MedKoo Cat#: 461936 | Name: Scirpusin A

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Scirpusin A is a hydroxystilbene dimer from the rhizome of Scirpus fluviatilis and Xinjiang wine grape. It is structurally related to resveratrol and other stilbene oligomers, which often exhibit bioactive properties. Scirpusin A, like other stilbenes, has been reported to exhibit strong antioxidant properties due to its phenolic structure. It can scavenge free radicals and may contribute to cellular protection against oxidative stress. Some studies suggest that Scirpusin A can modulate inflammatory pathways, potentially by inhibiting NF-κB activation, thereby reducing the expression of pro-inflammatory cytokines.

Chemical Structure

Scirpusin A
Scirpusin A
CAS#69297-51-4

Theoretical Analysis

MedKoo Cat#: 461936

Name: Scirpusin A

CAS#: 69297-51-4

Chemical Formula: C28H22O7

Exact Mass: 470.1366

Molecular Weight: 470.47

Elemental Analysis: C, 71.48; H, 4.71; O, 23.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Scirpusin A; Scirpusin-A;
IUPAC/Chemical Name
(E)-4-(3-(3,5-dihydroxyphenyl)-6-hydroxy-4-(4-hydroxystyryl)-2,3-dihydrobenzofuran-2-yl)benzene-1,2-diol
InChi Key
VJVQHVVOEFJLIO-DAFODLJHSA-N
InChi Code
InChI=1S/C28H22O7/c29-19-6-2-15(3-7-19)1-4-16-9-22(32)14-25-26(16)27(18-10-20(30)13-21(31)11-18)28(35-25)17-5-8-23(33)24(34)12-17/h1-14,27-34H/b4-1+
SMILES Code
OC1=CC=C(C2OC3=CC(O)=CC(/C=C/C4=CC=C(O)C=C4)=C3C2C5=CC(O)=CC(O)=C5)C=C1O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 470.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Kong Q, Ren X, Jiang L, Pan Y, Sun C. Scirpusin A, a hydroxystilbene dimer from Xinjiang wine grape, acts as an effective singlet oxygen quencher and DNA damage protector. J Sci Food Agric. 2010 Apr 15;90(5):823-8. doi: 10.1002/jsfa.3890. PubMed PMID: 20355118. 2: Sim Y, Choi JG, Gu PS, Ryu B, Kim JH, Kang I, Jang DS, Oh MS. Identification of Neuroactive Constituents of the Ethyl Acetate Fraction from Cyperi Rhizoma Using Bioactivity-Guided Fractionation. Biomol Ther (Seoul). 2016 Jul 1;24(4):438-45. doi: 10.4062/biomolther.2016.091. PubMed PMID: 27350341; PubMed Central PMCID: PMC4930289. 3: Tran HH, Nguyen MC, Le HT, Nguyen TL, Pham TB, Chau VM, Nguyen HN, Nguyen TD. Inhibitors of α-glucosidase and α-amylase from Cyperus rotundus. Pharm Biol. 2014 Jan;52(1):74-7. doi: 10.3109/13880209.2013.814692. Epub 2013 Sep 18. PubMed PMID: 24044731. 4: Pawlus AD, Sahli R, Bisson J, Rivière C, Delaunay JC, Richard T, Gomès E, Bordenave L, Waffo-Téguo P, Mérillon JM. Stilbenoid profiles of canes from Vitis and Muscadinia species. J Agric Food Chem. 2013 Jan 23;61(3):501-11. doi: 10.1021/jf303843z. Epub 2013 Jan 11. PubMed PMID: 23270496. 5: Yang GX, Zhou JT, Li YZ, Hu CQ. Anti-HIV bioactive stilbene dimers of Caragana rosea. Planta Med. 2005 Jun;71(6):569-71. PubMed PMID: 15971132. 6: Tisserant LP, Hubert J, Lequart M, Borie N, Maurin N, Pilard S, Jeandet P, Aziz A, Renault JH, Nuzillard JM, Clément C, Boitel-Conti M, Courot E. (13)C NMR and LC-MS Profiling of Stilbenes from Elicited Grapevine Hairy Root Cultures. J Nat Prod. 2016 Nov 23;79(11):2846-2855. Epub 2016 Nov 14. PubMed PMID: 27933900. 7: Rivière C, Papastamoulis Y, Fortin PY, Delchier N, Andriamanarivo S, Waffo-Teguo P, Kapche GD, Amira-Guebalia H, Delaunay JC, Mérillon JM, Richard T, Monti JP. New stilbene dimers against amyloid fibril formation. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3441-3. doi: 10.1016/j.bmcl.2009.09.074. Epub 2009 Sep 24. PubMed PMID: 20452207. 8: Chassy AW, Bueschl C, Lee H, Lerno L, Oberholster A, Barile D, Schuhmacher R, Waterhouse AL. Tracing flavonoid degradation in grapes by MS filtering with stable isotopes. Food Chem. 2015 Jan 1;166:448-55. doi: 10.1016/j.foodchem.2014.06.002. Epub 2014 Jun 9. PubMed PMID: 25053079. 9: Lee SK, Mbwambo ZH, Chung H, Luyengi L, Gamez EJ, Mehta RG, Kinghorn AD, Pezzuto JM. Evaluation of the antioxidant potential of natural products. Comb Chem High Throughput Screen. 1998 Apr;1(1):35-46. PubMed PMID: 10499128. 10: Hong EH, Heo EY, Song JH, Kwon BE, Lee JY, Park Y, Kim J, Chang SY, Chin YW, Jeon SM, Ko HJ. Trans-scirpusin A showed antitumor effects via autophagy activation and apoptosis induction of colorectal cancer cells. Oncotarget. 2017 Jun 20;8(25):41401-41411. doi: 10.18632/oncotarget.17388. PubMed PMID: 28489607; PubMed Central PMCID: PMC5522333. 11: Wang CY, Lam SH, Tseng LH, Lee SS. Rapid screening of lignans from Phyllanthus myrtifolius and stilbenoids from Syagrus romanzoffiana by HPLC-SPE-NMR. Phytochem Anal. 2011 Jul-Aug;22(4):352-60. doi: 10.1002/pca.1286. Epub 2011 Feb 19. PubMed PMID: 21337650. 12: Shao B, Guo HZ, Cui YJ, Liu AH, Yu HL, Guo H, Xu M, Guo DA. Simultaneous determination of six major stilbenes and flavonoids in Smilax china by high performance liquid chromatography. J Pharm Biomed Anal. 2007 Jul 27;44(3):737-42. Epub 2007 Mar 14. PubMed PMID: 17475435. 13: Yin X, Yu J, Kong Q, Ren X. Mechanism of isomers and analogues of resveratrol dimers selectively quenching singlet oxygen by UHPLC-ESI-MS(2). Food Chem. 2017 Dec 15;237:1101-1111. doi: 10.1016/j.foodchem.2017.06.021. Epub 2017 Jun 15. PubMed PMID: 28763956. 14: Sáez V, Pastene E, Vergara C, Mardones C, Hermosín-Gutiérrez I, Gómez-Alonso S, Gómez MV, Theoduloz C, Riquelme S, von Baer D. Oligostilbenoids in Vitis vinifera L. Pinot Noir grape cane extract: Isolation, characterization, in vitro antioxidant capacity and anti-proliferative effect on cancer cells. Food Chem. 2018 Nov 1;265:101-110. doi: 10.1016/j.foodchem.2018.05.050. Epub 2018 May 10. PubMed PMID: 29884360.