MedKoo Cat#: 584511 | Name: Kievitone

Description:

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

Kievitone is a naturally-occurring, highly hydroxylated isoflavanoid that inhibits the proliferation of breast cancer cell lines.

Chemical Structure

Kievitone
Kievitone
CAS#40105-60-0

Theoretical Analysis

MedKoo Cat#: 584511

Name: Kievitone

CAS#: 40105-60-0

Chemical Formula: C20H20O6

Exact Mass: 356.1260

Molecular Weight: 356.37

Elemental Analysis: C, 67.41; H, 5.66; O, 26.94

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.
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Related CAS #
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Synonym
Kievitone
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-
InChi Key
MERHMOCEIBOOMA-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H20O6/c1-10(2)3-5-13-16(23)8-17(24)18-19(25)14(9-26-20(13)18)12-6-4-11(21)7-15(12)22/h3-4,6-8,14,21-24H,5,9H2,1-2H3
SMILES Code
O=C1C(C2=CC=C(O)C=C2O)COC3=C(C/C=C(C)\C)C(O)=CC(O)=C13
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 356.37 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: Hoffman R. Potent inhibition of breast cancer cell lines by the isoflavonoid kievitone: comparison with genistein. Biochem Biophys Res Commun. 1995 Jun 15;211(2):600-6. PubMed PMID: 7794275. 2: Boué SM, Burow ME, Wiese TE, Shih BY, Elliott S, Carter-Wientjes CH, McLachlan JA, Bhatnagar D. Estrogenic and antiestrogenic activities of phytoalexins from red kidney bean (Phaseolus vulgaris L.). J Agric Food Chem. 2011 Jan 12;59(1):112-20. doi: 10.1021/jf102255u. Epub 2010 Dec 6. PubMed PMID: 21133423. 3: Eerdunbayaer, Orabi MA, Aoyama H, Kuroda T, Hatano T. Structures of new phenolics isolated from licorice, and the effectiveness of licorice phenolics on vancomycin-resistant Enterococci. Molecules. 2014 Aug 25;19(9):13027-41. doi: 10.3390/molecules190913027. PubMed PMID: 25157467. 4: Li D, Chung KR, Smith DA, Schardl CL. The Fusarium solani gene encoding kievitone hydratase, a secreted enzyme that catalyzes detoxification of a bean phytoalexin. Mol Plant Microbe Interact. 1995 May-Jun;8(3):388-97. PubMed PMID: 7655061. 5: Turbek CS, Li DX, Choi GH, Schardl CL, Smith DA. Induction and purification of kievitone hydratase from Fusarium solani f. sp. phaseoli. Phytochemistry. 1990;29(9):2841-6. PubMed PMID: 1366757. 6: Pankhurst CE, Biggs DR. Sensitivity of Rhizobium to selected isoflavonoids. Can J Microbiol. 1980 Apr;26(4):542-5. PubMed PMID: 7378947. 7: Whitehead IM, Dey PM, Dixon RA. Differential patterns of phytoalexin accumulation and enzyme induction in wounded and elicitor-treated tissues ofPhaseolus vulgaris. Planta. 1982 Mar;154(2):156-64. doi: 10.1007/BF00387910. PubMed PMID: 24275977. 8: Goossens JF, Vendrig JC. Effects of abscisic acid, cytokinins, and light on isoflavonoid phytoalexin accumulation inPhaseolus vulgaris L. Planta. 1982 Sep;154(5):441-6. doi: 10.1007/BF01267811. PubMed PMID: 24276272. 9: Turbek CS, Smith DA, Schardl CL. An extracellular enzyme from Fusarium solani f. sp. phaseoli which catalyses hydration of the isoflavonoid phytoalexin, phaseollidin. FEMS Microbiol Lett. 1992 Jul 1;73(1-2):187-90. PubMed PMID: 1521768. 10: Robbins MP, Bolwell GP, Dixon RA. Metabolic changes in elicitor-treated bean cells. Selectivity of enzyme induction in relation to phytoalexin accumulation. Eur J Biochem. 1985 May 2;148(3):563-9. PubMed PMID: 3996394. 11: Hatano T, Shintani Y, Aga Y, Shiota S, Tsuchiya T, Yoshida T. Phenolic constituents of licorice. VIII. Structures of glicophenone and glicoisoflavanone, and effects of licorice phenolics on methicillin-resistant Staphylococcus aureus. Chem Pharm Bull (Tokyo). 2000 Sep;48(9):1286-92. PubMed PMID: 10993226. 12: Engleder M, Horvat M, Emmerstorfer-Augustin A, Wriessnegger T, Gabriel S, Strohmeier G, Weber H, Müller M, Kaluzna I, Mink D, Schürmann M, Pichler H. Recombinant expression, purification and biochemical characterization of kievitone hydratase from Nectria haematococca. PLoS One. 2018 Feb 8;13(2):e0192653. doi: 10.1371/journal.pone.0192653. eCollection 2018. PubMed PMID: 29420618; PubMed Central PMCID: PMC5805349. 13: Suga H, Ikeda S, Taga M, Kageyama K, Hyakumachi M. Electrophoretic karyotyping and gene mapping of seven formae speciales in Fusarium solani. Curr Genet. 2002 Jul;41(4):254-60. Epub 2002 Jul 5. PubMed PMID: 12172966. 14: Rogers KR, Albert F, Anderson AJ. Lipid peroxidation is a consequence of elicitor activity. Plant Physiol. 1988 Feb;86(2):547-53. PubMed PMID: 16665944; PubMed Central PMCID: PMC1054521. 15: Akiyama K, Kawazu K, Kobayashi A. A novel method for chemo-enzymatic synthesis of elicitor-active chitosan oligomers and partially N-deacetylated chitin oligomers using N-acylated chitotrioses as substrates in a lysozyme-catalyzed transglycosylation reaction system. Carbohydr Res. 1995 Dec 27;279:151-60. PubMed PMID: 8593620. 16: Bell JN, Ryder TB, Wingate VP, Bailey JA, Lamb CJ. Differential accumulation of plant defense gene transcripts in a compatible and an incompatible plant-pathogen interaction. Mol Cell Biol. 1986 May;6(5):1615-23. PubMed PMID: 3785174; PubMed Central PMCID: PMC367688. 17: Bolwell GP, Robbins MP, Dixon RA. Metabolic changes in elicitor-treated bean cells. Enzymic responses associated with rapid changes in cell wall components. Eur J Biochem. 1985 May 2;148(3):571-8. PubMed PMID: 3996395. 18: Younis G, Awad A, Dawod RE, Yousef NE. Antimicrobial activity of yeasts against some pathogenic bacteria. Vet World. 2017 Aug;10(8):979-983. doi: 10.14202/vetworld.2017.979-983. Epub 2017 Aug 24. PubMed PMID: 28919693; PubMed Central PMCID: PMC5591489. 19: Engleder M, Pichler H. On the current role of hydratases in biocatalysis. Appl Microbiol Biotechnol. 2018 Jul;102(14):5841-5858. doi: 10.1007/s00253-018-9065-7. Epub 2018 May 21. Review. PubMed PMID: 29785499; PubMed Central PMCID: PMC6013536.