cis-Resveratrol
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MedKoo CAT#: 556208

CAS#: 61434-67-1

Description: Resveratrol (E-3,5,4'-trihydroxystilbene) is a polyphenol found in red wine that has been shown to have multiple anti-cancer properties. cis-(Z)- and trans-(E)-isomers of resveratrol occur in nature. cis-Resveratrol produces anti-inflammatory effects by inhibiting canonical and non-canonical inflammasomes in macrophages. cis-Resveratrol has a significant modulatory effect on the NF-kappaB signaling pathway. cis-Resveratrol at micromolar concentrations significantly attenuates several components of the macrophage response to proinflammatory stimuli (notably, production of O(2)(.-)(-) and of the proinflammatory mediators NO(.-) and PGE(2),

Chemical Structure

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cis-Resveratrol
CAS# 61434-67-1
Instruction

Theoretical Analysis

MedKoo Cat#: 556208
Name: cis-Resveratrol
CAS#: 61434-67-1
Chemical Formula: C14H12O3
Exact Mass: 228.08
Molecular Weight: 228.247
Elemental Analysis: C, 73.67; H, 5.30; O, 21.03

Price and Availability

Size Price Availability Quantity
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 1950 2 Weeks
500mg USD 2950 2 Weeks
1g USD 4250 2 Weeks
2g USD 6950 2 Weeks
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Synonym: cis-Resveratrol; (Z)-Resveratrol;

IUPAC/Chemical Name: 5[(1Z)-2-(4-hydroxyphenyl)ethenyl]-1,3-benzenediol

InChi Key: LUKBXSAWLPMMSZ-UPHRSURJSA-N

InChi Code: InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H/b2-1-

SMILES Code: OC1=CC(/C=C\C2=CC=C(O)C=C2)=CC(O)=C1

Appearance: To be determined

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 228.25 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Mota-Lugo E, Dolores-Hernández M, Morales-Hipólito EA, Blanco-Alcántara IA, Cuatecontzi-Flores H, López-Arellano R. Development and Validation of a Stability-Indicating HPLC Method for the Simultaneous Determination of trans-Resveratrol and cis-Resveratrol in an Injectable Solution. J Anal Methods Chem. 2021 Nov 13;2021:8402157. doi: 10.1155/2021/8402157. PMID: 34812295; PMCID: PMC8605923.


2: VanAntwerp IR, Phelps LE, Peuler JD, Kopf PG. Effects of trans- versus cis- resveratrol on adrenergic contractions of the rat tail artery and role of endothelium. Physiol Rep. 2021 Jan;8(24):e14666. doi: 10.14814/phy2.14666. PMID: 33369273; PMCID: PMC7758980.


3: Cheng H, Dong H, Wusigale, Liang L. A comparison of β-casein complexes and micelles as vehicles for trans-/cis-resveratrol. Food Chem. 2020 Nov 15;330:127209. doi: 10.1016/j.foodchem.2020.127209. Epub 2020 Jun 7. PMID: 32535314.


4: Wang F, Chatterjee S. Dominant Carbons in trans- and cis-Resveratrol Isomerization. J Phys Chem B. 2017 May 11;121(18):4745-4755. doi: 10.1021/acs.jpcb.7b02115. Epub 2017 Apr 26. PMID: 28402662.


5: Morris VL, Toseef T, Nazumudeen FB, Rivoira C, Spatafora C, Tringali C, Rotenberg SA. Anti-tumor properties of cis-resveratrol methylated analogs in metastatic mouse melanoma cells. Mol Cell Biochem. 2015 Apr;402(1-2):83-91. doi: 10.1007/s11010-014-2316-8. Epub 2015 Jan 8. PMID: 25567208; PMCID: PMC4323743.


6: Omar JM, Yang H, Li S, Marquardt RR, Jones PJ. Development of an improved reverse-phase high-performance liquid chromatography method for the simultaneous analyses of trans-/cis-resveratrol, quercetin, and emodin in commercial resveratrol supplements. J Agric Food Chem. 2014 Jun 25;62(25):5812-7. doi: 10.1021/jf5001277. Epub 2014 Jun 17. PMID: 24894567.


7: Huang TT, Lai HC, Chen YB, Chen LG, Wu YH, Ko YF, Lu CC, Chang CJ, Wu CY, Martel J, Ojcius DM, Chong KY, Young JD. cis-Resveratrol produces anti- inflammatory effects by inhibiting canonical and non-canonical inflammasomes in macrophages. Innate Immun. 2014 Oct;20(7):735-50. doi: 10.1177/1753425913507096. Epub 2013 Oct 22. PMID: 24149798.


8: Nour V, Trandafir I, Muntean C. Ultraviolet irradiation of trans-resveratrol and HPLC determination of trans-resveratrol and cis-resveratrol in Romanian red wines. J Chromatogr Sci. 2012 Nov-Dec;50(10):920-7. doi: 10.1093/chromsci/bms091. Epub 2012 Jun 11. PMID: 22689901.


9: Paulo L, Domingues F, Queiroz JA, Gallardo E. Development and validation of an analytical method for the determination of trans- and cis-resveratrol in wine: analysis of its contents in 186 Portuguese red wines. J Agric Food Chem. 2011 Mar 23;59(6):2157-68. doi: 10.1021/jf105004y. Epub 2011 Mar 1. PMID: 21361293.


10: Rius C, Abu-Taha M, Hermenegildo C, Piqueras L, Cerda-Nicolas JM, Issekutz AC, Estañ L, Cortijo J, Morcillo EJ, Orallo F, Sanz MJ. Trans- but not cis- resveratrol impairs angiotensin-II-mediated vascular inflammation through inhibition of NF-κB activation and peroxisome proliferator-activated receptor- gamma upregulation. J Immunol. 2010 Sep 15;185(6):3718-27. doi: 10.4049/jimmunol.1001043. Epub 2010 Aug 13. PMID: 20709957.


11: Cvejic JM, Djekic SV, Petrovic AV, Atanackovic MT, Jovic SM, Brceski ID, Gojkovic-Bukarica LC. Determination of trans- and cis-resveratrol in Serbian commercial wines. J Chromatogr Sci. 2010 Mar;48(3):229-34. doi: 10.1093/chromsci/48.3.229. PMID: 20223091.


12: Iwuchukwu OF, Nagar S. Cis-resveratrol glucuronidation kinetics in human and recombinant UGT1A sources. Xenobiotica. 2010 Feb;40(2):102-8. doi: 10.3109/00498250903406754. PMID: 20017604.


13: Mikulski D, Górniak R, Molski M. A theoretical study of the structure- radical scavenging activity of trans-resveratrol analogues and cis-resveratrol in gas phase and water environment. Eur J Med Chem. 2010 Mar;45(3):1015-27. doi: 10.1016/j.ejmech.2009.11.044. Epub 2009 Nov 27. PMID: 20004046.


14: Camont L, Cottart CH, Rhayem Y, Nivet-Antoine V, Djelidi R, Collin F, Beaudeux JL, Bonnefont-Rousselot D. Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions. Anal Chim Acta. 2009 Feb 16;634(1):121-8. doi: 10.1016/j.aca.2008.12.003. Epub 2008 Dec 6. PMID: 19154820.


15: Campos-Toimil M, Elíes J, Alvarez E, Verde I, Orallo F. Effects of trans- and cis-resveratrol on Ca2+ handling in A7r5 vascular myocytes. Eur J Pharmacol. 2007 Dec 22;577(1-3):91-9. doi: 10.1016/j.ejphar.2007.08.003. Epub 2007 Aug 14. PMID: 17822692.


16: Campos-Toimil M, Elíes J, Orallo F. Trans- and cis-resveratrol increase cytoplasmic calcium levels in A7r5 vascular smooth muscle cells. Mol Nutr Food Res. 2005 May;49(5):396-404. doi: 10.1002/mnfr.200400108. PMID: 15830338.


17: Leiro J, Arranz JA, Fraiz N, Sanmartín ML, Quezada E, Orallo F. Effect of cis-resveratrol on genes involved in nuclear factor kappa B signaling. Int Immunopharmacol. 2005 Feb;5(2):393-406. doi: 10.1016/j.intimp.2004.10.006. PMID: 15652768.


18: Careri M, Corradini C, Elviri L, Nicoletti I, Zagnoni I. Liquid chromatography-electrospray tandem mass spectrometry of cis-resveratrol and trans-resveratrol: development, validation, and application of the method to red wine, grape, and winemaking byproducts. J Agric Food Chem. 2004 Nov 17;52(23):6868-74. doi: 10.1021/jf049219d. PMID: 15537288.


19: Leiro J, Alvarez E, Arranz JA, Laguna R, Uriarte E, Orallo F. Effects of cis-resveratrol on inflammatory murine macrophages: antioxidant activity and down-regulation of inflammatory genes. J Leukoc Biol. 2004 Jun;75(6):1156-65. doi: 10.1189/jlb.1103561. Epub 2004 Feb 24. PMID: 14982945.


20: Aumont V, Krisa S, Battaglia E, Netter P, Richard T, Mérillon JM, Magdalou J, Sabolovic N. Regioselective and stereospecific glucuronidation of trans- and cis-resveratrol in human. Arch Biochem Biophys. 2001 Sep 15;393(2):281-9. doi: 10.1006/abbi.2001.2496. PMID: 11556815.


21: Lin CH, Chen YH. On-line identification of trans- and cis-resveratrol by nonaqueous capillary electrophoresis/fluorescence spectroscopy at 77 K. Electrophoresis. 2001 Aug;22(12):2574-9. doi: 10.1002/1522-2683(200107)22:12<2574::AID-ELPS2574>3.0.CO;2-M. PMID: 11519961.


22: Bertelli AA, Giovannini L, Stradi R, Urien S, Tillement JP, Bertelli A. Kinetics of trans- and cis-resveratrol (3,4',5-trihydroxystilbene) after red wine oral administration in rats. Int J Clin Pharmacol Res. 1996;16(4-5):77-81. PMID: 9172004.


23: Bertelli AA, Giovannini L, Stradi R, Bertelli A, Tillement JP. Plasma, urine and tissue levels of trans- and cis-resveratrol (3,4',5-trihydroxystilbene) after short-term or prolonged administration of red wine to rats. Int J Tissue React. 1996;18(2-3):67-71. PMID: 9063768.


24: Bertelli AA, Giovannini L, Bernini W, Migliori M, Fregoni M, Bavaresco L, Bertelli A. Antiplatelet activity of cis-resveratrol. Drugs Exp Clin Res. 1996;22(2):61-3. PMID: 8998912.