC=C3)=O)[C@@]2(C)CCC1

InChI

1S/C14H16O3/c1-9-4-3-6-14(2)11(9)13(15)17-12(14)10-5-7-16-8-10/h5,7-8,12H,3-4,6H2,1-2H3/t12-,14+/m0/s1

InChI key

XYYAFLHHHZVPRN-GXTWGEPZSA-N

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General description

Fraxinellone is a terpenoid found in the root bark of Dictamnus albus. It belongs to a small group of degraded limonoids.[1][2]

Biochem/physiol Actions

Fraxinellone possesses neuroprotective and vasorelaxing activities as well as anti-inflammatory properties.[3] Fraxinellone has been used as a potent therapeutic for T-cell-mediated liver disorders in humans.[1]

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SLBM4224

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Fraxinellone inhibits lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 expression by negatively regulating nuclear factor-kappa B in RAW 264.7 macrophages cells.
Kim J H, et al.
Biological & Pharmaceutical Bulletin, 32(6), 1062-1068 (2009)
Antimutagenic Activity of Isofraxinellone from Dictamnus dasycarpus
Miyazawa M, et al.
Journal of Agricultural and Food Chemistry, 43(6), 1428-1431 (1995)
Selective triggering of apoptosis of concanavalin A-activated T cells by fraxinellone for the treatment of T-cell-dependent hepatitis in mice
Sun Y, et al.
Biochemical Pharmacology, 77(11), 1717-1724 (2009)

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