Flavanone
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MedKoo CAT#: 540135

CAS#: 487-26-3

Description: Flavanone is found in various plant sources. It inhibits proliferation of tumor cells and may decrease oxidative damagae, inhibit angiogenesis, and suppress growth of bacteria.

Chemical Structure

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Flavanone
CAS# 487-26-3
Instruction

Theoretical Analysis

MedKoo Cat#: 540135
Name: Flavanone
CAS#: 487-26-3
Chemical Formula: C15H12O2
Exact Mass: 224.08
Molecular Weight: 224.250
Elemental Analysis: C, 80.34; H, 5.39; O, 14.27

Price and Availability

Size Price Availability Quantity
5g USD 250 2 Weeks
10g USD 350 2 Weeks
25g USD 500 2 Weeks
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Synonym: Flavanone ; NSC 50393; NSC50393; NSC-50393

IUPAC/Chemical Name: 2-phenylchroman-4-one

InChi Key: ZONYXWQDUYMKFB-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H12O2/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2

SMILES Code: O=C1CC(C2=CC=CC=C2)OC3=CC=CC=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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 224.25 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Kean RJ, Lamport DJ, Dodd GF, Freeman JE, Williams CM, Ellis JA, Butler LT, Spencer JP. Chronic consumption of flavanone-rich orange juice is associated with cognitive benefits: an 8-wk, randomized, double-blind, placebo-controlled trial in healthy older adults. Am J Clin Nutr. 2015 Mar;101(3):506-14. doi: 10.3945/ajcn.114.088518. Epub 2015 Jan 14. PubMed PMID: 25733635.

2: Schär MY, Curtis PJ, Hazim S, Ostertag LM, Kay CD, Potter JF, Cassidy A. Orange juice-derived flavanone and phenolic metabolites do not acutely affect cardiovascular risk biomarkers: a randomized, placebo-controlled, crossover trial in men at moderate risk of cardiovascular disease. Am J Clin Nutr. 2015 May;101(5):931-8. doi: 10.3945/ajcn.114.104364. Epub 2015 Mar 18. PubMed PMID: 25788001; PubMed Central PMCID: PMC4409690.

3: Ding F, Peng W. Biological activity of natural flavonoids as impacted by protein flexibility: an example of flavanones. Mol Biosyst. 2015 Apr;11(4):1119-33. doi: 10.1039/c4mb00662c. PubMed PMID: 25673513.

4: Sharma M, Akhtar N, Sambhav K, Shete G, Bansal AK, Sharma SS. Emerging potential of citrus flavanones as an antioxidant in diabetes and its complications. Curr Top Med Chem. 2015;15(2):187-95. Review. PubMed PMID: 25547100.

5: Lv J, Zha X, Pang S, Jia H, Zhang Y, Shang J. Synthesis and melanogenesis evaluation of 3',4',7-trihydroxyflavanone derivatives and characterization of flavanone-BODIPY. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1607-10. doi: 10.1016/j.bmcl.2015.01.072. Epub 2015 Feb 13. PubMed PMID: 25748162.

6: Memon AH, Ismail Z, Al-Suede FS, Aisha AF, Hamil MS, Saeed MA, Laghari M, Majid AM. Isolation, Characterization, Crystal Structure Elucidation of Two Flavanones and Simultaneous RP-HPLC Determination of Five Major Compounds from Syzygium campanulatum Korth. Molecules. 2015 Aug 4;20(8):14212-33. doi: 10.3390/molecules200814212. PubMed PMID: 26248073.

7: Shin KC, Nam HK, Oh DK. Hydrolysis of flavanone glycosides by β-glucosidase from Pyrococcus furiosus and its application to the production of flavanone aglycones from citrus extracts. J Agric Food Chem. 2013 Nov 27;61(47):11532-40. doi: 10.1021/jf403332e. Epub 2013 Nov 14. PubMed PMID: 24188428.

8: Tomás-Navarro M, Vallejo F, Sentandreu E, Navarro JL, Tomás-Barberán FA. Volunteer stratification is more relevant than technological treatment in orange juice flavanone bioavailability. J Agric Food Chem. 2014 Jan 8;62(1):24-7. doi: 10.1021/jf4048989. Epub 2013 Dec 23. PubMed PMID: 24344926.

9: Constantin RP, Constantin RP, Bracht A, Yamamoto NS, Ishii-Iwamoto EL, Constantin J. Molecular mechanisms of citrus flavanones on hepatic gluconeogenesis. Fitoterapia. 2014 Jan;92:148-62. doi: 10.1016/j.fitote.2013.11.003. Epub 2013 Nov 15. PubMed PMID: 24239748.

10: Pereira-Caro G, Oliver CM, Weerakkody R, Singh T, Conlon M, Borges G, Sanguansri L, Lockett T, Roberts SA, Crozier A, Augustin MA. Chronic administration of a microencapsulated probiotic enhances the bioavailability of orange juice flavanones in humans. Free Radic Biol Med. 2015 Jul;84:206-14. doi: 10.1016/j.freeradbiomed.2015.03.010. Epub 2015 Mar 20. PubMed PMID: 25801290.

11: Rendeiro C, Dong H, Saunders C, Harkness L, Blaze M, Hou Y, Belanger RL, Corona G, Lovegrove JA, Spencer JP. Flavanone-rich citrus beverages counteract the transient decline in postprandial endothelial function in humans: a randomised, controlled, double-masked, cross-over intervention study. Br J Nutr. 2016 Dec;116(12):1999-2010. doi: 10.1017/S0007114516004219. Epub 2017 Jan 9. PubMed PMID: 28065188.

12: Nagasawa A, Wakisaka E, Kidena H, Nomura T, Hotta M, Taguchi H, Moriwaki S. t-Flavanone Improves the Male Pattern of Hair Loss by Enhancing Hair-Anchoring Strength: A Randomized, Double-Blind, Placebo-Controlled Study. Dermatol Ther (Heidelb). 2016 Mar;6(1):59-68. doi: 10.1007/s13555-016-0101-1. Epub 2016 Feb 20. PubMed PMID: 26897375; PubMed Central PMCID: PMC4799041.

13: Gao TY, Jin X, Tang WZ, Wang XJ, Zhao YX. New geranylated flavanones from the fruits of Paulownia catalpifolia Gong Tong with their anti-proliferative activity on lung cancer cells A549. Bioorg Med Chem Lett. 2015 Sep 1;25(17):3686-9. doi: 10.1016/j.bmcl.2015.06.035. Epub 2015 Jun 17. PubMed PMID: 26115572.

14: Patel NK, Bairwa K, Gangwal R, Jaiswal G, Jachak SM, Sangamwar AT, Bhutani KK. 2'-Hydroxy flavanone derivatives as an inhibitors of pro-inflammatory mediators: Experimental and molecular docking studies. Bioorg Med Chem Lett. 2015 May 1;25(9):1952-5. doi: 10.1016/j.bmcl.2015.03.025. Epub 2015 Mar 14. PubMed PMID: 25824662.

15: Cassidy A, Bertoia M, Chiuve S, Flint A, Forman J, Rimm EB. Habitual intake of anthocyanins and flavanones and risk of cardiovascular disease in men. Am J Clin Nutr. 2016 Sep;104(3):587-94. doi: 10.3945/ajcn.116.133132. Epub 2016 Aug 3. PubMed PMID: 27488237; PubMed Central PMCID: PMC4997299.

16: Goetz ME, Judd SE, Hartman TJ, McClellan W, Anderson A, Vaccarino V. Flavanone Intake Is Inversely Associated with Risk of Incident Ischemic Stroke in the REasons for Geographic and Racial Differences in Stroke (REGARDS) Study. J Nutr. 2016 Nov;146(11):2233-2243. Epub 2016 Sep 21. PubMed PMID: 27655760; PubMed Central PMCID: PMC5086785.

17: Overwin H, Wray V, Seeger M, Sepúlveda-Boza S, Hofer B. Flavanone and isoflavone glucosylation by non-Leloir glycosyltransferases. J Biotechnol. 2016 Sep 10;233:121-8. doi: 10.1016/j.jbiotec.2016.06.026. Epub 2016 Jun 30. PubMed PMID: 27374405.

18: Sharma M, Akhtar N, Sambhav K, Shete G, Bansal AK, Sharma SS. Emerging Potential Of Citrus Flavanones As An Antioxidant In Diabetes And Its Complications. Curr Top Med Chem. 2014 Dec 9. [Epub ahead of print] PubMed PMID: 25496274.

19: Seo J, Ryu JY, Han J, Ahn JH, Sadowsky MJ, Hur HG, Chong Y. Amino acid substitutions in naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4 result in regio- and stereo-specific hydroxylation of flavanone and isoflavanone. Appl Microbiol Biotechnol. 2013 Jan;97(2):693-704. doi: 10.1007/s00253-012-3962-y. Epub 2012 Mar 6. PubMed PMID: 22391970.

20: Freischmidt A, Untergehrer M, Ziegler J, Knuth S, Okpanyi S, Müller J, Kelber O, Weiser D, Jürgenliemk G. Quantitative analysis of flavanones and chalcones from willow bark. Pharmazie. 2015 Sep;70(9):565-8. PubMed PMID: 26492639.