3,3',4',5,6,7,8-heptamethoxyflavoneCAS# 1178-24-1 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1178-24-1 | SDF | Download SDF |
| PubChem ID | 150893 | Appearance | Beige powder |
| Formula | C22H24O9 | M.Wt | 432.4 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Synonyms | 3-methoxynobiletin | ||
| Solubility | Soluble in DMSO and methanol; insoluble in water | ||
| Chemical Name | 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one | ||
| SMILES | COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)OC)OC | ||
| Standard InChIKey | SSXJHQZOHUYEGD-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 3,3',4',5,6,7,8-Heptamethoxyflavone(HMF) has neuroprotective, chemopreventive, anti-allergic, anti-inflammatory, immunomodulatory, anti-aging and photoprotective effects; it inhibits collagenase activity and induces type I procollagen synthesis in HDFn cells, and against nitric oxide (NO) carcinogenesis. |
| Targets | TNF-α | IL Receptor | gp120/CD4 | NO | MMP(e.g.TIMP) | MAPK | ERK | JNK | TGF-β/Smad |
| In vitro | 3,5,6,7,8,3',4'-Heptamethoxyflavone, a Citrus Flavonoid, Inhibits Collagenase Activity and Induces Type I Procollagen Synthesis in HDFn Cells.[Pubmed: 29470423]Int J Mol Sci. 2018 Feb 22;19(2). pii: E620.Citrus fruits contain various types of flavonoids with powerful anti-aging and photoprotective effects on the skin, and have thus been attracting attention as potential, efficacious skincare agents. |
| In vivo | Anti-inflammatory activity of an orange peel polymethoxylated flavone, 3',4',3,5,6,7,8-heptamethoxyflavone, in the rat carrageenan/paw edema and mouse lipopolysaccharide-challenge assays.[Pubmed: 18816060 ]J Agric Food Chem. 2008 Oct 22;56(20):9399-403.The anti-inflammatory properties of 3',4',3,5,6,7,8-heptamethoxyflavone (3,3',4',5,6,7,8-heptamethoxyflavone ,HMF), a citrus polymethoxylated flavone, were studied in the bacterial lipopolysaccharide (LPS)-challenge/tumor necrosis factor-alpha (TNFalpha) response in mice and in the carrageenan/paw edema assay in rats. Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants.[Pubmed: 11163102]Cancer Lett. 2001 Feb 10;163(1):7-9.
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| Animal Research | 3,5,6,7,8,3',4'-Heptamethoxyflavone reduces interleukin-4 production in the spleen cells of mice.[Pubmed: 27108879 ]3,5,6,7,8,3',4'-Heptamethoxyflavone, a citrus flavonoid, on protection against memory impairment and neuronal cell death in a global cerebral ischemia mouse model.[Pubmed: 24657445 ]Neurochem Int. 2014 May;70:30-8.
Biomed Res. 2016;37(2):95-9.In our previous studies, we reported anti-inflammatory functions of 3,5,6,7,8,3',4'-heptamethoxyflavone (3,3',4',5,6,7,8-heptamethoxyflavone ,HMF), which is a polymethoxyflavone rich in various citrus fruits. |
3,3',4',5,6,7,8-heptamethoxyflavone Dilution Calculator
3,3',4',5,6,7,8-heptamethoxyflavone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.3127 mL | 11.5634 mL | 23.1267 mL | 46.2535 mL | 57.8168 mL |
| 5 mM | 0.4625 mL | 2.3127 mL | 4.6253 mL | 9.2507 mL | 11.5634 mL |
| 10 mM | 0.2313 mL | 1.1563 mL | 2.3127 mL | 4.6253 mL | 5.7817 mL |
| 50 mM | 0.0463 mL | 0.2313 mL | 0.4625 mL | 0.9251 mL | 1.1563 mL |
| 100 mM | 0.0231 mL | 0.1156 mL | 0.2313 mL | 0.4625 mL | 0.5782 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants.[Pubmed:11163102]
Cancer Lett. 2001 Feb 10;163(1):7-9.
Nobiletin and 3,5,6,7,8,3',4'-heptamethoxyflavone (HPT), isolated from the peel of Citrus plants, were examined for the anti-tumor-initiating activity on two-stage carcinogenesis of mouse skin tumors induced by a nitric oxide donor, (+/-)-(E)-methyl-2-[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexenamide, as an initiator and 12-O-tetradecanoylphorbol-13-acetate as a promoter. HPT exhibited the remarkable anti-tumor-initiating effect on mouse skin and it suggested the possibility of HPT being a chemopreventive agent against nitric oxide (NO) carcinogenesis.
3,5,6,7,8,3',4'-Heptamethoxyflavone reduces interleukin-4 production in the spleen cells of mice.[Pubmed:27108879]
Biomed Res. 2016;37(2):95-9.
In our previous studies, we reported anti-inflammatory functions of 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF), which is a polymethoxyflavone rich in various citrus fruits. Here, we investigated the immunomodulatory function of HMF in mice. HMF administration (50 mg/kg, i.p., 2 times/week) tended to reduce the production of antigen-specific IgE induced by ovalbumin in combination with aluminum hydroxide gel. Fluorescence-activated cell sorting analysis revealed the reduction of interleukin-4(+)CD4(+) spleen cells and sustained presence of interferon-gamma(+)CD4(+) spleen cells in mice administered HMF, whereas the ratio of CD4(+)CD8(-) versus CD4(-)CD8(+) spleen cells was not affected. Interleukin-4 release from CD3/CD28-stimulated spleen cells of mice administered HMF was reduced, whereas interferon-gamma release was not affected. These results suggest that HMF has an immunomodulatory function via reduced interleukin-4 expression.
Anti-inflammatory activity of an orange peel polymethoxylated flavone, 3',4',3,5,6,7,8-heptamethoxyflavone, in the rat carrageenan/paw edema and mouse lipopolysaccharide-challenge assays.[Pubmed:18816060]
J Agric Food Chem. 2008 Oct 22;56(20):9399-403.
The anti-inflammatory properties of 3',4',3,5,6,7,8-heptamethoxyflavone (HMF), a citrus polymethoxylated flavone, were studied in the bacterial lipopolysaccharide (LPS)-challenge/tumor necrosis factor-alpha (TNFalpha) response in mice and in the carrageenan/paw edema assay in rats. In each of these trials, HMF administered by intraperitoneal (ip) injection exhibited anti-inflammatory activity, whereas HMF administered orally (po) produced no effects. The inhibition observed in the LPS-challenge/TNFalpha assay correlated with the HMF levels in the blood sera of mice dosed (ip) with either 33 or 100 mg/kg body weight. Low levels of HMF (0.035 +/- 0.024 ppm) were detected in the blood sera of mice dosed orally [100 mg of HMF (suspended in vegetable oil)/kg], whereas ip injection led to higher levels (0.517 +/- 0.051 ppm). This may account for the different levels of anti-inflammatory effects observed in mice following ip vs oral HMF administration. HMF metabolites, including a number of mono- and di-demethylated HMF metabolites and their glucuronic acid conjugates, were also detected, but results of these studies suggest that the glucuronidated metabolites of HMF are inactive in these inflammation models.
3,5,6,7,8,3',4'-Heptamethoxyflavone, a Citrus Flavonoid, Inhibits Collagenase Activity and Induces Type I Procollagen Synthesis in HDFn Cells.[Pubmed:29470423]
Int J Mol Sci. 2018 Feb 22;19(2). pii: ijms19020620.
Citrus fruits contain various types of flavonoids with powerful anti-aging and photoprotective effects on the skin, and have thus been attracting attention as potential, efficacious skincare agents. Here, we aimed to investigate the chemical composition of Citrus unshiu and its protective effects on photoaging. We isolated and identified a bioactive compound, 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF), from C. unshiu peels using ethanol extraction and hexane fractionation. HMF inhibited collagenase activity and increased type I procollagen content in UV-induced human dermal fibroblast neonatal (HDFn) cells. HMF also suppressed the expression of matrix metalloproteinases 1 (MMP-1) and induced the expression of type I procollagen protein in UV-induced HDFn cells. Additionally, HMF inhibited ultraviolet B (UVB)-induced phosphorylation of the mitogen-activated protein kinases (MAPK) cascade signaling components-ERK, JNK, and c-Jun-which are involved in the induction of MMP-1 expression. Furthermore, HMF affected the TGF-beta/Smad signaling pathway, which is involved in the regulation of type I procollagen expression. In particular, HMF induced Smad3 protein expression and suppressed Smad7 protein expression in UV-induced HDFn cells in a dose-dependent manner. These findings suggest a role for Citrusunshiu in the preparation of skincare products in future.
3,5,6,7,8,3',4'-Heptamethoxyflavone, a citrus flavonoid, on protection against memory impairment and neuronal cell death in a global cerebral ischemia mouse model.[Pubmed:24657445]
Neurochem Int. 2014 May;70:30-8.
The present study evaluated the effects of treatment with the citrus flavonoid, 3,5,6,7,8,3',4'-heptamethoxyflavone (HMF) on protection against memory impairment and neuronal death in a global cerebral ischemia mouse model. The results showed that HMF, administrated for three days immediately after ischemic surgery, protected against ischemia-induced memory dysfunction, rescued neuronal cell death in the CA1 cell layer, increased the production of BDNF, stimulated the autophosphorylation of CaMK II and suppressed microglial activation in the hippocampus. These results suggest that HMF has a neuroprotective effect after brain ischemia by inducing BDNF production and anti-inflammatory effects.
