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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. 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. Isohumulone During the brewing process, humulone degrades to ''cis-'' and ''trans-''isohumulone. These “alpha acids” survive the boiling process, although numerous oxidized derivatives are produced. The iso-alpha acids are significantly more soluble than humulone at the pH levels typically present in the brewing pr ...
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Humulone Synthesis
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. 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. Isohumulone During the brewing process, humulone degrades to ''cis-'' and ''trans-''isohumulone. These “alpha acids” survive the boiling process, although numerous oxidized derivatives are produced. The iso-alpha acids are significantly more soluble than humulone at the pH levels typically present in the brewing proce ...
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Hops
Hops are the flowers (also called seed cones or strobiles) of the hop plant '' Humulus lupulus'', a member of the Cannabaceae family of flowering plants. They are used primarily as a bittering, flavouring, and stability agent in beer, to which, in addition to bitterness, they impart floral, fruity, or citrus flavours and aromas. Hops are also used for various purposes in other beverages and herbal medicine. The hops plants have separate female and male plants, and only female plants are used for commercial production. The hop plant is a vigorous, climbing, herbaceous perennial, usually trained to grow up strings in a field called a hopfield, hop garden (in the South of England), or hop yard (in the West Country and United States) when grown commercially. Many different varieties of hops are grown by farmers around the world, with different types used for particular styles of beer. The first documented use of hops in beer is from the 9th century, though Hildegard of Bingen, ...
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Alpha Acid
Alpha acids (α acids) are a class of chemical compounds primarily of importance to the production of beer. They are found in the resin glands of the flowers of the hop plant and are the source of hop bitterness. Alpha acids may be isomerized to form iso-alpha acids by the application of heat in solution. Iso-alpha acids (iso-α-acids) are typically produced in beer from the addition of hops to the boiling wort. The degree of isomerization and the amount of bitter flavor produced by the addition of hops is highly dependent on the length of time the hops are boiled. Longer boil times will result in isomerization of more alpha acids and thus increased bitterness. Common alpha acids include humulone, adhumulone, cohumulone, posthumulone, and prehumulone. The most common iso-α-acids are ''cis''- and ''trans''-isohumulone. Bittering The alpha acid "rating" on hops indicates the amount of alpha acid as a percentage of total weight of the hop. Hops with a higher alpha ...
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Isohumulone
Isohumulones are chemical compounds that contribute to the bitter taste of beer and are in the class of compounds known as iso-alpha acids. They are found in hops. Beer The bitterness of beer is measured according to the International Bitterness Units scale, with one IBU corresponding to one part-per-million of isohumulone. When beer is exposed to light, these compounds can decompose in a reaction catalyzed by riboflavin to generate free-radical species by the homolytic cleavage of the exocyclic carbon-carbon bond. The cleaved acyl side-chain radical then decomposes further, expelling carbon monoxide and generating 1,1-dimethylallyl radical. This radical can finally react with sulfur-containing amino acids, such as cysteine, to create 3-methylbut-2-ene-1-thiol, a thiol which causes beer to develop a "skunky" flavor. Formation Isohumulones are generated by the isomerization of humulone.Esslinger, H. M. and Narziss, L. 2003. “Beer.” in ''Ullmann's Encyclopedia of Ind ...
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Humulus Lupulus
''Humulus lupulus'', the common hop or hops, is a species of flowering plant in the hemp family Cannabinaceae, native to Europe, western Asia and North America. It is a perennial, herbaceous climbing plant which sends up new shoots in early spring and dies back to a cold-hardy rhizome in autumn. It is dioecious (having separate male and female plants). As the female cone-shaped flowers (hops) are used to preserve and flavor beer, the species is widely cultivated by the brewing industry. Description ''Humulus lupulus'' is a perennial herbaceous plant up to tall, living up to 20 years. It has simple leaves with 3–5 deep lobes that can be opposite or alternate. The species is triggered by the longer summer days to flower, usually around July or August. The plant is dioecious, with male and female flowers on separate plants. The fragrant flowers are wind-pollinated. The staminate (male) flowers do not have petals, while the pistillate (female) flowers have petals envelopin ...
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Isoprenoid
The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of eucalyptus, the flavors of cinnamon, cloves, and ginger, the yellow color in sunflowers, and the red color in tomatoes. Well-known terpenoids include citral, menthol, camphor, salvinorin A in the plant ''Salvia div ...
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Vinylogy
In organic chemistry, vinylogy is the transmission of electronic effects through a conjugated organic bonding system. The concept was introduced in 1926 by Ludwig Claisen to explain the acidic properties of formylacetone and related ketoaldehydes. Its adjectival form, vinylogous, is used to describe functional groups in which the standard moieties of the group are separated by a carbon–carbon double bond. For example, a carboxylic acid with a carbon-carbon double bond (, a "vinyl" moiety; actually a vinylene group) between a carbonyl group () and a hydroxyl group () is referred to as a ''vinylogous'' carboxylic acid. Due to the transmission of electronic information through conjugation, ''vinylogous'' functional groups often possess "''analogous''" reactivity or chemical properties compared to the parent functional group. Hence, vinylogy is a useful heuristic for the prediction of the behavior of systems that are structurally similar but contain intervening C=C bonds that are ...
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In Vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology and its subdisciplines are traditionally done in labware such as test tubes, flasks, Petri dishes, and microtiter plates. Studies conducted using components of an organism that have been isolated from their usual biological surroundings permit a more detailed or more convenient analysis than can be done with whole organisms; however, results obtained from ''in vitro'' experiments may not fully or accurately predict the effects on a whole organism. In contrast to ''in vitro'' experiments, '' in vivo'' studies are those conducted in living organisms, including humans, and whole plants. Definition ''In vitro'' ( la, in glass; often not italicized in English usage) studies are conducted using components of an organism that have been isolated f ...
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GABAA Receptor
The GABAA receptor (GABAAR) is an ionotropic receptor and ligand-gated ion channel. Its endogenous ligand is γ-aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Upon opening, the GABAA receptor on the postsynaptic cell is selectively permeable to chloride ions (Cl−) and, to a lesser extent, bicarbonate ions (HCO3−). Depending on the membrane potential and the ionic concentration difference, this can result in ionic fluxes across the pore. If the membrane potential is higher than the equilibrium potential (also known as the reversal potential) for chloride ions, when the receptor is activated Cl− will flow into the cell. This causes an inhibitory effect on neurotransmission by diminishing the chance of a successful action potential occurring at the postsynaptic cell. The reversal potential of the GABAA-mediated inhibitory postsynaptic potential (IPSP) in normal solution is −70 mV, contrasting the GABAB IPSP (-100 mV). ...
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Antibacterial
An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of such infections. They may either kill or inhibit the growth of bacteria. A limited number of antibiotics also possess antiprotozoal activity. Antibiotics are not effective against viruses such as the common cold or influenza; drugs which inhibit viruses are termed antiviral drugs or antivirals rather than antibiotics. Sometimes, the term ''antibiotic''—literally "opposing life", from the Greek roots ἀντι ''anti'', "against" and βίος ''bios'', "life"—is broadly used to refer to any substance used against microbes, but in the usual medical usage, antibiotics (such as penicillin) are those produced naturally (by one microorganism fighting another), whereas non-antibiotic antibacterials (such as sulfonamides and anti ...
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