Hops, terpenes from

Terpenes were originally named after turpentine, the volatile oil from pine trees used in oil painting, whose major constituent is a-pinene. The term was rather vaguely used for all the volatile oily compounds, insoluble in water and usually with resiny smells from plants. The oils distilled from plants, which often contain perfumery or flavouring materials, are called essential oils and these too contain terpenes. Examples include camphor from the camphor tree, used to preserve clothes from moths, humulene from hops, which helps to give beer its flavour, and phytol, found in many plants. 

Karahanaenone, a terpene isolated from oil of hops, has been. synthesized by the thermal reaction shown. Identify the kind of pericyclic reaction, and explain how karahanaenone is formed. 

In a later study, the aroma constituents of a Bavarian (Pilsener) beer brewed in Hallertau, near Munich, which possessed a desirable fine hop aroma, was examined [58]. Neither the terpenes and sesquiterpenes nor the methyl esters characterized in hop oil were detected but fraction IV (Table 13.6), which contained terpenoids and sesquiterpenoids, possessed an intensive pleasant hoppy odour. Noteworthy amongst the identified constituents are the cyclic ethers (80)-(86) first found in Japanese hops, the flowery notes of which contribute to hop aroma, and the sesquiterpenoids derived from humulene such as humulene epoxide I, humulene epoxide II, humulol, and humulenol II. Similar results were found with American beers [60, 86]. Humuladienone (79)... 

SoRM, F., J. Mleziva, Z. Arnold, and J. Pliva Terpenes. XIII. Sesquiterpenes from the Essential Oil of Hops. Collect. Czech. Chem. Commun. 14, 699 (1949). 

Female inflorescences (cones) of hop carry glandular trichomes that contain volatiles derived from terpenes and fatty acids and a... 

The primary aromatic substances in beer are derived from raw materials (barley or hops) that confer the beer s typical odour and taste. Bitter acids of hops have a bitter taste (see Section 8.3.5.1.3), but hop cones also contain 0.3-1% m/m of terpenoids (60-80% of hop essential oil), which have a considerable influence on the smell of beer. The main components of aromatic hop oils are sesquiterpenic hydrocarbons in which a-humulene, P-caryophyllene and famesene dominate. The major monoter-penic hydrocarbon is myrcene. For example, the essential oil content of fine aromatic varieties, such as Saaz, is 0.8% m/m, of which 23% is myrcene, 20.5% a-humulene, 14% famesene 6% and P-caryophyUene. Significant components of the hop aroma in beer are mainly isomeric terpenoid monoepoxides resulting from autoxidation and diepoxides of a-humulene and fS-caryophyUene, but also other terpenoids. Important components of hops odour are also various alcohols (such as geraniol and hnalool), esters (ethyl 2-methylpropanoate, methyl 2-methylbutanoate, propyl 2-methylbutanoate and esters of terpenic alcohols, such as geranyl isobutanoate), hydrocarbons, aldehydes and ketones formed by oxidation of fatty acids, such as (3E,5Z)-undeca-l,3,5-triene, (Z)-hex-3-enal, nonanal, (Z)-octa-l,5-dien-3-one, their epoxides, such as ( )-4,5-epoxydec-2-enal and sulfur compounds. Other important components of hops are so-called polyphenols (condensed tannins) that influence the beer s taste and have antioxidant effects. Less important compounds are waxes and other hpids. Hop products, such as powder, pellets and extracts (by extraction with carbon... 

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