Apigenin 7-glucoside Chemical Properties

Melting point:

230-237°C

Boiling point:

788.9±60.0 °C(Predicted)

Density 

1.642±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly, Sonicated), Methanol (Slightly)

pka

6.13±0.40(Predicted)

form 

Solid

color 

Pale Yellow to Yellow

BRN 

65669

Stability:

Hygroscopic

InChIKey

KMOUJOKENFFTPU-YUVSVTSJNA-N

SMILES

C1(C2=CC=C(O)C=C2)OC2=C(C(=CC(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C2)O)C(=O)C=1 |&1:17,20,22,24,r|

LogP

-0.040 (est)

CAS DataBase Reference

578-74-5(CAS DataBase Reference)

Safety Information

Safety Statements 

34/35

WGK Germany 

3

F 

3-10

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

Apigenin 7-glucoside Usage And Synthesis

Chemical Properties

White crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from patchouli, agrimony, water chestnut, and paper mulberry leaves.

Uses

Apigenin 7-Glucoside is a by-product during the synthesis of Isorhoifolin (I819700), a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects.

Application

Apigenin 7-glucoside is a flavonoid with anti-inflammatory and anxiolytic activities. It inhibits LPS-induced nitric oxide production in RAW 264.7 cells when used at concentrations ranging from 0.16 to 10 μM. In vivo, apigenin 7-glucoside (10 mg/kg) reduces pulmonary edema and lung inflammation in a mouse model of LPS-induced acute lung injury. It also increases the number of entries and the time spent in the open arms of the elevated plus maze in rats, indicating anxiolytic activity.

Definition

ChEBI: A glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage.

Biological Functions

Apigenin 7-glucoside inhibited HL-60 cell growth, dose- and time-dependently, but did not cause apoptosis. The distribution of cells at different stages in the cell cycle indicated an accumulation of treated cells in the G2/M phase. Moreover, apigenin 7-glucoside induced granulocytic differentiation of HL-60 cells[1].

Synthesis

Compound 1 (CAS: 119249-30-8, 150 mg, 0.25 mmol) was dissolved in a mixture of methanol (20 mL) and 30% ammonia (5 mL) under stirring conditions. The reaction mixture was stirred continuously for 12 hours at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate/methanol (3:1, v/v) as eluent to afford the target product 5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-benzopyran-4-one , a yellow solid (78 mg, 72% yield). The melting point of the product was 234-236°C (literature value: 238-239°C). The infrared spectrum (KBr pressed sheet, cm^-1 ) showed characteristic absorption peaks: 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895. the NMR hydrogen spectrum (400 MHz, DMSO-d6) δ: 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-5), 10.47 (s, 1H). 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 6.45 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1.6 Hz, 1.6 Hz), 6.85 (d, J = 1.6 Hz, 1.6 Hz, 1.6 Hz, 1.6 Hz, 1.6 Hz). 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H H-3,4,5,6). NMR carbon spectrum (100 MHz, DMSO-d6) δ: 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1. The calculated value of [M + Na]+ C21H20O10Na by high resolution mass spectrometry (HRMS) was 455.3665 and the measured value was 455.3649.

References

[1] Eri Nakazaki. “Proteomic study of granulocytic differentiation induced by apigenin 7-glucoside in human promyelocytic leukemia HL-60 cells.” European Journal of Nutrition 52 1 (2013): 25–35.

Apigenin 7-glucoside(578-74-5)Related Product Information

• APIGENIN-7-GLUCURONIDE
• Apigenin 7-O-(2G-rhaMnosyl)gentiobioside
• APIIN
• Apigenin
• 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL
• AMYLOGLUCOSIDASE
• CHLOROPHOSPHONAZO III
• Polydextrose
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• Hematoxylin
• evocarpine
• Sodium ferulic
• apigenin 7-O-(6-O-malonylglucoside)
• 5-[(β-D-Glucopyranosyl)oxy]-4',7-dihydroxyflavone
• Oxalic acid
• 6-beta-D-Glucopyranosyl-8-beta-D-xylopyranosylapigenin
• Apigenin 6-C-α-L-arabinopyranosyl-8-C-β-D-xylopyranoside