| Identification | More | [Name]
Isorhamnetin | [CAS]
480-19-3 | [Synonyms]
3,5,7,4'-TETRAHYDROXY-3'-METHOXYFLAVONE
3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4-BENZOPYRONE
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-one
3,5,7-trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
3'-METHOXY-3,4',5,7-TETRAHYDROXYFLAVONE
3'-METHOXY-3,5,7,4'-TETRAHYDROXYFLAVONE
3-METHYLQUERCETIN
ISOHAMNETIN
ISORHAMNETIN
2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-4h-1-benzopyran-4-on
3,4’,5,7-tetrahydroxy-3’-methoxy-flavon
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-on
3’-methoxy-3,4’,5,7-tetrahydroxy-flavon
3’-methoxyquercetin
c.i.75680
isorhamnetol
ISOHAMNETIN:3'-METHOXY-3,4',5,7-TETRAHYDRO-XY-FLAVONE
3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one
QUERCETIN-3-METHYLETHER
QUERCETIN-3-ORTHO-METHYLETHER | [EINECS(EC#)]
207-545-5 | [Molecular Formula]
C31H42O7 | [MDL Number]
MFCD00017310 | [Molecular Weight]
526.66 | [MOL File]
480-19-3.mol |
| Questions And Answer | Back Directory | [Preparation]
The extraction method for isorhamnetin from sea buckthorn pomace using ultrasound is based on the principle that ultrasound induces cavitation between the solvent and the sample, leading to the formation, growth, bursting, and compression of bubbles in the solution. This facilitates solute diffusion and increases the mass transfer rate of the target compound from the solid phase to the liquid phase. Ultrasonic extraction can significantly shorten the extraction time and improve the extraction rate of active ingredients and the utilization rate of raw materials. The extraction process involves: accurately weighing approximately 1.0 g of sea buckthorn pomace → adding the extraction solution → ultrasonic extraction → filtration → adjusting the volume of the filtrate → isorhamnetin extraction. The optimal process for extracting isorhamnetin from sea buckthorn pomace is as follows: at 50℃, with an ultrasonic frequency of 40 kHz, extraction is performed twice using an extraction solution of ethyl acetate (V): 95% ethanol (V: 4:6), for 1 hour each time, with a solid-liquid ratio of 1:25. Using this method, the extracted isorhamnetin content can reach 5.09 mg·g⁻¹. Chemical synthesis: Starting with quercetin (Ⅰ), acetylation, benzylation, and methylation reactions yielded quercetin pentaacetate (Ⅱ) and 4',7-di-O-benzylquercetin (Ⅲ), 4',7-di-O-benzylquercetin triacetate (Ⅳ), and 4',7-di-O-benzyl-3'-methylquercetin (Ⅴ) intermediates, respectively. Compound (Ⅴ) was then benzylated to yield isorhamnetin (Ⅵ). | [Description]
Isorhamnetin is a flavonoid, which occurs naturally in plants and it is also a metabolite of quercetin.
Isorhamnetin has anti-inflammatory effect as it can reduce the formation of large amounts of nitric oxide by the inhibition the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for inducible nitric oxide synthase. Isorhamnetin is also reported to have effect in inducing the expression of neurofilaments, and it potentiated the NGF-induced neurite outgrowth and neurofilament expression, which could be a new direction in searching potential candidates as new drugs or food supplements for neurodegenerative diseases.
| [References]
[1] Mari Hämäläinen, Riina Nieminen, Pia Vuorela, Marina Heinonen and Eeva Moilanen, Anti-Inflammatory Effects of Flavonoids: Genistein, Kaempferol, Quercetin, and Daidzein Inhibit STAT-1 and NF-κB Activations, Whereas Flavone, Isorhamnetin, Naringenin, and Pelargonidin Inhibit only NF-κB Activation along with Their Inhibitory Effect on iNOS Expression and NO Production in Activated Macrophages, Mediators of Inflammation, 2007, vol. 2007, Article ID 45673
[2] Sherry L. Xu, Roy C. Y. Choi, Kevin Y. Zhu, Ka-Wing Leung, Ava J. Y. Guo, Dan Bi, Hong Xu, David T. W. Lau, Tina T. X. Dong and Karl W. K. Tsim, Isorhamnetin, A Flavonol Aglycone from Ginkgo biloba L., Induces Neuronal Differentiation of Cultured PC12 Cells: Potentiating the Effect of Nerve Growth Factor, Evidence-Based Complementary and Alternative Medicine, 2012, vol. 2012, Article ID 278273
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| Chemical Properties | Back Directory | [Melting point ]
307°C | [Boiling point ]
599.4±50.0 °C(Predicted) | [density ]
1.634±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml | [form ]
neat | [pka]
6.31±0.40(Predicted) | [color ]
Light yellow to Amber to Dark green | [BRN ]
44723 | [Stability:]
Hygroscopic | [Cosmetics Ingredients Functions]
SKIN PROTECTING | [InChI]
InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3 | [InChIKey]
IZQSVPBOUDKVDZ-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(O)C(OC)=C2)OC2=CC(O)=CC(O)=C2C(=O)C=1O | [LogP]
1.760 (est) | [CAS DataBase Reference]
480-19-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS08 | [Signal word ]
Warning | [Hazard statements ]
H351 | [Precautionary statements ]
P281-P280 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [RTECS ]
LK9275450 | [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Chemical Properties]
Beige to lighet yellow powder | [Uses]
A metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2
signaling pathways. | [Uses]
Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects. | [Application]
Isorhamnetin is a metabolite of the flavanoid Quercetin with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways. | [Definition]
ChEBI: A monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. | [benefits]
Isorhamnetin may have potential benefits in inhibiting the onset and treatment of neuroinflammatory diseases. Isorhamnetin is not that much studied than quercetin. However, the few that exist indicate that isorhamnetin has similar health benefits: it may reduce the risk of cancer, improve heart health and ease diabetes complications. | [General Description]
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate. | [Biochem/physiol Actions]
Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway. | [storage]
Store at -20°C |
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| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
China Langchem Inc.
|
| Telephone: |
0086-21-58956006 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList19141/0_EN.htm |
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