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MedKoo Cat#: 561306 | Name: 8-Prenylnaringenin

Description:

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

8-Prenylnaringenin, also known as Sophoraflavanone B, is prenylflavonoid phytoestrogen and an inhibitor of human estrogen receptor ERα and ERß. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at ERα and ERβ, and acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.

Chemical Structure

8-Prenylnaringenin
8-Prenylnaringenin
CAS#53846-50-7

Theoretical Analysis

MedKoo Cat#: 561306

Name: 8-Prenylnaringenin

CAS#: 53846-50-7

Chemical Formula: C20H20O5

Exact Mass: 340.1311

Molecular Weight: 340.38

Elemental Analysis: C, 70.58; H, 5.92; O, 23.50

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
8-Prenylnaringenin; 8Prenylnaringenin; 8 Prenylnaringenin; Sophoraflavanone B; Flavaprenin; YS04;
IUPAC/Chemical Name
(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
InChi Key
LPEPZZAVFJPLNZ-SFHVURJKSA-N
InChi Code
InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
SMILES Code
O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3C/C=C(C)\C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 340.38 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: Venturelli S, Burkard M, Biendl M, Lauer UM, Frank J, Busch C. Prenylated chalcones and flavonoids for the prevention and treatment of cancer. Nutrition. 2016 Nov-Dec;32(11-12):1171-8. doi: 10.1016/j.nut.2016.03.020. Epub 2016 Apr 8. Review. PubMed PMID: 27238957. 2: Abdi F, Kazemi F, Ramezani Tehrani F, Roozbeh N. Protocol for systematic review and meta-analysis: hop (Humulus lupulus L.) for menopausal vasomotor symptoms. BMJ Open. 2016 Apr 22;6(4):e010734. doi: 10.1136/bmjopen-2015-010734. Review. PubMed PMID: 27105715; PubMed Central PMCID: PMC4853989. 3: Busch C, Noor S, Leischner C, Burkard M, Lauer UM, Venturelli S. Anti-proliferative activity of hop-derived prenylflavonoids against human cancer cell lines. Wien Med Wochenschr. 2015 Jun;165(11-12):258-61. doi: 10.1007/s10354-015-0355-8. Epub 2015 Apr 30. Review. PubMed PMID: 25925225. 4: Depypere HT, Comhaire FH. Herbal preparations for the menopause: beyond isoflavones and black cohosh. Maturitas. 2014 Feb;77(2):191-4. doi: 10.1016/j.maturitas.2013.11.001. Epub 2013 Nov 19. Review. PubMed PMID: 24314619. 5: Chen W, Becker T, Qian F, Ring J. Beer and beer compounds: physiological effects on skin health. J Eur Acad Dermatol Venereol. 2014 Feb;28(2):142-50. doi: 10.1111/jdv.12204. Epub 2013 Jun 27. Review. PubMed PMID: 23802910. 6: Keiler AM, Zierau O, Kretzschmar G. Hop extracts and hop substances in treatment of menopausal complaints. Planta Med. 2013 May;79(7):576-9. doi: 10.1055/s-0032-1328330. Epub 2013 Mar 19. Review. PubMed PMID: 23512496. 7: Zanoli P, Zavatti M. Pharmacognostic and pharmacological profile of Humulus lupulus L. J Ethnopharmacol. 2008 Mar 28;116(3):383-96. doi: 10.1016/j.jep.2008.01.011. Epub 2008 Jan 20. Review. PubMed PMID: 18308492. 8: Stevens JF, Page JE. Xanthohumol and related prenylflavonoids from hops and beer: to your good health! Phytochemistry. 2004 May;65(10):1317-30. Review. PubMed PMID: 15231405. 9: Cos P, De Bruyne T, Apers S, Vanden Berghe D, Pieters L, Vlietinck AJ. Phytoestrogens: recent developments. Planta Med. 2003 Jul;69(7):589-99. Review. PubMed PMID: 12898412. 10: Fugh-Berman A. "Bust enhancing" herbal products. Obstet Gynecol. 2003 Jun;101(6):1345-9. Review. PubMed PMID: 12798545.