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Send EmailCitric Acid Esters of Mono and Diglyceride, Mono and Diglyceride Citrate Esters, Citro Glycerides, Citric Acid Glycerides, E472c, 36291-32-4
E472c – CITRIC ACID ESTERS OF MONO- AND DIGLYCERIDES
PRODUCT IDENTIFIER INFORMATION
| Parameter | Information |
|---|---|
| Product Name | Citric Acid Esters of Mono- and Diglycerides |
| E Number | E472c |
| CAS Number | 36291-32-4 |
| EC Number (EINECS) | Not registered (polymeric mixture) |
| Molecular Formula | Variable |
| Molecular Weight | ~350-700 g/mol |
| Chemical Class | Non-ionic, amphiphilic emulsifier |
SECTION 1: CHEMICAL IDENTITY AND DESCRIPTION
| Parameter | Information |
|---|---|
| Chemical Name | Citric Acid Esters of Mono- and Diglycerides |
| Synonyms | Mono- and Diglyceride Citrate Esters, CitroGlycerides, Citric Acid Glycerides |
| Chemical Class | Non-ionic, amphiphilic emulsifier |
| CAS Number | 36291-32-4 |
| EC Number (EINECS) | Not registered (polymeric mixture) |
| E Number | E472c |
| Appearance | Cream white to light yellow, waxy solid, beads, granules, or powder |
| Odor | Slight, characteristic (citric acid note) |
| Physical State (20°C) | Solid (waxy) or granules/powder |
| Raw Material Source | Vegetable or animal fatty acids (variable) |
SECTION 2: PHYSICAL PROPERTIES
| Property | Value |
|---|---|
| Physical State (20°C) | Solid (waxy) or granules/powder |
| Appearance | Cream white to light yellow, waxy solid, beads, granules, or powder |
| Odor | Slight, characteristic |
| Melting Point | 40 – 55 °C |
| Density (60°C) | ~0.95 – 1.05 g/cm3 |
| Solubility in Cold Water | Dispersible (opaque emulsion) |
| Solubility in Hot Water (>50°C) | Partially soluble / dispersible |
| Solubility in Vegetable Oils | Soluble (hot) |
| Solubility in Ethanol (96%) | Soluble (hot) |
| Solubility in Acetone | Soluble (hot) |
| Solubility in Chloroform | Soluble |
| HLB Value | ~6 – 10 |
| pH (1:10 dispersion) | 3.5 – 5.5 |
SECTION 3: CHEMICAL PROPERTIES
| Property | Information |
|---|---|
| Chemical Class | Mono/diglyceride ester (non-ionic, amphiphilic) |
| Functional Groups | Ester (-COOR), hydroxyl (-OH), carboxyl (-COOH) |
| Chemical Structure | Glycerol + Fatty Acids + Citric Acid |
| Stability | Stable under normal storage conditions; protect from light and moisture |
| Hygroscopicity | Moderate (absorbs moisture) |
| Incompatible Materials | Strong oxidizing agents, strong acids, strong bases |
Chemical Structure (Schematic):
CH2-O-CO-R (Fatty Acid)
CH-O-CO-R (Fatty Acid) or -OH
CH2-O-CO-CH2-C(OH)(COOH)-CH2-COOH (Citric Acid)
SECTION 4: TECHNOLOGICAL MECHANISM OF ACTION
4.1. Emulsion Stabilization Mechanism
| Parameter | Description |
|---|---|
| Interfacial Activity | Amphiphilic structure (hydrophobic fatty acid chains + hydrophilic citric acid groups) |
| Emulsion Type | Stabilizes oil-in-water (O/W) emulsions |
| HLB Value | ~6-10 (hydrophilic character dominant) |
| Mechanism | Adsorbs at oil-water interface reducing interfacial tension; forms steric barrier preventing coalescence |
4.2. Chelation (Metal Binding) and Antioxidant Synergy (Unique Property)
| Parameter | Description |
|---|---|
| Chelation Effect | Citric acid groups bind metal ions (Fe2+, Cu2+) |
| Mechanism | Binds transition metals that catalyze oxidative rancidity |
| Result | Delays lipid oxidation; increases oxidative stability of fat-containing products |
| Synergy | Works synergistically with added antioxidants (tocopherols, ascorbyl palmitate) |
4.3. Water Holding Capacity and Texture Improvement
| Parameter | Description |
|---|---|
| Effect | Increases water holding capacity in dough and products |
| Mechanism | Citric acid groups form hydrogen bonds with water molecules |
| Result | Softer texture, improved shelf life, reduced moisture loss |
4.4. Gluten Interaction Mechanism
| Parameter | Description |
|---|---|
| Interaction Type | Hydrogen bonds, ionic interactions |
| Target Molecules | Gluten proteins (gliadin and glutenin) |
| Effect | Strengthens gluten network; increases elasticity |
| Result | Improved gas retention capacity, better volume |
4.5. Starch Retrogradation Delay Mechanism
| Parameter | Description |
|---|---|
| Interaction Type | Adsorption on starch granule surface |
| Effect | Prevents recrystallization (retrogradation) of amylose and amylopectin chains |
| Result | Staling delayed; product shelf life extended |
4.6. Fat Crystallization Control Mechanism
| Parameter | Description |
|---|---|
| Interaction Type | Adsorption on triglyceride crystal growth surfaces |
| Effect | Promotes β' form retention; prevents transition to undesirable β form |
| Result | Smooth texture, homogeneous crystallization |
SECTION 5: FOOD APPLICATIONS AND DOSAGE
| Application | Function | Recommended Dosage | Suitability |
|---|---|---|---|
| Bread and Bakery Products | Texture improvement, volume, softness | 0.2-0.5% of flour | High |
| Cakes and Sponge Cakes | Moisture retention, texture softness, volume | 0.3-0.8% of flour | High |
| Margarine and Spreadable Fats | Emulsion stabilization, oxidative stability | 0.3-1.0% of total fat | High |
| Sauces and Salad Dressings | Viscosity control, separation prevention | 0.1-0.3% of total product | High |
| Ice Cream and Dairy Products | Ice crystal control, mouthfeel, stability | 0.05-0.15% of mix | High |
| Whipped Creams | Foam stabilization, cream consistency | 0.1-0.3% of total product | High |
| Confectionery | Crystallization control, texture improvement | 0.2-0.5% of total product | Medium |
| Meat Products (Sausages) | Fat-water stabilization, texture | 0.3-0.5% of total product | Medium |
| Instant Soups and Sauces | Fat-water stabilization, homogeneity | 0.1-0.3% of total product | High |
| Bakery Fillings and Creams | Stabilization, oxidative protection | 0.2-0.5% of total product | High |
SECTION 6: NON-FOOD APPLICATIONS
| Application | Function | Suitability |
|---|---|---|
| Cosmetics | Co-emulsifier in O/W creams and lotions, chelator | Medium |
| Pharmaceuticals (Topical) | Thickener, stabilizer in creams and ointments | Medium |
| Agrochemicals | Co-emulsifier in emulsifiable concentrate (EC) formulations | Medium |
| Bioplastics | Internal lubricant in starch-based bioplastics | Low |
| Food Packaging | Antioxidant synergist in active packaging | Low |
SECTION 7: COMPARISON WITH OTHER EMULSIFIERS
| Property | E472c | E472d | E472e (DATEM) | E477 (PGME) |
|---|---|---|---|---|
| HLB Value | ~6-10 | ~6-10 | ~8-12 | ~2-4 |
| Emulsion Type | O/W | O/W | O/W | W/O |
| Chelation Effect | Yes (Citrate) | No | No | No |
| Antioxidant Synergy | Yes | No | No | No |
| Gluten Interaction | Medium | Medium | Very Strong | None |
| Water Holding Capacity | High | High | Medium | Low |
| Acidic Environment Activity | High | High | Medium | Low |
| Temperature Resistance | >180°C | >180°C | >200°C | >200°C |
| Oxidative Stability | Enhanced | Standard | Standard | Standard |
| Main Use | Bakery, fats, sauces, dairy, antioxidant protection | Bakery, dairy, sauces | Industrial bread | Cakes, creams |
Key Differences:
-
E472c (Citric Acid Esters): Distinguished from others by metal ion binding (chelation) property. Prevents oxidative rancidity; ideal for fat-containing products requiring long shelf life.
-
E472d (Tartaric Acid Esters): High water holding capacity.
-
E472e (DATEM): Strongest gluten interaction; maximum volume.
-
E477 (PGME): Lipophilic; ideal for cakes and W/O emulsions.
SECTION 8: QUALITY SPECIFICATIONS (FOOD GRADE)
| Parameter | Specification (E472c) |
|---|---|
| Appearance | Cream white to light yellow, waxy solid, beads, granules, or powder |
| Identification (IR) | Positive (ester and citric acid peaks) |
| Acid Value (mg KOH/g) | ≤ 6.0 |
| Saponification Value (mg KOH/g) | 280 – 380 |
| Total Citric Acid (molar) | ≥ 12.0% |
| Iodine Value | Variable (depending on fatty acid source) |
| Hydroxyl Value | 30 – 70 mg KOH/g |
| Free Glycerol | ≤ 1.0% |
| Free Citric Acid | ≤ 0.5% |
| Water Content | ≤ 2.0% |
| Ash Content | ≤ 0.5% |
| Melting Point | 40 – 55 °C |
| pH (1:10 dispersion) | 3.5 – 5.5 |
| Heavy Metals (as Pb) | ≤ 10 ppm |
| Residual Solvents | Meets ICH Q3C requirements |
SECTION 9: MICROBIOLOGICAL SPECIFICATIONS
| Parameter | Specification |
|---|---|
| Total Mesophilic Aerobic Bacteria | ≤ 1,000 CFU/g |
| Yeast and Mold | ≤ 100 CFU/g |
| Salmonella spp. | Negative in 25g |
| Escherichia coli | Negative in 10g |
| Enterobacteriaceae | ≤ 10 CFU/g |
| Staphylococcus aureus | Negative in 1g |
| Bacillus cereus | ≤ 100 CFU/g |
| Coliform Bacteria | ≤ 10 CFU/g |
SECTION 10: PRODUCTION METHOD
| Stage | Process | Conditions |
|---|---|---|
| 1 | Glycerol + Fatty Acids → Mono/Diglyceride (E471) | 200-250°C, inert atmosphere (N2), alkaline catalyst |
| 2 | Mono/Diglyceride + Citric Acid → E472c | 100-150°C, vacuum, acidic catalyst (p-TSA) |
| 3 | Neutralization | pH neutralization with alkaline solution |
| 4 | Washing | Hot water washing (removal of excess acid and catalyst) |
| 5 | Drying | Vacuum drying (water content ≤ 2.0%) |
| 6 | Purification | Molecular distillation (to increase monoester ratio, optional) |
| 7 | Cooling and Forming | Cooling + Beading/Granulation/Powdering |
SECTION 11: STORAGE AND SHELF LIFE
| Parameter | Information |
|---|---|
| Storage Conditions | Cool (15-25°C), dry, well-ventilated area |
| Container Requirements | Tightly closed, original packaging (hygroscopic) |
| Keep Away From | Moisture (hygroscopic), direct sunlight (UV degradation), strong oxidizing agents |
| Shelf Life | 24 months (unopened original packaging under recommended conditions) |
| Stability Note | Color change (yellowing) may occur; protect from light and moisture |
SECTION 12: PACKAGING OPTIONS
| Packaging Type | Quantity |
|---|---|
| Kraft bag with PE inner liner | 25 kg |
| Plastic pail (powder/granules) | 20 kg |
| Big-Bag | 500 – 1000 kg |
| IBC Tank (melted, hot fill) | 1000 kg |
| Isotank (melted, hot fill) | 20 – 25 tons |
SECTION 13: SAFETY AND HEALTH INFORMATION
GHS Classification:
| Hazard Class | Category | H-Statement |
|---|---|---|
| Acute Toxicity (Oral) | Category 4 | H302 |
| Skin Irritation | Category 2 | H315 |
| Eye Irritation | Category 2A | H319 |
Signal Word: WARNING
Hazard Statements:
| Code | Statement |
|---|---|
| H302 | Harmful if swallowed |
| H315 | Causes skin irritation |
| H319 | Causes serious eye irritation |
Precautionary Statements:
| Code | Statement |
|---|---|
| P261 | Avoid breathing dust |
| P280 | Wear protective gloves/eye protection |
| P301+P312 | IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell |
| P302+P352 | IF ON SKIN: Wash with plenty of water and soap |
| P305+P351+P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing |
First Aid Measures:
| Exposure Route | Action to Take |
|---|---|
| Inhalation | Move to fresh air. Seek medical attention if respiratory irritation persists. |
| Skin Contact | Wash with plenty of water and soap. Remove contaminated clothing. |
| Eye Contact | Rinse immediately with plenty of water for at least 15 minutes. Seek medical attention. |
| Ingestion | Rinse mouth. Do not induce vomiting. Seek medical attention. |
SECTION 14: CRITICAL COMPLIANCE STATEMENTS
| Criterion | Description |
|---|---|
| Halal/Kosher Compliance | Depends on raw material source (vegetable/animal). Certificate must be requested. |
| GMO Status | GMO-Free certification possible (depends on raw material source). |
| Nanoparticle Content | Does not contain (EU 1169/2011 compliant). |
| Allergen Warning | Gluten-free. However, must be labeled if used in wheat-based products. |
| Vegan/Vegetarian | Depends on raw material source (suitable if vegetable-based). |
| Citric Acid Source | Synthetic (petrochemical) or fermentation-derived (natural, via Aspergillus niger). |
SECTION 15: REGULATORY STATUS
| Region / Authority | Status |
|---|---|
| European Union | Approved food additive as E472c (Regulation (EC) No 1333/2008) |
| USA (FDA) | GRAS (21 CFR 184.1101) |
| JECFA (FAO/WHO) | Approved; ADI: 0-25 mg/kg body weight |
| Turkey | Approved under Turkish Food Codex Regulation on Food Additives |
| REACH | Generally exemption or limited registration obligation as food additive |
| WGK (Germany) | 1 (low hazard to water) |
SECTION 16: TRANSPORTATION INFORMATION
| Parameter | Information |
|---|---|
| UN Number | Not regulated (not hazardous) |
| Hazard Class | Not applicable |
| ADR/RID | Not regulated |
| IMDG Code | Not regulated |
| IATA (Air) | Not regulated |
| Marine Pollutant | No |
| Transport Temperature (Solid) | Ambient temperature |
| Transport Temperature (Melted) | 60-70°C (hot fill) |
SECTION 17: FIREFIGHTING MEASURES
| Parameter | Information |
|---|---|
| Fire Hazard | Combustible solid (waxy structure) |
| Suitable Extinguishing Media | Water mist (fog), CO2, dry chemical powder, alcohol-resistant foam |
| Special Hazards | Releases CO, CO2, citric acid derivatives when heated |
| Decomposition Products | CO, CO2, citric acid derivatives |
| Protective Equipment | Self-contained breathing apparatus (SCBA), full protective clothing |
SECTION 18: ACCIDENTAL RELEASE AND CLEANUP
| Parameter | Information |
|---|---|
| Personal Protection | Nitrile gloves, safety goggles, dust mask (N95) |
| Cleanup Methods | Collect mechanically (sweeping or with spatula) |
| Important Warning | DO NOT WASH WITH WATER (enters sewer, creates wastewater load) |
| Environmental Precautions | Prevent entry into drains, soil, and surface water |
| Waste Disposal | According to local regulations; incineration or landfill at licensed disposal facilities |
SECTION 19: ENVIRONMENTAL INFORMATION
| Parameter | Information |
|---|---|
| Biodegradability | Readily biodegradable (ester bonds hydrolyze) |
| Aquatic Toxicity | Low toxicity |
| Bioaccumulation | Not expected (low log P) |
SECTION 20: OTHER NAMES AND SYNONYMS
| Type | Name |
|---|---|
| English Names | Citric Acid Esters of Mono- and Diglycerides, Mono- and Diglyceride Citrate Esters, CitroGlycerides |
| E Number | E472c |
| CAS Number | 36291-32-4 |
| HLB Value | ~6-10 |
| Trade Names | Grindsted® Citrate Esters, Palsgaard® 2000 series, ADM® E472c |
SECTION 21: SELECTION GUIDE
| Criterion | E472c | E472d | E472e (DATEM) | E477 (PGME) |
|---|---|---|---|---|
| Primary Strength | Chelation, antioxidant protection | Water retention | Gluten strengthening | Foam stabilization |
| Best Application | Margarine, fats, sauces, bakery | Bread, cakes, dairy | Industrial bread | Cakes, creams |
| HLB Value | ~6-10 | ~6-10 | ~8-12 | ~2-4 |
| Emulsion Type | O/W | O/W | O/W | W/O |
| Chelation Effect | Yes (Citrate) | No | No | No |
| Oxidative Stability | Enhanced | Standard | Standard | Standard |
| Water Holding Capacity | High | High | Medium | Low |
| Gluten Interaction | Medium | Medium | Very Strong | None |
| Temperature Resistance | >180°C | >180°C | >200°C | >200°C |
Selection Summary:
-
Antioxidant protection, oxidative stability, fat-containing products, long shelf life → Choose E472c
-
Soft texture, moisture retention, shelf life extension → Choose E472d
-
Maximum volume, strong gluten, industrial efficiency → Choose E472e (DATEM)
-
Cakes, creams, foam stabilization → Choose E477 (PGME)
SECTION 22: SUMMARY AND CRITICAL WARNINGS
Product Summary:
| Parameter | Value |
|---|---|
| Product | Citric Acid Esters of Mono- and Diglycerides (E472c) |
| CAS | 36291-32-4 |
| Appearance | Cream white to light yellow, waxy solid, beads, granules, or powder |
| Melting Point | 40-55 °C |
| HLB Value | ~6-10 |
| Main Sector | Food (bakery, oils and fats, sauces, dairy products) |
Key Properties:
| Property | Description |
|---|---|
| Emulsifier Type | Non-ionic, amphiphilic (O/W) |
| HLB Value | ~6-10 (hydrophilic) |
| Primary Effect | Chelation (metal binding), antioxidant synergy |
| Secondary Effect | Emulsion stabilization, water retention, staling delay |
| Acidic Character | pH 3.5-5.5 (due to citric acid content) |
Critical Warnings:
| No | Warning |
|---|---|
| 1 | E472c is the only emulsifier in the E472 series with metal ion chelation properties. This property provides antioxidant protection in fat-containing products and extends shelf life. |
| 2 | Works synergistically with added antioxidants (tocopherols, ascorbyl palmitate, BHA, BHT); enhances oxidative stability of margarine, spreadable fats, and frying oils. |
| 3 | HLB ~6-10, ideal for O/W emulsions. Preferred in products requiring oxidative stability. |
| 4 | Do not confuse with E472d: E472c provides antioxidant protection; E472d provides water retention. Both have similar HLB but different functional mechanisms. |
| 5 | Do not confuse with E472e (DATEM): DATEM provides maximum volume and gluten strengthening; E472c provides oxidative stability. |
| 6 | Overdosing (above 1.0%) may cause dough to become sticky and weak. Recommended dosages must be strictly followed. |
| 7 | Citric acid content provides acidic pH (3.5-5.5); suitable for acidic products (sauces, salad dressings). |
| 8 | For Halal/Kosher certification, raw material source (vegetable/animal) and certificate must be requested from supplier. |
| 9 | Hygroscopic (absorbs moisture). After opening, store in airtight containers in a dry environment. |
| 10 | Thermal decomposition begins above 180°C; for high-temperature processes, DATEM (E472e) alternative should be considered. |
| 11 | Approved by EU (E472c), USA (GRAS), JECFA (ADI: 0-25 mg/kg). Approved in Turkish Food Codex. |
| 12 | GMO-Free certification possible. Gluten-free; however, must be labeled if used in wheat-based products. |
LEGAL DISCLAIMER: This Technical Data Sheet (TDS) is for informational purposes only and has been prepared based on available technical data. The user is responsible for determining the suitability of the product for their specific application and for complying with all local, national, and international regulations. The source of fatty acids (vegetable or animal) affects Halal and Kosher certification. For complete safety, storage, handling, transportation, disposal, and regulatory compliance information, refer to the official Safety Data Sheet (SDS/MSDS) provided by the manufacturer/supplier. The user is responsible for testing the product in their own processes and applications.
