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L(+)-Tartaric acid

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CAS:87-69-4
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Related articles

  • Biosynthesis of L(+)-tartaric acid
  • L(+)-Tartaric acid (TA) is the primary nonfermentable soluble acid in grapes and the principal acid in wine, contributing impo....
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L(+)-Tartaric acid Basic information
Product Name:L(+)-Tartaric acid
Synonyms:DIHYDROXYSUCCINIC ACID;DEXTROTARTARIC ACID;ACIDUM TARTARICUM;2,3-DIHYDROXYDUTANEDIOIC ACID;(2R,3R)-(+)-TARTARIC ACID;d-alpha,beta-dihydroxysuccinicacid;dextro-rotation-2,3-dihydroxybutanedioicacid;Kyselina 2,3-dihydroxybutandiova
CAS:87-69-4
MF:C4H6O6
MW:150.09
EINECS:201-766-0
Product Categories:Food additive and acidulant;intermediates;Chiral Compound;Amino Acids;Nutritional Supplements;Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;Chiral Compounds;87-69-4;bc0001
Mol File:87-69-4.mol
L(+)-Tartaric acid Structure
L(+)-Tartaric acid Chemical Properties
Melting point 170-172 °C(lit.)
alpha 12 º (c=20, H2O)
Boiling point 191.59°C (rough estimate)
density 1.76
bulk density1000kg/m3
vapor density 5.18 (vs air)
vapor pressure <5 Pa (20 °C)
FEMA 3044 | TARTARIC ACID (D-, L-, DL-, MESO-)
refractive index 12.5 ° (C=5, H2O)
Fp 210 °C
storage temp. Store at +5°C to +30°C.
solubility H2O: soluble1M at 20°C, clear, colorless
form Solid
pka2.98, 4.34(at 25℃)
color White or colorless
PH3.18(1 mM solution);2.55(10 mM solution);2.01(100 mM solution);
Odorat 100.00 %. odorless
Odor Typeodorless
biological sourceVitis vinifera
Optical Rotation[α]20/D +13.5±0.5°, c = 10% in H2O
Water Solubility 1390 g/L (20 ºC)
Merck 14,9070
JECFA Number621
BRN 1725147
Dielectric constant35.9(-10℃)
Stability:Stable. Incompatible with oxidizing agents, bases, reducing agents. Combustible.
Cosmetics Ingredients FunctionsFRAGRANCE
BUFFERING
InChI1S/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
InChIKeyFEWJPZIEWOKRBE-JCYAYHJZSA-N
SMILESO[C@H]([C@@H](O)C(O)=O)C(O)=O
LogP-1.43
CAS DataBase Reference87-69-4(CAS DataBase Reference)
NIST Chemistry ReferenceButanedioic acid, 2,3-dihydroxy- [r-(r*,r*)]-(87-69-4)
EPA Substance Registry SystemTartaric acid (87-69-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38-41
Safety Statements 26-36-37/39-36/37/39
WGK Germany 3
RTECS WW7875000
Autoignition Temperature797 °F
Hazard Note Irritant
TSCA TSCA listed
HS Code 29181200
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Dam. 1
MSDS Information
ProviderLanguage
L(+)-Dihydroxysuccinic acid English
SigmaAldrich English
ACROS English
ALFA English
L(+)-Tartaric acid Usage And Synthesis
Chemical PropertiesTartaric acid occurs as colorless monoclinic crystals, or a white or almost white crystalline powder. It is odorless, with an extremely tart taste. L-(+)-Tartaric Acid is a naturally occurring chemical compound found in berries, grapes and various wines. It provides antioxidant properties and contributes to the sour taste within these products.
UsesIn the soft drink industry, confectionery products, bakery products, gelatin desserts, as an acidulant. In photography, tanning, ceramics, manufacture of tartrates. The common commercial esters are the diethyl and dibutyl derivatives used for lacquers and in textile printing. Pharmaceutic aid (buffering agent).
Uses L(+)-Tartaric acid is widely utilized in pharmaceutical industries. It is used in soft drinks, confectionaries, food products, gelatin desserts and as a buffering agent. It forms a compound, TiCl2(O-i-Pr)2 with Diels-Alder catalyst and acta as a chelate agent in metal industries. Owing to its efficient chelating property towards metal ions, it is used in farming and metal industries for complexing micronutrients and for cleaning metal surfaces, respectively.
Production MethodsTartaric acid occurs naturally in many fruits as the free acid or in combination with calcium, magnesium, and potassium.
Commercially, L-(+)-tartaric acid is manufactured from potassium tartrate (cream of tartar), a by-product of wine making. Potassium tartrate is treated with hydrochloric acid, followed by the addition of a calcium salt to produce insoluble calcium tartrate. This precipitate is then removed by filtration and reacted with 70% sulfuric acid to yield tartaric acid and calcium sulfate.
DefinitionChEBI: L-tartaric acid is a tetraric acid that is butanedioic acid substituted by hydroxy groups at positions 2 and 3. It is a conjugate acid of a L-tartrate(1-). It is an enantiomer of a D-tartaric acid.
General DescriptionL(+)-Tartaric acid belongs to the group of carboxylic acids, and is abundantly found in grapes and wine. It is widely used in drugs, food, and beverage industry.
Flammability and ExplosibilityNot classified
Pharmaceutical ApplicationsTartaric acid is used in beverages, confectionery, food products, and pharmaceutical formulations as an acidulant. It may also be used as a sequestering agent and as an antioxidant synergist. In pharmaceutical formulations, it is widely used in combination with bicarbonates, as the acid component of effervescent granules, powders, and tablets.
Tartaric acid is also used to form molecular compounds (salts and cocrystals) with active pharmaceutical ingredients to improve physicochemical properties such as dissolution rate and solubility.
Biochem/physiol ActionsL-(+)-Tartaric acid serves as a donor ligand for biological processes. It is used as a food additive in candies and soft drinks to impart a sour taste.
Safety ProfileModerately toxic by intravenous route. Mildly toxic by ingestion. Reaction with silver produces the unstable silver tartrate. When heated to decomposition it emits acrid smoke and irritating fumes.
Safety L(+)-Tartaric acid is widely used in food products and oral, topical, and parenteral pharmaceutical formulations. It is generally regarded as a nontoxic and nonirritant material; however, strong tartaric acid solutions are mildly irritant and if ingested undiluted may cause gastroenteritis.
An acceptable daily intake for L-(+)-tartaric acid has not been set by the WHO, although an acceptable daily intake of up to 30 mg/kg body-weight for monosodium L-(+)-tartrate has been established. LD50 (mouse, IV): 0.49 g/kg.
storageThe bulk material is stable and should be stored in a well-closed container in a cool, dry place.
IncompatibilitiesTartaric acid is incompatible with silver and reacts with metal carbonates and bicarbonates (a property exploited in effervescent preparations).
Regulatory StatusGRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (IM and IV injections; oral solutions, syrups and tablets; sublingual tablets; topical films; rectal and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
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