PRODUCTS

GRAPE ACID

Grape acid market can be primarily divided into D-Grape acid, L-Grape acid and DL Tataric acid.
Grape 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.
Naturally occurring Grape acid is a useful raw material in organic chemical synthesis.

CAS Number: 87-69-4
EC Number: 205-695-6
Molecular Formula: C4H6O6
Molecular Weight (g/mol): 150.09

Synonyms: (+)-L-Tartaric acid, (+)-Tartaric acid, 87-69-4, L-(+)-Tartaric acid, L-Tartaric acid, L(+)-Tartaric acid, tartaric acid, (2R,3R)-2,3-dihydroxysuccinic acid, (2R,3R)-2,3-dihydroxybutanedioic acid, (R,R)-Tartaric acid, Threaric acid, L-threaric acid, Dextrotartaric acid, Natural tartaric acid, Acidum tartaricum, DL-Tartaric acid, (2R,3R)-(+)-Tartaric acid, (+)-(R,R)-Tartaric acid, Tartaric acid, L-, Rechtsweinsaeure, Kyselina vinna, (2R,3R)-Tartaric acid, (R,R)-(+)-Tartaric acid, tartrate, Succinic acid, 2,3-dihydroxy, Weinsteinsaeure, L-2,3-Dihydroxybutanedioic acid, 133-37-9, (2R,3R)-rel-2,3-Dihydroxysuccinic acid, 1,2-Dihydroxyethane-1,2-dicarboxylic acid, EINECS 201-766-0, (+)-Weinsaeure, NSC 62778, FEMA No. 3044, INS NO.334, DTXSID8023632, UNII-W4888I119H, CHEBI:15671, Kyselina 2,3-dihydroxybutandiova, AI3-06298, Lamb protein (fungal), INS-334, (+/-)-Tartaric Acid, Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, (R,R)-tartrate, NSC-62778, W4888I119H, Tartaric acid (VAN), Kyselina vinna [Czech], DTXCID203632, E 334, E-334, RR-tartaric acid, (+)-(2R,3R)-Tartaric acid, Tartaric acid, L-(+)-, EC 201-766-0, TARTARIC ACID (L(+)-), Tartaric acid [USAN:JAN], Weinsaeure, BAROS COMPONENT TARTARIC ACID, L-2,3-DIHYDROXYSUCCINIC ACID, MFCD00064207, C4H6O6, L-tartarate, 4J4Z8788N8, 138508-61-9, (2R,3R)-2,3-Dihydroxybernsteinsaeure, TARTARIC ACID COMPONENT OF BAROS, Resolvable tartaric acid, d-alpha,beta-Dihydroxysuccinic acid, TARTARIC ACID (II), TARTARIC ACID [II], 144814-09-5, Kyselina 2,3-dihydroxybutandiova [Czech], REL-(2R,3R)-2,3-DIHYDROXYBUTANEDIOIC ACID, TARTARIC ACID (MART.), TARTARIC ACID [MART.], (1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid, TARTARIC ACID (USP-RS), TARTARIC ACID [USP-RS], BUTANEDIOIC ACID, 2,3-DIHYDROXY-, (R-(R*,R*))-, Tartaric acid D,L, Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-, TARTARIC ACID (EP MONOGRAPH), TARTARIC ACID [EP MONOGRAPH], Tartarate, DL-TARTARICACID, 132517-61-4, L(+) tartaric acid, (2RS,3RS)-Tartaric acid, 2,3-dihydroxy-succinic acid, Traubensaeure, Vogesensaeure, Weinsaure, acide tartrique, acido tartarico, tartaric-acid, para-Weinsaeure, L-Threaric aci, 4ebt, NSC 148314, NSC-148314, (r,r)-tartarate, (+)-tartarate, l(+)tartaric acid, Tartaric acid; L-(+)-Tartaric acid, Tartaric acid (TN), (+-)-Tartaric acid, Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-, L-(+) tartaric acid, (2R,3R)-Tartarate, 1d5r, DL TARTARIC ACID, TARTARICUM ACIDUM, 2,3-dihydroxy-succinate, TARTARIC ACID,DL-, SCHEMBL5762, TARTARIC ACID, DL-, Tartaric acid (JP17/NF), TARTARIC ACID [FCC], TARTARIC ACID [JAN], d-a,b-Dihydroxysuccinic acid, TARTARIC ACID [INCI], MLS001336057, L-TARTARIC ACID [MI], TARTARIC ACID [VANDF], DL-TARTARIC ACID [MI], CCRIS 8978, L-(+)-Tartaric acid, ACS, TARTARIC ACID [WHO-DD], CHEMBL1236315, L-(+)-Tartaric acid, BioXtra, TARTARICUM ACIDUM [HPUS], UNII-4J4Z8788N8, (2R,3R)-2,3-tartaric acid, CHEBI:26849, HMS2270G22, Pharmakon1600-01300044, TARTARIC ACID, DL- [II], TARTARIC ACID, (+/-)-, TARTARIC ACID,DL- [VANDF], HY-Y0293, STR02377, TARTARIC ACID [ORANGE BOOK], EINECS 205-105-7, Tox21_300155, (2R,3R)-2,3-dihydroxysuccinicacid, NSC759609, s6233, AKOS016843282, L-(+)-Tartaric acid, >=99.5%, CS-W020107, DB09459, NSC-759609, (2R,3R)-2,3-dihydroxy-succinic acid, Butanedioic acid, 2,3-dihydroxy-; Butanedioic acid, 2,3-dihydroxy-, (R-(R*,R*))-, CAS-87-69-4, L-(+)-Tartaric acid, AR, >=99%, (R*,R*)-2,3-dihydroxybutanedioic acid, NCGC00247911-01, NCGC00254043-01, BP-31012, SMR000112492, SBI-0207063.P001, (2R,3R)-rel-2,3-dihydroxybutanedioic acid, NS00074184, T0025, EN300-72271, (R*,R*)-(+-)-2,3-dihydroxybutanedioic acid, C00898, D00103, D70248, L-(+)-Tartaric acid, >=99.7%, FCC, FG, L-(+)-Tartaric acid, ACS reagent, >=99.5%, L-(+)-Tartaric acid, BioUltra, >=99.5% (T), J-500964, J-520420, L-(+)-Tartaric acid, ReagentPlus(R), >=99.5%, L-(+)-Tartaric acid, SAJ first grade, >=99.5%, L-(+)-Tartaric acid, tested according to Ph.Eur., Butanedioic acid, 2,3-dihydroxy-, (R*,R*)-(+-)-, L-(+)-Tartaric acid, JIS special grade, >=99.5%, L-(+)-Tartaric acid, natural, >=99.7%, FCC, FG, L-(+)-Tartaric acid, p.a., ACS reagent, 99.0%, L-(+)-Tartaric acid, Vetec(TM) reagent grade, 99%, Q18226455, F8880-9012, Z1147451717, Butanedioic acid, 2,3-dihydroxy-, (theta,theta)-(+-)-, 000189E3-11D0-4B0A-8C7B-31E02A48A51F, L-(+)-Tartaric acid, puriss. p.a., ACS reagent, >=99.5%, L-(+)-Tartaric acid, certified reference material, TraceCERT(R), Tartaric acid, United States Pharmacopeia (USP) Reference Standard, L-(+)-Tartaric acid, anhydrous, free-flowing, Redi-Dri(TM), ACS reagent, >=99.5%, L-(+)-Tartaric acid, p.a., ACS reagent, reag. ISO, reag. Ph. Eur., 99.5%, Tartaric Acid, Pharmaceutical Secondary Standard; Certified Reference Material

Grape acid is an organic acid found in many vegetables and fruits such as bananas, and grapes, but also in bananas, citrus, and tamarinds.
Grape acid is also known as 2,3-dihydroxysuccinic acid or Racemic acid.

Grape acid is used to generate carbon dioxide.
Grape acid is a diprotic aldaric acid which is crystalline white.
Baking powder is a mixture of Grape acid with sodium bicarbonate.

Grape acid is widely used in the field of pharmaceuticals.
High doses of Grape acid can lead to paralysis or death.

Grape acid is one of the least antimicrobial of the organic acids known to inactivate fewer microorganisms and inhibit less microbial growth in comparison with most other organic acids (including acetic, ascorbic, benzoic, citric, formic, fumaric, lactic, levulinic, malic, and propionic acids) in the published scientific literature.

Grape acid is a tetraric acid, which is butanedioic acid substituted with hydroxy groups at the 2 and 3 positions.
Grape acid has a role as a human xenobiotic metabolite and a plant metabolite.
Grape acid is a conjugate acid of 3-carboxy-2,3-dihydroxypropanoate.

Grape 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.
Grape acid salt, potassium bitartrate, commonly known as cream of tartar, develops naturally in the process of fermentation.

Grape acid is commonly mixed with sodium bicarbonate and is sold as baking powder used as a leavening agent in food preparation.
Grape acid itself is added to foods as an antioxidant E334 and to impart Grape acid distinctive sour taste.

Grape acid is an organic acid that naturally occurs in many fruits, most notably in grapes but also in bananas and citrus fruits.
Grape acid is a white, crystalline solid which can easily be dissolved in water.

Approx. 50 % of the produced Grape acid is subsequently used by the food and pharmaceutical industry, the other half is used in technical applications.
When added to food or beverage products, Grape acid is denoted by E-number E 334.

Besides that, Grape acid and its derivatives are often used in the field of pharmaceuticals or as a chelating agent in the farming and metal industry.

Naturally occurring Grape acid is a useful raw material in organic chemical synthesis.
Grape acid, an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

Grape acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.
Tartaric is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

L-Grape acid is a Grape acid.
Grape acid is a conjugate acid of a L-tartrate(1-).
Grape acid is an enantiomer of a D-Grape acid.

Grape acid is a white crystalline diprotic organic acid.
Grape acid occurs naturally in many plants, particularly in grapes, bananas, and tamarinds.
Grape acid is also one of the main acids found in wine.

Grape acid can be added to food when a sour taste is desired.
Grape acid is also used as an antioxidant.

Salts of Grape acid are known as tartarates.
Grape acid is a dihydroxy derivative of succinic acid.

Grape acid is found in cream of tartar and baking powder.
Grape acid is used in silvering mirrors, tanning leather, and in Rochelle Salt.
In medical analysis, Grape acid is used to make solutions for the determination of glucose.

Grape acid (2,3-dihydroxybutanedioic acid) is a naturally occurring dicarboxylic acid containing two stereocenters.
Grape acid exists as a pair of enantiomers and an achiral meso compound.

The dextrorotatory enantiomer of (R,R)-L-(+)-Grape acid is widely distributed in nature.
Grape acid is present in many fruits (fruit acid), and Grape acid monopotassium salt is found as a deposit during the fermentation of grape juice.

Pure levorotatory (S,S)-d-(−)-Grape acid is rare.
Grape acid is a historical compound, dating back to when Louis Pasteur separated Grape acid into two enantiomers with a magnifying lens and a pair of tweezers more than 160 years ago.

Grape acid is manufactured from potassium hydrogen tartrate (wine tartar, cream of tartar – a by-product of the wine-making industry) via the calcium salt.
(S,S)-Grape acid is also available commercially; Grape acid can be obtained from the racemic acid by several resolution procedures or from d-xylose.

The highly functionalized and C2-symmetric Grape acid molecule is perfectly tailored for applications as a resolving agent and chiral ligand.
In fact, Grape acid is the most frequently used resolving agent for racemic amines.

Grape acid has a stronger, sharper taste than citric acid.
Although Grape acid is renowned for its natural occurrence in grapes, Grape acid also occurs in apples, cherries, papaya, peach, pear, pineapple, strawberries, mangos, and citrus fruits.

Grape acid is used preferentially in foods containing cranberries or grapes, notably wines, jellies, and confectioneries.
Commercially, Grape acid is prepared from the waste products of the wine industry and is more expensive than most acidulants, including citric and malic acids.

l-Grape acid is an abundant constituent of many fruits such as grapes and bananas and exhibits a slightly astringent and refreshing sour taste.
Grape acid is one of the main acids found in wine.

Grape acid is added to other foods to give a sour taste and is normally used with other acids such as citric acid and malic acid as an additive in soft drinks, candies, and so on.
Grape acid is produced by acid hydrolysis of calcium tartrate, which is prepared from potassium tartrate obtained as a by-product during wine production.
Optically active Grape acid is used for the chiral resolution of amines and also as an asymmetric catalyst.

Grape acid is the most water-soluble of the solid acidulants.
Grape acid contributes a strong tart taste that enhances fruit flavors, particularly grape and lime.

This dibasic acid is produced from potassium acid tartrate, which has been recovered from various by-products of the wine industry, including press cakes from fermented and partially fermented grape juice, lees (the dried, slimy sediments in wine fermentation vats), and argols (the crystalline crusts formed in vats during the second fermentation step of wine making).
The major European wine-producing countries, Spain, Germany, Italy, and France, use more of the acid than the United States.

Grape acid is often used as an acidulant in grape- and lime-flavored beverages, gelatin desserts, jams, jellies, and hard sour confectionery.
The acidic monopotassium salt, more commonly known as ‘cream of tartar,’ is used in baking powders and leavening systems.
Because Grape acid has limited solubility at lower temperatures, cream of tartar does not react with bicarbonate until the baking temperatures are reached; this ensures maximum development of volume in the finished product.

Grape acid, a dicarboxylic acid, one of the most widely distributed of plant acids, with a number of food and industrial uses.
Along with several of Grape acid salts, cream of tartar (potassium hydrogen tartrate) and Rochelle salt (potassium sodium tartrate), Grape acid is obtained from by-products of wine fermentation.

In a partially purified form, tartar was known to the ancient Greeks and Romans; the free acid was first isolated in 1769 by Swedish chemist Carl Wilhelm Scheele.
The lees, or sediments, and other waste products from fermentation are heated and neutralized with calcium hydroxide; the precipitated calcium tartrate is then treated with sulfuric acid to produce free Grape acid.

Rochelle salt is prepared from the crude crystalline potassium acid salt, called argol, by neutralization with sodium carbonate.
Purified cream of tartar comes chiefly from the filtrates from production of the acid and Rochelle salt.
A third salt, tartar emetic (antimony potassium tartrate), is made from the potassium acid salt and antimony oxide.

Three stereoisomeric forms of Grape acid exist:
(1) dextrorotatory Grape acid (D-Grape acid) found in grapes and several other fruits,
(2) levorotatory Grape acid (L-Grape acid) obtained chiefly by resolution of racemic Grape acid,
(3) a meso or achiral form.

Racemic Grape acid (an equal mixture of D- and L-Grape acid) is prepared commercially by the molybdenum- or tungsten-catalyzed oxidation of maleic anhydride with hydrogen peroxide.

Study of the crystallographic, chemical, and optical properties of the Grape acids by French chemist and microbiologist Louis Pasteur laid the basis for modern ideas of stereoisomerism.

The various Grape acids and the common tartrate salts are all colourless, crystalline solids readily soluble in water.
Grape acid is widely used as an acidulant in carbonated drinks, effervescent tablets, gelatin desserts, and fruit jellies.

Grape acid has many industrial applications—e.g., in cleaning and polishing metals, in calico printing, in wool dyeing, and in certain photographic printing and development processes.
Rochelle salt is used in silvering mirrors, in processing cheese, and in compounding mild cathartics.

Cream of tartar is incorporated into baking powders, hard candies, and taffies; and Grape acid is employed in the cleaning of brass, the electrolytic tinning of iron and steel, and the coating of other metals with gold and silver.
Tartar emetic is used as an insecticide and a dyeing mordant.

Grape acid is an organic acid.
Grape acid is also known as 2,3-dihydroxysuccinic acid or Racemic acid.
Grape acid is in use to generate carbon dioxide.

Grape acid is a diprotic aldaric acid.
Grape acid is an alpha-hydroxy-carboxylic acid and is a dihydroxyl derivative of succinic acid.

Grape acid is widely in use in the field of pharmaceuticals.
A High dose of Grape acid can affect our body to a great extent.

Grape acid is a white and crystalline that occurs naturally in many fruits and vegetables and most notably in grapes.
Grape acid is also present in bananas, tamarinds, and citrus.
The salt i.e., potassium bitartrate also called cream of tartar, develops naturally in the process of fermentation.

Grape acid is commonly mixed with sodium bicarbonate and is sold as a baking powder that is in use as a leavening agent in food preparation.
The Grape acid is added to foods being an antioxidant i.e., E334 and to impart Grape acid distinctive sour taste.

Grape acid, sometimes called racemic acid, is an organic compound that naturally occurs in plants, wine, and many fruits, such as grapes, tamarinds, citrus, and bananas.
The acid is available as a white solid that’s soluble in water.
Grape acid salt, commonly referred to as cream of tartar, is created naturally through fermentation.

Grape acid is made from potassium acid tartrate obtained from different by-products of the wine industry, such as lees, argol, and press cakes from fermented grape juice.
This dibasic acid is usually mixed with sodium bicarbonate and is available as baking powder commonly used as a food additive.

Forms of Grape acid:
Grape acid is a strong dicarboxylic acid with a molecular formula of C4H6O6.

Grape acid exists in three forms:
L-Grape acid
D-Grape acid
MesoGrape acid

All these forms of Grape acid have the same chemical formula but different atom arrangements.
Again, L-Grape acid occurs naturally, while mesoGrape acid and D-Grape acid are synthetically produced.

Uses of Grape acid:
Grape acid is Levo form of dextrorotatory Grape acid.
Grape acid is found throughout nature and classified as a fruit acid.

Grape acid is used in soft drinks and foods, as an acidulant, complexing agent, pharmaceutic aid (buffering agent), in photography, tanning, ceramics, and to make tartrates.
Diethyl and dibutyl ester derivatives are commercially significant for use in lacquers and in textile printing.

Grape acid is used as an intermediate, in construction and ceramics applications, in cleaning products, cosmetics/personal care products, and metal surface treatments (including galvanic and electroplating products).
Grape acid is used as a flavoring agent, anticaking agent, drying agent, firming agent, humectant, leavening agent, and pH control agent for foods.

Grape acid is used to improve the taste of oral medications.
Grape acid is used to chelate metal ions such as magnesium and calcium.

Grape acid is used in recipes as a leavening agent along with baking soda.
Grape acid is used as an antioxidant.

Grape acid is as one of the important acids in wine.
Grape acid is used in foods to give a sour taste.

Grape acid is sometimes used to induce vomiting.
Grape acid is used to make silver mirrors.

In its ester form, Grape acid is used in the dyeing of textiles.
Grape acid is used in the tanning of leather.

Grape acid is used in candies.
In its cream form, Grape acid is used as a stabilizer in food.

Food industry:
Grape acid is used as acidifier and natural preservative for marmalades, ice cream, jellies, juices, preserves, and beverages.
Grape acid is used as effervescent for carbonated water.
Grape acid is used as emulsifier and preservative in the bread-making industry and in the preparation of candies and sweets.

Oenology:
Grape acid is used as an acidifier.
Grape acid is used in musts and wines to prepare wines that are more balanced from the point of view of taste, the result being an increase in their degree of acidity and a decrease in their pH content.

Pharmaceuticals industry:
Grape acid is used as an excipient for the preparation of effervescent tablets.

Construction industry:
Grape acid is used in cement, plaster, and plaster of Paris to retard drying and facilitate the handling of these materials.

Cosmetics industry:
Grape acid is used as a basic component of many natural body crèmes.

Chemical sector:
Grape acid is used in galvanic baths.
Grape acid is used in electronics industry.

Grape acid is used as mordant in the textile industry.
Grape acid is used as an anti-oxidant in industrial greases.

Industry Uses:
Processing aids not otherwise specified

Consumer Uses:
Processing aids not otherwise specified

Industrial Processes with risk of exposure:
Electroplating
Painting (Pigments, Binders, and Biocides)
Leather Tanning and Processing
Photographic Processing
Textiles (Printing, Dyeing, or Finishing)

Usage Areas of Grape acid:
Grape acid, this crystalline acid, is commonly seen in plants and fruits.
The chemical formula of Grape acid, an organic acid, is C4H6O6 and its density is 1.788g/cm.

Grape acid is used in different branches of industry, especially industry.
Grape acid is generally preferred for the fermentation of wine and is formed as a byproduct of potassium during fermentation.

Grape acid is frequently used in wool dyeing, polishing, gelatin, desserts and sodas.
Apart from this, antimony potassium tartar is generally preferred and used as a mordant with insecticides.

Grape acid, which is mostly found in grape fruits, also occurs in some fruits other than grapes.
However, the Grape acids seen in these fruits are called dextro Grape acid.

Grape acid, which is formed from the mixture of raceme, is called levo.
Grape acids are among the water-soluble dicarboxylic acids.

Grape acid is used to give a sour taste to foods.
Grape acid, E334, is a good antioxidant.

The most common use of Grape acid is in soda production.
Grape acid, which is used to flavor soda, is an indispensable component of soda.

Grape acid is preferred for dyeing wool.
Grape acid can be used for polishing, polishing and cleaning metals.

Grape acid is used to release carbon dioxide in bakery products.
Grape acid, an indispensable ingredient in gelatin desserts, is generally preferred as a thickener in products such as meringue, Turkish delight and whipped cream.

The form of Grape acid obtained from grapes is generally preferred in pastry.
Grape acid can be preferred over baking powder for rising cakes.

Grape acid, which is frequently found in fruits and has a tart and strong taste, is preferred for winemaking and fermentation of wine.
Grape acid is used in making marmalade and jams.

Applications of Grape acid:
Grape acid and its derivatives have a plethora of uses in the field of pharmaceuticals.
For example, Grape acid has been used in the production of effervescent salts, in combination with citric acid, to improve the taste of oral medications.

The potassium antimonyl derivative of the acid known as tartar emetic is included, in small doses, in cough syrup as an expectorant.
Grape acid also has several applications for industrial use.

The acid has been observed to chelate metal ions such as calcium and magnesium.
Therefore, the acid has served in the farming and metal industries as a chelating agent for complexing micronutrients in soil fertilizer and for cleaning metal surfaces consisting of aluminium, copper, iron, and alloys of these metals, respectively.

Grape acid is used in fuels and fuel additives, laboratory chemicals, lubricants and lubricant additives, coating agents and surface treatment agents.
Grape acid is used in processing aids and petroleum production specific processing aids.

Grape acid is used in ink, toner and coloring products, laboratory use, lubricants and greases.
Grape acid is found in cream of tartar, which is used in making candies and frostings for cakes.

Grape acid is also used in baking powder where Grape acid serves as the source of acid that reacts with sodium bicarbonate (baking soda).
This reaction produces carbon dioxide gas and lets products “rise,” but Grape acid does so without the “yeast” taste that can result from using active yeast cultures as a source of the carbon dioxide gas.

Grape acid is used in silvering mirrors, tanning leather, and in the making of Rochelle Salt, which is sometimes used as a laxative.
Blue prints are made with ferric tartarte as the source of the blue ink.

In medical analysis, Grape acid is used to make solutions for the determination of glucose.
Common esters of Grape acid are diethyl tartarate and dibutyl tartrate.
Both are made by reacting Grape acid with the appropriate alcohol, ethanol or n-butanol.

In the reaction the Hydrogen of the COOH acid group is replaced with an ethyl group (diethyl tartarate) or butyl group (dibutyl tartarate.
These esters are used in manufacturing lacquer and in dyeing textiles.

Grape acid in wine:
Grape acid may be most immediately recognizable to wine drinkers as the source of "wine diamonds", the small potassium bitartrate crystals that sometimes form spontaneously on the cork or bottom of the bottle.
These "tartrates" are harmless, despite sometimes being mistaken for broken glass, and are prevented in many wines through cold stabilization (which is not always preferred since Grape acid can change the wine's profile).
The tartrates remaining on the inside of aging barrels were at one time a major industrial source of potassium bitartrate.

Grape acid plays an important role chemically, lowering the pH of fermenting "must" to a level where many undesirable spoilage bacteria cannot live, and acting as a preservative after fermentation.
In the mouth, Grape acid provides some of the tartness in the wine, although citric and malic acids also play a role.

Grape acid in fruits:
Grapes and tamarinds have the highest levels of Grape acid concentration.
Other fruits with Grape acid are bananas, avocados, prickly pear fruit, apples, cherries, papayas, peaches, pears, pineapples, strawberries, mangoes and citrus fruits.

Results from a study showed that in citrus (oranges, lemons and mandarins), fruits produced in organic farming contain higher levels of Grape acid than fruits produced in conventional agriculture.

Trace amounts of Grape acid have been found in cranberries and other berries.
Grape acid is also present in the leaves and pods of Pelargonium plants and beans.

Retarding Agent:
Grape acid is widely used as a retarding agent in oilfield applications as well as in cementitious-based systems.
Grape acid works by slowing the setting of cement by impeding certain reactions during the hydration of the cement process.
Grape acid retards various steps, including ettringite formation and C3A hydration.

Food Additive:
Grape acid also has many uses in the food industry.
As an acidulant, Grape acid offers a pleasant sour taste and gives food a sharp flavor.

Grape acid also serves as a preservative food agent and can help set gels.
Grape acid is usually added to most products, including carbonated beverages, gelatin, fruit jellies, and effervescent tablets.
Grape acid is also used as an ingredient in candy and various brands of baking powders and leavening systems to make goods rise.

Industrial Applications:
Grape acid has many industrial applications.
Grape acid’s used in gold and silver plating, making blue ink for blueprints, tanning leather, and cleaning and polishing metals.
Grape acid’s also one of the ingredients in Rochelle Salt, which is luxuriant and reacts with silver nitrate to form the silvering in mirrors.

Commercial Application:
The by-products obtained from the fermentation of wine during the production of Grape acid are heated with calcium hydroxide.
This causes calcium tartrate to develop a residue, which is further treated with sulfuric acid to form a mixture of Grape acid and calcium sulfate.
Once the mixture is separated, Grape acid is purified and used for commercial production.

Other Grape acid uses include pharmaceutical applications to produce effervescent salt that helps enhance the taste of oral medications.
Grape acid’s also used in the metals and farming industry as a chelating agent for cleaning metal surfaces and adding nutrients to the soil.

Derivatives of Grape acid:

Important derivatives of Grape acid include:
Sodium ammonium tartrate, the first material separated into Grape acid enantiomers
Cream of tartar (potassium bitartrate), used in cooking
Rochelle salt (potassium sodium tartrate), which has unusual optical properties
Tartar emetic (antimony potassium tartrate), a resolving agent.
Diisopropyl tartrate is used as a co-catalyst in asymmetric synthesis.

Grape acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death.
As a food additive, Grape acid is used as an antioxidant with E number E334; tartrates are other additives serving as antioxidants or emulsifiers.

When cream of tartar is added to water, a suspension results which serves to clean copper coins very well, as the tartrate solution can dissolve the layer of copper(II) oxide present on the surface of the coin.
The resulting copper(II)-tartrate complex is easily soluble in water.

Production of Grape acid:

L-(+)-Grape acid:
The L-(+)-Grape acid isomer of Grape acid is industrially produced in the largest amounts.
Grape acid is obtained from lees, a solid byproduct of fermentations.
The former byproducts mostly consist of potassium bitartrate (KHC4H4O6).

This potassium salt is converted to calcium tartrate (CaC4H4O6) upon treatment with calcium hydroxide "milk of lime" (Ca(OH)2):
KH(C4H4O6) + Ca(OH)2 -> Ca(C4H4O6) + KOH + H2O

In practice, higher yields of calcium tartrate are obtained with the addition of calcium chloride.

Calcium tartrate is then converted to Grape acid by treating the salt with aqueous sulfuric acid:
Ca(C4H4O6) + H2SO4 -> H2(C4H4O6) + CaSO4

Racemic Grape acid:
Racemic Grape acid can be prepared in a multistep reaction from maleic acid.

In the first step, the maleic acid is epoxidized by hydrogen peroxide using potassium tungstate as a catalyst.
HO2CC2H2CO2H + H2O2 → OC2H2(CO2H) 2

In the next step, the epoxide is hydrolyzed.
OC2H2(CO2H)2 + H2O → (HOCH)2(CO2H)2

meso-Grape acid:
A mixture of racemic acid and meso-Grape acid is formed when dextro-Grape acid is heated in water at 165 °C for about 2 days.

meso-Grape acid can also be prepared from dibromosuccinic acid using silver hydroxide:
HO2CCHBrCHBrCO2H + 2 AgOH → HO2CCH(OH)CH(OH)CO2H + 2 AgBr

meso-Grape acid can be separated from residual racemic acid by crystallization, the racemate being less soluble.

General Manufacturing Information of Grape acid:

Industry Processing Sectors:
Computer and Electronic Product Manufacturing
Construction
Not Known or Reasonably Ascertainable

Stereochemistry of Grape acid:
Naturally occurring form of the acid is dextro Grape acid or L-(+)-Grape acid (obsolete name d-Grape acid).
Because Grape acid is available naturally, Grape acid is cheaper than its enantiomer and the meso isomer.

The dextro and levo prefixes are archaic terms.
Modern textbooks refer to the natural form as (2R,3R)-Grape acid (L-(+)-Grape acid), and its enantiomer as (2S,3S)-Grape acid (D-(-)-Grape acid).
The meso diastereomer is referred to as (2R,3S)-Grape acid or (2S,3R)-Grape acid.

Dextro and levo form monoclinic sphenoidal crystals and orthorhombic crystals.
Racemic Grape acid forms monoclinic and triclinic crystals (space group P1).

Anhydrous meso Grape acid form two anhydrous polymorphs: triclinic and orthorhombic.
Monohydrated meso Grape acid crystallizes as monoclinic and triclinic polymorphys depending on the temperature at which crystallization from aqueous solution occurs.
Grape acid in Fehling's solution binds to copper(II) ions, preventing the formation of insoluble hydroxide salts.

History of Grape acid:
Grape acid has been known to winemakers for centuries.
However, the chemical process for extraction was developed in 1769 by the Swedish chemist Carl Wilhelm Scheele.

Grape acid played an important role in the discovery of chemical chirality.
This property of Grape acid was first observed in 1832 by Jean Baptiste Biot, who observed Grape acid ability to rotate polarized light.

Louis Pasteur continued this research in 1847 by investigating the shapes of sodium ammonium tartrate crystals, which he found to be chiral.
By manually sorting the differently shaped crystals, Pasteur was the first to produce a pure sample of levoGrape acid.

Pharmacology and Biochemistry of Grape acid:

Pharmacodynamics:
Grape acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration.
Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography.
In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

Route of Elimination:
Only about 15-20% of consumed Grape acid is secreted in the urine unchanged.

Metabolism / Metabolites:
Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract, primarily in the large instestine.

Human Metabolite Information of Grape acid:

Tissue Locations:
Adipose Tissue
Platelet
Prostate

Cellular Locations:
Cytoplasm

Reactivity of Grape acid:
L-(+)-Grape acid, can participate in several reactions.

As shown the reaction scheme below, dihydroxymaleic acid is produced upon treatment of L-(+)-Grape acid with hydrogen peroxide in the presence of a ferrous salt.
HO2CCH(OH)CH(OH)CO2H + H2O2 → HO2CC(OH)C(OH)CO2H + 2 H2O

Dihydroxymaleic acid can then be oxidized to tartronic acid with nitric acid.

Accidental Release Measures of Grape acid:

Spillage Disposal:

Personal protection:
Particulate filter respirator adapted to the airborne concentration of Grape acid.
Sweep spilled substance into covered containers.

If appropriate, moisten first to prevent dusting.
Store and dispose of according to local regulations.

Identifiers of Grape acid:
CAS Number:
R,R-isomer: 87-69-4
S,S-isomer: 147-71-7
racemic: 133-37-9
meso-isomer: 147-73-9
ChEBI: CHEBI:15674

ChEMBL:
ChEMBL333714
ChEMBL1200861

ChemSpider: 852
DrugBank: DB01694
ECHA InfoCard: 100.121.903
E number: E334 (antioxidants, ...)
KEGG: C00898
MeSH: tartaric+acid
PubChem CID: 875 unspecified isomer
UNII: W4888I119H
CompTox Dashboard (EPA): DTXSID5046986
InChI: InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
Key: FEWJPZIEWOKRBE-UHFFFAOYSA-N
InChI=1/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)
Key: FEWJPZIEWOKRBE-UHFFFAOYAZ
SMILES: O=C(O)C(O)C(O)C(=O)O

CAS number: 147-71-7
EC number: 205-695-6
Hill Formula: C₄H₆O₆
Chemical formula: HOOCCH(OH)CH(OH)COOH
Molar Mass: 150.09 g/mol
HS Code: 2918 12 00

CAS: 87-69-4
Molecular Formula: C4H6O6
Molecular Weight (g/mol): 150.09
MDL Number: MFCD00064207
InChI Key: FEWJPZIEWOKRBE-UHFFFAOYNA-N
PubChem CID: 444305
ChEBI: CHEBI:15671
SMILES: OC(C(O)C(O)=O)C(O)=O

Properties of Grape acid:
Chemical formula:
C4H6O6 (basic formula)
HO2CCH(OH)CH(OH)CO2H (structural formula)

Molar mass: 150.087 g/mol
Appearance: White powder

Density:
1.737 g/cm3 (R,R- and S,S-)
1.79 g/cm3 (racemate)
1.886 g/cm3 (meso)

Melting point:
169, 172 °C (R,R- and S,S-)
206 °C (racemate)
165-6 °C (meso)

Solubility in water:
1.33 kg/L (L or D-tartaric)
0.21 kg/L (DL, racemic)
1.25 kg/L ("meso")

Acidity (pKa): L(+) 25 °C: pKa1= 2.89, pKa2= 4.40
meso 25 °C: pKa1= 3.22, pKa2= 4.85
Conjugate base: Bitartrate
Magnetic susceptibility (χ): −67.5·10−6 cm3/mol

Density: 1.8 g/cm3 (20 °C)
Flash point: 210 °C
Ignition temperature: 425 °C
Melting Point: 172 - 174 °C
Solubility: 1394 g/l

grade: ACS reagent
Quality Level: 200
vapor density: 5.18 (vs air)
Assay: ≥99.5%

form:
crystalline powder
crystals

optical activity: [α]20/D +12.4°, c = 20 in H2O
optical purity: ee: 99% (GLC)
autoignition temp.: 797 °F

impurities:
≤0.002% S compounds
≤0.005% insolubles

ign. residue: ≤0.02%
mp: 170-172 °C (lit.)

anion traces:
chloride (Cl-): ≤0.001%
oxalate (C2O42-): passes test
phosphate (PO43-): ≤0.001%

cation traces:
Fe: ≤5 ppm
heavy metals (as Pb): ≤5 ppm

SMILES string: O[C@H]([C@@H](O)C(O)=O)C(O)=O
InChI: 1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1
InChI key: FEWJPZIEWOKRBE-JCYAYHJZSA-N

Molecular Weight: 150.09 g/mol
XLogP3-AA: -1.9
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 6
Rotatable Bond Count: 3
Exact Mass: 150.01643791 g/mol
Monoisotopic Mass: 150.01643791 g/mol
Topological Polar Surface Area: 115Å²
Heavy Atom Count: 10
Complexity: 134
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Grape acid:
Assay (acidimetric): ≥ 99.0 %
Melting range (lower value): ≥ 166 °C
Melting range (upper value): ≤ 169 °C
Spec. rotation [α²0/D (c=10 in water): -14.0 - -12.0 °
Identity (IR): passes test

Melting Point: 168.0°C to 172.0°C
Color: White or Colorless
Assay Percent Range: 99+%
Linear Formula: HO2CCH(OH)CH(OH)CO2H
Solubility Information: Solubility in water: 1390g/L (20°C).
Other solubilities: soluble in methanol, ethanol, propanol and, glycerol, 4g/L ether, insoluble in chloroform
IUPAC Name: 2,3-dihydroxybutanedioic acid
Formula Weight: 150.09
Percent Purity: ≥99%
Quantity: 500 g
Flash Point: 210°C
Infrared Spectrum: Authentic
Loss on Drying: 0.5% (1g, 105°C) max.
Packaging: Plastic bottle
Physical Form: Crystals or Crystalline Powder
Chemical Name or Material: L(+)-Grape acid

Related compounds of Grape acid:
2,3-Butanediol
Cichoric acid

Other cations:
Monosodium tartrate
Disodium tartrate
Monopotassium tartrate
Dipotassium tartrate

Related carboxylic acids:
Butyric acid
Succinic acid
Dimercaptosuccinic acid
Malic acid
Maleic acid
Fumaric acid

Names of Grape acid:

Preferred IUPAC name:
2,3-Dihydroxybutanedioic acid

Other names:
Tartaric acid
2,3-Dihydroxysuccinic acid
Threaric acid
Racemic acid
Uvic acid
Paratartaric acid
Winestone