Hyperforin | cyclic terpene ketone | GABA reuptake inhibitor | CAS#11079-53-1

MedKoo Cat#: 126053 | Name: Hyperforin

Description:

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

Hyperforin is a cyclic terpene ketone that is a prenylated carbobicyclic acylphloroglucinol derivative. It has a role as a GABA reuptake inhibitor, a plant metabolite, an anti-inflammatory agent, an antidepressant, an antibacterial agent, an antineoplastic agent and an apoptosis inducer.

Chemical Structure

Hyperforin

CAS#11079-53-1 (free base)

Theoretical Analysis

MedKoo Cat#: 126053

Name: Hyperforin

CAS#: 11079-53-1 (free base)

Chemical Formula: C35H52O4

Exact Mass: 536.3866

Molecular Weight: 536.80

Elemental Analysis: C, 78.31; H, 9.76; O, 11.92

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 #

238074-03-8 (DCHA) 11079-53-1 (free base)

Synonym

hyperforin; hiperforina; hyperforine;

IUPAC/Chemical Name

(1R,5S,6R,7S)-4-hydroxy-5-isobutyryl-6-methyl-1,3,7-tris(3-methylbut-2-en-1-yl)-6-(4-methylpent-3-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

InChi Key

IWBJJCOKGLUQIZ-HQKKAZOISA-N

InChi Code

InChI=1S/C35H52O4/c1-22(2)13-12-19-33(11)27(16-14-23(3)4)21-34(20-18-25(7)8)30(37)28(17-15-24(5)6)31(38)35(33,32(34)39)29(36)26(9)10/h13-15,18,26-27,38H,12,16-17,19-21H2,1-11H3/t27-,33+,34+,35-/m0/s1

SMILES Code

CC(C)C(=O)[C@]12C(=O)[C@](CC=C(C)C)(C[C@H](CC=C(C)C)[C@@]1(C)CCC=C(C)C)C(=O)C(CC=C(C)C)=C2O

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 536.80 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: Li XX, Yan Y, Zhang J, Ding K, Xia CY, Pan XG, Shi YJ, Xu JK, He J, Zhang WK. Hyperforin: A natural lead compound with multiple pharmacological activities. Phytochemistry. 2023 Feb;206:113526. doi: 10.1016/j.phytochem.2022.113526. Epub 2022 Nov 26. PMID: 36442576. 2: Chen S, Liu X, Peng C, Tan C, Sun H, Liu H, Zhang Y, Wu P, Cui C, Liu C, Yang D, Li Z, Lu J, Guan J, Ke X, Wang R, Bo X, Xu X, Han J, Liu J. The phytochemical hyperforin triggers thermogenesis in adipose tissue via a Dlat-AMPK signaling axis to curb obesity. Cell Metab. 2021 Mar 2;33(3):565-580.e7. doi: 10.1016/j.cmet.2021.02.007. PMID: 33657393. 3: Zhang S, Zhang J, Yu J, Chen X, Zhang F, Wei W, Zhang L, Chen W, Lin N, Wu Y. Hyperforin Ameliorates Imiquimod-Induced Psoriasis-Like Murine Skin Inflammation by Modulating IL-17A-Producing γδ T Cells. Front Immunol. 2021 May 5;12:635076. doi: 10.3389/fimmu.2021.635076. PMID: 34025642; PMCID: PMC8131513. 4: Bouron A. Cellular neurobiology of hyperforin. Phytother Res. 2023 Nov 14. doi: 10.1002/ptr.8063. Epub ahead of print. PMID: 37963759. 5: Beerhues L. Hyperforin. Phytochemistry. 2006 Oct;67(20):2201-7. doi: 10.1016/j.phytochem.2006.08.017. Epub 2006 Sep 14. PMID: 16973193. 6: Friedland K, Harteneck C. Hyperforin: To Be or Not to Be an Activator of TRPC(6). Rev Physiol Biochem Pharmacol. 2015;169:1-24. doi: 10.1007/112_2015_25. PMID: 26384487. 7: Gaid M, Biedermann E, Füller J, Haas P, Behrends S, Krull R, Scholl S, Wittstock U, Müller-Goymann C, Beerhues L. Biotechnological production of hyperforin for pharmaceutical formulation. Eur J Pharm Biopharm. 2018 May;126:10-26. doi: 10.1016/j.ejpb.2017.03.024. Epub 2017 Apr 2. PMID: 28377273. 8: Liu S, Yu B, Dai J, Chen R. Targeting the biological activity and biosynthesis of hyperforin: a mini-review. Chin J Nat Med. 2022 Oct;20(10):721-728. doi: 10.1016/S1875-5364(22)60189-4. PMID: 36307194. 9: Madabushi R, Frank B, Drewelow B, Derendorf H, Butterweck V. Hyperforin in St. John's wort drug interactions. Eur J Clin Pharmacol. 2006 Mar;62(3):225-33. doi: 10.1007/s00228-006-0096-0. Epub 2006 Feb 14. PMID: 16477470. 10: Yang S, Zhong S, Deng Z, Xie T, Yin G, Wang L, Liu J, Yang J, Long Z, Jiang X, Tan J. Hyperforin regulates renal fibrosis via targeting the PI3K-AKT/ICAM1 axis. Cell Signal. 2023 Aug;108:110691. doi: 10.1016/j.cellsig.2023.110691. Epub 2023 Apr 26. PMID: 37116554.