Lupiwighteone | CAS#104691-86-3 | isoflavone

MedKoo Cat#: 145625 | Name: Lupiwighteone

Description:

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

Lupiwighteone has anticancer effects in prostate cancer cells and neuroblastoma cells. Lupiwighteone treatment decreases the viability of MCF-7 and MDA-MB-231 cells. Lupiwighteone treatment results in apoptotic cell death in breast cancer cells. Treatment with lupiwighteone induces caspase-dependent apoptosis.

Chemical Structure

Lupiwighteone

CAS#104691-86-3

Theoretical Analysis

MedKoo Cat#: 145625

Name: Lupiwighteone

CAS#: 104691-86-3

Chemical Formula: C20H18O5

Exact Mass: 338.1200

Molecular Weight: 338.36

Elemental Analysis: C, 71.00; H, 5.36; O, 23.64

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Lupiwighteone; 8-Prenylgenistein;

IUPAC/Chemical Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

InChi Key

YGCCASGFIOIXIN-UHFFFAOYSA-N

InChi Code

1S/C20H18O5/c1-11(2)3-8-14-16(22)9-17(23)18-19(24)15(10-25-20(14)18)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3

SMILES Code

CC(C)=CCC1=C2OC=C(C(=O)C2=C(O)C=C1O)C3=CC=C(O)C=C3

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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 338.36 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

1: Won YS, Seo KI. Lupiwighteone induces caspase-dependent and -independent apoptosis on human breast cancer cells via inhibiting PI3K/Akt/mTOR pathway. Food Chem Toxicol. 2020 Jan;135:110863. doi: 10.1016/j.fct.2019.110863. Epub 2019 Oct 8. PMID: 31604113. 2: Ren J, Yang J, Xu Y, Huang Q, Yang M, Hu K. Lupiwighteone induces cell cycle arrest and apoptosis and activates the Nrf2/ARE pathway in human neuroblastoma cells. Biomed Pharmacother. 2015 Feb;69:153-61. doi: 10.1016/j.biopha.2014.11.016. Epub 2014 Nov 21. PMID: 25661352. 3: Ren J, Huang Q, Xu Y, Yang M, Yang J, Hu K. Isoflavone lupiwighteone induces cytotoxic, apoptotic, and antiangiogenic activities in DU-145 prostate cancer cells. Anticancer Drugs. 2015 Jul;26(6):599-611. doi: 10.1097/CAD.0000000000000224. PMID: 25734831. 4: Hu K, Zhang J, Zhang Y, Wu X, Jin X, Mao S, Ding P, Wu S, Ren J. Lupiwighteone as an Antitumor Agent Reverses Multidrug Resistance in K562/ADR Cells by Regulating Cellular Prion Protein-Oct4 Axis. Anticancer Agents Med Chem. 2024;24(20):1514-1524. doi: 10.2174/0118715206316284240807100226. PMID: 39129165. 5: Biondi DM, Rocco C, Ruberto G. Dihydrostilbene derivatives from Glycyrrhiza glabra leaves. J Nat Prod. 2005 Jul;68(7):1099-102. doi: 10.1021/np050034q. PMID: 16038558. 6: Wei S, Wu W, Ji Z. New antifungal pyranoisoflavone from Ficus tikoua Bur. Int J Mol Sci. 2012;13(6):7375-7382. doi: 10.3390/ijms13067375. Epub 2012 Jun 14. PMID: 22837700; PMCID: PMC3397532. 7: Polbuppha I, Suthiphasilp V, Maneerat T, Charoensup R, Limtharakul T, Cheenpracha S, Pyne SG, Laphookhieo S. Macluracochinones A-E, antimicrobial flavonoids from Maclura cochinchinensis (Lour.) Corner. Phytochemistry. 2021 Jul;187:112773. doi: 10.1016/j.phytochem.2021.112773. Epub 2021 Apr 16. PMID: 33873019. 8: Erasto P, Bojase-Moleta G, Majinda RR. Antimicrobial and antioxidant flavonoids from the root wood of Bolusanthus speciosus. Phytochemistry. 2004 Apr;65(7):875-80. doi: 10.1016/j.phytochem.2004.02.011. PMID: 15081287. 9: Xie YT, Xiong SH, Bian Y, Wang Y, Guan RQ, Suo XY, DU MR, Liu YP, Fu YH. [Chemical constituents from Artocarpus incisus and their inhibitory effects on proliferation of synoviocytes in vitro]. Zhongguo Zhong Yao Za Zhi. 2022 Sep;47(17):4665-4673. Chinese. doi: 10.19540/j.cnki.cjcmm.20220506.203. PMID: 36164873. 10: Xiaoli L, Naili W, Sau WM, Chen AS, Xinsheng Y. Four new isoflavonoids from the stem bark of Erythrina variegata. Chem Pharm Bull (Tokyo). 2006 Apr;54(4):570-3. doi: 10.1248/cpb.54.570. PMID: 16595969. 11: Ali MS, Ali MI, Onocha PA, Ahmed Z. bis-Sigmodiol: a new prenylflavanone dimer from Erythrina sigmoidea Hua (Fabaceae) of Nigeria. J Asian Nat Prod Res. 2011 Feb;13(2):182-7. doi: 10.1080/10286020.2010.546352. PMID: 21279883. 12: Liu CY, Deng P, Wang B, Liu AH, Wang MG, Li SW, Chen LL, Mao SC. Coumaronochromones, flavanones, and isoflavones from the twigs and leaves of Erythrina subumbrans inhibit PTP1B and nitric oxide production. Phytochemistry. 2023 Feb;206:113550. doi: 10.1016/j.phytochem.2022.113550. Epub 2022 Dec 5. PMID: 36481312. 13: Yang YF, Peng SX, Wang KY, Zhu CT, Zhong HS, Che FY. [Effect of Mailuo Shutong Pills in treatment of ischemic stroke based on network pharmacological analysis and experimental verification]. Zhongguo Zhong Yao Za Zhi. 2022 Dec;47(23):6466-6475. Chinese. doi: 10.19540/j.cnki.cjcmm.20220706.401. PMID: 36604893.