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Tiliroside

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Tiliroside Basic information

Product Name:
Tiliroside
Synonyms:
  • Kaempferol 3-O-β-D-(6?″-O-(E)-p-coumaroyl)glucopyranoside
  • 3-(4-hydroxyphenyl)-2-propenoicaci6’-esterwith3-(beta-d-glucopyranosylo
  • xy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4h-1-benzopyran-4-one
  • KAEMPFEROL-3-(P-COUMARYL)GLUCOSIDE
  • TILIROSIDE
  • 6''-O-trans-p-CouMaroylastragalin
  • 1-O-[5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl]-β-D-glucopyranose 6-[3-(4-hydroxyphenyl)propenoate]
  • 2-(4-Hydroxyphenyl)-3-[6-O-[3-(4-hydroxyphenyl)acryloyl]-β-D-glucopyranosyloxy]-5,7-dihydroxy-4H-1-benzopyran-4-one
CAS:
20316-62-5
MF:
C30H26O13
MW:
594.52
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • Flavanols
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
20316-62-5.mol
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Tiliroside Chemical Properties

Melting point:
257-260°C
Boiling point:
943.9±65.0 °C(Predicted)
Density 
1.68±0.1 g/cm3(Predicted)
Flash point:
311℃
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
DMSO : 250 mg/mL (420.51 mM; Need ultrasonic)
form 
Solid
pka
6.20±0.40(Predicted)
color 
Yellow
optical activity
[α]/D -65±8°, c = 0.1 in methanol
InChIKey
DVGGLGXQSFURLP-TXAASVHYNA-N
SMILES
C1(OC2=C(C(O)=CC(O)=C2)C(=O)C=1O[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](COC(=O)/C=C/C2=CC=C(O)C=C2)O1)O)C1C=CC(O)=CC=1 |&1:14,15,17,18,20,r|
LogP
3.830 (est)
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Safety Information

WGK Germany 
3
HS Code 
29389090
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Tiliroside Usage And Synthesis

Description

Tiliroside (kaempferol 3-O-β-d-glucopyranoside-6-p-coumaril ester) is a glycosidic flavonoid, and it is contained in several medicinal and dietary plants, such as linden, rose hip and strawberry. Tiliroside possesses anti-inflammatory, antioxidant, anticarcinogenic, cytochrome P450 inhibitory and hepatoprotective activities[1].

Uses

Tiliroside is an antioxidant, antiproliferating, and free radical scavenger agent.

Definition

ChEBI: Tribuloside is a glycosyloxyflavone that is kaempferol attached to a 6-O-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]-beta-D-glucopyranosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite. It is a glycosyloxyflavone, a cinnamate ester, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol and a trans-4-coumaric acid.

References

[1] Tsuyoshi Goto . “Tiliroside, a glycosidic flavonoid, ameliorates obesity-induced metabolic disorders via activation of adiponectin signaling followed by enhancement of fatty acid oxidation in liver and skeletal muscle in obese–diabetic mice.” Journal of Nutritional Biochemistry 23 7 (2012): Pages 768-776.

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