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Kaempferitrin

HCID 5486199
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Basic information

CAS
482-38-2
Standard SMILES
C[C@@H]1O[C@@H](Oc2cc(O)c3c(=O)c(O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)c(-c4ccc(O)cc4)oc3c2)[C@H](O)[C@H](O)[C@H]1O
InChIKey
PUPKKEQDLNREIM-QNSQPKOQSA-N
Molecular formula
C27H30O14
Average molar mass
578.5 g/mol
Monoisotopic mass
578.16355563

Overview

Kaempferol 3,7-di-O-alpha-L-rhamnoside is a glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis. It has a role as an antidepressant, a hypoglycemic agent, an antineoplastic agent, a bone density conservation agent, an immunomodulator, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a polyphenol, an alpha-L-rhamnoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol.

Names & identifiers

Preferred name
Kaempferitrin
IUPAC
5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]chromen-4-one
English name
KAEMPFERITRIN
Molecular formula
C27H30O14
Molecular weight
578.52

Names & synonyms

Kaempferitrin482-38-2LespenefrilKaempferol 3,7-dirhamnosidelespenephrilKaempferol 3,7-bisrhamnosideKaempferol-dirhamnosideVPV01U3R59DTXSID901974584H-1-Benzopyran-4-one, 3,7-bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-3,7-Bis((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy]chromen-4-one
Show more names
Kaempherol 3,7-bismannosideKAEMPFERITRIN(P)Kaempferitrin-RMKaempferitrin (LespedinKaeMpferol3,7bisrhaMnosideKAEMPFEROL-3,7-DIRHAMNOSIDE
3,7-Bis[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one3,7-bis-(alpha-6-deoxymannopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)chromen-4-oneRefChem:40778DTXCID00119949LespedinLespenephrylgrosvenorine II

Properties

Computed structural properties

XLogP
-0.1
Topological polar surface area
225 Ų
Hydrogen bond donors
8
Hydrogen bond acceptors
14
Rotatable bonds
5
Heavy atoms
41
Formal charge
0
Complexity
968

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Melting Point202 - 203 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
202 · 202~203℃
Boiling point
908.6 · 908.6±65.0 °C(Predicted)
Density
1.7 · 1.70
storage temp.
-20 °C · -20°C
solubility
125 mg/mL · DMSO : 125 mg/mL (216.07 mM; Need ultrasonic)
pka
5.81 · 5.81±0.40(Predicted)
form
powder
color
white to beige
biological source
(Cinnamomum sp.)
Stability
Hygroscopic
Major Application

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
WGK 3
hs_code
29389090
Signal word
Warning
Symbol(GHS)
GHS07,GHS02
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302+H312+H332-H315-H319-H228
Precautionary statements
P501-P261-P270-P240-P210-P241-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm
Applications · 3 items

DescriptionKaempferitrin is a flavonoid glycoside that has been found in B. pinnatum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 8.73 μg/ml) and is active against the bacteria S. aureus, P. aeruginosa, and S. typhi, as well as the fungi C. albicans, C. parapsilosis, and C. neoformans (MICs = 16-32 μg/ml). Kaempferitrin inhibits LPS-and IFN-γ-induced nitric oxide (NO) production in isolated mouse macrophages (IC50 = 40 μM). It decreases blood glucose levels in a rat model of alloxan-induced diabetes when administered at a dose of 100 mg/kg.

UsesKaempferitirin is a glycoside of Kaempferol (K100000), a plant flavonoid that exhibits antioxidant properties and is known to reduce risks of various types cancer and cardiovascular diseases. Kaempferitirin have been isolated as natural products from plants such as Hedyotis Verticilata.

General DescriptionThis substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Additional notes · 1 item

DefinitionChEBI: Kaempferol 3,7-di-O-alpha-L-rhamnoside is a glycosyloxyflavone that is kaempferol attached to alpha-L-rhamnopyranosyl residues at positions 3 and 7 respectively via glycosidic linkages. It has been isolated from the aerial parts of Vicia faba and Lotus edulis. It has a role as a bone density conservation agent, a hypoglycemic agent, an immunomodulator, an anti-inflammatory agent, an antineoplastic agent, a plant metabolite, an apoptosis inducer and an antidepressant. It is an alpha-L-rhamnoside, a monosaccharide derivative, a dihydroxyflavone, a glycosyloxyflavone and a polyphenol. It is functionally related to a kaempferol.

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Compound notes

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Database identifiers

CAS
482-38-2
PubChem CID
5486199
DTXSID
DTXSID90197458
ChEMBL
CHEMBL251766
ChEBI
CHEBI:68883
UNII
VPV01U3R59
Nikkaji
J94.496C
food and beverages
InChIKey
PUPKKEQDLNREIM-QNSQPKOQSA-N
SMILES
OC(C=C1)=CC=C1C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)C(C4=C(O)C=C(O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)C=C4O2)=O
FDA UNII
1 U3R59 · VPV01U3R59
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07,GHS02
Signal word
Warning
Hazard statements
302 · H302+H312+H332-H315-H319-H228
Precautionary statements
501 · P501-P261-P270-P240-P210-P241-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312
Safety Statements
24 · 24/25
WGK Germany
3 · WGK 3
HS Code
29389090 · 29389090
Storage Class
11 · 11 - Combustible Solids