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Humulone information


Humulone
Names
Preferred IUPAC name
(6S)-3,5,6-Trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one[1]
Other names
α-Lupulic acid; α-Bitter acid
Identifiers
CAS Number
  • 26472-41-3 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 391214
ECHA InfoCard 100.043.371 Edit this at Wikidata
PubChem CID
  • 442911
UNII
  • KHB4767H3K
CompTox Dashboard (EPA)
  • DTXSID501019081 DTXSID50946227, DTXSID501019081 Edit this at Wikidata
InChI
  • InChI=1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1
SMILES
  • O=C(\C1=C(/O)\C(=C(\O)[C@](O)(C1=O)C\C=C(/C)C)C\C=C(/C)C)CC(C)C
Properties
Chemical formula
C21H30O5
Molar mass 362.466 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Humulone (α-lupulic acid), a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops (Humulus lupulus).[2] Humulone is a prevalent member of the class of compounds known as alpha acids, which collectively give hopped beer its characteristic bitter flavor.

  1. ^ Urban, Jan; Dahlberg, Clinton; Carroll, Brian; Kaminsky, Werner (2013). "Absolute Configuration of Beer's Bitter Compounds". Angew. Chem. Int. Ed. 52 (5): 1553–1555. doi:10.1002/anie.201208450. PMC 3563212. PMID 23239507.
  2. ^ De Keukeleire, J; Ooms, G; Heyerick, A; Roldan-Ruiz, I; Van Bockstaele, E; De Keukeleire, D (2003). "Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.)". Journal of Agricultural and Food Chemistry. 51 (15): 4436–41. doi:10.1021/jf034263z. PMID 12848522.

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Humulone

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Humulone (α-lupulic acid), a vinylogous type of organic acid, is a bitter-tasting chemical compound found in the resin of mature hops (Humulus lupulus)...

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Hops

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chemical compound within hops are the alpha acids or humulones. During wort boiling, the humulones are thermally isomerized into iso-alpha acids or isohumulones...

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Tetrahydrocannabinol

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for THCA biosynthesis is similar to that which produces the bitter acid humulone in hops. It can also be produced in genetically modified yeast. Cannabidiol...

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Alpha acid

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alpha acids and thus increased bitterness. Common alpha acids include humulone, adhumulone, cohumulone, posthumulone, and prehumulone. The most common...

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Humulus

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acylphloroglucinol derivatives. Bitter acids are divided into the alpha-acids, with humulone the major compound, and the beta-acids, with lupulone the major compound;...

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Phloroglucinol

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Humulone is a phloroglucinol derivative with three isoprenoid side-chains. Two side-chains are prenyl groups and one is an isovaleryl group. Humulone...

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Terpenoid

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Paclitaxel is a diterpenoid anticancer drug. Terpineols are monoterpenoids. Humulones are classified as sesquiterpenoids. Retinol is a diterpenoid. Hinokitiol...

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C21H30O5

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a corticosteroid 5α-Dihydroaldosterone Dihydrocortisone Hydrocortisone Humulone 18-Hydroxycorticosterone Isohumulone This set index page lists chemical...

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Meroterpene

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genus Humulus and Cannabis produce terpenophenolic metabolites, such as humulone and tetrahydrocannabinol respectively. Other examples of terpenophenolics...

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Isohumulone

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a "skunky" flavor. Isohumulones are generated by the isomerization of humulone. Beer chemistry Urban, Jan; Dahlberg, Clinton; Carroll, Brian; Kaminsky...

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Humulus lupulus

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bitter acids in hops. A 13C-NMR and 2H-NMR study on the building blocks of humulone". European Journal of Biochemistry. 263 (2): 447–454. doi:10.1046/j.1432-1327...

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Beer measurement

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provided by compounds such as humulones, or alpha acids from hops used during brewing. During the brewing process, humulone undergoes isomerization to form...

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Beer chemistry

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ales comes from a family of compounds called alpha-acids (also called humulones) and beta-acids (also called lupulones). Generally, brewers believe that...

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Sesquiterpene

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Humulones are sesquiterpenoids that give "hoppy" flavor to beer....

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List of hop varieties

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unknown. The alpha acid content is relatively high—11.5 to 13.5%—but its co-humulone content and its beta acid range are also high. Low-cohumulone American...

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TAS2R1

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T2R1 were identified in BitterDB, among them L-amino acids, peptides, humulones, small molecules etc. Taste receptor GRCh38: Ensembl release 89: ENSG00000169777...

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