Sanshodiol

CAS# 54854-91-0

Sanshodiol

2D Structure

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Quality Control of Sanshodiol

3D structure

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Sanshodiol

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Chemical Properties of Sanshodiol

Cas No. 54854-91-0 SDF Download SDF
PubChem ID 14237706 Appearance Powder
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-[4-(1,3-benzodioxol-5-ylmethyl)-3-(hydroxymethyl)oxolan-2-yl]-2-methoxyphenol
SMILES COC1=C(C=CC(=C1)C2C(C(CO2)CC3=CC4=C(C=C3)OCO4)CO)O
Standard InChIKey GRYMYKQGSSTJBA-UHFFFAOYSA-N
Standard InChI InChI=1S/C20H22O6/c1-23-18-8-13(3-4-16(18)22)20-15(9-21)14(10-24-20)6-12-2-5-17-19(7-12)26-11-25-17/h2-5,7-8,14-15,20-22H,6,9-11H2,1H3
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 Sanshodiol

The stem bark of Xanthoxylum piperitum DC.

Biological Activity of Sanshodiol

DescriptionStandard reference

Protocol of Sanshodiol

Structure Identification
Chemical & Pharmaceutical Bulletin,1974,22(11) :2650-5.

Studies on Xanthoxylun spp. II. Constituents of the bark of Xanthoxylum piperitum DC.[Reference: WebLink]


METHODS AND RESULTS:
The stem bark of Xanthoxylum piperitum DC. was phytochemically examined and five new lignans, viz., xanthoxylol (3), piperitol (5), their γ, γ-dimethylallyl ethers (6, 7) and Sanshodiol (8) were isolated besides l-asarinin (1) and l-sesamin (2) and their structures were determined.
CONCLUSIONS:
Phytosterol, γ-fagarine, skimmianine, syringaldehyde, piperonylic acid, menisperine, laurifoline and magnoflorine were also isolated from the same source.

Sanshodiol Dilution Calculator

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Sanshodiol Molarity Calculator

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Preparing Stock Solutions of Sanshodiol

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 Sanshodiol

Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.[Pubmed:12003531]

J Org Chem. 2002 May 17;67(10):3242-8.

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether 1b, acuminatin methyl ether 1e, and Sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin 1i, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.

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