Fertaric acid

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Fertaric acid
Fertaric acid.svg
(2S,3S)-stereoisomer
Names
IUPAC name
2-Hydroxy-3-{[(2E)-3-(4-hydroxy-3methoxyphenyl)prop-2-enoyl]oxy}butandioic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+
    Key: XIWXUSFCUBAMFH-HWKANZROSA-N
  • 2S,3S,trans:InChI=1S/C14H14O9/c1-22-9-6-7(2-4-8(9)15)3-5-10(16)23-12(14(20)21)11(17)13(18)19/h2-6,11-12,15,17H,1H3,(H,18,19)(H,20,21)/b5-3+/t11-,12-/m0/s1
    Key: XIWXUSFCUBAMFH-SCBUBVSKSA-N
  • Oc1ccc(cc1OC)/C=C/C(=O)OC(C(=O)O)C(O)C(=O)O
  • 2S,3S,trans:COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]([C@@H](C(=O)O)O)C(=O)O)O
Properties
C14H14O9
Molar mass 326.257 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fertaric acid is a hydroxycinnamic acid found in wine and grapes. [1] It is an ester formed from ferulic acid bound to tartaric acid.

It is a metabolite of caftaric acid after caftaric acid has been fed to rats. Fertaric acid is then found in plasma, kidney, and urine. [2]

Related Research Articles

<span class="mw-page-title-main">Grape</span> Fruit growing on woody vines in clusters

A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus Vitis. Grapes are a non-climacteric type of fruit, generally occurring in clusters.

<span class="mw-page-title-main">Tartaric acid</span> Organic acid found in many fruits

Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados, and citrus. Its salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation. Potassium bitartrate is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation. The acid itself is added to foods as an antioxidant E334 and to impart its distinctive sour taste. Naturally occurring tartaric acid is a useful raw material in organic chemical synthesis. Tartaric acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics and is a dihydroxyl derivative of succinic acid.

<span class="mw-page-title-main">Noble rot</span> Grey fungus affecting wine grapes

Noble rot is the beneficial form of a grey fungus, Botrytis cinerea, affecting wine grapes. Infestation by Botrytis requires warm and humid conditions, typically around 20 degrees celcius and above 80% humidity. If the weather stays wet, the undesirable form, "bunch rot" or "grey rot", adversely affects winemaking by disrupting fermentation and changing the taste, aroma, and appearance of the final wine Grapes typically become infected with Botrytis when they are ripe. If they are then exposed to drier conditions and become partially raisined, this form of infection is known as noble rot. Grapes picked at a certain point during infestation can produce particularly fine and concentrated sweet wine. Wines produced by this method are known as botrytized wines, and are considered a distinct category of dessert wines.

<span class="mw-page-title-main">Winemaking</span> Production of wine

Winemaking, wine-making, 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. There is evidence that suggests that the earliest wine production took place in Georgia and Iran around 6000 to 5000 B.C. The science of wine and winemaking is known as oenology. A winemaker may also be called a vintner. The growing of grapes is viticulture and there are many varieties of grapes.

<span class="mw-page-title-main">Grape seed oil</span> Liquid fat derived from grape seeds

Grape seed oil is a vegetable oil derived from the seeds of grapes. Grape seeds are a winemaking by-product, and oil made from the seeds is commonly used as an edible oil.

<span class="mw-page-title-main">Sémillon</span> Variety of grape

Sémillon is a golden-skinned grape used to make dry and sweet white wines, mostly in France and Australia. Its thin skin and susceptibility to botrytis make it dominate the sweet wine region Sauternes AOC and Barsac AOC.

<span class="mw-page-title-main">Aligoté</span> Variety of grape

Aligoté is a white grape used to make dry white wines, especially in the Burgundy region of France where it was first recorded in the 18th century. Since it is tolerant to cold, this variety is also cultivated in Eastern European countries. In 2004, it was the 22nd most planted vine variety in the world at 45,000 hectares.

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<span class="mw-page-title-main">Acids in wine</span>

The acids in wine are an important component in both winemaking and the finished product of wine. They are present in both grapes and wine, having direct influences on the color, balance and taste of the wine as well as the growth and vitality of yeast during fermentation and protecting the wine from bacteria. The measure of the amount of acidity in wine is known as the “titratable acidity” or “total acidity”, which refers to the test that yields the total of all acids present, while strength of acidity is measured according to pH, with most wines having a pH between 2.9 and 3.9. Generally, the lower the pH, the higher the acidity in the wine. There is no direct connection between total acidity and pH. In wine tasting, the term “acidity” refers to the fresh, tart and sour attributes of the wine which are evaluated in relation to how well the acidity balances out the sweetness and bitter components of the wine such as tannins. Three primary acids are found in wine grapes: tartaric, malic, and citric acids. During the course of winemaking and in the finished wines, acetic, butyric, lactic, and succinic acids can play significant roles. Most of the acids involved with wine are fixed acids with the notable exception of acetic acid, mostly found in vinegar, which is volatile and can contribute to the wine fault known as volatile acidity. Sometimes, additional acids, such as ascorbic, sorbic and sulfurous acids, are used in winemaking.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

Phenolic compounds—natural phenol and polyphenols—occur naturally in wine. These include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

<span class="mw-page-title-main">Chicoric acid</span> Chemical compound

Chicoric acid is a hydroxycinnamic acid, an organic compound of the phenylpropanoid class and occurs in a variety of plant species. It is a derivative of both caffeic acid and tartaric acid.

This glossary of winemaking terms lists some of terms and definitions involved in making wine, fruit wine, and mead.

<span class="mw-page-title-main">Caftaric acid</span> Chemical compound

Caftaric acid is a non-flavonoid phenolic compound.

<span class="mw-page-title-main">Oenin</span> Chemical compound

Oenin is an anthocyanin. It is the 3-glucoside of malvidin. It is one of the red pigments found in the skin of purple grapes and in wine.

<span class="mw-page-title-main">Ripeness in viticulture</span> How the term "ripe" is used in viticulture and winemaking

In viticulture, ripeness is the completion of the ripening process of wine grapes on the vine which signals the beginning of harvest. What exactly constitutes ripeness will vary depending on what style of wine is being produced and what the winemaker and viticulturist personally believe constitutes ripeness. Once the grapes are harvested, the physical and chemical components of the grape which will influence a wine's quality are essentially set so determining the optimal moment of ripeness for harvest may be considered the most crucial decision in winemaking.

<span class="mw-page-title-main">Syringic acid</span> Chemical compound

Syringic acid is a naturally occurring phenolic compound and dimethoxybenzene that is commonly found as a plant metabolite.

<span class="mw-page-title-main">Grape reaction product</span> Chemical compound

The grape reaction product is a phenolic compound explaining the disappearance of caftaric acid from grape must during processing. It is also found in aged red wines. Its enzymatic production by polyphenol oxidase is important in limiting the browning of musts, especially in white wine production. The product can be recreated in model solutions.

References

  1. Branka Mozetič; Irma Tomažič; Andreja Škvarč; Polonca Trebše (2006). "Determination of Polyphenols in White grape Berries cv. Rebula" (PDF). Acta Chim. Slov. 53: 58–64. Archived from the original (PDF) on 2011-08-07.
  2. Vanzo, A; Cecotti, R; Vrhovsek, U; Torres, AM; Mattivi, F; Passamonti, S (2007). "The fate of trans-caftaric acid administered into the rat stomach". Journal of Agricultural and Food Chemistry. 55 (4): 1604–11. doi:10.1021/jf0626819. PMID   17300159.