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CAS 25422-83-7

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Isoadhumulone

Description:
Isoadhumulone is a chemical compound primarily known for its role as a bittering agent in beer, derived from the hops plant. It is a type of iso-alpha acid, formed during the brewing process when hops are boiled, leading to the isomerization of humulone. Isoadhumulone is characterized by its distinct bitter flavor, which contributes to the overall taste profile of beer. It is less stable than some other iso-alpha acids, which can affect its bitterness over time. In addition to its flavoring properties, isoadhumulone has been studied for its potential antimicrobial effects, which can influence the preservation of beer. The compound is soluble in alcohol and has a relatively low solubility in water, making it more effective in alcoholic beverages. Its chemical structure includes a series of carbon rings and functional groups that contribute to its reactivity and interaction with other compounds in the brewing process. Overall, isoadhumulone plays a crucial role in the sensory characteristics of beer, particularly in terms of bitterness and stability.
Formula:C21H30O5
InChI:InChI=1S/C21H30O5/c1-7-14(6)18(23)17-19(24)15(10-8-12(2)3)21(26,20(17)25)16(22)11-9-13(4)5/h8-9,14-15,25-26H,7,10-11H2,1-6H3
InChI key:InChIKey=QHRQNLXYMFCGPB-UHFFFAOYSA-N
SMILES:C(CC=C(C)C)(=O)C1(O)C(CC=C(C)C)C(=O)C(C(C(CC)C)=O)=C1O
Synonyms:
  • 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-
  • 2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(2-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-
  • 3,4-Dihydroxy-2-(2-Methylbutanoyl)-5-(3-Methylbut-2-En-1-Yl)-4-(4-Methylpent-3-Enoyl)Cyclopent-2-En-1-One
  • 3,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-2-cyclopenten-1-one
  • 3-Penten-1-one, 1-[1,2-dihydroxy-5-(3-methyl-2-butenyl)-3-(2-methylbutyryl)-4-oxo-2-cyclopenten-1-yl]-4-methyl-
  • Isoadhumulone
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