(+)-humulone

Also known as alpha-humulon, (6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone, alpha-bitter acid, alpha-lupulic acid, humulone

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). Humulone is a prevalent member of the class of compounds known as alpha acids, which collectively give hopped beer its characteristic bitter flavor.

Chemical data

Formula: C21H30O5
Molecular weight: 362.5 g/mol
IUPAC name: (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
SMILES: CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
InChIKey: VMSLCPKYRPDHLN-OAQYLSRUSA-N
XLogP: 4.2
Polar surface area: 94.8 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: alpha acid
Mass: 362.209324

Show 5 more facts

chemical formula: C₂₁H₃₀O₅
canonical SMILES: CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
isomeric SMILES: CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
has characteristic: bitterness
found in taxon: Humulus lupulus

Sources (3)

via Wikidata · CC0

~2 min read

Encyclopedic overview

6 sections

Contents

Chemistry
Isohumulone
Laboratory synthesis
Biosynthesis
Research
References

== Chemistry == In terms of structure, humulone is a phloroglucinol derivative with three isoprenoid side-chains. Two side-chains are prenyl groups and one is an isovaleryl group. The acidity of the ring enol moieties that give rise to its designation as an acid lie in their vinylogous relationship with the ring and side chain carbonyl functional groups.

Excerpted from Wikipedia’s “(+)-humulone” article, available under the CC BY-SA 4.0 licence.