Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones
Humulones are a family of homolog natural products obtained from the strobiles of humulus lupulus, or hops plants. Structurally, they consist of substituted phloroglucinols with two isoprenyl side chains, a carbonyl group and a quaternary ring carbon substituted with a hydroxyl group. The three most...
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MDPI AG
2025-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/5/1002 |
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| author | Bruce C. Hamper Bradley Gallow Gregory Giovine Trevor Smith |
| author_facet | Bruce C. Hamper Bradley Gallow Gregory Giovine Trevor Smith |
| author_sort | Bruce C. Hamper |
| collection | DOAJ |
| description | Humulones are a family of homolog natural products obtained from the strobiles of humulus lupulus, or hops plants. Structurally, they consist of substituted phloroglucinols with two isoprenyl side chains, a carbonyl group and a quaternary ring carbon substituted with a hydroxyl group. The three most prominent homologs are n-, co- and ad-humulone, containing isobutyl, isopropyl and secbutyl ketone groups, respectively. When solutions of humulones are exposed to UV light, they undergo stereoselective isomerization to the five-membered ring trans-isohumulones. A photoreactor was assembled from strip LEDs in close contact with UV-transparent tubing. This reactor allowed continuous-flow chemical synthesis of the isohumulones. The yield, conversion and product throughput are compared for the humulones, using LEDs emitting white, blue and ultraviolet light (visible, 400 nm, and 365 nm, respectively). Using an optimized continuous-flow reactor, a throughput of 0.43 g/h was obtained for trans-n-isohumulone. |
| format | Article |
| id | doaj-art-e4b542577a6f47c7b9e8ff0ca0c79354 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-e4b542577a6f47c7b9e8ff0ca0c793542025-08-20T02:53:22ZengMDPI AGMolecules1420-30492025-02-01305100210.3390/molecules30051002Continuous-Flow Photochemical Isomerization of Humulones to IsohumulonesBruce C. Hamper0Bradley Gallow1Gregory Giovine2Trevor Smith3Department of Chemistry & Biochemistry, University of Missouri-St. Louis, 43 Benton Ct., St. Louis, MO 63121, USADepartment of Chemistry & Biochemistry, University of Missouri-St. Louis, 43 Benton Ct., St. Louis, MO 63121, USADepartment of Chemistry & Biochemistry, University of Missouri-St. Louis, 43 Benton Ct., St. Louis, MO 63121, USADepartment of Chemistry & Biochemistry, University of Missouri-St. Louis, 43 Benton Ct., St. Louis, MO 63121, USAHumulones are a family of homolog natural products obtained from the strobiles of humulus lupulus, or hops plants. Structurally, they consist of substituted phloroglucinols with two isoprenyl side chains, a carbonyl group and a quaternary ring carbon substituted with a hydroxyl group. The three most prominent homologs are n-, co- and ad-humulone, containing isobutyl, isopropyl and secbutyl ketone groups, respectively. When solutions of humulones are exposed to UV light, they undergo stereoselective isomerization to the five-membered ring trans-isohumulones. A photoreactor was assembled from strip LEDs in close contact with UV-transparent tubing. This reactor allowed continuous-flow chemical synthesis of the isohumulones. The yield, conversion and product throughput are compared for the humulones, using LEDs emitting white, blue and ultraviolet light (visible, 400 nm, and 365 nm, respectively). Using an optimized continuous-flow reactor, a throughput of 0.43 g/h was obtained for trans-n-isohumulone.https://www.mdpi.com/1420-3049/30/5/1002humuloneisohumulonephotochemistryflow chemistrygreen chemistryphotoisomerization |
| spellingShingle | Bruce C. Hamper Bradley Gallow Gregory Giovine Trevor Smith Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones Molecules humulone isohumulone photochemistry flow chemistry green chemistry photoisomerization |
| title | Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones |
| title_full | Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones |
| title_fullStr | Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones |
| title_full_unstemmed | Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones |
| title_short | Continuous-Flow Photochemical Isomerization of Humulones to Isohumulones |
| title_sort | continuous flow photochemical isomerization of humulones to isohumulones |
| topic | humulone isohumulone photochemistry flow chemistry green chemistry photoisomerization |
| url | https://www.mdpi.com/1420-3049/30/5/1002 |
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