E476 POLYGLYCERYL-3-PENTARICINOLEATE

E476 Polyglyceryl-3-Pentaricinoleate is a synthetic, lipophilic, nonionic emulsifier produced by the esterification of polyglycerol with polycondensed ricinoleic acid fatty acids derived from castor oil, forming a colorless to light yellow viscous liquid that is soluble in fats and oils but insoluble in water and ethanol, widely used in chocolate, confectionery, margarine, spreads, sauces, baked goods, cosmetics, and pharmaceutical formulations.
E476 Polyglyceryl-3-Pentaricinoleate works by decreasing the friction between solid particles such as cocoa, sugar, and milk in molten chocolate, reducing yield stress so that chocolate flows more easily and approaches the behavior of a Newtonian fluid, and it is used at low levels below 0.5% in combination with lecithin to achieve optimal flow, processing, and texture properties.
E476 Polyglyceryl-3-Pentaricinoleate is also used as a water-in-oil emulsifier in margarine, spreads, salad dressings, and sauces to stabilize emulsions and prevent phase separation, and in cosmetics as a lipophilic emulsifier, skin conditioner, viscosity controlling agent, stabilizer, thickener, and anticaking agent at concentrations of 0.1–3.0%.

CAS Number: 29894-35-7
EC Number: 608-428-5
Molecular Formula: C27H52O9
Molecular Weight: 520.70 g/mol

Synonyms: Polyglycerol Polyricinoleate, Polyglyceryl-3 Polyricinoleate, Polyglyceryl-3-Pentaricinoleate, PGPR, E476, E 476, Polyglycerol Esters of Polycondensed Fatty Acids from Castor Oil, Polyglycerol Esters of Interesterified Ricinoleic Acid, Glyceran Esters of Condensed Castor Oil Fatty Acids, Polyglycerin-Polyricinoleat, Polyglycerol-3 Polyricinoleate, Polyglycerol-3 Polyricinoleate-PG3PR, 1,2,3-Propanetriol polymer with (9Z,12R)-12-hydroxy-9-octadecenoic acid, 9-Octadecenoic acid 12-hydroxy- (9Z,12R)- polymer with 1,2,3-propanetriol, Admul 1408K, Admul WOL 1408K, Cithrol PG 3PR, Grindsted PGPR 90, Hexalyn PR 15, Nikkol Decaglyn PR 20, PGPR 4125, Polyglyceryl-3 Polyricinoleat mittlere Molmasse 2500 g/mol, Polyricinoléate de Polyglycéryle-3, Poliricinoleat de Poligliceril-3, Poligliseril-3 Polirisinoleat, CAS 29894-35-7

E476 Polyglyceryl-3-Pentaricinoleate is structurally composed of a short chain of glycerol molecules connected by ether bonds with ricinoleic acid side chains connected by ester bonds, giving it a low HLB value suitable for water-in-oil emulsion systems and making it strongly lipophilic with excellent oil-binding, viscosity-reducing, and surface tension-controlling properties.
E476 Polyglyceryl-3-Pentaricinoleate has been in use as a food additive since 1952 and is approved as Generally Recognized as Safe (GRAS) by the US FDA and by JECFA (FAO/WHO), and is permitted in the European Union in chocolate under Regulation (EC) No 1333/2008; it has also been re-evaluated by an EFSA panel in 2017 with a favorable safety outcome.

E476 Polyglyceryl-3-Pentaricinoleate is compatible with other emulsifiers, particularly lecithin (E322), with which it has a strong synergistic effect; when used together they achieve optimal flow and processing properties in chocolate, with E476 Polyglyceryl-3-Pentaricinoleate primarily controlling yield stress and lecithin primarily controlling plastic viscosity.
E476 Polyglyceryl-3-Pentaricinoleate has a LogP of approximately 5.701 (estimated), confirming its strongly lipophilic character, and is registered in the EPA Substance Registry System as 9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-, polymer with 1,2,3-propanetriol; a three-generation reproduction study in Wistar rats at 1.5% dietary incorporation showed no cumulative effect on reproductive performance.

Uses of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate is used in chocolate and compound chocolate manufacturing as a primary emulsifier to reduce viscosity, improve flow characteristics especially near the melting point, enhance the efficiency of chocolate coating processes in enrobing and dipping, improve mold filling and release in solid molded products, and facilitate air bubble discharge to prevent empty holes and pores.
E476 Polyglyceryl-3-Pentaricinoleate is used in chocolate production to allow a reduction in expensive cocoa butter content without compromising quality, as the solid particles in chocolate are suspended in cocoa butter and by reducing viscosity less cocoa butter is required, saving costs and resulting in a lower-fat product.

E476 Polyglyceryl-3-Pentaricinoleate is used in combination with lecithin in chocolate to achieve a synergistic viscosity-reducing effect superior to either emulsifier alone, promoting formation of smaller and more stable cocoa butter crystals for enhanced snap and gloss, and assisting during the tempering process to prevent fat bloom (white fat migration to the chocolate surface).
E476 Polyglyceryl-3-Pentaricinoleate is used in margarine and low-fat spreads as a water-in-oil emulsifier to reduce the viscosity of the fat phase, stabilize the emulsion between water and oil, prevent phase separation, improve spreadability even when refrigerated, and enable production of lower-fat margarine without compromising texture or spreadability.

E476 Polyglyceryl-3-Pentaricinoleate is used in fat-based spreads, cocoa-based spreads, nut-based spreads, and low-fat shortenings to stabilize water-in-oil emulsions, reduce oil content while preserving texture, and improve the stability of the fat phase in reduced-fat products.
E476 Polyglyceryl-3-Pentaricinoleate is used in salad dressings and emulsion-based sauces as an emulsifier to maintain homogeneous structure, prevent separation of oil and water phases, ensure a smooth and cohesive texture, and improve shelf life of the finished product.

E476 Polyglyceryl-3-Pentaricinoleate is used in fine bakery products, industrially produced pastries, and baked goods to improve fat dispersion within the dough or batter, improve texture and workability of fat-based icings and fillings, delay staling to maintain freshness over time, and enhance the plasticity of puff pastry margarine.
E476 Polyglyceryl-3-Pentaricinoleate is used in ice cream and soft ice cream formulations to impart the desired softness, stabilize water-in-oil emulsions, and create a smooth and consistent structure.

E476 Polyglyceryl-3-Pentaricinoleate is used in confectionery products such as cocoa-based candies, filled waffles, and candy coatings to provide a homogeneous structure, prevent crystallization and turbidity, improve flowability, and act as an anti-caking agent.
E476 Polyglyceryl-3-Pentaricinoleate is used in cosmetic and personal care products including lip balms, lipsticks, skin creams, protective hand creams, night creams, baby care products, sun protection products, and lotions as a lipophilic emulsifier that is particularly useful in buttery lip balms and other soft to low-viscosity water-in-oil emulsions with a pleasant, non-greasy skin feel.

E476 Polyglyceryl-3-Pentaricinoleate is used in cosmetics as a stabilizer, thickener, and anticaking agent that helps to adjust the surface tension and viscosity of products; it softens, hydrates, and nourishes the skin without damaging the skin's natural protective barrier and does not tend to oxidize, remaining stable throughout product life without change in color or odor.
E476 Polyglyceryl-3-Pentaricinoleate is used in pharmaceutical applications as an emulsifying agent in topical formulations, ointment and cream-based mixtures, and lipid-based drug delivery systems, and in industrial lubricants and coatings due to its excellent lipophilic and viscosity-reducing properties.

Benefits or Advantages of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate is used at very low concentrations below 0.5% to achieve significant viscosity reduction in chocolate and fat-based systems, providing a cost-effective solution that requires minimal product quantity to deliver maximal processing and texture benefits.
E476 Polyglyceryl-3-Pentaricinoleate enables manufacturers to reduce cocoa butter content in chocolate formulations by lowering viscosity of the chocolate mass, saving costs because cocoa butter is an expensive ingredient and resulting in a lower-fat product without sacrificing coverage quality, gloss, snap, or consumer appeal.

E476 Polyglyceryl-3-Pentaricinoleate has no bad odor, demonstrates good thermal stability, does not tend to oxidize, and remains stable throughout the shelf life of a product without changing color or odor, providing reliable performance across diverse temperature and humidity conditions.
E476 Polyglyceryl-3-Pentaricinoleate has been confirmed safe for human consumption by the FDA, JECFA, and EFSA, with safety data showing no evidence of interference with normal fat metabolism, growth, reproduction, or tissue maintenance; external use in cosmetics is generally considered safe and does not cause skin irritation or allergic reactions.

E476 Polyglyceryl-3-Pentaricinoleate is fully compatible with other emulsifiers commonly used in the food industry, particularly lecithin (E322), providing formulation flexibility and synergistic performance when used in combination; it works with all types of emulsifiers and can be used alone or in combination with co-emulsifiers and waxes.
E476 Polyglyceryl-3-Pentaricinoleate allows the viscosity of cosmetic formulations to be adjusted from liquid lotions to highly viscous creams depending on the ratio between the water and oil phases, providing versatile rheology control across a wide range of product textures.

Features of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate is a colorless to light yellow viscous liquid with a light characteristic mild odor, strongly lipophilic character, boiling point of approximately 416°C, insoluble in cold water and ethanol, soluble in hot fats and oils and in ether and hydrocarbons, and classified as a nonionic water-in-oil surfactant with emulsifying and viscosity-controlling functions.
E476 Polyglyceryl-3-Pentaricinoleate has a low HLB (hydrophilic-lipophilic balance) value and a LogP of approximately 5.701, consistent with its strongly lipophilic, water-in-oil emulsifier character, making it particularly effective for anhydrous and low-water formulations requiring a pleasant, non-greasy skin feel.

E476 Polyglyceryl-3-Pentaricinoleate prevents crystallization and turbidity in chocolate and fat-based systems, promotes formation of smaller and more stable cocoa butter crystals that provide enhanced snap and glossiness, and prevents fat bloom (fat migration to chocolate surface).
E476 Polyglyceryl-3-Pentaricinoleate does not tend to oxidize and remains stable throughout product shelf life without change in color or odor, and is compatible with all types of emulsifiers whether used alone or in combination with co-emulsifiers and waxes.

Chemical Properties of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate has the IUPAC name 1,2,3-Propanetriol, homopolymer, (9Z,12R)-12-hydroxy-9-octadecenoate, the molecular formula C27H52O9, and the molecular weight 520.70 g/mol; it is structurally a polyglycerol backbone with ricinoleic acid (12-hydroxy-9-octadecenoic acid) ester side chains connected by ether and ester bonds respectively.
E476 Polyglyceryl-3-Pentaricinoleate is a nonionic surfactant with both hydrophilic (polyglycerol ether chain) and lipophilic (ricinoleic acid ester chain) portions; its amphiphilic structure allows it to position itself at fat-water interfaces, reducing interfacial tension and enabling stable water-in-oil emulsions; its InChIKey is HUXYPHWJPJYMBC-NKUOOZJZNA-N.

E476 Polyglyceryl-3-Pentaricinoleate is chemically stable under normal storage and handling conditions, resistant to oxidation, and thermally stable under typical food processing temperatures; it is incompatible with strong oxidizing agents and concentrated acids or bases.
E476 Polyglyceryl-3-Pentaricinoleate thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, and irritating organic fumes; it has a boiling point of approximately 416°C and is not classified as flammable under normal handling conditions.

Production of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate is produced in a three-step industrial process: glycerol is heated above 200°C with an alkaline catalyst to form polyglycerol by polymerization via ether bond formation; castor oil fatty acids are separately heated above 200°C to produce interesterified ricinoleic fatty acids; and the two components are combined by esterification to yield the final product.
E476 Polyglyceryl-3-Pentaricinoleate is also produced using biotechnological methods with the mold Rhizopus arrhizus, and instead of castor oil fatty acids, fatty acids from soybean oil may be used as an alternative feedstock, providing formulation flexibility for different market requirements.

E476 Polyglyceryl-3-Pentaricinoleate quality is controlled through verification of purity (≥98–99%), acid value, viscosity, and color, aligned to regulatory requirements in the EU, US, and Codex Alimentarius markets; food-grade material is available to FCC and E476 specifications.
E476 Polyglyceryl-3-Pentaricinoleate is available as a viscous liquid or semi-solid depending on temperature and formulation, supplied in 25 kg cardboard boxes for food, cosmetic, and industrial applications.

Material Safety Data Sheet (MSDS) of E476 Polyglyceryl-3-Pentaricinoleate:

Handling of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate should be handled in accordance with good industrial hygiene and safety practices and in compliance with the applicable Safety Data Sheet.
E476 Polyglyceryl-3-Pentaricinoleate handling requires avoiding prolonged skin contact, eye contact, and generation of aerosol or mist during spraying or heating operations; the substance is non-irritating and non-sensitizing to the skin under normal conditions of use.

SDS of E476 Polyglyceryl-3-Pentaricinoleate:

Stability and Reactivity of E476 Polyglyceryl-3-Pentaricinoleate:

Chemical stability:
E476 Polyglyceryl-3-Pentaricinoleate is stable under normal storage and handling conditions; it does not tend to oxidize and remains stable throughout product shelf life.

Reactivity:
No dangerous reaction is expected under normal conditions of use.
E476 Polyglyceryl-3-Pentaricinoleate may react with strong oxidizing agents or concentrated acids and bases at elevated temperatures.

Conditions to avoid:
Excessive heat above processing temperatures.
Contact with strong oxidizing agents.
Contact with concentrated strong acids or bases.

Incompatible materials:
Strong oxidizing agents.
Concentrated strong acids.
Concentrated strong bases.

Hazardous decomposition products:
Carbon monoxide (CO).
Carbon dioxide (CO2).
Irritating organic fumes (under thermal decomposition or fire conditions).

Handling and Storage of E476 Polyglyceryl-3-Pentaricinoleate:

Handling:
Handle in accordance with good industrial hygiene and safety practices.
Avoid prolonged skin contact and eye contact.
Avoid inhalation of aerosol or mist if heated or sprayed.
Wash hands after handling.
If solidified at low temperature, warm gently to restore liquid state before use.

Storage:
Store in tightly sealed original containers in a cool, dry, well-ventilated area.
Protect E476 Polyglyceryl-3-Pentaricinoleate from excessive heat and direct sunlight.
E476 Polyglyceryl-3-Pentaricinoleate does not tend to oxidize and remains stable under recommended storage conditions.
Packaging: 25 kg cardboard box.

First Aid Measures of E476 Polyglyceryl-3-Pentaricinoleate:

Inhalation:
Move affected person to fresh air.
If aerosol or heated vapor causes respiratory irritation, seek medical advice.

Skin contact:
Wash affected skin with soap and water.
E476 Polyglyceryl-3-Pentaricinoleate is non-sensitizing to the skin; external use is generally considered safe.
Seek medical advice if unexpected irritation develops.

Eye contact:
Rinse immediately with plenty of clean water for at least 15 minutes while holding eyelids open.
Seek medical attention if irritation persists.

Ingestion:
E476 Polyglyceryl-3-Pentaricinoleate is non-toxic and highly digestible; it has been found to be utilized as an energy source.
Rinse mouth with water.
Seek medical advice if discomfort occurs.

Firefighting Measures of E476 Polyglyceryl-3-Pentaricinoleate:

Suitable extinguishing media:
Foam, dry chemical powder, carbon dioxide, or water spray.

Specific hazards:
E476 Polyglyceryl-3-Pentaricinoleate is combustible; thermal decomposition may produce carbon monoxide, carbon dioxide, and irritating organic fumes.

Protective equipment for firefighters:
Wear self-contained breathing apparatus (SCBA) and full protective clothing.

Firefighting instructions:
Cool exposed containers with water spray.
Prevent contaminated firefighting water from entering drains or waterways.

Accidental Release Measures of E476 Polyglyceryl-3-Pentaricinoleate:

Personal precautions:
Spilled E476 Polyglyceryl-3-Pentaricinoleate creates a slipping hazard due to its viscous, oily nature; contain immediately.
Avoid contact with eyes and skin.

Environmental precautions:
Prevent E476 Polyglyceryl-3-Pentaricinoleate from entering drains or waterways.

Methods for cleaning up:
Contain spill with inert absorbent material such as sand or vermiculite.
Collect into properly labeled waste containers for disposal according to local regulations.
Clean contaminated surfaces with detergent and water after collection.

Exposure Controls / Personal Protective Equipment of E476 Polyglyceryl-3-Pentaricinoleate:

Engineering controls:
Provide adequate ventilation, particularly when E476 Polyglyceryl-3-Pentaricinoleate is heated or sprayed.

Eye protection:
Wear safety glasses or goggles where splashing is possible.

Hand protection:
Wear chemical-resistant gloves for prolonged or repeated handling.

Skin and body protection:
Wear suitable protective clothing; remove contaminated clothing immediately.

Respiratory protection:
Not normally required under ambient conditions.
Use suitable respirator if aerosol or mist is generated during heating or spraying.

Hygiene measures:
Wash hands after handling E476 Polyglyceryl-3-Pentaricinoleate and before eating, drinking, or smoking.

Identifiers of E476 Polyglyceryl-3-Pentaricinoleate:
CAS Number: 29894-35-7
EC Number: 608-428-5
ECHA InfoCard: 100.117.615
E Number: E476
IUPAC Name: 1,2,3-Propanetriol, homopolymer, (9Z,12R)-12-hydroxy-9-octadecenoate
Molecular Formula: C27H52O9
Molecular Weight: 520.70 g/mol
InChIKey: HUXYPHWJPJYMBC-NKUOOZJZNA-N
LogP: 5.701 (estimated)
INCI Name: Polyglyceryl-3 Polyricinoleate
INCI Functions: Anticaking; Emulsifying; Skin Conditioning; Viscosity Controlling
GHS Classification: Not classified as hazardous
US FDA: GRAS
EU: Approved food additive E476 under Regulation (EC) No 1333/2008
JECFA: Safe; ADI 7.5 mg/kg body weight/day
HLB: Low (water-in-oil emulsifier)
Ionic character: Nonionic

Properties of E476 Polyglyceryl-3-Pentaricinoleate:
Physical state: Liquid (viscous; may be semi-solid at low temperatures)
Appearance: Colorless to light yellow viscous liquid
Odor: Light characteristic; mild odor
Form: Liquid
Color: Colorless to light yellow
Solubility in water: Insoluble (cold water and ethanol)
Solubility in fats/oils: Soluble
Solubility in ether and hydrocarbons: Soluble
Boiling point: ~416°C
LogP: 5.701 (estimated)
HLB value: Low (W/O emulsifier)
Ionic character: Nonionic
Thermal stability: Good; does not tend to oxidize
Oxidative stability: High; does not change color or odor over product shelf life
Cosmetic use concentration: 0.1–3.0%
Food use level: ≤0.5%
GHS Classification: Not classified

Specifications of E476 Polyglyceryl-3-Pentaricinoleate:
Product name: E476 Polyglyceryl-3-Pentaricinoleate (Polyglycerol Polyricinoleate)
CAS Number: 29894-35-7
EC Number: 608-428-5
E Number: E476
Molecular Formula: C27H52O9
Molecular Weight: 520.70 g/mol
INCI Name: Polyglyceryl-3 Polyricinoleate
Appearance: Colorless to light yellow viscous liquid
Purity: ≥98–99%
Odor: Light characteristic
Solubility in water: Insoluble
Solubility in fats/oils: Soluble
Grades available: Food grade (FCC/E476); cosmetic grade; technical grade
Packaging: 25 kg cardboard box
Storage: Cool, dry, well-ventilated; sealed original containers

Names of E476 Polyglyceryl-3-Pentaricinoleate:
E476 Polyglyceryl-3-Pentaricinoleate
Polyglyceryl-3-Pentaricinoleate
Polyglycerol Polyricinoleate
Polyglyceryl-3 Polyricinoleate
Polyglycerol-3 Polyricinoleate
Polyglycerol-3 Polyricinoleate-PG3PR
PGPR
E476
E 476
Admul 1408K
Admul WOL 1408K
Cithrol PG 3PR
Grindsted PGPR 90
Hexalyn PR 15
Nikkol Decaglyn PR 20
PGPR 4125
Polyglycerin-polyricinoleate
Polyglycerol Esters of Polycondensed Fatty Acids from Castor Oil
Polyglycerol Esters of Interesterified Ricinoleic Acid
Glyceran Esters of Condensed Castor Oil Fatty Acids
Polyricinoléate de Polyglycéryle-3
Poliricinoleat de Poligliceril-3
Poligliseril-3 Polirisinoleat
CAS 29894-35-7