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MedKoo Cat#: 564553 | Name: Bisdemethoxycurcumin
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Description:

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

Bisdemethoxycurcumin is a natural inhibitor of NF-kappaB, MMP-2, and MMP--9 pathways. Bisdemethoxycurcumin suppresses migration and invasion of human cervical cancer HeLa cells.

Chemical Structure

Bisdemethoxycurcumin
Bisdemethoxycurcumin
CAS#24939-16-0

Theoretical Analysis

MedKoo Cat#: 564553

Name: Bisdemethoxycurcumin

CAS#: 24939-16-0

Chemical Formula: C19H16O4

Exact Mass: 308.1049

Molecular Weight: 308.33

Elemental Analysis: C, 74.01; H, 5.23; O, 20.76

Price and Availability

Size Price Availability Quantity
2g USD 350.00 2 Weeks
5g USD 550.00 2 Weeks
25g USD 1,250.00 2 Weeks
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Related CAS #
33171-05-0
Synonym
Curcumin III, Bisdemethoxycurcumin
IUPAC/Chemical Name
(1E,6E)-1,7-Bis(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione
InChi Key
PREBVFJICNPEKM-YDWXAUTNSA-N
InChi Code
InChI=1S/C19H16O4/c20-16-7-1-14(2-8-16)5-11-18(22)13-19(23)12-6-15-3-9-17(21)10-4-15/h1-12,20-21H,13H2/b11-5+,12-6+
SMILES Code
O=C(CC(/C=C/C1=CC=C(O)C=C1)=O)/C=C/C2=CC=C(O)C=C2
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 308.33 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
1: Yang J, Zhang B, Qin Z, Li S, Xu J, Yao Z, Zhang X, Gonzalez FJ, Yao X. Efflux excretion of bisdemethoxycurcumin-O-glucuronide in UGT1A1-overexpressing HeLa cells: Identification of breast cancer resistance protein (BCRP) and multidrug resistance-associated proteins 1 (MRP1) as the glucuronide transporters. Biofactors. 2018 Oct 17. doi: 10.1002/biof.1452. [Epub ahead of print] PubMed PMID: 30334318. 2: Fu M, Fu S, Ni S, Wang D, Hong T. Inhibitory effects of bisdemethoxycurcumin on mast cell-mediated allergic diseases. Int Immunopharmacol. 2018 Dec;65:182-189. doi: 10.1016/j.intimp.2018.10.005. Epub 2018 Oct 10. PubMed PMID: 30316076. 3: Liao CL, Chu YL, Lin HY, Chen CY, Hsu MJ, Liu KC, Lai KC, Huang AC, Chung JG. Bisdemethoxycurcumin Suppresses Migration and Invasion of Human Cervical Cancer HeLa Cells via Inhibition of NF-ĸB, MMP-2 and -9 Pathways. Anticancer Res. 2018 Jul;38(7):3989-3997. doi: 10.21873/anticanres.12686. PubMed PMID: 29970522. 4: Tedesco S, Zusso M, Facci L, Trenti A, Boscaro C, Belluti F, Fadini GP, Skaper SD, Giusti P, Bolego C, Cignarella A. Bisdemethoxycurcumin and Its Cyclized Pyrazole Analogue Differentially Disrupt Lipopolysaccharide Signalling in Human Monocyte-Derived Macrophages. Mediators Inflamm. 2018 Feb 8;2018:2868702. doi: 10.1155/2018/2868702. eCollection 2018. PubMed PMID: 29576743; PubMed Central PMCID: PMC5822910. 5: Mohammadi F, Moeeni M, Mahmudian A, Hassani L. Inhibition of amyloid fibrillation of lysozyme by bisdemethoxycurcumin and diacetylbisdemethoxycurcumin. Biophys Chem. 2018 Apr;235:56-65. doi: 10.1016/j.bpc.2018.02.005. Epub 2018 Feb 12. PubMed PMID: 29477768. 6: Kong R, Kang OH, Seo YS, Zhou T, Kim SA, Shin DW, Kwon DY. MAPKs and NF κB pathway inhibitory effect of bisdemethoxycurcumin on phorbol 12 myristate 13 acetate and A23187 induced inflammation in human mast cells. Mol Med Rep. 2018 Jan;17(1):630-635. doi: 10.3892/mmr.2017.7852. Epub 2017 Oct 20. PubMed PMID: 29115448. 7: Hathout RM, El-Ahmady SH, Metwally AA. Curcumin or bisdemethoxycurcumin for nose-to-brain treatment of Alzheimer disease? A bio/chemo-informatics case study. Nat Prod Res. 2017 Oct 12:1-10. doi: 10.1080/14786419.2017.1385017. [Epub ahead of print] PubMed PMID: 29022380. 8: Wang HJ, Yang ZX, Dai XT, Chen YF, Yang HP, Zhou XD. Bisdemethoxycurcumin sensitizes cisplatin-resistant lung cancer cells to chemotherapy by inhibition of CA916798 and PI3K/AKT signaling. Apoptosis. 2017 Sep;22(9):1157-1168. doi: 10.1007/s10495-017-1395-x. PubMed PMID: 28677094. 9: Shao Y, Zhu W, Da J, Xu M, Wang Y, Zhou J, Wang Z. Bisdemethoxycurcumin in combination with α-PD-L1 antibody boosts immune response against bladder cancer. Onco Targets Ther. 2017 May 22;10:2675-2683. doi: 10.2147/OTT.S130653. eCollection 2017. PubMed PMID: 28579805; PubMed Central PMCID: PMC5449128. 10: Enomoto A, Yamada J, Morita A, Miyagawa K. Bisdemethoxycurcumin enhances X-ray-induced apoptosis possibly through p53/Bcl-2 pathway. Mutat Res. 2017 Mar;815:1-5. doi: 10.1016/j.mrgentox.2016.12.005. Epub 2017 Jan 11. PubMed PMID: 28283087. 11: Mehanny M, Hathout RM, Geneidi AS, Mansour S. Studying the effect of physically-adsorbed coating polymers on the cytotoxic activity of optimized bisdemethoxycurcumin loaded-PLGA nanoparticles. J Biomed Mater Res A. 2017 May;105(5):1433-1445. doi: 10.1002/jbm.a.36028. Epub 2017 Feb 24. PubMed PMID: 28177570. 12: Ramezani M, Hatamipour M, Sahebkar A. Promising anti-tumor properties of bisdemethoxycurcumin: A naturally occurring curcumin analogue. J Cell Physiol. 2018 Feb;233(2):880-887. doi: 10.1002/jcp.25795. Epub 2017 May 16. Review. PubMed PMID: 28075008. 13: Yang H, Fan S, An Y, Wang X, Pan Y, Xiaokaiti Y, Duan J, Li X, Tie L, Ye M, Li X. Bisdemethoxycurcumin exerts pro-apoptotic effects in human pancreatic adenocarcinoma cells through mitochondrial dysfunction and a GRP78-dependent pathway. Oncotarget. 2016 Dec 13;7(50):83641-83656. doi: 10.18632/oncotarget.13272. PubMed PMID: 27845899; PubMed Central PMCID: PMC5347794. 14: Mohammadi F, Moeeni M. Investigation of the binding interactions of Bisdemethoxycurcumin, Diacetylcurcumin and Diacetylbisdemethoxycurcumin with bovine α-lactalbumin by experimental and theoretical analysis. J Biomol Struct Dyn. 2017 Dec;35(16):3486-3498. doi: 10.1080/07391102.2016.1259588. Epub 2016 Dec 1. PubMed PMID: 27829316. 15: Adeyeni TA, Khatwani N, San K, Ezekiel UR. BMI1 is downregulated by the natural compound curcumin, but not by bisdemethoxycurcumin and dimethoxycurcumin. Physiol Rep. 2016 Aug;4(16). pii: e12906. doi: 10.14814/phy2.12906. PubMed PMID: 27550987; PubMed Central PMCID: PMC5002914. 16: Pei H, Yang Y, Cui L, Yang J, Li X, Yang Y, Duan H. Bisdemethoxycurcumin inhibits ovarian cancer via reducing oxidative stress mediated MMPs expressions. Sci Rep. 2016 Jun 28;6:28773. doi: 10.1038/srep28773. PubMed PMID: 27349797; PubMed Central PMCID: PMC4923879. 17: Zhang YQ, Yang ZG, Ding W, Luo JX. Synergistic inhibitory effect of scopoletin and bisdemethoxycurcumin on Tetranychus cinnabarinus (Boisduval) (Acari: Tetranychidae). Z Naturforsch C. 2016;71(1-2):1-8. doi: 10.1515/znc-2014-4131. PubMed PMID: 26824978. 18: Lai CS, Chen YY, Lee PS, Kalyanam N, Ho CT, Liou WS, Yu RC, Pan MH. Bisdemethoxycurcumin Inhibits Adipogenesis in 3T3-L1 Preadipocytes and Suppresses Obesity in High-Fat Diet-Fed C57BL/6 Mice. J Agric Food Chem. 2016 Feb 3;64(4):821-30. doi: 10.1021/acs.jafc.5b05577. Epub 2016 Jan 25. PubMed PMID: 26777574. 19: Pettinari R, Marchetti F, Pettinari C, Condello F, Petrini A, Scopelliti R, Riedel T, Dyson PJ. Organometallic rhodium(III) and iridium(III) cyclopentadienyl complexes with curcumin and bisdemethoxycurcumin co-ligands. Dalton Trans. 2015 Dec 21;44(47):20523-31. doi: 10.1039/c5dt03037d. Epub 2015 Nov 9. PubMed PMID: 26548708. 20: Benediktsdottir BE, Baldursson O, Gudjonsson T, Tønnesen HH, Masson M. Curcumin, bisdemethoxycurcumin and dimethoxycurcumin complexed with cyclodextrins have structure specific effect on the paracellular integrity of lung epithelia in vitro. Biochem Biophys Rep. 2015 Nov 10;4:405-410. doi: 10.1016/j.bbrep.2015.11.004. eCollection 2015 Dec. PubMed PMID: 29124231; PubMed Central PMCID: PMC5669517.

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