MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 112073 | Name: Colupulone
Featured

Description:

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

Colupulone is a β-acid that activates the pregnane X receptor (PXR).

Chemical Structure

Colupulone
CAS#468-27-9

Theoretical Analysis

MedKoo Cat#: 112073

Name: Colupulone

CAS#: 468-27-9

Chemical Formula: C25H36O4

Exact Mass: 400.2614

Molecular Weight: 400.56

Elemental Analysis: C, 74.96; H, 9.06; O, 15.98

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 1,250.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Colupulone; co-lupulone; NSC 650561; NSC650561; NSC-650561
IUPAC/Chemical Name
3,5-dihydroxy-4-isobutyryl-2,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
InChi Key
GEXOPZHAKQAGLU-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H36O4/c1-15(2)9-10-19-22(27)20(21(26)18(7)8)24(29)25(23(19)28,13-11-16(3)4)14-12-17(5)6/h9,11-12,18,27,29H,10,13-14H2,1-8H3
SMILES Code
O=C(C(C(O)=C1C/C=C(C)\C)=C(C(C/C=C(C)\C)(C1=O)C/C=C(C)\C)O)C(C)C
Appearance
Solid powder
Purity
≥95% (mixture of isomers)
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

Preparing Stock Solutions

The following data is based on the product molecular weight 400.56 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: Makri A, Papachristos DP, Michaelakis A, Vidali VP. Colupulone, colupone and novel deoxycohumulone geranyl analogues as larvicidal agents against Culex pipiens. Pest Manag Sci. 2022 Oct;78(10):4217-4222. doi: 10.1002/ps.7039. Epub 2022 Jul 8. PMID: 35705833. 2: Li Y, Dalabasmaz S, Gensberger-Reigl S, Heymich ML, Krofta K, Pischetsrieder M. Identification of colupulone and lupulone as the main contributors to the antibacterial activity of hop extracts using activity-guided fractionation and metabolome analysis. Food Res Int. 2023 Jul;169:112832. doi: 10.1016/j.foodres.2023.112832. Epub 2023 Apr 17. PMID: 37254407. 3: Mannering GJ, Shoeman JA, Shoeman DW. Effects of colupulone, a component of hops and brewers yeast, and chromium on glucose tolerance and hepatic cytochrome P450 in nondiabetic and spontaneously diabetic mice. Biochem Biophys Res Commun. 1994 May 16;200(3):1455-62. doi: 10.1006/bbrc.1994.1614. PMID: 8185600. 4: Shipp EB, Mehigh CS, Helferich WG. The effect of colupulone (a HOPS beta- acid) on hepatic cytochrome P-450 enzymatic activity in the rat. Food Chem Toxicol. 1994 Nov;32(11):1007-14. doi: 10.1016/0278-6915(94)90140-6. PMID: 7959454. 5: Bharate JB, Batarseh YS, Wani A, Sharma S, Vishwakarma RA, Kaddoumi A, Kumar A, Bharate SB. Synthesis and P-glycoprotein induction activity of colupulone analogs. Org Biomol Chem. 2015 May 21;13(19):5488-96. doi: 10.1039/c5ob00554j. PMID: 25875530. 6: Teotico DG, Bischof JJ, Peng L, Kliewer SA, Redinbo MR. Structural basis of human pregnane X receptor activation by the hops constituent colupulone. Mol Pharmacol. 2008 Dec;74(6):1512-20. doi: 10.1124/mol.108.050732. Epub 2008 Sep 2. PMID: 18768384; PMCID: PMC2584763. 7: Mannering GJ, Shoeman JA, Deloria LB. Identification of the antibiotic hops component, colupulone, as an inducer of hepatic cytochrome P-4503A in the mouse. Drug Metab Dispos. 1992 Mar-Apr;20(2):142-7. PMID: 1352202. 8: Kolenc Z, Langerholc T, Hostnik G, Ocvirk M, Štumpf S, Pintarič M, Košir IJ, Čerenak A, Garmut A, Bren U. Antimicrobial Properties of Different Hop (Humulus lupulus) Genotypes. Plants (Basel). 2022 Dec 26;12(1):120. doi: 10.3390/plants12010120. PMID: 36616249; PMCID: PMC9824274. 9: Haseleu G, Intelmann D, Hofmann T. Identification and RP-HPLC-ESI-MS/MS quantitation of bitter-tasting beta-acid transformation products in beer. J Agric Food Chem. 2009 Aug 26;57(16):7480-9. doi: 10.1021/jf901759y. PMID: 19627140. 10: Kao TH, Wu GY. Simultaneous determination of prenylflavonoid and hop bitter acid in beer lee by HPLC-DAD-MS. Food Chem. 2013 Nov 15;141(2):1218-26. doi: 10.1016/j.foodchem.2013.04.032. Epub 2013 Apr 18. PMID: 23790907. 11: Killeen DP, Andersen DH, Beatson RA, Gordon KC, Perry NB. Vibrational spectroscopy and chemometrics for rapid, quantitative analysis of bitter acids in hops (Humulus lupulus). J Agric Food Chem. 2014 Dec 31;62(52):12521-8. doi: 10.1021/jf5042728. Epub 2014 Dec 18. PMID: 25485767. 12: Simpson WJ, Smith AR. Factors affecting antibacterial activity of hop compounds and their derivatives. J Appl Bacteriol. 1992 Apr;72(4):327-34. doi: 10.1111/j.1365-2672.1992.tb01843.x. PMID: 1517174. 13: Gaid M, Füller J, Müller-Goymann C. The Petroleum Ether Extract from Hypericum perforatum Root Cultures Exhibits Potent Antiproliferative Activity in Human Keratinocytes and Fibroblasts. Planta Med. 2019 May;85(7):591-598. doi: 10.1055/a-0806-7735. Epub 2018 Dec 4. PMID: 30513539. 14: Paguet AS, Siah A, Lefèvre G, Moureu S, Cadalen T, Samaillie J, Michels F, Deracinois B, Flahaut C, Alves Dos Santos H, Etienne-Debaecker A, Rambaud C, Chollet S, Molinié R, Fontaine JX, Waterlot C, Fauconnier ML, Sahpaz S, Rivière C. Multivariate analysis of chemical and genetic diversity of wild Humulus lupulus L. (hop) collected in situ in northern France. Phytochemistry. 2023 Jan;205:113508. doi: 10.1016/j.phytochem.2022.113508. Epub 2022 Nov 10. PMID: 36370882. 15: Patzak J, Nesvadba V, Krofta K, Henychova A, Marzoev AI, Richards K. Evaluation of genetic variability of wild hops (Humulus lupulus L.) in Canada and the Caucasus region by chemical and molecular methods. Genome. 2010 Jul;53(7):545-57. doi: 10.1139/g10-024. PMID: 20616876. 16: Zawadzki A, Alloo C, Grossi AB, do Nascimento ESP, Almeida LC, Bogusz Junior S, Skibsted LH, Cardoso DR. Effect of hop β-acids as dietary supplement for broiler chickens on meat composition and redox stability. Food Res Int. 2018 Mar;105:210-220. doi: 10.1016/j.foodres.2017.10.072. Epub 2017 Dec 20. PMID: 29433209. 17: Saugspier M, Dorn C, Czech B, Gehrig M, Heilmann J, Hellerbrand C. Hop bitter acids inhibit tumorigenicity of hepatocellular carcinoma cells in vitro. Oncol Rep. 2012 Oct;28(4):1423-8. doi: 10.3892/or.2012.1925. Epub 2012 Jul 20. PMID: 22825405. 18: Schulz C, Chiheb C, Pischetsrieder M. Quantification of co-, n-, and ad- lupulone in hop-based dietary supplements and phytopharmaceuticals and modulation of their contents by the extraction method. J Pharm Biomed Anal. 2019 May 10;168:124-132. doi: 10.1016/j.jpba.2019.02.022. Epub 2019 Feb 16. PMID: 30807916. 19: Kac J, Zakrajsek J, Mlinaric A, Kreft S, Filipic M. Determination of xanthohumol in hops (Humulus lupulus L.) by nonaqueous CE. Electrophoresis. 2007 Mar;28(6):965-9. doi: 10.1002/elps.200600494. PMID: 17309054. 20: Shen C, Sofos JN. Antilisterial activity of hops beta acids in broth with or without other antimicrobials. J Food Sci. 2008 Nov;73(9):M438-42. doi: 10.1111/j.1750-3841.2008.00962.x. PMID: 19021815.