Identification of the Compounds Responsible for the Sweat-Like Odor in Hop (Humulus lupulus L.) Volatile Oil

Miyazato, Hironari

doi:10.5539/jfr.v2n5p34

Cited by 3 publications

(3 citation statements)

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“…The five-membered ring radical fragment is the precursor of humulinic acids, well-known degradation products of isohumulones (Figure ). Concomitant formation of a short-lived reactive ketene in such a mechanism should be readily scavenged by water resulting in 4-methyl-3-pentenoic acid as a flavor-active substance, which reminds of old, oxidized hops. , …”

Section: Discussionmentioning

confidence: 99%

“…Concomitant formation of a short-lived reactive ketene in such a mechanism should be readily scavenged by water resulting in 4-methyl-3-pentenoic acid as a flavor-active substance, which reminds of old, oxidized hops. 30,38 Six-membered ring hop acids are a different story, as the impact of ageing was very pronounced. Mainly the lupulones, in their salt form, must be very reducing and it is thought that alkaline conditions induce lability of some of the involved functionalities.…”

Section: ■ Discussionmentioning

confidence: 99%

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Radical Intermediates in the Degradation of Hop Acids

Berton¹,

Verbeke

Durme

et al. 2021

J. Agric. Food Chem.

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Radical formation in isohumulones was investigated under different types of stress, including temperature, transition metal ions, and hydrogen peroxide. Including dihydroisohumulones and tetrahydroisohumulones, as relevant analogues, allowed us to evaluate critical functionalities in radical formation. Using spin-trapping methodology with 5,5-dimethyl-1-pyrroline N-oxide and N-tert-butyl-α-phenylnitrone as relevant traps, followed by simulation of corresponding spin adducts, identification of incipient radicals was attempted. The isohexenoyl side chain in isohumulones, but not present in dihydro- and tetrahydroisohumulones, was most sensitive to radical formation. Kinetic profiles further demonstrated that radical formation in this moiety was accelerated in the presence of ferrous ions. Reactivity of parent six-membered-ring humulones in radical formation was different, as scavenging of free radical species was more important. Lupulones, despite similarity with humulones, showed a different behavior with an obvious radical decay pathway during ageing, mainly ascribed to radical formation on the ring structure. Quantification of final spin adducts allowed us to determine absolute importance of the different degradation pathways. Eventually, mechanisms are presented explaining why isohumulones are more prone to radical processes in (aut)oxidation and thermal decay than close relatives such as dihydroisohumulones.

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Section: Discussionmentioning

confidence: 99%

Section: ■ Discussionmentioning

confidence: 99%

Radical Intermediates in the Degradation of Hop Acids

Berton¹,

Verbeke

Durme

et al. 2021

J. Agric. Food Chem.

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“…Les S-méthylthio -acétate, -butanoate, -isovalérate, -pentanoate, -hexanoate, -heptanoate, -décanoate et -(E)-4-méthyl-3-hexénoate (responsables de notes de légumes cuits, de fromage, d'ananas ou de rance) sont présents dans les huiles essentielles de cônes de houblons (Figure 9a-h ; Tableau 4 ; Seaton et al, 1981 ;Lermusieau et al, 2001 ;Gijs et al, 2003 ;Miyazato, 2013). La voie de biosynthèse de ces thioesters n'y a toutefois pas été investiguée.…”

Section: Les Thioestersunclassified

Revue sur les analogies et les différences relevées entre un cône de houblon et une baie de raisin : arômes soufrés et azotés

Cibaka

Gros²,

Collin

2017

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Cet article est distribué suivant les termes et les conditions de la licence CC-BY (http://creativecommons.org/licenses/by/4.0/ deed.fr) Introduction. Plusieurs similitudes peuvent être relevées entre le cône de houblon et la baie de raisin. Nous nous focaliserons dans cet article sur leurs arômes soufrés et azotés. Littérature. Bien qu'initialement développées sur la vigne, les recherches sur les thiols polyfonctionnels ont abouti à l'identification d'un grand nombre d'analogues odorants dans le houblon. Parmi ceux-ci, le 3-sulfanylhexan-1-ol (3SHol) caractérisé par des arômes de pamplemousse ou de fruit de la passion est retrouvé à la fois dans le cône de houblon (72-117 µg . kg -1 ) et dans le moût de raisin (66-121 ng . l -1 ). Des concentrations souvent au-dessus du seuil de perception sont atteintes dans la bière (jusque 200 ng . l -1 ) ou dans le vin (jusque 6 000 ng . l -1 ), suite à la dégradation de précurseurs cystéinés et glutathionés durant la fermentation. Le cône de houblon renferme également de nombreux thiophènes et épisulfures d'origine terpénique, ainsi que des sulfures, polysulfures et thioesters aux arômes d'oignon, de verdure ou de fromage. Par contre, la présence de méthoxypyrazines n'est relevée à ce jour que dans le raisin. Conclusions. Plusieurs analogies sont relevées entre les thiols polyfonctionnels du cône de houblon et de la baie de raisin. Les thiophènes, épisulfures, sulfures, polysulfures et thioesters sont principalement retrouvés dans le cône de houblon, alors que les méthoxypyrazines ne sont observées que dans le raisin. Mots-clés. Raisin, vigne, cône, houblon, bière, vin, thiols, pyrazine, flaveur, fermentation alcoolique. Similarities and differences between hop cones and grape berries: sulfur and nitrogen aromas. A review Introduction.Similarities can be found between the flavors of hop cones and grapes. The present paper will focus on their sulfur and nitrogen odorants. Literature. Although initially investigated in vines, recent research has led to the identification of a larger number of polyfunctional thiols in hop cones. These have included the pleasant-smelling grapefruit-or passion fruit-like 3-sulfanylhexan-1-ol. Surprisingly, to date, the occurrence of sulfides, polysulfides and thioesters (onion, vegetable or cheese-like flavors), as well as various thiophenes and terpenic episulfides has been described extensively only in the hop literature, while methoxypyrazines have been described only in vine cultivars. Conclusions. Among the sulfur and nitrogen odorants, many similarities have been observed between hop and grape polyfunctional thiols. Thiophenes, episulfides, sulfides, polysulfides and thioesters are mainly found in hop cones, while methoxypyrazines have been described only in grape.

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Influence of hop harvest date of the ‘Mandarina Bavaria’ hop variety on the sensory evaluation of dry‐hopped top‐fermented beer

Schnaitter¹,

Wimmer²,

Kollmannsberger³

et al. 2016

J. Inst. Brew.

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To impart a special hop aroma to beer, dry‐hopping is a technique that is becoming more and more popular with commercial breweries. Nevertheless, until now little was known about the factors that influence the reproducibility (and consistent product quality) of dry‐hopping with flavour varieties. One factor that could influence the sensory impressions and aroma profile compositions of dry‐hopped beers is the hop harvest date. Therefore, to determine the effects of different harvest dates of the flavour variety ‘Mandarina Bavaria’ on the aroma of top‐fermented beer, laboratory‐scale dry‐hopping trials were performed. Besides tasting sessions of brewed beers, relative quantities of selected hop‐derived, as well as beer‐originated aroma compounds, were investigated by headspace–solid‐phase microextraction–gas chromatography–mass spectrometry. Duo–trio tests between the beers hopped with pellets of different harvest dates showed no significant differences (α = 0.05) between them. In addition, these beers had similar profiles in a five‐point profile tasting scheme. On the other hand, relative concentrations of some hop‐derived aroma compounds – especially myrcene, which is known to be able to contribute to beer flavour – increased corresponding to a later harvest date, while beer originated volatiles were not different between the beers. Analytical results combined with the results of sensory evaluations led to the conclusion that the harvest date of Mandarina Bavaria was not a dominant factor in the dry‐hopping aroma of top‐fermented beers. High amounts of fermentation by‐products are likely responsible for masking effects resulting in no sensory distinctness between the samples with different hop aroma compound concentrations. Copyright © 2016 The Institute of Brewing & Distilling

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Identification of the Compounds Responsible for the Sweat-Like Odor in Hop (Humulus lupulus L.) Volatile Oil

Cited by 3 publications

References 25 publications

Radical Intermediates in the Degradation of Hop Acids

Radical Intermediates in the Degradation of Hop Acids

Revue sur les analogies et les différences relevées entre un cône de houblon et une baie de raisin : arômes soufrés et azotés

Influence of hop harvest date of the ‘Mandarina Bavaria’ hop variety on the sensory evaluation of dry‐hopped top‐fermented beer

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