Apigenin 7-glucoside

Product Name: Apigenin 7-glucoside
CAS No.: 578-74-5
Chemical Name: Apigenin 7-glucoside
Synonyms: COSMOSIIN;APIGETRIN;APIGENIN-7-O-GLUCOSIDE;COSMETIN;APIGENIN-7-GLUCOSIDE;Apigenin-7-O-β-D-glucoside;Apigenin-7-O-β-D-glucopyranoside;apigenin 7-O-β-D-glucoside;Cosmosioside;Apigenin 7-O-β-glucoside
CBNumber: CB8468248
Molecular Formula: C21H20O10
Formula Weight: 432.38
MOL File: 578-74-5.mol

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Apigenin 7-glucoside Property

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)

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Safety

Safety Statements: 34/35
WGK Germany: 3
F: 3-10
HS Code: 29389090

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: Y0001777
Product name: Apigenin 7-glucoside
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 25 mg
Price: $236
Updated: 2025/07/31

Sigma-Aldrich

Product number: 44692
Product name: Apigenin 7-glucoside
Purity: analytical standard
Packaging: 5mg
Price: $242
Updated: 2025/07/31

Sigma-Aldrich

Product number: 44692
Product name: Apigenin 7-glucoside
Purity: analytical standard
Packaging: 25mg
Price: $807.5
Updated: 2025/07/31

Sigma-Aldrich

Product number: 00720585
Product name: Apigenin 7-glucoside
Purity: primary pharmaceutical reference standard
Packaging: 10mg
Price: $738
Updated: 2025/07/31

Cayman Chemical

Product number: 26813
Product name: Apigenin 7-glucoside
Packaging: 10mg
Price: $108
Updated: 2024/03/01

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Apigenin 7-glucoside Chemical Properties,Usage,Production

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

119249-30-8

578-74-5

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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Bonerge(Hunan) Lifescience Co., Ltd.

Product: Apigenin 7-glucoside 578-74-5
Price: US $0.00/kg
Min. Order: 25kg
Purity: 99%
Supply Ability: 8 tons
Release date: 2023-06-02

Shaanxi Haibo Biotechnology Co., Ltd

Product: Apigenin 7-glucoside 578-74-5
Price: US $0.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 2000ton
Release date: 2023-09-07

Shanghai Standard Technology Co., Ltd.

Product: Apigenin 7-glucoside 578-74-5
Price: US $0.00/mg
Min. Order: 5mg
Purity: ≥98%(HPLC)
Supply Ability: 10 g
Release date: 2019-11-22

578-74-5, Apigenin 7-glucosideRelated Search:

APIGENIN-7-GLUCURONIDE Apigenin 7-O-(2G-rhaMnosyl)gentiobioside APIIN Apigenin 2,5-DIDEOXY-2,5-IMINO-D-MANNITOL AMYLOGLUCOSIDASE CHLOROPHOSPHONAZO III Polydextrose L-Aspartic acid L-Theanine 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

COSMETIN

4H-1-Benzopyran-4-one,7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)

Apigenin 7-beta-D-glucoside

Apigenin 7-glucoside SynonyMs:Apigetrin

Apigenin 7-b-D-glucoside

4H-1-Benzopyran-4-one,7-(b-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-

Apigenin 7-glucoside, >=98%

Apigetrin(Apigenin-7-O-glucoside)

5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Apigenin 7-glucoside, 98%, from Dendranthema indicum (L.) Des Moul.

5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-4-one

Apigenin 7-glucoside, BR

Apigenin, 7-β-D-glucopyranoside

COSMIIN

COSMOSIIN

APIGENIN-7-O-GLUCOSIDE

APIGENIN-7-GLUCOSIDE

APIGETRIN

7-O-BETA-D-GLUCOPYRANOSYLOXY-4',5-DIHYDROXYFLAVONE

7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

4H-1-Benzopyran-4-one, 7- (.beta.-D-glucopyranosyloxy)-5-hydroxy-2-(4- hydroxyphenyl)-

APIGENIN-7-O-GLUCOSIDE WITH HPLC

Apigetrin, Cosmosiin

Apigenin 7-β-D-glucoside

Cosmosioside

4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)- (9ci)

7-o-(beta-D-Glucosyl)apigenin

Apigenin, 7-beta-D-glucopyranoside

Cosemetin

APIGENIN-7-GLUCOSIDE (COSMOSIIN)(P)

APIGENIN-7-O-GLUCOSIDE hplc

Apigenin-7-O-β-D-glucopyranoside

APIGENIN-7-O-GLUCOSIDE (COSMOSIIN)(P)

APIGENIN-7-O-GLUCOSIDE (COSMOSIIN)(SH)

Apigenin-7-O-β-D-glucoside

Apigenin 7-glucoside (Apigenin-7-O-β-D-glucopyranoside

Apigenin 7-glucoside CRS

Thalictiin

5-Hydroxy-2-(4-hydroxyphenyl)-7-((2S,3S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one

apigenin 7-O-β-D-glucoside

Apigenin 7-O-β-glucoside

Apigenin 7-glucoside USP/EP/BP

5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Apigetrin (Apigenin-7-O-β-D-glucopyranoside

7-(β-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-...

Cosmoside

Apigenin 7-glucoside-RM

Apigenin-7-O-Glucoside(P)

Apigenin 7-glucoside, 10 mM in DMSO

Apigenin-7-O-β-D-glucopyranoside

578-74-5

547-74-5

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