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(-)-Epipinoresinol

CAS# 10061-38-8

(-)-Epipinoresinol

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Quality Control of (-)-Epipinoresinol

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Chemical structure

(-)-Epipinoresinol

3D structure

Chemical Properties of (-)-Epipinoresinol

Cas No. 10061-38-8 SDF Download SDF
PubChem ID 12309639 Appearance Cryst.
Formula C20H22O6 M.Wt 358.4
Type of Compound Lignans Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 4-[(3R,3aS,6S,6aS)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
SMILES COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
Standard InChIKey HGXBRUKMWQGOIE-FQZPYLGXSA-N
Standard InChI InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3/t13-,14-,19-,20+/m1/s1
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 (-)-Epipinoresinol

The rhizomes of Polygonatum sibiricum Red.

Protocol of (-)-Epipinoresinol

Structure Identification
Natural Product Sciences, 2010, 16(1):15-19.

Lignans from Lonicerae caulis.[Reference: WebLink]


METHODS AND RESULTS:
A new 2,7'-cyclolignan named lonicerinol (1) along with eight known lignans, (-)-Epipinoresinol(2), (-)-pinoresinol (3), -hydroxypinoresinol (4), 7R,8S-dihydrodehydrodiconiferyl alcohol (5), ()-neo-olivil (6), (+)-isolariciresinol (7), 3-methoxy-8,4'-oxyneoligna-3',4,7,9,9'-pentol (8), and (-)-pinoresinol 4-O-glucoside (9), were isolated from the caulis of Lonicera japonica THUNB. (Caprifoliaceae). All of these constituents except for (-)-pinoresinol (3) and -hydroxypinoresinol (4) are reported for the first time from the genus Lonicera.
CONCLUSIONS:
The structures and absolute configurations of these compounds were determined on the basis of spectroscopic analysis, including CD and 1D- and 2D-NMR techniques and chemical methods.

(-)-Epipinoresinol Dilution Calculator

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(-)-Epipinoresinol Molarity Calculator

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Preparing Stock Solutions of (-)-Epipinoresinol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7902 mL 13.9509 mL 27.9018 mL 55.8036 mL 69.7545 mL
5 mM 0.558 mL 2.7902 mL 5.5804 mL 11.1607 mL 13.9509 mL
10 mM 0.279 mL 1.3951 mL 2.7902 mL 5.5804 mL 6.9754 mL
50 mM 0.0558 mL 0.279 mL 0.558 mL 1.1161 mL 1.3951 mL
100 mM 0.0279 mL 0.1395 mL 0.279 mL 0.558 mL 0.6975 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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References on (-)-Epipinoresinol

Optimized conversion of antiproliferative lignans pinoresinol and epipinoresinol: Their simultaneous isolation and identification by centrifugal partition chromatography and high performance liquid chromatography.[Pubmed:28384606]

J Chromatogr B Analyt Technol Biomed Life Sci. 2017 May 1;1052:142-149.

High amount of the valuable lignan pinoresinol (PR) was determined in Carduus nutans fruit (7.8mg/g) for the first time. A preparative separation method using two consecutive, identical steps of centrifugal partition chromatography (CPC) was developed in order (i) to isolate PR and (ii) to subsequently isolate PR and its 7' epimer epipinoresinol (EPR) simultaneously after an optimized acid treatment which resulted in PR epimerization forming equal amounts of PR and EPR, from C. nutans fruit. As optimal conditions, a two-phase solvent system consisting of methyl tert-butyl ether:acetone:water (4:3:3, v/v/v) for CPC separation, and an acid treatment performed at 50 degrees C for 30min for the epimerization were applied. Thus, 33.7mg and 32.8mg PR and EPR, in as high as 93.7% and 92.3% purity, were isolated from 10.0gC. nutans fruit, representing 86.4% and 84.1% efficiency, respectively. Conversion characteristic of PR and EPR in acidic medium, determined as a function of time and temperature of acid treatment provides their unambiguous identification by on-line high performance liquid chromatography (HPLC). Antiproliferative assay of isolated PR and EPR in two different types of colon cancer cell lines (HCT116 and SW480) confirmed that both epimers caused a more significant decrease of viability in HCT116 cells than in SW480 cells, suggesting their similar mechanism of antiproliferative action.

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