8-Prenylnaringenin

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

MedKoo CAT#: 561306

CAS#: 53846-50-7

Description: 8-Prenylnaringenin 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.


Price and Availability

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8-Prenylnaringenin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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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


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


Technical Data

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).

Harmonized System Code:
293490


References

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.