Rhamnazin

Modify Date: 2025-08-20 11:23:06

Rhamnazin Structure
Rhamnazin structure
Common Name Rhamnazin
CAS Number 552-54-5 Molecular Weight 330.29
Density 1.5±0.1 g/cm3 Boiling Point 591.6±50.0 °C at 760 mmHg
Molecular Formula C17H14O7 Melting Point 214-215℃
MSDS N/A Flash Point 221.2±23.6 °C

 Use of Rhamnazin


Rhamnazin is an orally active inhibitor of VEGFR2 signaling with an IC50 of 4.68 μM against VEGFR2 kinase. Rhamnazin shows potent antiangiogenic activity and antitumor efficacy[1]. Rhamnazin shows antioxidant and anti-inflammatory properties[2].

 Names

Name 3',7-Di-O-methyl Quercetin
Synonym More Synonyms

 Rhamnazin Biological Activity

Description Rhamnazin is an orally active inhibitor of VEGFR2 signaling with an IC50 of 4.68 μM against VEGFR2 kinase. Rhamnazin shows potent antiangiogenic activity and antitumor efficacy[1]. Rhamnazin shows antioxidant and anti-inflammatory properties[2].
Related Catalog
Target

VEGFR2:4.68 μM (IC50)

In Vitro Rhamnazin (5-40 μM) 抑制 VEGF 诱导的 HUVECs 增殖、迁移和成管[1]。 Rhamnazin (0-20 μM) 降低 VEGFR-2 酪氨酸激酶活性和 VEGFR-2 信号通路[1]。 Rhamnazin (0-40 μM; 24 h) 抑制乳腺癌细胞增殖和 VEGFR2 信号通路[1]。 Cell Migration Assay [1] Cell Line: HUVECs Concentration: 0, 10, 15 and 20 μM Incubation Time: 6 h Result: Strongly inhibited the migration of HUVECs. Western Blot Analysis[1] Cell Line: HUVECs Concentration: 0, 10, 15 and 20 μM Incubation Time: 24 h Result: Decreased VEGF binding to VEGFR2. Reduced VEGF-stimulated phosphorylation of VEGFR2 and its downstream MAPK, AKT, and STAT3 in HUVECs in a concentrationdependent manner. Cell Proliferation Assay[1] Cell Line: HCC1937, T-47D, SK-BR-3, MCF-7 and MDA-MB-231 Concentration: 0, 10, 15, 20, 30 and 40 μM Incubation Time: 24 h Result: Inhibited cell growth with IC50s of 19, 27, 32, 41 and 64 μM against MDA-MB-231, MCF-7, SK-BR-3, T-47D and HCC1937 in the presence of VEGF, respectively.
In Vivo Rhamnazin (200 mg/kg; i.g.; daily for 25 days) 抑制小鼠乳腺癌生长和血管生成[1]。 Rhamnazin (5-20 mg/kg; i.p.; once) 在大鼠急性肺损伤模型中显示出较强的抗氧化和抗炎作用[2]。 Animal Model: BALB/c nude mice, breast cancer xenograft model[1] Dosage: 200 mg/kg Administration: Intragastric administration, daily for 25 days Result: Dramatically suppressed tumor volumes by 47% compared with the vehicle group. Showed a significant reduction of pVEGFR2Tyr951-positive cells in tumors. Resulted in downregulation of VEGFR2 downstream molecules phosphorylation including MAPK, AKT and STAT3.
References

[1]. Yu Y, et al. Rhamnazin, a novel inhibitor of VEGFR2 signaling with potent antiangiogenic activity and antitumor efficacy. Biochem Biophys Res Commun. 2015 Mar 20;458(4):913-9.  

[2]. Wu G, et al. ANTIOXIDANT AND ANTI-INFLAMMATORY EFFECTS OF RHAMNAZIN ON LIPOPOLYSACCHARIDE-INDUCED ACUTE LUNG INJURY AND INFLAMMATION IN RATS. Afr J Tradit Complement Altern Med. 2017 Jun 5;14(4):201-212.  

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 591.6±50.0 °C at 760 mmHg
Melting Point 214-215℃
Molecular Formula C17H14O7
Molecular Weight 330.29
Flash Point 221.2±23.6 °C
Exact Mass 330.073944
PSA 109.36000
LogP 2.26
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.681

 Safety Information

HS Code 2914509090

 Synthetic Route

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Itokawa,H.; Oshida,Y. Phytochemistry (Elsevier), 1981 , vol. 20, p. 2421

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Kim, Bong-Gyu; Lee, Youngshim; Hur, Hor-Gil; Lim, Yoongho; Ahn, Joong-Hoon Phytochemistry, 2006 , vol. 67, # 4 p. 387 - 394

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Kuhn; Loew Chemische Berichte, 1944 , vol. 77/79, p. 211,213

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Rao; Seshadri Journal of the Chemical Society, 1946 , p. 771

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Anand et al. Proceedings - Indian Academy of Sciences, Section A, 1949 , # 29 p. 203,207

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Nair, G. Aravindakshan; Joshua, C. P.; Nair, A. G. Ramachandran Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981 , vol. 20, # 10 p. 939

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Rhamnazin Structure

Rhamnazin

CAS#:552-54-5

Literature: Rao; Seshadri Journal of the Chemical Society, 1946 , p. 771

 Customs

HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

 Synonyms

3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one
Rhamnazin
3,4',5-Trihydroxy-3',7-dimethoxyflavone
3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
Flavone, 3,4',5-trihydroxy-3',7-dimethoxy-
T66 BO EVJ CR DQ CO1& DQ GQ IO1
3,5-Dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4H-chromen-4-one
3',7-Dimethylquercetin
rhamnacene
4H-1-Benzopyran-4-one, 3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-
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