Wine chemistry
   HOME

TheInfoList



OR:

Wine Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...
is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through
photosynthesis Photosynthesis is a process used by plants and other organisms to convert light energy into chemical energy that, through cellular respiration, can later be released to fuel the organism's activities. Some of this chemical energy is stored i ...
, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season.
Anthocyanins Anthocyanins (), also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical com ...
give grapes a red color and protection against
ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30  PHz) to 400 nm (750  THz), shorter than that of visible light, but longer than X-rays. UV radiation ...
light.
Tannins Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' (from Anglo-Norman ''tanner'', f ...
add bitterness and astringency which acts to defend vines against pests and grazing animals. Environmental factors such as soil, rainfall and fog affect flavor in ways that can be described collectively as "character" or the French term “
terroir (, ; from ''terre'', "land") is a French term used to describe the environmental factors that affect a crop's phenotype, including unique environment contexts, farming practices and a crop's specific growth habitat. Collectively, these contex ...
”. As
climate change In common usage, climate change describes global warming—the ongoing increase in global average temperature—and its effects on Earth's climate system. Climate change in a broader sense also includes previous long-term changes to ...
disrupts long-established patterns of temperature and precipitation in wine-growing regions and causes more extreme weather events, the rate at which sugars, acids and secondary compounds develop during the growing season can be disrupted. Hotter temperatures and an earlier growing season can push chemistry of berries towards higher sugar content, less acids and differences in aromas. Other factors such as smoke taint from fires can negatively impact chemistry and flavor, resulting in flaws and
wine faults A wine fault or defect is an unpleasant characteristic of a wine often resulting from poor winemaking practices or storage conditions, and leading to wine spoilage. Many of the compounds that cause wine faults are already naturally present in wine ...
that can make the wines undrinkable.


Types of natural molecules present in wine

* Acids in wine *
Phenolic compounds in wine The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include ...
* Proteins in wine * Sugars in wine *
Yeast assimilable nitrogen Yeast assimilable nitrogen or YAN is the combination of free amino nitrogen (FAN), ammonia (NH3) and ammonium (NH4+) that is available for a yeast, e.g. the wine yeast ''Saccharomyces cerevisiae'', to use during fermentation. Outside of the f ...
*
Minerals In geology and mineralogy, a mineral or mineral species is, broadly speaking, a solid chemical compound with a fairly well-defined chemical composition and a specific crystal structure that occurs naturally in pure form.John P. Rafferty, ed ...
* Dissolved gas (CO2) *
Monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...
s and
sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modificat ...
s such as
linalool Linalool () refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent (floral, with a touch of ...
and α-terpineol *
Glutathione Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, pe ...
(reduced and oxidized)


Volatiles

*
Methoxypyrazines Methoxypyrazines are a class of chemical compounds that produce odors. The odors tend to be undesirable, as in the case of certain wines, or as defensive chemicals used by insects such as ''Harmonia axyridis'' which produces isopropyl methoxy pyr ...
* Esters:
Ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound with the formula , simplified to . This colorless liquid has a characteristic sweet smell (similar to pear drops) and is used in glues ...
is the most common ester in wine, being the product of the most common volatile organic acid — acetic acid, and the ethyl alcohol generated during the fermentation. * Norisoprenoids, such as C13-norisoprenoids found in grape (''
Vitis vinifera ''Vitis vinifera'', the common grape vine, is a species of flowering plant, native to the Mediterranean region, Central Europe, and southwestern Asia, from Morocco and Portugal north to southern Germany and east to northern Iran. There are curr ...
'') or
wine Wine is an alcoholic drink typically made from fermented grapes. Yeast consumes the sugar in the grapes and converts it to ethanol and carbon dioxide, releasing heat in the process. Different varieties of grapes and strains of yeasts are m ...
, can be produced by fungal peroxidases or
glycosidase Glycoside hydrolases (also called glycosidases or glycosyl hydrolases) catalyze the hydrolysis of glycosidic bonds in complex sugars. They are extremely common enzymes with roles in nature including degradation of biomass such as cellulose (c ...
s.


Other molecules found in wine


Preservatives

* Ascorbic acid is used during wine making * Sulfur dioxide (SO2), a preservative often added to wine


Fining agents

Gum arabic Gum arabic, also known as gum sudani, acacia gum, Arabic gum, gum acacia, acacia, Senegal gum, Indian gum, and by other names, is a natural gum originally consisting of the hardened sap of two species of the ''Acacia'' tree, '' Senegalia se ...
has been used in the past as fining agent. List of additives permitted for use in the production of wine under European Union law:


Others

* Melatonin * Wine lactone * Anthocyanone A, a degradation product of malvidin under acidic conditions


Wine faults

A wine fault or defect is an unpleasant characteristic of a wine often resulting from poor
winemaking Winemaking or vinification is the production of wine, starting with the selection of the fruit, its fermentation into alcohol, and the bottling of the finished liquid. The history of wine-making stretches over millennia. The science of wine and ...
practices or storage conditions, and leading to wine spoilage. Many of the compounds that cause wine faults are already naturally present in wine but at insufficient concentrations to adversely affect it. However, when the concentration of these compounds greatly exceeds the sensory threshold, they replace or obscure the flavors and aromas that the wine should be expressing (or that the winemaker wants the wine to express). Ultimately the quality of the wine is reduced, making it less appealing and sometimes undrinkable.M. Baldy ''"The University Wine Course" Third Edition pgs 37-39, 69-80, 134-140 The Wine Appreciation Guild 2009 The yeast ''
Brettanomyces ''Brettanomyces'' is a non-spore forming genus of yeast in the family Saccharomycetaceae, and is often colloquially referred to as "Brett". The genus name ''Dekkera'' is used interchangeably with ''Brettanomyces'', as it describes the teleomorp ...
'' produces an array of metabolites when growing in wine, some of which are volatile
phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it ...
ic compounds. ''Brettanomyces'' converts ''p''-coumaric acid to 4-vinylphenol via the enzyme cinnamate decarboxylase.Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol
at etslabs.com
4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme vinyl phenol reductase. 4-Ethylphenol causes a wine fault at a concentration of greater than 140 µg/L. Other compounds produced by ''Brettanomyces'' that cause wine faults include 4-ethylguaiacol and isovaleric acid.
Coumaric acid Coumaric acid is a phenolic derivative of cinnamic acid Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Cl ...
is sometimes added to
microbiological media Microbiology () is the scientific study of microorganisms, those being unicellular (single cell), multicellular (cell colony), or acellular (lacking cells). Microbiology encompasses numerous sub-disciplines including virology, bacteriology, pr ...
, enabling the positive identification of ''Brettanomyces'' by smell.
Geraniol Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in w ...
is a by-product of the metabolism of
sorbate Sorbic acid, or 2,4-hexadienoic acid, is a natural organic compound used as a food preservative. It has the chemical formula and the structure . It is a colourless solid that is slightly soluble in water and sublimes readily. It was first isol ...
.
Fusel alcohol Fusel alcohols or fuselol, also sometimes called fusel oils in Europe, are mixtures of several higher alcohols (those with more than two carbons, chiefly amyl alcohol) produced as a by-product of alcoholic fermentation. The word ''Fusel'' is Ge ...
s are a mixture of several alcohols (chiefly amyl alcohol) produced as a by-product of alcoholic fermentation.


See also

* Beer chemistry *
Food chemistry Food chemistry is the study of chemical processes and interactions of all biological and non-biological components of foods. The biological substances include such items as meat, poultry, lettuce, beer, milk as examples. It is similar to biochemist ...
* Premature oxidation *
Congener (alcohol) In the alcoholic beverages industry, congeners are substances, other than the desired type of alcohol, ethanol, produced during fermentation. These substances include small amounts of chemicals such as methanol and other alcohols (known as fusel a ...
, such as
tryptophol Tryptophol is an aromatic alcohol that induces sleep in humans. It is found in wine as a secondary product of ethanol fermentation. It was first described by Felix Ehrlich in 1912. It is also produced by the trypanosomal parasite in sleeping si ...


Notes


References

* ''Comprehensive Natural Products II — Chemistry and Biology'', chapter 3.26 – Chemistry of Wine, volume 3, pages 1119–1172. Véronique Cheynier, Rémi Schneider, Jean-Michel Salmon and Hélène Fulcrand,


External links


''Wine Chemistry and Biochemistry'', by M. Victoria Moreno-Arribas, Carmen Polo and María Carmen Polo, on Google books''Mass Spectrometry in Grape and Wine Chemistry'', by Riccardo Flamini and Pietro Traldi, on Google books
* Antoine de Saporta ''La Chimie des vins : les vins naturels, les vins manipulés et falsifiés'' (1889)
Google Books
{{Food chemistry