Calcium tartrate

Last updated
Calcium tartrate
Calcium L-tartrate Structural Formula V1.svg
Names
IUPAC name
2,3-Dihydroxybutanedioic acid calcium salt
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.656 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 221-621-5
E number E354 (antioxidants, ...)
PubChem CID
UNII
  • InChI=1S/C4H6O6.Ca/c5-1(3(7)8)2(6)4(9)10;/h1-2,5-6H,(H,7,8)(H,9,10);/q;+2/p-2 Yes check.svgY
    Key: GUPPESBEIQALOS-UHFFFAOYSA-L Yes check.svgY
  • InChI=1/C4H6O6.Ca/c5-1(3(7)8)2(6)4(9)10;/h1-2,5-6H,(H,7,8)(H,9,10);/q;+2/p-2
    Key: GUPPESBEIQALOS-NUQVWONBAP
  • [Ca+2].O=C([O-])C(O)C(O)C([O-])=O
Properties
CaC4H4O6
Molar mass 190.16484 g/mol (anhydrous)
260.21 g/mol (tetrahydrate)
Appearance hygroscopic white powder
or colorless crystals
Density 1.817 g/cm3 (tetrahydrate)
Melting point tetrahydrate decomposes at 160 °C
anhydrous decomposes at 650 °C
0.037 g/100 ml (0 °C) 0.2 g/100 ml (85 °C)
Structure
d or l rhombic
dl triclinic
Hazards
Safety data sheet (SDS) Calcium tartrate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Calcium tartrate, exactly calcium L-tartrate, is a byproduct of the wine industry, prepared from wine fermentation dregs. [1] [2] [3] It is the calcium salt of L-tartaric acid, an acid most commonly found in grapes. [4] Its solubility decreases with lower temperature, which results in the forming of whitish (in red wine often reddish) crystalline clusters as it precipitates. As E number E354, it finds use as a food preservative and acidity regulator. Like tartaric acid, calcium tartrate has two asymmetric carbons, hence it has two chiral isomers and a non-chiral isomer (meso-form). Most calcium tartrate of biological origin is the chiral levorotatory (–) isomer.

Related Research Articles

<span class="mw-page-title-main">Stereoisomerism</span> When molecules have the same atoms and bond structure but differ in 3D orientation

In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer.

<span class="mw-page-title-main">Stereochemistry</span> Subdiscipline of chemistry

Stereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which by definition have the same molecular formula and sequence of bonded atoms (constitution), but differ in the geometric positioning of the atoms in space. For this reason, it is also known as 3D chemistry—the prefix "stereo-" means "three-dimensionality".

In chemistry, a racemic mixture or racemate, is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates.

<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. It 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">Enantiomer</span> Stereoisomers that are nonsuperposable mirror images of each other

In chemistry, an enantiomer – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are nonsuperposable onto their own mirror image. Enantiomers are much like one's right and left hands; without mirroring one of them, hands cannot be superposed onto each other. No amount of reorientation in three spatial dimensions will allow the four unique groups on the chiral carbon to line up exactly. The number of stereoisomers a molecule has can be determined by the number of chiral carbons it has.

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

Potassium tartrate, dipotassium tartrate or argol has formula K2C4H4O6. It is the potassium salt of tartaric acid. It is often confused with potassium bitartrate, also known as cream of tartar. As a food additive, it shares the E number E336 with potassium bitartrate.

In chemistry, racemization is a conversion, by heat or by chemical reaction, of an optically active compound into a racemic form. This creates a 1:1 molar ratio of enantiomers and is referred to as a racemic mixture. Plus and minus forms are called Dextrorotation and levorotation. The D and L enantiomers are present in equal quantities, the resulting sample is described as a racemic mixture or a racemate. Racemization can proceed through a number of different mechanisms, and it has particular significance in pharmacology as different enantiomers may have different pharmaceutical effects.

<span class="mw-page-title-main">Meso compound</span> Optically inactive isomer in a set of stereoisomers

A meso compound or meso isomer is an optically inactive isomer in a set of stereoisomers, at least two of which are optically active. This means that despite containing two or more stereocenters, the molecule is not chiral. A meso compound is superposable on its mirror image. Two objects can be superposed if all aspects of the objects coincide and it does not produce a "(+)" or "(-)" reading when analyzed with a polarimeter. The name is derived from the Greek mésos meaning “middle”.

<span class="mw-page-title-main">Potassium bitartrate</span> Chemical salt used in cooking as cream of tartar

Potassium bitartrate, also known as potassium hydrogen tartrate, with formula KC4H5O6, is a chemical compound with a number of uses.

<span class="mw-page-title-main">Chirality (chemistry)</span> Geometric property of some molecules and ions

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

<span class="mw-page-title-main">Racemic acid</span>

Racemic acid is an old name for an optically inactive or racemic form of tartaric acid. It is an equal mixture of two mirror-image isomers (enantiomers), optically active in opposing directions. It occurs naturally in grape juice.

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

Calcium lactate is a white crystalline salt with formula C
6
H
10
CaO
6
, consisting of two lactate anions H
3
C
(CHOH)CO
2
for each calcium cation Ca2+
. It forms several hydrates, the most common being the pentahydrate C
6
H
10
CaO
6
·5H
2
O
.

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

A tartrate is a salt or ester of the organic compound tartaric acid, a dicarboxylic acid. The formula of the tartrate dianion is OOC-CH(OH)-CH(OH)-COO or C4H4O62−.

Chiral resolution, or enantiomeric resolution, is a process in stereochemistry for the separation of racemic mixture into their enantiomers. It is an important tool in the production of optically active compounds, including drugs. Another term with the same meaning is optical resolution.

<span class="mw-page-title-main">Absolute configuration</span> Stereochemistry term

Absolute configuration refers to the spatial arrangement of atoms within a chiral molecular entity and its resultant stereochemical description. Absolute configuration is typically relevant in organic molecules where carbon is bonded to four different substituents. This type of construction creates two possible enantiomers. Absolute configuration uses a set of rules to describe the relative positions of each bond around the chiral center atom. The most common labeling method uses the descriptors R or S and is based on the Cahn–Ingold–Prelog priority rules. R and S refer to rectus and sinister, Latin for right and left, respectively.

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

Diethyl tartrate is an organic compound with the formula (HOCHCO2Et)2 (Et = ethyl). Three stereoisomers exist, R,R-, S,S-, and R,S (=S,R-). They are the ethyl esters of the respective R,R-, S,S-, and R,S-tartaric acids. The R,R- and S,S- isomers are enantiomeric, being mirror images. The meso stereoisomer is not chiral. The chiral isomer is far more common.

<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">Isomer</span> Chemical compounds with the same molecular formula but different atomic arrangements

In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Diamond and graphite are a familiar example; they are isomers of carbon. Isomerism refers to the existence or possibility of isomers.

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

Metatartaric acid is a food additive. Chemically, it is a polymeric lactone of variable composition and different molecular weights obtained through a dehydration reaction by heating tartaric acid.

Dibutyl tartrate is a di-ester of tartaric acid and butanol. It has been used as a chiral oil to separate enantiomers in chromatography. Another use is in farinographs. Yet another use is as a plasticizer. The material is classed as "green" as it is made from natural products, and is biodegradable.

References

  1. Zoecklein, Bruce; Fugelsang, Kenneth C.; Gump, Barry H.; Nury, Fred S. (2013-11-09). Wine Analysis and Production. Springer Science & Business Media. p. 228. ISBN   978-1-4757-6967-8.
  2. Roeber, Eugene Franz; Parmelee, Howard Coon (1915). Metallurgical & Chemical Engineering. Electrochemical Publishing Company. p. 616.
  3. Ribéreau-Gayon, Pascal; Glories, Yves; Maujean, Alain; Dubourdieu, Denis (2006-05-01). Handbook of Enology, Volume 2: The Chemistry of Wine - Stabilization and Treatments. John Wiley & Sons. pp. 39–40. ISBN   978-0-470-01038-9.
  4. "Calcium tartrate". InXight Drugs. National Center for Advancing Translational Sciences.