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APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE

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APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE Basic information

Product Name:
APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE
Synonyms:
  • 8-(α-L-Arabinopyranosyl)-6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  • Shaftoside
  • Apigenin 8-C-α-L-arabinoside 6-C-β-D-glucoside
  • 6-C-beta-D-Glucosyl-8-C-alpha-L-arabinosylapigenin
  • 4',5,7-Trihydroxy-6-(β-D-glucopyranosyl)-8-(α-L-arabinopyranosyl)flavone
  • Schaftoside, 98%, from Desmodium styracifolium (Osbeck) Merr.
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]-8-[(2S,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl]-4H-chromen-4-one (non-preferred name)
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2ytetrahydH-chromen-4-one (non-preferred name)
CAS:
51938-32-0
MF:
C26H28O14
MW:
564.5
EINECS:
218-362-5
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
  • plant extract
  • Tri-substituted Flavones
Mol File:
51938-32-0.mol
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APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE Chemical Properties

Melting point:
228℃
Boiling point:
935.0±65.0 °C(Predicted)
Density 
1.766
storage temp. 
2-8°C
solubility 
DMSO : 250 mg/mL (442.88 mM; Need ultrasonic)
form 
Solid
pka
5.70±0.40(Predicted)
color 
Yellow
InChIKey
NIABBGMPPWXWOJ-JQSBCWDXSA-N
SMILES
OC1=C([C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)C(O)=C2C(C=C(C3C=CC(O)=CC=3)OC2=C1[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O)=O |&1:3,4,5,7,9,30,33,35,37,r|
LogP
0.040 (est)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
RTECS 
DJ2977250
HS Code 
29389090
Storage Class
11 - Combustible Solids
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APIGENIN-6-GLUCOSIDE-8-ARABINOSIDE Usage And Synthesis

Chemical Properties

White crystalline powder, soluble in methanol, derived from Desmodium styracifolium.

Uses

Schaftoside is an inhibitor of cholestorol gallstone formation. Prevents hepatic fatty degeneration in mice.

Definition

ChEBI: A C-glycosyl compound that is apigenin substituted by beta-D-glucopyranosyl and an alpha-L-arabinopyranosyl moieties at positions 6 and 8 via C-glycos dic linkages.

Synthesis

An efficient method for the isolation of charophyllosides in the following steps:

(1) Take 2 kg of extract of Guangqian with content of about 20% and add 40% ethanol solution to formulate a sample solution of 60 mg/ml;

(2) Place the above sample solution in the crystallization kettle, open the CO2 gas cylinder in the supercritical device, pass CO2 to the crystallization kettle to reach the predetermined temperature 60 ?? and the pressure of 10MPa, turn off the gas cylinder, turn on the regulator to control the balance of the pressure, and the cycle of crystallization for 120min, collect the Crystals I;

(3) Dissolve the above crystals in 40% ethanol solution to form a sample solution of 60mg/ml, and repeat the crystallization 2 times according to the above conditions to obtain crystal III.

(4) The product 227g of 93.3% Xaveratoside can be obtained by high performance liquid chromatography.

IC 50

TLR4

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