Humulone

Structural formula
General
Surname	Humulone
other names	α-lupulinic acid; α-hop bitter acid; α-humulone; (6 R ) -3,5,6-trihydroxy-4,6-bis (3-methyl-2-butenyl) -2- (3-methyl-1-oxobutyl) -2,4-cyclohexadien-1-one ( IUPAC ) ;
Molecular formula	C 21 H 30 O 5
External identifiers / databases
EC number	247-725-0
ECHA InfoCard	100.043.371
PubChem	442911
Wikidata	Q419456
properties
Molar mass	362.47 g mol −1
Physical state	firmly
Melting point	66 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Humulone (also α-lupulinic acid ) is a bacteriostatic bitter substance .

Occurrence

Hops ( humulus lupulus )

The resin of the ripe hops Humulus lupulus contains humulone. Its rearrangement products (especially cis - and trans -isohumulone), which are created by heating, give the beer its characteristic bitter taste. It is counted among the hop bitter substances .

Degradation of humulone to cis and trans isohumulone

Structurally, humulone is a hydroxyphloroglucine with three isoprenoid side chains. An anti-inflammatory effect of humulone was shown to suppress the transcription of the gene belonging to cyclooxygenase-2 ( COX-2 ), which inhibits the formation of prostaglandins .

Web links

The importance of the hops ingredients for beer brewing and health (PDF; 960 kB)

Individual evidence

↑ Entry on Humulones. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Briggs, DE, CA Boulton, PA Brookes, and R. Stevens, Brewing Science and Practice. 2004, Cambridge, UK: Woodhead Publishing Limited, ISBN 978-0-8493-2547-2 .
↑ K. Yamamoto, J. Wang, S. Yamamoto, H. Tobe: Suppression of Cyclooxygenase-2 Gene Transcription by Humulone. In: Kenneth V. Honn, Lawrence J. Marnett, Santosh Nigam, Edward Dennis, Charles Serhan (Eds.): Eicosanoids and other bioactive lipids in cancer, inflammation, and radiation injury, Volume 5. Springer, 2002, ISBN 978-0 -306-47283-1 , pp. 73-76.

[roempp-1] Entry on Humulones. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Briggs, DE, CA Boulton, PA Brookes, and R. Stevens, Brewing Science and Practice. 2004, Cambridge, UK: Woodhead Publishing Limited, ISBN 978-0-8493-2547-2 .

[4] K. Yamamoto, J. Wang, S. Yamamoto, H. Tobe: Suppression of Cyclooxygenase-2 Gene Transcription by Humulone. In: Kenneth V. Honn, Lawrence J. Marnett, Santosh Nigam, Edward Dennis, Charles Serhan (Eds.): Eicosanoids and other bioactive lipids in cancer, inflammation, and radiation injury, Volume 5. Springer, 2002, ISBN 978-0 -306-47283-1 , pp. 73-76.