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Keywords
- 7437-55-0
- 8-geranyloxypsoralen
- High quality
Quick Details
- ProName: 8-geranyloxypsoralen
- CasNo: 7437-55-0
- Molecular Formula: C21H22O4
- Appearance: detailed see specifications
- Application: analysis,activity test,Botanical Refer...
- DeliveryTime: 1-3 working days after confirming
- PackAge: According to the clients requirement.
- Port: China main port
- ProductionCapacity: /
- Purity: HPLC≥98%
- Storage: Store at 2~8°C
- Transportation: by air or by ocean shipping
- LimitNum: 0
- Plant of Origin: Chinese herbal medicine
- Testing Method: NMR/MS/HPLC
- Product Ecification: 1mg-1kg
- Heavy Metal: <10ppm
- Voluntary Standards: Company standard
Superiority
Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.
Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
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D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library
1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
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5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries
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.
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.
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.
Details
Chemical Properties of 8-Geranyloxypsoralen
| Cas No. | 7437-55-0 | ||
| PubChem ID | 5317564 | Appearance | White powder |
| Formula | C21H22O4 | M.Wt | 338.4 |
| Type of Compound | Coumarins | Storage | Desiccate at -20°C |
| Solubility | Soluble in acetonitrile and chloroform | ||
| Chemical Name | 9-[(2E)-3,7-dimethylocta-2,6-dienoxy]furo[3,2-g]chromen-7-one | ||
| SMILES | CC(=CCCC(=CCOC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2)C)C | ||
| Standard InChIKey | SOVNCTNQAWWYAQ-OQLLNIDSSA-N | ||
| 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. |
||
| 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. |
||
| 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. | ||
Source of 8-Geranyloxypsoralen
The herbs of Seseli mairei Wolff
Biological Activity of 8-Geranyloxypsoralen
| Description | 8-Geranyloxypsoralen inhibits β-secretase (BACE1) activity in non-competitive manner, with the IC(50) values <25.0 uM, it can induce vasorelaxation on rat arterial tissues. 8-Geranyloxypsoralen possesses nematicidal activities, the median lethal concentrations (LC(50)) is 188.3 mg/ L against B. xylophilus and is 117.5 mg/L against P. redivivus. |
| Targets | BACE | P450 (e.g. CYP17) | Antifection |
| In vitro |
Nematicidal coumarins from Heracleum candicans Wall.[Pubmed: 18569707 ] Nat Prod Res. 2008 May 20;22(8):666-71. The root extract of Heracleum candicans Wall. exhibited antagonistic activities against nematodes Bursaphelenchus xylophilus (Steiner et Buhrer) Nickle and Panagrellus redivivus (Linn.) Goodey. Vasodilation and radical-scavenging activity of imperatorin and selected coumarinic and flavonoid compounds from genus Casimiroa.[Pubmed: 24309287] Phytomedicine. 2014 Apr 15;21(5):586-94. Hypertension is a very widespread condition which is not strictly considered as an illness but if not countered, progressively causes damage to all tissues and loss in their functionality. For this reason the find of new antihypertensive agents is prominent and medicinal plants and their derivatives are valuable for the purpose. The genus Casimiroa (Rutaceae) includes plants from Central America and Mexico; among these, Casimiroa edulis Llave et Lex. and Casimiroa pubescens Ramirez are the most relevant species, even for their medicinal uses. The decoction of leaves and seeds is traditionally taken as a tea mainly to lower blood pressure. |
Protocol of 8-Geranyloxypsoralen
| Kinase Assay |
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.[Pubmed: 22222157] Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.[Pubmed: 16481174] Bioorg Med Chem. 2006 Jun 1;14(11):3865-71. Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency. Bioorg Med Chem. 2012 Jan 15;20(2):784-8. The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of β-secretase (BACE1) activity. |
Preparing Stock Solutions of 8-Geranyloxypsoralen
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.9551 mL | 14.7754 mL | 29.5508 mL | 59.1017 mL | 73.8771 mL |
| 5 mM | 0.591 mL | 2.9551 mL | 5.9102 mL | 11.8203 mL | 14.7754 mL |
| 10 mM | 0.2955 mL | 1.4775 mL | 2.9551 mL | 5.9102 mL | 7.3877 mL |
| 50 mM | 0.0591 mL | 0.2955 mL | 0.591 mL | 1.182 mL | 1.4775 mL |
| 100 mM | 0.0296 mL | 0.1478 mL | 0.2955 mL | 0.591 mL | 0.7388 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. | |||||
References on 8-Geranyloxypsoralen
Synthesis of 8-geranyloxypsoralen analogues and their evaluation as inhibitors of CYP3A4.[Pubmed:16481174]
Bioorg Med Chem. 2006 Jun 1;14(11):3865-71.
Furanocoumarins have been shown to inhibit CYP3A4 in vitro with varying degrees of potency. In this study, we report the effects of a series of novel furanocoumarins based on the naturally occurring derivative 8-geranylepoxypsoralen which has been shown to be a more potent inhibitor of CYP3A4 than its 5-position-substituted counterpart bergamottin. Compounds were designed, synthesised and tested for their ability to inhibit CYP3A4 activity in human liver microsomes using testosterone as the marker substrate. Both the saturated and unsaturated phenolic furanocoumarin derivatives were found to be inactive. However, the 8-alkyloxy-furanocoumarin analogues were shown to inhibit CYP3A4 activity in a dose dependent manner, with IC(50) values ranging from 0.78+/-0.11 to 3.93+/-0.53 microM. The reduced furan derivative dihydro-8-Geranyloxypsoralen showed a 4-fold decrease in inhibitory potency, suggesting that the furan moiety plays a role in the interaction between these compounds and CYP3A4.
Nematicidal coumarins from Heracleum candicans Wall.[Pubmed:18569707]
Nat Prod Res. 2008 May 20;22(8):666-71.
The root extract of Heracleum candicans Wall. exhibited antagonistic activities against nematodes Bursaphelenchus xylophilus (Steiner et Buhrer) Nickle and Panagrellus redivivus (Linn.) Goodey. Through bioassay-guided fractionations, three coumarins were obtained from the extract of H. candicans and determined to be 8-Geranyloxypsoralen (1), imperatorin (2), and heraclenin (3) based on spectra data. All three compounds possessed nematicidal activities against the two tested nematodes. The median lethal concentrations (LC(50)) of compounds 1-3 at 72 h were 188.3, 161.7, and 114.7 mg L(-1) respectively against B. xylophilus and were 117.5, 179.0, and 148.7 mg L(-1) respectively against P. redivivus. This is the first report about species in the Umbelliferae family that possesses nematicidal activity.
Structure-activity relationships for naturally occurring coumarins as beta-secretase inhibitor.[Pubmed:22222157]
Bioorg Med Chem. 2012 Jan 15;20(2):784-8.
The present study was demonstrated to evaluate the effects of naturally occurring coumarins (NOCs) including simple coumarins, furanocoumarins, and pyranocoumarins on the inhibition of beta-secretase (BACE1) activity. Of 41 NOCs examined, some furanocoumarins inhibited BACE1 activity, but simple coumarins and pyranocoumarins did not affect. The most potent inhibitor was 5-geranyloxy-8-methoxypsoralen (31), which has an IC(50) value of 9.9 muM. Other furanocoumarin derivatives, for example, 8-geranyloxy-5-methoxypsoralen (35), 8-Geranyloxypsoralen (24), and bergamottin (18) inhibited BACE1 activity, with the IC(50) values <25.0 muM. Analyses of the inhibition mechanism by Dixon plots and Cornish-Bowden plots showed that compounds 18, 31 and 35 were mixed-type inhibitor. The kinetics of inhibition of BACE1 by coumarins 24 was non-competitive inhibitors.
Description
8-Geranyloxypsoralen is a furanocoumarin isolated from grapefruit, acts as a potent inhibitor of P450 3A4 (CYP3A4) with an IC50 of 3.93 μM.
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