WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 406634
Description: Embelin is the only known non-peptide small-molecule X-linked inhibitor of the apoptosis protein (XIAP) - an anti-apoptotic protein considered a promising cancer therapeutic target. Embelin acts as an NF-κB blocker and potential suppressor of tumorigenesis. It also exhibits potent cytotoxic, antioxidant and cancer chemopreventive effects. Given the potential uses of embelin, it is recommended that further investigations take place to properly explore its pharmacological and clinical effects.
MedKoo Cat#: 406634
Chemical Formula: C17H26O4
Exact Mass: 294.18311
Molecular Weight: 294.39
Elemental Analysis: C, 69.36; H, 8.90; O, 21.74
Synonym: NSC91874; NSC91874; NSC 91874; Embelin; Emberine; Embelic acid.
IUPAC/Chemical Name: 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
InChi Key: IRSFLDGTOHBADP-UHFFFAOYSA-N
InChi Code: InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
SMILES Code: O=C1C(O)=C(CCCCCCCCCCC)C(C(O)=C1)=O
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 to 10 mM in ethanol with gentle warming and to 100 mM in DMSO, not soluble in water
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
The following data is based on the product molecular weight 294.39 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: Zhou XL, Huang L, Cao J. Embelin Reduces Systemic Inflammation and Ameliorates Organ Injuries in Septic Rats Through Downregulating STAT3 and NF-κB Pathways. Inflammation. 2015 Feb 15. [Epub ahead of print] PubMed PMID: 25682469.
2: Narayanaswamy R, Shymatak M, Chatterjee S, Wai LK, Arumugam G. Inhibition of Angiogenesis and Nitric Oxide Synthase (NOS), by Embelin & Vilangin Using in vitro, in vivo & in Silico Studies. Adv Pharm Bull. 2014 Dec;4(Suppl 2):543-8. doi: 10.5681/apb.2014.080. Epub 2014 Dec 31. PubMed PMID: 25671187; PubMed Central PMCID: PMC4312403.
3: Joy B, Kumar SN, Radhika AR, Abraham A. Embelin (2,5-Dihydroxy-3-undecyl-p-benzoquinone) for photodynamic therapy: study of their cytotoxicity in cancer cells. Appl Biochem Biotechnol. 2015 Jan;175(2):1069-79. doi: 10.1007/s12010-014-1266-7. Epub 2014 Oct 31. PubMed PMID: 25359675.
4: Yang T, Lan J, Huang Q, Chen X, Sun X, Liu X, Yang P, Jin T, Wang S, Mou X. Embelin sensitizes acute myeloid leukemia cells to TRAIL through XIAP inhibition and NF-κB inactivation. Cell Biochem Biophys. 2015 Jan;71(1):291-7. doi: 10.1007/s12013-014-0197-9. PubMed PMID: 25358405.
5: Dhanjal JK, Nigam N, Sharma S, Chaudhary A, Kaul SC, Grover A, Wadhwa R. Embelin inhibits TNF-α converting enzyme and cancer cell metastasis: molecular dynamics and experimental evidence. BMC Cancer. 2014 Oct 22;14:775. doi: 10.1186/1471-2407-14-775. PubMed PMID: 25336399; PubMed Central PMCID: PMC4210574.
6: Hu R, Yang Y, Liu Z, Jiang H, Zhu K, Li J, Xu W. The XIAP inhibitor Embelin enhances TRAIL-induced apoptosis in human leukemia cells by DR4 and DR5 upregulation. Tumour Biol. 2015 Feb;36(2):769-77. doi: 10.1007/s13277-014-2702-6. Epub 2014 Oct 8. PubMed PMID: 25293521.
7: Singh B, Guru SK, Sharma R, Bharate SS, Khan IA, Bhushan S, Bharate SB, Vishwakarma RA. Synthesis and anti-proliferative activities of new derivatives of embelin. Bioorg Med Chem Lett. 2014 Oct 15;24(20):4865-70. doi: 10.1016/j.bmcl.2014.08.052. Epub 2014 Sep 1. PubMed PMID: 25240254.
8: Joy B, Nishanth Kumar S, Soumya MS, Radhika AR, Vibin M, Abraham A. Embelin (2,5-dihydroxy-3-undecyl-p-benzoquinone): a bioactive molecule isolated from Embelia ribes as an effective photodynamic therapeutic candidate against tumor in vivo. Phytomedicine. 2014 Sep 25;21(11):1292-7. doi: 10.1016/j.phymed.2014.07.001. Epub 2014 Jul 30. PubMed PMID: 25172792.
9: Poojari RJ. Embelin, a small molecule quinone with a co-clinical power for castrate-resistant prostate cancer. Front Pharmacol. 2014 Aug 8;5:184. doi: 10.3389/fphar.2014.00184. eCollection 2014. PubMed PMID: 25152733; PubMed Central PMCID: PMC4126039.
10: Peng M, Huang B, Zhang Q, Fu S, Wang D, Cheng X, Wu X, Xue Z, Zhang L, Zhang D, Da Y, Dai Y, Yang Q, Yao Z, Qiao L, Zhang R. Embelin inhibits pancreatic cancer progression by directly inducing cancer cell apoptosis and indirectly restricting IL-6 associated inflammatory and immune suppressive cells. Cancer Lett. 2014 Nov 28;354(2):407-16. doi: 10.1016/j.canlet.2014.08.011. Epub 2014 Aug 13. PubMed PMID: 25128650.