Sesamol | CAS#533-31-3 | HepG2 inhibitor

MedKoo Cat#: 463776 | Name: Sesamol

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Description:

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

Sesamol is a lignan originally isolated from S. indicum that has diverse biological activities, including antioxidant, antibacterial, anticancer, and anti-obesity properties. Sesamol scavenges 2,2-diphenyl-1-picrylhydrazyl radicals with an IC50 value of 5.44 μg/ml and is active against B. cereus and S. aureus. It also inhibits the growth of HepG2 human hepatocellular carcinoma cells in a concentration-dependent manner. Sesamol reduces weight gain and hepatic steatosis in a mouse model of obesity induced by a high-fat diet (HFD).

Chemical Structure

Sesamol

CAS#533-31-3

Theoretical Analysis

MedKoo Cat#: 463776

Name: Sesamol

CAS#: 533-31-3

Chemical Formula: C7H6O3

Exact Mass: 138.0317

Molecular Weight: 138.12

Elemental Analysis: C, 60.87; H, 4.38; O, 34.75

Price and Availability

Size	Price	Availability
10g	USD 250.00	2 Weeks
25g	USD 400.00	2 Weeks
50g	USD 600.00	2 Weeks
100g	USD 900.00	2 Weeks

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Related CAS #

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Synonym

Sesamol; NSC 59256; NSC59256; NSC-59256;

IUPAC/Chemical Name

benzo[d][1,3]dioxol-5-ol

InChi Key

LUSZGTFNYDARNI-UHFFFAOYSA-N

InChi Code

InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2

SMILES Code

OC1=CC=C2OCOC2=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

>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:

Sesamol has anticancer properties. Sesamol inactivated Wnt/β-catenin signaling and sesamol induced Wnt inhibitory factor 1 (WIF1), expression and WIF1 artificial knockdown abrogated the inactivation of Wnt/β-catenin signaling by sesamol exposure in triple negative breast cancer cells. Promoter region de-methylation was responsible for WIF1 up-regulation by sesamol administration. Reference: Biochem Pharmacol. 2022 Dec;206:115299. https://pubmed.ncbi.nlm.nih.gov/36244446/

In vivo activity:

Sesamol might be a prospective therapeutic candidate for hepatic fibrosis treatment. Sesamol could regulate hepatic fibrosis by inhibiting fibrogenesis, autophagy and inflammation. Sesamol significantly reversed hepatic fibrosis via FXR/LXR and autophagy. In C57BL/6 mice, sesamol reduced serum transaminase, histopathology changes, fibrogenesis, autophagy markers and inflammatory cytokines caused by TAA. Reference: Phytomedicine. 2023 Oct 13;123:155145. https://pubmed.ncbi.nlm.nih.gov/37976698/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	217.20
	DMSO	30.0	217.20
	Ethanol	30.0	217.20

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 138.12 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. Ma X, Hu X, Zhu Y, Jin H, Hu G, Ding L, Ning S. Sesamol inhibits proliferation, migration and invasion of triple negative breast cancer via inactivating Wnt/β-catenin signaling. Biochem Pharmacol. 2022 Dec;206:115299. doi: 10.1016/j.bcp.2022.115299. Epub 2022 Oct 13. PMID: 36244446. 2. Xiong J, Sheng J, Wei Y, Sun Z, Xiao X, Zhang L. Sesamol Augments Paclitaxel-Induced Apoptosis in Human Cervical Cancer Cell Lines. Nutr Cancer. 2022;74(10):3692-3700. doi: 10.1080/01635581.2022.2079684. Epub 2022 May 31. PMID: 35639488. 3. Jiang Y, Hou L, Dou J, Xuan M, Cui Z, Lian L, Nan J, Wu Y. Sesamol as a potential candidate for the treatment of hepatic fibrosis, based on its regulation of FXR/LXR axis-mediated inhibition of autophagy through crosstalk between hepatic cells and macrophage. Phytomedicine. 2023 Oct 13;123:155145. doi: 10.1016/j.phymed.2023.155145. Epub ahead of print. PMID: 37976698. 4. El-Sayyad SM, El-Ella DMA, Hafez MM, Al-Mokaddem AK, Ali BM, Awny MM, El-Emam SZ. Sesamol defends neuronal damage following cerebral ischemia/reperfusion: a crosstalk of autophagy and Notch1/NLRP3 inflammasome signaling. Inflammopharmacology. 2023 Oct 17. doi: 10.1007/s10787-023-01355-1. Epub ahead of print. PMID: 37848698.

In vitro protocol:

In vivo protocol:

1. Jiang Y, Hou L, Dou J, Xuan M, Cui Z, Lian L, Nan J, Wu Y. Sesamol as a potential candidate for the treatment of hepatic fibrosis, based on its regulation of FXR/LXR axis-mediated inhibition of autophagy through crosstalk between hepatic cells and macrophage. Phytomedicine. 2023 Oct 13;123:155145. doi: 10.1016/j.phymed.2023.155145. Epub ahead of print. PMID: 37976698. 2. El-Sayyad SM, El-Ella DMA, Hafez MM, Al-Mokaddem AK, Ali BM, Awny MM, El-Emam SZ. Sesamol defends neuronal damage following cerebral ischemia/reperfusion: a crosstalk of autophagy and Notch1/NLRP3 inflammasome signaling. Inflammopharmacology. 2023 Oct 17. doi: 10.1007/s10787-023-01355-1. Epub ahead of print. PMID: 37848698.

1: Damiens A, Alebrahim MT, Léonard E, Fayeulle A, Furman C, Hilbert JL, Siah A, Billamboz M. Sesamol-based terpenoids as promising bio-sourced crop protection compounds against the wheat pathogen Zymoseptoria tritici. Pest Manag Sci. 2021 Jan 8. doi: 10.1002/ps.6269. Epub ahead of print. PMID: 33415837. 2: Zhang P, Wang Y, Wang H, Cao J. Sesamol alleviates chronic intermittent hypoxia-induced cognitive deficits via inhibiting oxidative stress and inflammation in rats. Neuroreport. 2021 Jan 13;32(2):105-111. doi: 10.1097/WNR.0000000000001564. PMID: 33323839. 3: Han L, Li J, Wang S, Cheng W, Ma L, Liu G, Han D, Niu L. The inhibitory effects of sesamol and sesamolin on the glycidyl esters formation during deodorization of vegetables oils. J Sci Food Agric. 2020 Dec 4. doi: 10.1002/jsfa.10989. Epub ahead of print. PMID: 33275282. 4: Gourishetti K, Keni R, Nayak PG, Jitta SR, Bhaskaran NA, Kumar L, Kumar N, Krishnadas N, Shenoy RR. Sesamol-Loaded PLGA Nanosuspension for Accelerating Wound Healing in Diabetic Foot Ulcer in Rats. Int J Nanomedicine. 2020 Nov 23;15:9265-9282. doi: 10.2147/IJN.S268941. PMID: 33262587; PMCID: PMC7695744. 5: Zhou S, Zou H, Huang G, Chen G. Preparations and antioxidant activities of sesamol and it's derivatives. Bioorg Med Chem Lett. 2021 Jan 1;31:127716. doi: 10.1016/j.bmcl.2020.127716. Epub 2020 Nov 26. PMID: 33249134. 6: El-Emam SZ. Sesamol Alleviates the Cytotoxic Effect of Cyclophosphamide on Normal Human Lung WI-38 Cells via Suppressing RAGE/NF-κB/Autophagy Signaling. Nat Prod Bioprospect. 2020 Nov 20. doi: 10.1007/s13659-020-00286-6. Epub ahead of print. PMID: 33216292. 7: Ohno KI, Sato K, Kumano M, Watanabe K, Fujimura T. Electrochemical Detection of Sesamol Dimer and its Application to Measurement of Radicals. Anal Sci. 2020 Oct 23. doi: 10.2116/analsci.20N027. Epub ahead of print. PMID: 33100301. 8: Li X , Dong S , Bai W , Jia J , Gu R , Zhao C , Liu X , Wang Y . Metabolic and transcriptional regulation of phenolic conversion and tocopherol biosynthesis during germination of sesame (Sesamum indicum L.) seeds. Food Funct. 2020 Nov 18;11(11):9848-9857. doi: 10.1039/d0fo01706j. PMID: 33090159. 9: Chamorro-Arenas D, Salgado-Moreno G, Martinez-Mendieta L, Quintero L, Godínez-Chaparro B, Sartillo-Piscil F. Stereoselective Synthesis and Antiallodynic Activity of 3-Hydroxylated Paroxetines. ChemMedChem. 2020 Oct 19. doi: 10.1002/cmdc.202000674. Epub ahead of print. PMID: 33078572. 10: Zhao B, Xia B, Li X, Zhang L, Liu X, Shi R, Kou R, Liu Z, Liu X. Sesamol Supplementation Attenuates DSS-Induced Colitis via Mediating Gut Barrier Integrity, Inflammatory Responses, and Reshaping Gut Microbiome. J Agric Food Chem. 2020 Sep 30;68(39):10697-10708. doi: 10.1021/acs.jafc.0c04370. Epub 2020 Sep 16. PMID: 32893621. 11: C Palheta I, R Ferreira L, K L Vale J, P P Silva O, M Herculano A, R H M Oliveira K, Neto AMJC, M Campos J, B R Santos C, S Borges R. Alkylated Sesamol Derivatives as Potent Antioxidants. Molecules. 2020 Jul 21;25(14):3300. doi: 10.3390/molecules25143300. PMID: 32708143; PMCID: PMC7397082. 12: Wei SM, Wang RY, Chen YS. Sesamol Protects Testis from Ischemia-Reperfusion Injury through Scavenging Reactive Oxygen Species and Upregulating CREMτ Expression. Oxid Med Cell Longev. 2020 Jun 17;2020:9043806. doi: 10.1155/2020/9043806. PMID: 32655774; PMCID: PMC7320277. 13: Ashooriha M, Khoshneviszadeh M, Khoshneviszadeh M, Rafiei A, Kardan M, Yazdian-Robati R, Emami S. Kojic acid-natural product conjugates as mushroom tyrosinase inhibitors. Eur J Med Chem. 2020 Sep 1;201:112480. doi: 10.1016/j.ejmech.2020.112480. Epub 2020 Jun 16. PMID: 32652434. 14: Alazoumi KKM, Ahmed A, Alamery SF, Shamsi A, Ahmad B, Islam A, Farooqi H. Effect of Antioxidants on Heavy Metals Induced Conformational Altera-tion of Cytochrome C And Myoglobin. Protein Pept Lett. 2020 Jun 10. doi: 10.2174/0929866527666200610134442. Epub ahead of print. PMID: 32520671. 15: Lee DH, Chang SH, Yang DK, Song NJ, Yun UJ, Park KW. Sesamol Increases Ucp1 Expression in White Adipose Tissues and Stimulates Energy Expenditure in High- Fat Diet-Fed Obese Mice. Nutrients. 2020 May 18;12(5):1459. doi: 10.3390/nu12051459. PMID: 32443555; PMCID: PMC7284577. 16: Castro-González LM, Alvarez-Idaboy JR, Galano A. Computationally Designed Sesamol Derivatives Proposed as Potent Antioxidants. ACS Omega. 2020 Apr 13;5(16):9566-9575. doi: 10.1021/acsomega.0c00898. PMID: 32363309; PMCID: PMC7191856. 17: Majdaeen M, Banaei A, Abedi-Firouzjah R, Ebrahimnejad Gorji K, Ataei G, Momeni F, Zamani H. Investigating the radioprotective effect of sesamol oral consumption against gamma irradiation in mice by micronucleus and alkaline comet assays. Appl Radiat Isot. 2020 May;159:109091. doi: 10.1016/j.apradiso.2020.109091. Epub 2020 Feb 22. PMID: 32250765. 18: Liou CJ, Chen YL, Yu MC, Yeh KW, Shen SC, Huang WC. Sesamol Alleviates Airway Hyperresponsiveness and Oxidative Stress in Asthmatic Mice. Antioxidants (Basel). 2020 Apr 1;9(4):295. doi: 10.3390/antiox9040295. PMID: 32244835; PMCID: PMC7222203. 19: Kim AY, Yun CI, Lee JG, Kim YJ. Determination and Daily Intake Estimation of Lignans in Sesame Seeds and Sesame Oil Products in Korea. Foods. 2020 Mar 30;9(4):394. doi: 10.3390/foods9040394. PMID: 32235516; PMCID: PMC7230771. 20: Ghadge GA, Gourishetti K, Chamallamudi MR, Nampurath GK, Nandakumar K, Kumar N. Sesamol protects MIN6 pancreatic beta cells against simvastatin-induced toxicity by restoring mitochondrial membrane potentials. 3 Biotech. 2020 Apr;10(4):149. doi: 10.1007/s13205-020-2146-1. Epub 2020 Mar 2. PMID: 32181111; PMCID: PMC7052092.