486-62-4, Ononin,
CAS:486-62-4
C22H22O9 / 430.405
MFCD00017464
Ononin is a furocoumarin that has been shown to have significant cytotoxicity in vitro. It also has the ability to modulate the response of cells to various stimuli by binding to DNA and activating transcription. Ononin can be found in pueraria lobata, which is a plant that is native to Japan and China, as well as in other plants such as kidney beans, ligustrum fruit, and fructus quinquefolii. The chemical structure of ononin has similarities with biochanin A, a compound found in black cohosh, which has been used for centuries for its purported anti-inflammatory properties.
Ononin is a glycoside isoflavone that has been found in soybeans and A. mongholicus and has anti-inflammatory and neuroprotective activities. Ononin (5 µM) inhibits LPS-induced production of nitrite, prostaglandin E2 (PGE2;), and the pro-inflammatory cytokines IL-1β, IL-6, and TNF-α by RAW 264.7 macrophages. It also inhibits glutamate-induced toxicity in rat adrenal PC12 cells when used at a concentration of 0.025 µg/ml.
Ononin analytical standard provided with w/w absolute assay, to be used for quantitative titration.
Ononin, also known as ononoside, belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. Ononin exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Within the cell, ononin is primarily located in the cytoplasm. Outside of the human body, ononin can be found in chickpea, pulses, and soy bean. This makes ononin a potential biomarker for the consumption of these food products.
CAS Number | 486-62-4 |
Product Name | Ononin |
IUPAC Name | 3-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
Molecular Formula | C22H22O9 |
Molecular Weight | 430.4 g/mol |
InChI | InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1 |
InChI Key | MGJLSBDCWOSMHL-MIUGBVLSSA-N |
SMILES | COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O |
Solubility | Soluble in DMSO |
Synonyms | Ononin, Formononetin 7-O-β-D-Glucopyranoside, Formononetin Glucoside, Formononetin 7-O-Glucoside |
Canonical SMILES | COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O |
Isomeric SMILES | COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O |
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