KAEMPFEROL-3-O-RUTINOSIDE Chemical Properties

Melting point:

200°C (dec.)

Boiling point:

941.7±65.0 °C(Predicted)

Density 

1.76

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

6.20±0.40(Predicted)

color 

Off-White to Yellow

biological source

plant (Clematis cultivar)

Stability:

Hygroscopic

InChIKey

RTATXGUCZHCSNG-FVJKAJKWNA-N

SMILES

C1(O[C@H]2[C@H](O)[C@H]([C@H](O)[C@@H](CO[C@@H]3O[C@H]([C@H](O)[C@@H](O)[C@H]3O)C)O2)O)C(=O)C2=C(C=C(O)C=C2O)OC=1C1C=CC(O)=CC=1 |&1:2,3,5,6,8,11,13,14,16,18,r|

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-45-24/25

WGK Germany 

3

HS Code 

29389090

KAEMPFEROL-3-O-RUTINOSIDE Usage And Synthesis

Description

Nicotiflorin is a flavonoid that has been found in I. glandulifera and has antioxidant and neuroprotective activities. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) and ABTS radicals with EC₅₀ values of 0.52 and 0.48 mg/ml, respectively, in cell-free assays. Nicotiflorin (1 μM) prevents hydrogen peroxide-induced decreases in tyrosine hydroxylase activity in PC12 cells and cell death in primary rat mesencephalic neurons. It decreases infarct volume by 24.5, 45.8, and 63.2% when administered at doses of 2.5, 5, and 10 mg/kg, respectively, in a rat model of cerebral ischemia-reperfusion injury induced by transient middle central artery occlusion (MCAO).

Chemical Properties

Light yellow needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Sophora japonica seeds and safflower.

Uses

Kaempferol 3-O-β -Rutinoside is a flavonoid antioxidant compound from Cichorium spinosum L. ecotype plants and also may display anti-diabetic activity. It is a component of many plant species including Helianthemum ruficomum.

Definition

ChEBI: Kaempferol-3-rutinoside is a kaempferol O-glucoside that is kaempferol attached to a rutinosyl [6-deoxy-alpha-L-mannosyl-(1->6)-beta-D-glucosyl] residue at position 3 via a glycosidic linkage. It has been isolated from the leaves of Solanum campaniforme. It has a role as a metabolite, a radical scavenger and a plant metabolite. It is a rutinoside, a trihydroxyflavone, a disaccharide derivative and a kaempferol O-glucoside.

General Description

Kaempferol 3-O-β -rutinoside is a bitter tasting flavonol glycoside that was isolated from flowers of a Clematis cultivar.

in vivo

References

[1] KATARZYNA SZEWCZYK . Phenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities[J]. Natural Product Research, 2019, 33 19: Pages 2851-2855. DOI: 10.1080/14786419.2018.1499644
[2] WEI QU . Kaempferol Derivatives Prevent Oxidative Stress–Induced Cell Death in a DJ-1–Dependent Manner[J]. Journal of pharmacological sciences, 2009, 110 2: Pages 191-200. DOI: 10.1254/jphs.09045fp
[3] RUNPING LI . Nicotiflorin reduces cerebral ischemic damage and upregulates endothelial nitric oxide synthase in primarily cultured rat cerebral blood vessel endothelial cells[J]. Journal of ethnopharmacology, 2006, 107 1: Pages 143-150. DOI: 10.1016/j.jep.2006.04.024

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