E471 (Mono- and Diglycerides of Fatty Acids) are fatty acid derivatives commonly used as emulsifiers in food products. They are formed by reacting glycerol with natural fatty acids, which can be derived from either vegetable or animal sources. E471 is used to improve the texture and stability of food products by helping to blend and maintain emulsions of water and fats.

Chemical Composition and Structure

Mono- and diglycerides of fatty acids are created when one or two fatty acid chains are attached to a glycerol molecule. Depending on whether one or two fatty acids are bonded, mono- or diglycerides are formed. The fatty acids can be either saturated or unsaturated, and the source can vary, affecting the final properties of the compound.

Physical Properties

Mono- and diglycerides of fatty acids are usually solid or semi-solid at room temperature. They can range from clear to slightly yellowish in appearance and are odorless and tasteless. They are soluble in oils and fats but insoluble in water, although they act as effective emulsifiers to stabilize mixtures of water and fats in many food products.

It is found in the human body as a by-product of the breakdown of fats.

Production Process

E471 is produced by reacting glycerol with fatty acids through direct esterification or transesterification. The fatty acids can be sourced from vegetable oils, such as soybean or palm oil, or from animal fats. After the reaction, the product is purified and prepared for use in food applications. 

• Selection of Raw Materials: Fatty acids and glycerols are obtained from plant or animal sources. Common fats used include vegetable oils such as palm, soybean, or sunflower oil.

• Hydrolysis of Fats: Triglycerides, which are the main form of fats and oils, undergo a hydrolysis process where they are separated into fatty acids and glycerol. This can be accomplished through treatment with hot water or the use of enzymes.

• Esterification: The free fatty acids are then combined with glycerol in an esterification process. This is achieved by heating the fatty acids with glycerol in the presence of a catalyst, usually an acid, to promote the formation of mono- and diglycerides.

• Purification: The produced mono- and diglycerides are purified to remove any impurities and chemical residues. This may include distillation or filtration to ensure a high-quality product.

• Quality Control and Packaging: Finally, E471 undergoes quality control checks to verify its purity and functional properties. After analysis, they are packaged for distribution and use in food products.

From where it is extracted

Derived from glycerin and from fatty acids, such as soybean oil, but also from rapeseed oil, palm oil and other oils. As the name implies, the generic term "fatty acids" does not make it possible to trace what type of oil is used, whether saturated, unsaturated or hydrogenated, or genetically modified and it can be derived from animal fats. 

From fungi lipase as Malassezia globosa, Penicillium camembertii, Aspergillus oryzae (1)

What it is used for

Food products. It serves as a thickener, non-ionic emulsifier and stabiliser in order to refine softness and increase volume: bread, croissants, chocolate, cakes, biscuits, ice cream, pasta, panettone, corn flakes, food supplements, chips, crackers, etc.

 A 2024 study warns about the risk of developing cancer with high intakes of emulsifiers, (including E440, Pectin, E471 mono- and diglycerides of fatty acids, carrageenan, E407, sodium carbonate E500) (2).  

Plastic. PVC lubricant, EPE foaming agent, PE antifogging agent.

Pharmaceutical and cosmetics. Thickener, non-ionic emulsifier and stabiliser

Safety

The estimated combined intake of E 470a, E 471 and E 477 at the maximum permitted levels could lead to a maximum total exposure of 84 mg/kg body weight (bw) per day for toddlers and 20 mg/kg bw per day for adults. Using a reference body weight of 12 kg for toddlers and of 70 kg for adults, the highest amount of emulsifiers ingested per person per day would be 1,008 mg for toddlers and 1,400 mg for adults. As a conservative approach, it could be assumed that these doses could be consumed on a single occasion (3).

Glycerol monostearate studies

Typical optimal characteristics of E471 commercial product

Molecular Formula: C₂₁H₄₂O₄

Molecular  Weight : 358.563

CAS : 123-94-4  31566-31-1   22610-63-5   14811-92-8   85666-92-8   83138-62-9   37349-34-1

Synonyms :

Mono- and diacylglycerol, Glyceryl Monostearate, Monostearin, 1-Monostearoylglycerol, Glyceryl stearate, tegin, Stearic acid 1-monoglyceride, 2,3-dihydroxypropyl octadecanoate, Stearic acid alpha-monoglyceride

References________________________________________________________________________

(1) Yuan D, Lan D, Xin R, Yang B, Wang Y. Biochemical properties of a new cold-active mono- and diacylglycerol lipase from marine member Janibacter sp. strain HTCC2649. Int J Mol Sci. 2014 Jun 12;15(6):10554-66. doi: 10.3390/ijms150610554.

(2) Sellem, L., Srour, B., Javaux, G., Chazelas, E., Chassaing, B., Viennois, E., ... & Touvier, M. (2024). Food additive emulsifiers and cancer risk: Results from the French prospective NutriNet-Santé cohort. Plos Medicine, 21(2), e1004338.

Abstract. Emulsifiers are widely used food additives in industrially processed foods to improve texture and enhance shelf-life. Experimental research suggests deleterious effects of emulsifiers on the intestinal microbiota and the metabolome, leading to chronic inflammation and increasing susceptibility to carcinogenesis. However, human epidemiological evidence investigating their association with cancer is nonexistent. This study aimed to assess associations between food additive emulsifiers and cancer risk in a large population-based prospective cohort.

Coumoul X, Fezeu LK, Julia C, Kesse-Guyot E, Allès B, Galan P, Hercberg S, Deschasaux-Tanguy M, Touvier M. Food additive emulsifiers and risk of cardiovascular disease in the NutriNet-Santé cohort: prospective cohort study. BMJ. 2023 Sep 6;382:e076058. doi: 10.1136/bmj-2023-076058. PMID: 37673430; PMCID: PMC10480690.

(3) Scientific Opinion related to a notification from DuPont Nutrition Biosciences Aps on behenic acid from mustard seeds to be used in the manufacturing of certain emulsifiers pursuant to Article 21(2) of Regulation (EU) No 1169/2011 – for permanent exemption from labelling
First published: 15 November 2016
EFSA DOI: 10.2903/j.efsa.2016.4631