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

MedKoo CAT#: 540236

CAS#: 70872-29-6

Description: Isoxanthohumol is a less potent derivative of xanthohumol found in Humulus lupulus. It modulates signalling between endothelial cells and vascular smooth muscle cells, induces apoptosis in mature adipocytes, and inhibits differentiation of preadipocytes.


Chemical Structure

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Isoxanthohumol
CAS# 70872-29-6

Theoretical Analysis

MedKoo Cat#: 540236
Name: Isoxanthohumol
CAS#: 70872-29-6
Chemical Formula: C21H22O5
Exact Mass: 354.1467
Molecular Weight: 354.4
Elemental Analysis: C, 71.17; H, 6.26; O, 22.57

Price and Availability

Size Price Availability Quantity
10.0mg USD 430.0 2 Weeks
50.0mg USD 1080.0 2 Weeks
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Synonym: (2S)-4',7-Dihydroxy-5-methoxy-8-prenylflavanone; Isoxanthohumol

IUPAC/Chemical Name: (S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one

InChi Key: YKGCBLWILMDSAV-SFHVURJKSA-N

InChi Code: InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1

SMILES Code: O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=C1C(OC)=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

Preparing Stock Solutions

The following data is based on the product molecular weight 354.4 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

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1: Żołnierczyk AK, Mączka WK, Grabarczyk M, Wińska K, Woźniak E, Anioł M. Isoxanthohumol--Biologically active hop flavonoid. Fitoterapia. 2015 Jun;103:71-82. doi: 10.1016/j.fitote.2015.03.007. Epub 2015 Mar 12. PubMed PMID: 25771121.

2: Stompor M, Dancewicz K, Gabryś B, Anioł M. Insect Antifeedant Potential of Xanthohumol, Isoxanthohumol, and Their Derivatives. J Agric Food Chem. 2015 Aug 5;63(30):6749-56. doi: 10.1021/acs.jafc.5b02025. Epub 2015 Jul 27. PubMed PMID: 26176501.

3: Martinez SE, Davies NM. Enantiospecific pharmacokinetics of isoxanthohumol and its metabolite 8-prenylnaringenin in the rat. Mol Nutr Food Res. 2015 Sep;59(9):1674-89. doi: 10.1002/mnfr.201500118. Epub 2015 Jul 1. PubMed PMID: 26079861.

4: Gąsiorowska J, Teisseyre A, Uryga A, Michalak K. Inhibition of Kv1.3 Channels in Human Jurkat T Cells by Xanthohumol and Isoxanthohumol. J Membr Biol. 2015 Aug;248(4):705-11. doi: 10.1007/s00232-015-9782-0. Epub 2015 Feb 17. PubMed PMID: 25688010; PubMed Central PMCID: PMC4513206.

5: Quifer-Rada P, Martínez-Huélamo M, Chiva-Blanch G, Jáuregui O, Estruch R, Lamuela-Raventós RM. Urinary isoxanthohumol is a specific and accurate biomarker of beer consumption. J Nutr. 2014 Apr;144(4):484-8. doi: 10.3945/jn.113.185199. Epub 2014 Jan 29. PubMed PMID: 24477299.

6: Izzo G, Söder O, Svechnikov K. The prenylflavonoid phytoestrogens 8-prenylnaringenin and isoxanthohumol diferentially suppress steroidogenesis in rat Leydig cells in ontogenesis. J Appl Toxicol. 2011 Aug;31(6):589-94. doi: 10.1002/jat.1602. Epub 2010 Nov 9. PubMed PMID: 21061451.

7: Serwe A, Rudolph K, Anke T, Erkel G. Inhibition of TGF-β signaling, vasculogenic mimicry and proinflammatory gene expression by isoxanthohumol. Invest New Drugs. 2012 Jun;30(3):898-915. doi: 10.1007/s10637-011-9643-3. Epub 2011 Feb 22. PubMed PMID: 21340508.

8: Negrão R, Duarte D, Costa R, Soares R. Isoxanthohumol modulates angiogenesis and inflammation via vascular endothelial growth factor receptor, tumor necrosis factor alpha and nuclear factor kappa B pathways. Biofactors. 2013 Nov-Dec;39(6):608-22. doi: 10.1002/biof.1122. Epub 2013 Aug 1. PubMed PMID: 23904052.

9: Allsopp P, Possemiers S, Campbell D, Gill C, Rowland I. A comparison of the anticancer properties of isoxanthohumol and 8-prenylnaringenin using in vitro models of colon cancer. Biofactors. 2013 Jul-Aug;39(4):441-7. doi: 10.1002/biof.1084. Epub 2013 Jan 30. PubMed PMID: 23361834.

10: Fu ML, Wang W, Chen F, Dong YC, Liu XJ, Ni H, Chen QH. Production of 8-prenylnaringenin from isoxanthohumol through biotransformation by fungi cells. J Agric Food Chem. 2011 Jul 13;59(13):7419-26. doi: 10.1021/jf2011722. Epub 2011 Jun 10. PubMed PMID: 21634799.

11: Büchter C, Havermann S, Koch K, Wätjen W. Isoxanthohumol, a constituent of hop (Humulus lupulus L.), increases stress resistance in Caenorhabditis elegans dependent on the transcription factor DAF-16. Eur J Nutr. 2016 Feb;55(1):257-65. doi: 10.1007/s00394-015-0843-z. Epub 2015 Feb 3. PubMed PMID: 25644181.

12: Krajnović T, Kaluđerović GN, Wessjohann LA, Mijatović S, Maksimović-Ivanić D. Versatile antitumor potential of isoxanthohumol: Enhancement of paclitaxel activity in vivo. Pharmacol Res. 2016 Mar;105:62-73. doi: 10.1016/j.phrs.2016.01.011. Epub 2016 Jan 16. PubMed PMID: 26784390.

13: Dhooghe L, Naessens T, Heyerick A, De Keukeleire D, Vlietinck AJ, Pieters L, Apers S. Quantification of xanthohumol, isoxanthohumol, 8-prenylnaringenin, and 6-prenylnaringenin in hop extracts and derived capsules using secondary standards. Talanta. 2010 Dec 15;83(2):448-56. doi: 10.1016/j.talanta.2010.09.041. Epub 2010 Oct 1. PubMed PMID: 21111159.

14: Overk CR, Guo J, Chadwick LR, Lantvit DD, Minassi A, Appendino G, Chen SN, Lankin DC, Farnsworth NR, Pauli GF, van Breemen RB, Bolton JL. In vivo estrogenic comparisons of Trifolium pratense (red clover) Humulus lupulus (hops), and the pure compounds isoxanthohumol and 8-prenylnaringenin. Chem Biol Interact. 2008 Oct 22;176(1):30-9. doi: 10.1016/j.cbi.2008.06.005. Epub 2008 Jun 20. PubMed PMID: 18619951; PubMed Central PMCID: PMC2574795.

15: Magalhães PJ, Guido LF, Cruz JM, Barros AA. Analysis of xanthohumol and isoxanthohumol in different hop products by liquid chromatography-diode array detection-electrospray ionization tandem mass spectrometry. J Chromatogr A. 2007 May 25;1150(1-2):295-301. Epub 2006 Sep 7. PubMed PMID: 16962125.

16: Yang JY, Della-Fera MA, Rayalam S, Baile CA. Effect of xanthohumol and isoxanthohumol on 3T3-L1 cell apoptosis and adipogenesis. Apoptosis. 2007 Nov;12(11):1953-63. PubMed PMID: 17874298.

17: Guo J, Nikolic D, Chadwick LR, Pauli GF, van Breemen RB. Identification of human hepatic cytochrome P450 enzymes involved in the metabolism of 8-prenylnaringenin and isoxanthohumol from hops (Humulus lupulus L.). Drug Metab Dispos. 2006 Jul;34(7):1152-9. Epub 2006 Apr 12. PubMed PMID: 16611861.

18: Possemiers S, Rabot S, Espín JC, Bruneau A, Philippe C, González-Sarrías A, Heyerick A, Tomás-Barberán FA, De Keukeleire D, Verstraete W. Eubacterium limosum activates isoxanthohumol from hops (Humulus lupulus L.) into the potent phytoestrogen 8-prenylnaringenin in vitro and in rat intestine. J Nutr. 2008 Jul;138(7):1310-6. PubMed PMID: 18567753.

19: Kodama S, Yamamoto A, Sato A, Suzuki K, Yamashita T, Kemmei T, Taga A, Hayakawa K. Enantioseparation of isoxanthohumol in beer by hydroxypropyl-gamma-cyclodextrin-modified micellar electrokinetic chromatography. J Agric Food Chem. 2007 Aug 8;55(16):6547-52. Epub 2007 Jul 13. PubMed PMID: 17629302.

20: Liu M, Zhang W, Zhang W, Zhou X, Li M, Miao J. Prenylflavonoid Isoxanthohumol Sensitizes MCF-7/ADR Cells to Doxorubicin Cytotoxicity via Acting as a Substrate of ABCB1. Toxins (Basel). 2017 Jun 30;9(7). pii: E208. doi: 10.3390/toxins9070208. PubMed PMID: 28665335.