ChemicalBook--->CAS DataBase List--->17650-84-9

17650-84-9

17650-84-9 Structure

17650-84-9 Structure
IdentificationBack Directory
[Name]

KAEMPFEROL-3-O-RUTINOSIDE
[CAS]

17650-84-9
[Synonyms]

Nictoflorin
Nicotifiorin
NICOTIFLORIN
Nicotoflorin
Nicotiflorine
Nicotifloroside
Nictoflorin (incorr
Rutoside EP Impurity B
KAEMPFEROL-3-RUTINOSIDE
Kaempfeol-3-O-rutinoside
Kaempferol-3-O-rutinosid
Aempferol-3-O-rutinoside
KAEMPFEROL-3-O-RUTINOSIDE
KAEMPFEROL-3-RUTINOSIDE hplc
Kaempferol 3-rhamnoglucoside
Kaempferol-3-O-rutinosid ,98%
Kaempferol-3-O-beta-rutinoside
Rutoside Trihydrate EP Impurity B
KAEMPFEROL-3-O-RUTINOSIDE WITH HPLC
Kaempferol-3-O-rutinosid, ≥98.0%(HPLC)
KaeMpferol-3-O-rutinoside, Nicotiflorin
Kaempferol 3-O-β -Rutinoside (Nicotiflorin)
Nicotiflorin (Kaempferol-3-O-beta-Rutinoside)
3,4′,5,7-Tetrahydroxyflavone 3-rhamnoglucoside
KaeMpferol-3-O-rutinosid, froM CarthaMus tinctorius
Kaempferol-3-O-rutinosid, 98%, from Carthamus tinctorius L.
Rutoside Trihydrate Impurity 2(Rutoside Trihydrate EP Impurity B)
3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(4-hydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
3-[[6-O-(6-Deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-Mannopyranosyl)-b-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-
4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-
3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
[Molecular Formula]

C27H30O15
[MDL Number]

MFCD03427292
[MOL File]

17650-84-9.mol
[Molecular Weight]

594.52
Chemical PropertiesBack Directory
[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
[Cosmetics Ingredients Functions]

ANTIOXIDANT
SKIN CONDITIONING - EMOLLIENT
SKIN PROTECTING
[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 DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

22-45-24/25
[WGK Germany ]

3
[HS Code ]

29389090
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[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; Item No. 14805) and ABTS (Item No. 27317) 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]

At doses of 2.5, 5 and 10 mg/kg, nicotiflorin administered immediately after the onset of ischemia markedly reduces brain infarct volume and neurological deficits[2]. Nicotiflorin (2.5-10 mg/kg) administered after onset of ischemia markedly reduces brain infarct volume by 24.5-63.2% and neurological deficits[3].

[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
Spectrum DetailBack Directory
[Spectrum Detail]

KAEMPFEROL-3-O-RUTINOSIDE(17650-84-9)1HNMR
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