Sesamin | CAS#607-80-7 | anti-inflammatory

MedKoo Cat#: 584408 | Name: Sesamin

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Description:

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

Sesamin is a constituent of sesame oil that has been shown to lower cholesterol and inflammation.

Chemical Structure

Sesamin

CAS#607-80-7

Theoretical Analysis

MedKoo Cat#: 584408

Name: Sesamin

CAS#: 607-80-7

Chemical Formula: C20H18O6

Exact Mass: 354.1103

Molecular Weight: 354.36

Elemental Analysis: C, 67.79; H, 5.12; O, 27.09

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 190.00
5mg	USD 352.00
10mg	USD 580.00

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Related CAS #

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Synonym

Sesamin; AI3-00811; Asarinin; Episesamin; Fagarol; Sezamin

IUPAC/Chemical Name

1H,3H-Furo(3,4-c)furan, tetrahydro-1,4-bis(3,4-(methylenedioxy)phenyl)-, (1S,3aR,4S,6aR)- (8CI)

InChi Key

PEYUIKBAABKQKQ-AFHBHXEDSA-N

InChi Code

InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19+,20+/m0/s1

SMILES Code

[H][C@@]12[C@@](CO[C@@H]2C3=CC(OCO4)=C4C=C3)([H])[C@@H](C5=CC(OCO6)=C6C=C5)OC1

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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Sertraline is selective for serotonin transporter (SERT) over the norepinephrine and dopamine transporters (IC50s = 520 and 720 nM, respectively).

In vitro activity:

This study indicates that sesamin inhibits cervical cancer cell proliferation, and might be useful as an adjuvant in anti-cervical cancer treatments. Sesamin inhibited SiHa and HeLa cancer cell proliferation without affecting proliferation of normal Hs68 cells. Sesamin increased the sub-G1 phase ratio and apoptosis up to approximately 38.5% and 37.8%, respectively, induced p53 phosphorylation at serine-46 and serine-15, upregulated the levels of PUMA, Bax, and PTEN, and inhibited AKT phosphorylation at serine-473. Reference: Int J Med Sci. 2020 Aug 25;17(15):2292-2298. https://pubmed.ncbi.nlm.nih.gov/32922194/

In vivo activity:

Sesamin has potential to ameliorate the symptoms of diabetes. In a diabetes model in Wistar rats, sesamin reduced blood glucose levels, HbA1c, TG, and ALT and AST enzymes. Sesamin also increased insulin levels, SOD, CAT, and GPx activities. Reference: Molecules. 2023 Oct 25;28(21):7255. https://pubmed.ncbi.nlm.nih.gov/37959677/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	282.21

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 354.36 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

Formulation protocol:

1. Udomruk S, Wudtiwai B, Hla Shwe T, Phitak T, Pothacharoen P, Phimphilai M, Kongtawelert P. Sesamin suppresses advanced glycation end products induced microglial reactivity using BV2 microglial cell line as a model. Brain Res Bull. 2021 Jul;172:190-202. doi: 10.1016/j.brainresbull.2021.04.012. Epub 2021 Apr 21. PMID: 33894297. 2. Kuo TN, Lin CS, Li GD, Kuo CY, Kao SH. Sesamin inhibits cervical cancer cell proliferation by promoting p53/PTEN-mediated apoptosis. Int J Med Sci. 2020 Aug 25;17(15):2292-2298. doi: 10.7150/ijms.48955. PMID: 32922194; PMCID: PMC7484641. 3. Huang SM, Chuang CH, Rejano CJF, Tayo LL, Hsieh CY, Huang SK, Tsai PW. Sesamin: A Promising Therapeutic Agent for Ameliorating Symptoms of Diabetes. Molecules. 2023 Oct 25;28(21):7255. doi: 10.3390/molecules28217255. PMID: 37959677; PMCID: PMC10649669. 4. Du H, Tong S, Kuang G, Gong X, Jiang N, Yang X, Liu H, Li N, Xie Y, Xiang Y, Guo J, Li Z, Yuan Y, Wu S, Wan J. Sesamin Protects against APAP-Induced Acute Liver Injury by Inhibiting Oxidative Stress and Inflammatory Response via Deactivation of HMGB1/TLR4/NFκB Signal in Mice. J Immunol Res. 2023 Aug 24;2023:1116841. doi: 10.1155/2023/1116841. PMID: 37663051; PMCID: PMC10471453.

In vitro protocol:

In vivo protocol:

1. Huang SM, Chuang CH, Rejano CJF, Tayo LL, Hsieh CY, Huang SK, Tsai PW. Sesamin: A Promising Therapeutic Agent for Ameliorating Symptoms of Diabetes. Molecules. 2023 Oct 25;28(21):7255. doi: 10.3390/molecules28217255. PMID: 37959677; PMCID: PMC10649669. 2. Du H, Tong S, Kuang G, Gong X, Jiang N, Yang X, Liu H, Li N, Xie Y, Xiang Y, Guo J, Li Z, Yuan Y, Wu S, Wan J. Sesamin Protects against APAP-Induced Acute Liver Injury by Inhibiting Oxidative Stress and Inflammatory Response via Deactivation of HMGB1/TLR4/NFκB Signal in Mice. J Immunol Res. 2023 Aug 24;2023:1116841. doi: 10.1155/2023/1116841. PMID: 37663051; PMCID: PMC10471453.

1: Liang YT, Chen J, Jiao R, Peng C, Zuo Y, Lei L, Liu Y, Wang X, Ma KY, Huang Y, Chen ZY. Cholesterol-lowering activity of sesamin is associated with down-regulation on genes of sterol transporters involved in cholesterol absorption. J Agric Food Chem. 2015 Mar 25;63(11):2963-9. doi: 10.1021/jf5063606. Epub 2015 Mar 13. PubMed PMID: 25745846. 2: Monteiro EM, Chibli LA, Yamamoto CH, Pereira MC, Vilela FM, Rodarte MP, Pinto MA, do Amaral Mda P, Silvério MS, Araújo AL, de Araújo Ada L, Del-Vechio-Vieira G, de Sousa OV. Antinociceptive and anti-inflammatory activities of the sesame oil and sesamin. Nutrients. 2014 May 12;6(5):1931-44. doi: 10.3390/nu6051931. PubMed PMID: 24824289; PubMed Central PMCID: PMC4042560. 3: Jiang Z, Li S, Liu Y, Deng P, Huang J, He G. Sesamin induces melanogenesis by microphthalmia-associated transcription factor and tyrosinase up-regulation via cAMP signaling pathway. Acta Biochim Biophys Sin (Shanghai). 2011 Oct;43(10):763-70. doi: 10.1093/abbs/gmr078. Epub 2011 Sep 6. PubMed PMID: 21896570. 4: Kong X, Wang GD, Ma MZ, Deng RY, Guo LQ, Zhang JX, Yang JR, Su Q. Sesamin Ameliorates Advanced Glycation End Products-Induced Pancreatic β-Cell Dysfunction and Apoptosis. Nutrients. 2015 Jun 9;7(6):4689-704. doi: 10.3390/nu7064689. PubMed PMID: 26066015; PubMed Central PMCID: PMC4488808. 5: Ma L, Gong X, Kuang G, Jiang R, Chen R, Wan J. Sesamin ameliorates lipopolysaccharide/d-galactosamine-induced fulminant hepatic failure by suppression of Toll-like receptor 4 signaling in mice. Biochem Biophys Res Commun. 2015 May 29;461(2):230-6. doi: 10.1016/j.bbrc.2015.03.154. Epub 2015 Apr 9. PubMed PMID: 25866179. 6: Liu N, Wu C, Sun L, Zheng J, Guo P. Sesamin enhances cholesterol efflux in RAW264.7 macrophages. Molecules. 2014 Jun 6;19(6):7516-27. doi: 10.3390/molecules19067516. PubMed PMID: 24914897. 7: Tian J, Zhang R, Zhang H, Liu Y, Niu Y, Zhao L, Wang L, Guo H. [Protective effect of sesamin against myocardial injury induced by cadmium chloride in rats]. Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2014 May;32(5):357-60. Chinese. PubMed PMID: 25169091. 8: Xu P, Cai F, Liu X, Guo L. Sesamin inhibits lipopolysaccharide-induced proliferation and invasion through the p38-MAPK and NF-κB signaling pathways in prostate cancer cells. Oncol Rep. 2015 Jun;33(6):3117-23. doi: 10.3892/or.2015.3888. Epub 2015 Mar 31. PubMed PMID: 25845399. 9: Lin CH, Shen ML, Zhou N, Lee CC, Kao ST, Wu DC. Protective effects of the polyphenol sesamin on allergen-induced T(H)2 responses and airway inflammation in mice. PLoS One. 2014 Apr 22;9(4):e96091. doi: 10.1371/journal.pone.0096091. eCollection 2014. PubMed PMID: 24755955; PubMed Central PMCID: PMC3996011. 10: Hori H, Takayanagi T, Kamada Y, Shimoyoshi S, Ono Y, Kitagawa Y, Shibata H, Nagao M, Fujii W, Sakakibara Y. Genotoxicity evaluation of sesamin and episesamin. Mutat Res. 2011 Feb 3;719(1-2):21-8. doi: 10.1016/j.mrgentox.2010.10.001. Epub 2010 Oct 16. Erratum in: Mutat Res. 2011 Apr 3;721(2):211. PubMed PMID: 20937410. 11: Ide T. Combined effect of sesamin and soybean phospholipid on hepatic fatty acid metabolism in rats. J Clin Biochem Nutr. 2014 May;54(3):210-8. doi: 10.3164/jcbn.13-83. Epub 2014 Apr 12. PubMed PMID: 24894022; PubMed Central PMCID: PMC4042142. 12: Akl MR, Ayoub NM, Abuasal BS, Kaddoumi A, Sylvester PW. Sesamin synergistically potentiates the anticancer effects of γ-tocotrienol in mammary cancer cell lines. Fitoterapia. 2013 Jan;84:347-59. doi: 10.1016/j.fitote.2012.12.013. Epub 2012 Dec 22. PubMed PMID: 23266736. 13: Yasuda K, Sakaki T. How is sesamin metabolised in the human liver to show its biological effects? Expert Opin Drug Metab Toxicol. 2012 Jan;8(1):93-102. doi: 10.1517/17425255.2012.637917. Epub 2011 Nov 19. Review. PubMed PMID: 22098100. 14: Zlabek V, Vestergren AS, Trattner S, Wagner L, Pickova J, Zamaratskaia G. Stimulatory effect of sesamin on hepatic cytochrome P450 activities in Atlantic salmon (Salmo salar L.) is not directly associated with expression of genes related to xenobiotic metabolism. Xenobiotica. 2015;45(7):598-604. doi: 10.3109/00498254.2015.1007111. Epub 2015 Feb 12. PubMed PMID: 25673088. 15: Zhang M, Lee HJ, Park KH, Park HJ, Choi HS, Lim SC, Lee MK. Modulatory effects of sesamin on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. Neuropharmacology. 2012 Jun;62(7):2219-26. doi: 10.1016/j.neuropharm.2012.01.012. Epub 2012 Jan 24. PubMed PMID: 22293035. 16: Park HJ, Zhao TT, Lee KS, Lee SH, Shin KS, Park KH, Choi HS, Lee MK. Effects of (-)-sesamin on 6-hydroxydopamine-induced neurotoxicity in PC12 cells and dopaminergic neuronal cells of Parkinson's disease rat models. Neurochem Int. 2015 Apr-May;83-84:19-27. doi: 10.1016/j.neuint.2015.01.003. Epub 2015 Mar 3. PubMed PMID: 25747493. 17: Wagner L, Trattner S, Pickova J, Gómez-Requeni P, Moazzami AA. ¹H NMR-based metabolomics studies on the effect of sesamin in Atlantic salmon (Salmo salar). Food Chem. 2014 Mar 15;147:98-105. doi: 10.1016/j.foodchem.2013.09.128. Epub 2013 Oct 1. PubMed PMID: 24206691. 18: Siao AC, Hou CW, Kao YH, Jeng KC. Effect of sesamin on apoptosis and cell cycle arrest in human breast cancer mcf-7 cells. Asian Pac J Cancer Prev. 2015;16(9):3779-83. PubMed PMID: 25987037. 19: Zuo Y, Peng C, Liang Y, Ma KY, Chan HY, Huang Y, Chen ZY. Sesamin extends the mean lifespan of fruit flies. Biogerontology. 2013 Apr;14(2):107-19. doi: 10.1007/s10522-012-9413-4. Epub 2013 Jan 6. PubMed PMID: 23291977. 20: Fukunaga M, Ohnishi M, Shiratsuchi A, Kawakami T, Takahashi M, Motomura M, Egusa K, Urasaki T, Inoue A. Sesamin increases heme oxygenase-1 protein in RAW 264.7 macrophages through inhibiting its ubiquitination process. Eur J Pharmacol. 2014 Oct 15;741:214-21. doi: 10.1016/j.ejphar.2014.08.015. Epub 2014 Aug 26. PubMed PMID: 25169430.

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