Sinapine | CAS#18696-26-9 | radio-protective

MedKoo Cat#: 585212 | Name: Sinapine

Description:

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

Sinapine, an alkaloid from seeds of Brassica nigra, has antioxidant and radio-protective activities.

Chemical Structure

Sinapine

CAS#18696-26-9

Theoretical Analysis

MedKoo Cat#: 585212

Name: Sinapine

CAS#: 18696-26-9

Chemical Formula: C16H24NO5+

Exact Mass: 310.1649

Molecular Weight: 310.37

Elemental Analysis: C, 61.92; H, 7.79; N, 4.51; O, 25.77

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 #

No Data

Synonym

Sinapine

IUPAC/Chemical Name

Ethanaminium, 2-((3-(4-hydroxy-3,5-dimethoxyphenyl)-1-oxo-2-propenyl)oxy)-N,N,N-trimethyl-

InChi Key

HUJXHFRXWWGYQH-UHFFFAOYSA-O

InChi Code

InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1

SMILES Code

O=C(OCC[N+](C)(C)C)/C=C/C1=CC(OC)=C(O)C(OC)=C1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 310.37 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.

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: Guo Y, An H, Feng L, Liu Q, Wang S, Zhang T. Sinapine as an active compound for inhibiting the proliferation of Caco-2 cells via downregulation of P-glycoprotein. Food Chem Toxicol. 2014 May;67:187-92. doi: 10.1016/j.fct.2014.02.035. Epub 2014 Mar 5. PubMed PMID: 24607798. 2: Niu Y, Jiang M, Guo M, Wan C, Hu S, Jin H, Huang F. Characterization of the factors that influence sinapine concentration in rapeseed meal during fermentation. PLoS One. 2015 Jan 21;10(1):e0116470. doi: 10.1371/journal.pone.0116470. eCollection 2015. PubMed PMID: 25606856; PubMed Central PMCID: PMC4301875. 3: Zhou H, Huang Y, Hoshi T, Kashiwagi Y, Anzai J, Li G. Electrochemistry of sinapine and its detection in medicinal plants. Anal Bioanal Chem. 2005 Jun;382(4):1196-201. Epub 2005 May 20. PubMed PMID: 15906009. 4: Clauss K, Baumert A, Nimtz M, Milkowski C, Strack D. Role of a GDSL lipase-like protein as sinapine esterase in Brassicaceae. Plant J. 2008 Mar;53(5):802-13. Epub 2007 Nov 23. PubMed PMID: 18036206. 5: Wang SX, Oomah BD, McGregor DI. Application and Evaluation of Ion-Exchange UV Spectrophotometric Method for Determination of Sinapine in Brassica Seeds and Meals. J Agric Food Chem. 1998 Feb 16;46(2):575-579. PubMed PMID: 10554280. 6: Bhinu VS, Schäfer UA, Li R, Huang J, Hannoufa A. Targeted modulation of sinapine biosynthesis pathway for seed quality improvement in Brassica napus. Transgenic Res. 2009 Feb;18(1):31-44. doi: 10.1007/s11248-008-9194-3. Epub 2008 Jul 9. PubMed PMID: 18612839. 7: Clauss K, von Roepenack-Lahaye E, Böttcher C, Roth MR, Welti R, Erban A, Kopka J, Scheel D, Milkowski C, Strack D. Overexpression of sinapine esterase BnSCE3 in oilseed rape seeds triggers global changes in seed metabolism. Plant Physiol. 2011 Mar;155(3):1127-45. doi: 10.1104/pp.110.169821. Epub 2011 Jan 19. PubMed PMID: 21248075; PubMed Central PMCID: PMC3046574. 8: Yang M, Zheng C, Zhou Q, Liu C, Li W, Huang F. Influence of microwaves treatment of rapeseed on phenolic compounds and canolol content. J Agric Food Chem. 2014 Feb 26;62(8):1956-63. doi: 10.1021/jf4054287. Epub 2014 Feb 11. PubMed PMID: 24476101. 9: Harloff HJ, Lemcke S, Mittasch J, Frolov A, Wu JG, Dreyer F, Leckband G, Jung C. A mutation screening platform for rapeseed (Brassica napus L.) and the detection of sinapine biosynthesis mutants. Theor Appl Genet. 2012 Mar;124(5):957-69. doi: 10.1007/s00122-011-1760-z. Epub 2011 Dec 24. PubMed PMID: 22198204. 10: Kajla S, Mukhopadhyay A, Pradhan AK. Development of transgenic Brassica juncea lines for reduced seed sinapine content by perturbing phenylpropanoid pathway genes. PLoS One. 2017 Aug 7;12(8):e0182747. doi: 10.1371/journal.pone.0182747. eCollection 2017. PubMed PMID: 28787461; PubMed Central PMCID: PMC5546701. 11: Guo Y, Ding Y, Zhang T, An H. Sinapine reverses multi-drug resistance in MCF-7/dox cancer cells by downregulating FGFR4/FRS2α-ERK1/2 pathway-mediated NF-κB activation. Phytomedicine. 2016 Mar 15;23(3):267-73. doi: 10.1016/j.phymed.2015.12.017. Epub 2016 Jan 15. PubMed PMID: 26969380. 12: Huang D, Luo L, Jiang C, Han J, Wang J, Zhang T, Jiang J, Zhou Z, Chen H. Sinapine detection in radish taproot using surface desorption atmospheric pressure chemical ionization mass spectrometry. J Agric Food Chem. 2011 Mar 23;59(6):2148-56. doi: 10.1021/jf103725f. Epub 2011 Feb 18. PubMed PMID: 21332204. 13: Tzagoloff A. Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline. Plant Physiol. 1963 Mar;38(2):202-6. PubMed PMID: 16655775; PubMed Central PMCID: PMC549906. 14: Nair RB, Joy RW 4th, Kurylo E, Shi X, Schnaider J, Datla RS, Keller WA, Selvaraj G. Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds. Plant Physiol. 2000 Aug;123(4):1623-34. PubMed PMID: 10938378; PubMed Central PMCID: PMC59119. 15: Yu D, Huang X, Zou C, Li B, Duan J, Yin Q. Isolation and identification of sinapine-degrading bacteria from the intestinal tract of laying hens. Anim Nutr. 2016 Mar;2(1):57-62. doi: 10.1016/j.aninu.2016.02.002. Epub 2016 Mar 2. PubMed PMID: 29767072; PubMed Central PMCID: PMC5940989. 16: Huang J, Rozwadowski K, Bhinu VS, Schäfer U, Hannoufa A. Manipulation of sinapine, choline and betaine accumulation in Arabidopsis seed: towards improving the nutritional value of the meal and enhancing the seedling performance under environmental stresses in oilseed crops. Plant Physiol Biochem. 2008 Jul;46(7):647-54. doi: 10.1016/j.plaphy.2008.04.014. Epub 2008 Apr 25. PubMed PMID: 18515127. 17: Vermorel M, Hocquemiller R, Evrard J. Valorization of rapeseed meal. 5. Effects of sinapine and other phenolic compounds on food intake and nutrient utilization in growing rats. Reprod Nutr Dev. 1987;27(4):781-90. PubMed PMID: 3116621. 18: Li X, Han L, Li Y, Zhang J, Chen J, Lu W, Zhao X, Lai Y, Chen D, Wei G. Protective Effect of Sinapine against Hydroxyl Radical-Induced Damage to Mesenchymal Stem Cells and Possible Mechanisms. Chem Pharm Bull (Tokyo). 2016;64(4):319-25. doi: 10.1248/cpb.c15-00850. Epub 2016 Feb 3. PubMed PMID: 26842908. 19: Wolfram K, Schmidt J, Wray V, Milkowski C, Schliemann W, Strack D. Profiling of phenylpropanoids in transgenic low-sinapine oilseed rape (Brassica napus). Phytochemistry. 2010 Jul;71(10):1076-84. doi: 10.1016/j.phytochem.2010.04.007. Epub 2010 May 5. PubMed PMID: 20451226. 20: Milkowski C, Strack D. Sinapate esters in brassicaceous plants: biochemistry, molecular biology, evolution and metabolic engineering. Planta. 2010 Jun;232(1):19-35. doi: 10.1007/s00425-010-1168-z. Epub 2010 Apr 29. Review. PubMed PMID: 20428885.