Isopimpinellin CAS NO.482-27-9

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ProName: Isopimpinellin
CasNo: 482-27-9
Molecular Formula: C13H10O5=246.2
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

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
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
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;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
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 Isopimpinellin

Cas No.	482-27-9	SDF
PubChem ID	68079	Appearance	White-yellowish powder
Formula	C₁₃H₁₀O₅	M.Wt	246.2
Type of Compound	Coumarins	Storage	Desiccate at -20°C
Synonyms	5,8-Dimethoxypsoralen
Solubility	Soluble in acetone and chloroform; practically insoluble in water
Chemical Name	4,9-dimethoxyfuro[3,2-g]chromen-7-one
SMILES	COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
Standard InChIKey	DFMAXQKDIGCMTL-UHFFFAOYSA-N
Standard InChI	InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
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 Isopimpinellin

1 Apium sp. 2 Citrus sp. 3 Ferula sp. 4 Heracleum sp. 5 Pastinaca sp. 6 Petroselinum sp. 7 Pimpinella sp. 8 Ruta sp. 9 Stellera sp.

Biological Activity of Isopimpinellin

Description	Isopimpinellin has chemopreventive effects, it effectively inhibits mouse COH activity (IC50 values 19-40 microM).Isopimpinellin is a new inhibitor against the Leishmania APRT enzyme.
Targets	BACE \| Antifection
In vitro	Isopimpinellin is not phototoxic in a chick skin assay.[Pubmed: 8881335] Photochem Photobiol. 1996 Mar;63(3):306-7. METHODS AND RESULTS: Synthetic Isopimpinellin (5,8-dimethoxypsoralen), confirmed to contain as impurities only trace quantities at most of psoralen, bergapten (5-methoxypsoralen) and xanthotoxin (8-methoxypsoralen), is not phototoxic when tested in a chick skin bioassay system. These findings are at variance with earlier studies showing Isopimpinellin to be phototoxic against chick skin and support the conclusion that Isopimpinellin is photobiologically inactive. CONCLUSIONS: As recently proposed by others, the several reports of Isopimpinellin photoactivity are most likely attributable to contamination by small amounts of highly active psoralens such as bergapten or xanthotoxin. Isopimpinellin is not phototoxic to viruses and cells.[Pubmed: 3628561 ] Planta Med. 1987 Jun;53(3):306-7. Isopimpinellin is not phototoxic to viruses and cells. Redetermination and comparative structural study of isopimpinellin: A new inhibitor against the Leishmania APRT enzyme[Reference: WebLink] Acta Crystallographica, 2003, 59(10):o1506–8. The title compound (Isopimpinellin,alternative name 5,8-dimethoxypsoralen), C13H10O5, is a natural product extracted from Adiscanthus fusciflorus (Rutaceae). METHODS AND RESULTS: Our biochemical tests show that this compound has inhibitory activity against the enzyme adenine phosphoribosyltransferase (APRT) from Leishmania, a tropical parasite causing endemic disease in poor countries. It crystallizes in the centrosymmetric space group P2(1)/c, with one molecule in the asymmetric unit, and has at least two C-H...O intermolecular interactions, leading to the formation of centrosymmetric dimers.
In vivo	Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice.[Pubmed: 12376476] Carcinogenesis. 2002 Oct;23(10):1667-75. The current study was designed to evaluate the effects of oral administration of the citrus coumarin, Isopimpinellin, on skin tumor initiation by topically applied benzo[a]pyrene (B[a]P) and 7,12-dimethylbenz[a]anthracene (DMBA). METHODS AND RESULTS: To evaluate the effects of orally administered Isopimpinellin on skin tumor initiation by B[a]P and DMBA, its effects on DNA adduct formation were first evaluated. Female SENCAR mice were pre-treated twice with corn oil, or Isopimpinellin (70 mg/kg body wt per os) at 24 h and 2 h prior to topical treatment with B[a]P or DMBA. Another citrus coumarin, imperatorin, was also included in these experiments for comparison. Orally administered Isopimpinellin and imperatorin significantly inhibited B[a]P-DNA adduct formation by 37 and 26%, respectively. Imperatorin also blocked DMBA-DNA adduct formation by 43%. In a second dose-response study, orally administered Isopimpinellin (35, 70 and 150 mg/kg) blocked DMBA-DNA adduct formation by 23, 56 and 69%, respectively. For the tumor study, mice were pretreated orally with corn oil or Isopimpinellin at 24 and 2 h prior to initiation with DMBA, and 2 weeks later promotion began with 12-O-tetradecanoylphorbol-13-acetate (TPA). Isopimpinellin significantly reduced the mean number of papillomas per mouse by 49, 73 and 78% compared to corn oil controls at 30, 70 and 150 mg/kg body wt, respectively. Orally administered Isopimpinellin also significantly reduced the percentage of mice with papillomas at the highest dose tested (150 mg/kg). The effectiveness of Isopimpinellin given topically over a broad dose range against DMBA tumor initiation was also evaluated for comparison. As part of this study, several parameters of systemic toxicity were evaluated following oral dosing with Isopimpinellin and imperatorin. Mice were treated orally with corn oil, Isopimpinellin or imperatorin (35, 70 and 150 mg/kg body wt per os) once daily for four consecutive days, killed at 24 h after the last dose, and livers, lungs, and kidneys evaluated histologically. In addition, urinary parameters of nephrotoxicity, blood parameters of liver and kidney function, and thrombin clotting time were assayed. No significant changes in blood clotting, or renal or hepatic function were observed. There was, however, a significant increase in liver wt accompanied by cytoplasmic vacuolation of hepatocytes. There were no histopathological changes in lungs or kidneys. CONCLUSIONS: Overall, these data indicate that Isopimpinellin (and imperatorin) have chemopreventive effects when administered orally on skin tumor initiation by DMBA.

Protocol of Isopimpinellin

Structure Identification

J Oleo Sci. 2011;60(11):575-8.

Microbial transformation of Isopimpinellin by Glomerella cingulata.[Pubmed: 22027023]

METHODS AND RESULTS:
Microbial transformation studies conducted on Isopimpinellin (1) by the fungus Glomerella cingulata have revealed that 1 was metabolized to give the corresponding reduced acid, 5,8-dimethoxy-6,7-furano-hydrocoumaric acid (2). The structure of metabolite 2 was elucidated by high-resolution mass spectrometry (HR-MS), extensive NMR techniques, including (1)H NMR, (13)C NMR, (1)H-(1)H correlation spectroscopy (COSY), heteronuclear multiple quantum coherence (HMQC) and heteonuclear multiple bond coherence (HMBC).
CONCLUSIONS:
The biotransformed product 2 showed weak a in vitro β-secretase (BACE1) inhibitory effect.

Preparing Stock Solutions of Isopimpinellin

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	4.0617 mL	20.3087 mL	40.6174 mL	81.2348 mL	101.5435 mL
5 mM	0.8123 mL	4.0617 mL	8.1235 mL	16.247 mL	20.3087 mL
10 mM	0.4062 mL	2.0309 mL	4.0617 mL	8.1235 mL	10.1543 mL
50 mM	0.0812 mL	0.4062 mL	0.8123 mL	1.6247 mL	2.0309 mL
100 mM	0.0406 mL	0.2031 mL	0.4062 mL	0.8123 mL	1.0154 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.