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Tartaric Acid, L(+)-Tartaric Acid, Racemic Acid, Paratartaric Acid, Uvic Acid, DL-Tartrate, Dihydroxy Butanedioic Acid, Meso-Tartaric, E334, 87-69-4, 133-37-9, 147-73-9, 147-71-7

Tartaric Acid, L(+)-Tartaric Acid, Racemic Acid, Paratartaric Acid, Uvic Acid, DL-Tartrate, Dihydroxy Butanedioic Acid, Meso-Tartaric, E334, 87-69-4, 133-37-9, 147-73-9, 147-71-7

TARTARIC ACID (L(+)-NATURAL TARTARIC ACID, E334)

Tartaric Acid / L(+)-Tartaric Acid / 2,3-Dihydroxybutanedioic Acid / Racemic Acid / Paratartaric Acid / Uvic Acid / E334
CAS Numbers: 87-69-4 (L(+)-Natural); 133-37-9 (DL-Racemic)
EC Number: 201-766-0

SECTION 1: PRODUCT IDENTIFICATION AND CHEMICAL IDENTITY

Parameter Information
Product Name L(+)-Tartaric Acid (Natural Tartaric Acid)
Chemical Name (IUPAC) 2,3-Dihydroxybutanedioic Acid
Other Names L(+)-Tartaric Acid, Natural Tartaric Acid, Racemic Acid, Paratartaric Acid, Uvic Acid, DL-Tartrate, Dihydroxy Butanedioic Acid
CAS Number (L(+)-Natural) 87-69-4
CAS Number (DL-Racemic) 133-37-9
EC Number (EINECS) 201-766-0
E Number E334
Molecular Formula C₄H₆O₆ (HOOC–CH(OH)–CH(OH)–COOH)
Molecular Weight 150.09 g/mol
Chemical Class Organic dicarboxylic acid (dihydroxy)
Appearance White to off-white crystalline powder or colorless crystals
Odor Odorless
Taste Strongly acidic, sharp (sour)
Physical State (20°C) Solid (crystalline)
HS Code 2918.12
UN Number Not regulated (non-hazardous for transport)

Tartaric acid is a naturally occurring organic dicarboxylic acid widely distributed in plants, particularly in grapes, bananas, and tamarinds. The L(+)-isomer is the naturally occurring form, predominantly obtained as a by-product of the wine industry (from potassium bitartrate deposits). It is used extensively as an acidulant, flavor enhancer, antioxidant, and chelating agent in food, pharmaceutical, cosmetic, and industrial applications. It is approved as a food additive (E334) worldwide.

SECTION 2: SYNONYMS AND OTHER NAMES

Type Name
Turkish Names Tartarik Asit, L(+)-Doğal Tartarik Asit, Rasemik Asit, Paratartarik Asit
English Names Tartaric Acid, L(+)-Tartaric Acid, Natural Tartaric Acid, Racemic Acid, Paratartaric Acid, Uvic Acid
Chemical Names 2,3-Dihydroxybutanedioic Acid, 2,3-Dihydroxysuccinic Acid
E Number E334
CAS (L(+)-Natural) 87-69-4
CAS (DL-Racemic) 133-37-9
EC Number 201-766-0
HS Code 2918.12

SECTION 3: CHEMICAL STRUCTURE

3.1. Molecular Structure

Tartaric acid is a dicarboxylic acid with two hydroxyl groups attached to the chiral carbon atoms. It has two chiral centers, resulting in four stereoisomers.

Structural Formula:

        COOH
         |
       H - C - OH
         |
       HO - C - H
         |
        COOH

Simplified Representation:
HOOC–CH(OH)–CH(OH)–COOH

3.2. Molecular Formula

C₄H₆O₆

3.3. Molecular Weight

150.09 g/mol

3.4. Key Structural Features

Feature Description
Functional Groups Two carboxyl groups (-COOH), Two hydroxyl groups (-OH)
Chiral Centers Two (C2 and C3)
Stereoisomers L(+), D(-), DL-Racemic, Meso
Acidity Dicarboxylic acid (two acidic protons)
Chelating Ability Strong chelator for metal ions (Cu²⁺, Fe³⁺, Ca²⁺, Al³⁺)

SECTION 4: TARTARIC ACID STEREOISOMERS

Isomer CAS Number Optical Rotation Melting Point Occurrence
L(+)-Tartaric (Natural) 87-69-4 +12° to +13° 168–170°C Grapes, tamarind, wine
D(-)-Tartaric 147-71-7 -12° to -13° 168–170°C Synthetic/rare
DL-Racemic (Paratartaric) 133-37-9 206°C Synthetic mixture
Meso-Tartaric 147-73-9 140°C Synthetic

SECTION 5: PHYSICAL PROPERTIES

5.1. General Physical Properties

Property L(+)-Tartaric Acid DL-Racemic Tartaric Acid
Appearance White to off-white crystalline powder or colorless crystals White to off-white crystalline powder or colorless crystals
Physical State (20°C) Solid (crystalline) Solid (crystalline)
Odor Odorless Odorless
Taste Strongly acidic, sharp (sour) Strongly acidic, sharp (sour)
Density (20°C) 1.984 g/cm³ 1.984 g/cm³
Bulk Density 0.8–1.0 g/cm³ 0.8–1.0 g/cm³
Melting Point 168–170°C (decomposes) 206°C (decomposes)
Optical Rotation [α]D²⁰ +12° to +13° (20% w/w in water) 0° (racemic mixture)
Specific Rotation +12.0° to +13.0° -
Flash Point Non-flammable Non-flammable
Autoignition Temperature >400°C >400°C
pKa₁ (25°C) 3.04 3.04
pKa₂ (25°C) 4.37 4.37

5.2. Water Solubility

Temperature (°C) Solubility (g/100 mL water)
0°C 60.0
10°C 70.0
20°C 133.0
25°C 139.0
30°C 150.0
40°C 170.0
50°C 195.0
60°C 220.0
80°C 280.0
100°C 350.0

5.3. Solubility in Other Solvents

Solvent Solubility
Water Very soluble (133 g/100 mL at 20°C)
Absolute Ethanol Soluble (~20–30 g/100 mL)
Methanol Soluble
Acetone Slightly soluble
Glycerol Soluble
Diethyl Ether Insoluble
Chloroform Insoluble

5.4. Aqueous Solution Properties

Parameter Value
pH (1% solution, 20°C) 2.0–2.5
pH (10% solution, 20°C) 1.8–2.0
Heat of Dissolution Endothermic (water cools)
Buffering Capacity Moderate (effective pH range 2.5–4.5)

SECTION 6: CHEMICAL PROPERTIES AND REACTIVITY

6.1. Acid Dissociation Constants (pKa, 25°C)

Dissociation Step pKa Equation
First Dissociation 3.04 H₂C₄H₄O₆ ⇌ HC₄H₄O₆⁻ + H⁺
Second Dissociation 4.37 HC₄H₄O₆⁻ ⇌ C₄H₄O₆²⁻ + H⁺

6.2. Chemical Reactivity

Reaction Description
Neutralization with Bases Forms tartrate salts (potassium bitartrate – cream of tartar, sodium tartrate, calcium tartrate)
Esterification With alcohols → tartrate esters (diethyl tartrate, dibutyl tartrate)
With Sodium Bicarbonate NaHCO₃ + tartaric acid → effervescence (CO₂) – used in baking powder
Complexation with Metal Ions Forms complexes with Cu²⁺, Fe³⁺, Al³⁺, Ca²⁺
Dehydration (Heating) Decomposes to pyrotartaric acid, then to CO₂ + H₂O
Reduction To succinic acid or glyceric acid

6.3. Thermal Stability

Temperature Behavior
<150°C Stable
150–170°C Melts (168–170°C)
>170°C Decomposes (charring, CO₂, H₂O)
>200°C Complete decomposition

6.4. Stability

Parameter Behavior
Stability in Dry Air Indefinitely stable
Stability in Humid Air Slightly hygroscopic
Light Sensitivity Stable
Thermal Stability Decomposes above 170°C

6.5. Incompatibilities

Substance Hazard
Strong Oxidizing Agents (permanganates, chromates, peroxides, nitrates) Oxidation, fire/explosion risk
Strong Bases (NaOH, KOH) Neutralization (exothermic)
Metal Salts (iron, copper, aluminum) Complexation, corrosion
Sodium Bicarbonate (in presence of moisture) CO₂ release (effervescence)

SECTION 7: QUALITY SPECIFICATIONS (FOOD/PHARMACEUTICAL GRADE – L(+)-NATURAL)

Parameter Specification Test Method
Assay (C₄H₆O₆, on dry basis) 99.5–101.0% Titration
Loss on Drying (105°C, 2 hours) ≤ 0.5% Gravimetric
Residue on Ignition (Sulfated Ash) ≤ 0.1% Ashing (800°C)
Chloride (Cl) ≤ 0.01% Turbidimetric
Sulfate (SO₄) ≤ 0.02% Turbidimetric
Heavy Metals (as Pb) ≤ 10 ppm Colorimetric
Lead (Pb) ≤ 2 mg/kg Atomic Absorption
Arsenic (As) ≤ 3 ppm Atomic Absorption
Iron (Fe) ≤ 20 ppm Colorimetric
Calcium (Ca) ≤ 0.02% Atomic Absorption
Oxalate (C₂O₄) ≤ 0.01% Colorimetric
Specific Optical Rotation [α]D²⁰ +12.0° to +13.0° Polarimetry
Melting Point 168–170°C Capillary
pH (1% solution) 2.0–2.5 pH meter
Appearance White to off-white crystalline powder Visual

SECTION 8: PRODUCTION METHODS

8.1. Natural L(+)-Tartaric Acid (From Wine Industry By-products – Most Common)

Source Description
Raw Material Potassium bitartrate (cream of tartar) deposits from wine fermentation
Process Wine lees and tartrates are collected from wine barrels and tanks. Crude potassium bitartrate is purified by recrystallization. Converted to calcium tartrate by adding calcium chloride. Calcium tartrate is treated with sulfuric acid → L(+)-tartaric acid + calcium sulfate (gypsum). Purified by crystallization.
Purity 99.5–100.5% (food/pharmaceutical grade)

8.2. Synthetic DL-Tartaric Acid (Racemic)

Source Description
Process Oxidation of maleic acid or fumaric acid with hydrogen peroxide or potassium permanganate.
Purity 99.0–99.5% (technical grade)

8.3. Natural Occurrence

Source Tartaric Acid Content
Grapes and Wine 0.3–1.0%
Tamarind 8–18% (very high concentration)
Bananas, Citrus Fruits Trace amounts

SECTION 9: APPLICATIONS AND INDUSTRIAL USES

9.1. Food and Beverage Industry (E334 – Largest Application)

Application Function Typical Concentration
Carbonated Beverages (Soft Drinks) Acidulant, flavor enhancer 0.1–0.5%
Fruit Juices Acidity regulator, flavor enhancer 0.1–0.3%
Jams, Jellies, Marmalades Acidity regulator (pectin gelling) 0.1–0.5%
Confectionery and Candies Acidulant, tartness, flavor enhancer 0.5–2.0%
Baking Powder Acid component (reacts with bicarbonate → CO₂) 10–30% of baking powder
Wine Production Acidity adjustment, pH control, color stabilization 1–5 g/L
Canned Vegetables pH control, preservative 0.1–0.3%
Chewing Gum Acidulant, flavor enhancer 0.1–0.5%
Effervescent Tablets Acid component (with bicarbonate) 10–40%
Dried Fruits (Apricots, Grapes) Antioxidant, flavor enhancer, color stabilizer 0.1–0.5%

9.2. Baking Powder (Synergy with Sodium Bicarbonate)

Component Function Typical Ratio
Sodium Bicarbonate (NaHCO₃) Base (CO₂ source) 30–35%
Tartaric Acid Acid (reacts with bicarbonate) 20–30%
Corn Starch Filler, moisture absorber 30–40%

Reaction:
H₂C₄H₄O₆ + 2NaHCO₃ → Na₂C₄H₄O₆ + 2H₂O + 2CO₂↑

9.3. Pharmaceutical Applications

Application Function Typical Dosage
Effervescent Tablets (Vitamins, Analgesics, Antacids) Acid component (CO₂ source) 10–40% of tablet
Laxatives Active ingredient (as potassium bitartrate) 1–5 g
Antacids pH regulator, acidulant 5–15%
Cough Syrups pH regulator, flavor enhancer 0.1–1%
L-Carnitine Tartrate Salt form (enhances bioavailability) 50–80% L-carnitine tartrate
Oral Rehydration Salts pH buffer 0.5–2%

9.4. Wine and Beverage Industry (Critical Application)

Parameter Value
Natural Occurrence in Grapes 0.3–1.0%
Role in Wine Primary acid in wine (30–50% of total acidity)
pH Control Lowers pH (prevents bacterial growth, stabilizes color)
Tartrate Stabilization Prevents potassium bitartrate precipitation (wine diamonds)
Cold Stabilization Addition 50–200 mg/L (to prevent tartrate crystals)
Acidity Adjustment (High-pH Wines) 1–5 g/L

9.5. Industrial and Technical Applications

Application Function
Electroplating (Gold, Silver, Copper) Complexing agent, bath stabilizer
Metal Cleaning and Polishing Removes oxide layers, tarnish
Leather Tanning Masking agent in chrome tanning
Textile Dyeing Mordant, complexing agent
Photography Developer solution component
Concrete Admixture (Retarder) Extends setting time (plaster/gypsum)
Mirror Silvering (Tollens Test) Complexes silver ions in silvering solutions
Blue Ink Production Component in iron-gall inks
Water-Soluble Plastics Organic acid source for biodegradable polymers
Plaster/Gypsum Retarder Extends workability, retards setting

9.6. Cosmetics and Personal Care

Application Function Typical Concentration
Skin Care (Exfoliants) Mild exfoliant, pH regulator 0.5–5%
Sunscreens pH regulator, antioxidant 0.1–1%
Hair Care Products pH regulator, shine enhancer 0.1–1%
Facial Toners pH regulator, mild astringent 0.1–1%

9.7. Construction (Plaster and Gypsum Retarder)

Application Function Typical Concentration
Gypsum Plaster Retarder Extends setting time, improves workability 0.05–0.2% of plaster weight
Wall Plastering Prevents premature hardening 0.1–0.3%

SECTION 10: TARTARIC ACID VS. CITRIC ACID – COMPARISON

Property Tartaric Acid Citric Acid
Formula C₄H₆O₆ C₆H₈O₇
Molecular Weight 150.09 192.12
pKa₁ 3.04 3.13
pKa₂ 4.37 4.76
Acid Strength Slightly stronger Slightly weaker
Solubility (20°C) 133 g/100 mL 70 g/100 mL
Taste Very tart, sharp Mild, pleasant
Natural Source Grapes, tamarind Citrus fruits
Calcium Binding High (forms calcium tartrate) Medium (forms calcium citrate)
Effervescent Tablet Suitability Excellent Excellent
Use in Baking Powder Common (fast-acting) Common (delayed-acting)
Use in Wine Primary acid (natural) Rare (added for adjustment)
E Number E334 E330

SECTION 11: DERIVATIVES – TARTRATE SALTS

Salt Formula CAS Applications
Potassium Bitartrate (Cream of Tartar) KHC₄H₄O₆ 868-14-4 Baking powder, stabilizer, reducing agent
Sodium Tartrate Na₂C₄H₄O₆·2H₂O 6106-24-7 Buffer, sequestrant, food additive
Potassium Sodium Tartrate (Rochelle Salt) KNaC₄H₄O₆·4H₂O 304-59-6 Buffer, piezoelectric crystals
Calcium Tartrate CaC₄H₄O₆·4H₂O 3164-34-9 Effervescent tablets, antacid
Diethyl Tartrate C₄H₄O₆(C₂H₅)₂ 87-91-2 Plasticizer, chiral auxiliary
Dibutyl Tartrate C₄H₄O₆(C₄H₉)₂ 2050-27-3 Plasticizer

SECTION 12: TOXICOLOGY AND SAFETY

12.1. Acute Toxicity

Parameter Value Classification
Oral LD₅₀ (Rat) 5,000–7,500 mg/kg (low toxicity) Not classified
Dermal LD₅₀ (Rabbit) >2,000 mg/kg Not classified
Inhalation LC₅₀ Not determined (dust may be irritating) Not classified
Skin Irritation Mild irritant (powder) Not classified
Eye Irritation Moderate to severe irritant Eye Damage 1
Skin Sensitization Not a sensitizer Not classified

12.2. GHS Classification

Classification Category
Signal Word WARNING
Hazard Statements H319 – Causes serious eye irritation
Precautionary Statements P264, P280, P305+P351+P338, P337+P313

12.3. NFPA Rating

Health Flammability Reactivity
1 0 0

SECTION 13: PRECAUTIONARY STATEMENTS (P-CODES)

Code Statement
P264 Wash hands thoroughly after handling.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present.
P337+P313 If eye irritation persists: Get medical advice/attention.
P501 Dispose of contents/container in accordance with local regulations.

SECTION 14: FIRST AID MEASURES

Route of Exposure Action to Be Taken
Inhalation Move to fresh air.
Eye Contact Rinse with water for 15 minutes; remove contact lenses; seek medical attention if irritation persists.
Skin Contact Wash with soap and water.
Ingestion Rinse mouth; drink water (low toxicity).

SECTION 15: FIRE-FIGHTING MEASURES

Parameter Information
Fire Hazard Non-flammable
Suitable Extinguishing Media Water spray, CO₂, dry chemical powder, foam
Special Hazards Thermal decomposition produces toxic fumes (CO, CO₂)
Protective Equipment Self-contained breathing apparatus (SCBA), full protective clothing

SECTION 16: ACCIDENTAL RELEASE MEASURES

Parameter Information
Personal Protection Protective goggles, dust mask, gloves.
Cleaning Methods Collect dry using vacuum or sweeping. Avoid generating dust.
Environmental Precautions Prevent entry into drains, sewers, and water bodies.
Waste Disposal Dispose of in accordance with local regulations.

SECTION 17: STORAGE AND SHELF LIFE

Parameter Information
Storage Conditions Store in a cool, dry, and well-ventilated area at 5–30°C.
Container Requirements Keep tightly closed in original packaging (HDPE, PP, lined paper bags).
Materials to Avoid Moisture (slightly hygroscopic), strong oxidizers, strong bases.
Shelf Life 24–36 months (unopened, dry conditions).
Signs of Degradation Caking (moisture absorption), discoloration (yellowing).

SECTION 18: PACKAGING OPTIONS

Packaging Type Quantity Material
Kraft Bag + PE Liner 25 kg Paper / Polyethylene
Plastic Drum 25 kg HDPE
Fiber Drum 25 kg Cardboard / Plastic
Big-Bag (FIBC) 500 – 1000 kg Polypropylene
Small Pack 1 kg, 5 kg PE bag + box

SECTION 19: TRANSPORT INFORMATION

Regulation Classification
UN Number Not regulated (non-hazardous)
ADR/RID Not classified as dangerous goods
IMDG Not regulated
IATA Not regulated
Proper Shipping Name Tartaric acid (non-hazardous)

SECTION 20: ENVIRONMENTAL INFORMATION

Parameter Value
Biodegradability Readily biodegradable (OECD 301)
Aquatic Toxicity (Fish, LC₅₀, 96 h) 100–500 mg/L (low to moderate toxicity)
Daphnia magna (EC₅₀, 48 h) 50–200 mg/L
Algal Toxicity (EC₅₀, 72 h) 10–100 mg/L
Bioaccumulation Low (log P < 1)
Mobility in Soil High (high water solubility)
WGK Germany 1 (low hazard to water)
Disposal Method Landfill or incineration (non-hazardous waste)

SECTION 21: REGULATORY INFORMATION

Regulation Status
REACH (EU) Registered
TSCA (USA) Listed
FDA GRAS – food additive (E334) – 21 CFR § 184.1099
EFSA Permitted as food additive (E334)
USP / Ph. Eur. Monographed for pharmaceutical use

SECTION 22: OTHER NAMES AND SYNONYMS

Language Name
Turkish Tartarik Asit, L(+)-Doğal Tartarik Asit, Rasemik Asit, Paratartarik Asit
English Tartaric Acid, L(+)-Tartaric Acid, Natural Tartaric Acid, Racemic Acid, Paratartaric Acid, Uvic Acid
French Acide tartrique
German Weinsäure
Spanish Ácido tartárico

SECTION 23: QUICK REFERENCE TABLE

Property Value
Product Name L(+)-Tartaric Acid (E334)
CAS Number (L(+)-Natural) 87-69-4
Molecular Formula C₄H₆O₆
Molecular Weight 150.09 g/mol
Appearance White to off-white crystalline powder
Density 1.984 g/cm³
Melting Point 168–170°C
pH (1% solution) 2.0–2.5
Water Solubility (20°C) 133 g/100 mL
Optical Rotation [α]D²⁰ +12.0° to +13.0°
pKa₁ / pKa₂ 3.04 / 4.37
Assay (Food/Pharm Grade) 99.5–101.0%
E Number E334
Primary Applications Food additive (acidulant, baking powder), winemaking, pharmaceuticals (effervescent tablets), cosmetics, construction (plaster retarder), electroplating
GHS Signal Word WARNING
Hazard Statements H319 (Causes serious eye irritation)
Oral LD₅₀ (Rat) 5,000–7,500 mg/kg
Biodegradability Readily biodegradable
Shelf Life 24–36 months

SECTION 24: CRITICAL NOTICES AND BEST PRACTICES

CRITICAL NOTICES:

  1. Natural L(+)-Form: The L(+)-isomer (CAS 87-69-4) is the naturally occurring form and is preferred for food and pharmaceutical applications. The DL-racemic mixture (CAS 133-37-9) is synthetic and has different properties.

  2. High Water Solubility: Tartaric acid has very high water solubility (133 g/100 mL at 20°C), making it easy to incorporate into aqueous formulations.

  3. Strong Acidity: With pKa₁ of 3.04, it is a strong acidulant effective even at low concentrations. It provides a sharp, tart taste preferred in certain applications (wine, confectionery).

  4. Baking Powder: Tartaric acid reacts rapidly with sodium bicarbonate, making it ideal for fast-acting baking powders.

  5. Hygroscopic Nature: Tartaric acid is slightly hygroscopic. Store in airtight containers to prevent moisture absorption and caking.

  6. Eye Irritation: Powder may cause serious eye irritation (H319). Use protective goggles when handling bulk quantities.

  7. Chelating Properties: Tartaric acid forms strong complexes with metal ions (Cu²⁺, Fe³⁺, Ca²⁺, Al³⁺), making it useful for metal cleaning, electroplating, and as a sequestrant.

  8. Wine Industry: Tartaric acid is the primary acid in grapes and wine. It is used for acidity adjustment, tartrate stabilization, and pH control.

  9. Plaster Retarder: Tartaric acid is an effective gypsum/plaster retarder, extending workability time by up to several hours at low concentrations (0.05–0.2%).

  10. GRAS Status: L(+)-Tartaric acid is GRAS (Generally Recognized as Safe) and approved as food additive E334 worldwide (EU, USA, Codex).

BEST PRACTICE RECOMMENDATIONS:

  • Storage: Store in a cool, dry, and well-ventilated area at 5–30°C. Keep containers tightly closed to prevent moisture absorption.

  • Handling: Use protective goggles (risk of eye irritation) and dust mask in dusty environments.

  • Dissolution: Add to water with stirring; dissolution is endothermic (solution cools). Use warm water for faster dissolution.

  • Baking Powder Formulation: For fast-acting baking powder, use tartaric acid with sodium bicarbonate. For delayed action, use sodium aluminum sulfate or monocalcium phosphate.

  • Wine Application: Add 1–5 g/L for acidity adjustment. For tartrate stabilization, use 50–200 mg/L before cold stabilization.

  • Plaster Retardation: Use 0.05–0.2% of plaster weight to extend setting time. Higher concentrations may delay setting excessively.

  • Quality Control: Test for optical rotation to confirm L(+)-isomer identity. Monitor moisture content to prevent caking.

LEGAL DISCLAIMER:

This Technical Data Sheet (TDS) is for informational purposes only and is prepared based on available technical data. The user is solely responsible for determining the suitability of the product for their specific application and for complying with all local, national, and international regulations. For complete safety, storage, handling, transport, waste, and regulatory compliance information, the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier must be consulted. This document does not substitute professional or medical advice.

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