Oleyl erucate is a chemical compound, the ester resulting from the reaction of oleic alcohol with erucic acid, usually extracted  from plants belonging to the Brassicaceae family.

The name defines the structure of the molecule:

• Oleyl refers to the oleyl group, which is derived from oleic acid, a monounsaturated omega-9 fatty acid found in various animal and plant sources.
• Erucate refers to the ester or saline form of erucic acid, a monounsaturated omega-9 fatty acid found in some oils, such as rapeseed oil.

The synthesis process takes place in several stages:

• Esterification. Oleyl alcohol reacts with erucic acid in the presence of an acid catalyst, such as sulfuric acid (H2SO4). The reaction can be represented as follows

C18H36O (oleyl alcohol) + C22H42O2 (erucic acid) -> C40H76O2 (oleyl erucate) + H2O (water)

• Water removal. The above reaction is an equilibrium reaction, which means that it can proceed in both directions back and forth. To guide the reaction to completion (i.e., to maximize the production of oleyl erucate), the water produced in the reaction is often removed. This can be achieved through various methods, such as the use of a Dean-Stark apparatus or by carrying out the reaction under reduced pressure.
• Purification. Oleyl erucate crude may contain unreacted oleyl alcohol and erucic acid, as well as the acid catalyst. Therefore it must be purified to remove these impurities through various methods, such as distillation or extraction.
• Characterization. The final stage of the synthesis process is the characterization of the product to confirm its identity and purity. This can be done through various methods, such as infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS).

It appears as a colourless to yellowish transparent liquid.

What it is used for and where

Oleyl Erucate is an ester of oleic acid and erucic acid often used in cosmetics and personal care products for its emollient properties, which can help soften and smooth the skin. It can also provide a non-greasy feel to products and can help improve the spreadability of cosmetic formulations.

Cosmetics

Skin conditioning agent - Occlusive. This ingredient has the task of modifying the condition of the skin when it is damaged or dry by reducing flaking and restoring elasticity. It has a strong lipophilic character and is identified as an occlusive ingredient; it is generally composed of oily and fatty materials that remain on the skin surface and reduce trans epidermal water loss.

Skin conditioning agent - Emollient. Emollients have the characteristic of enhancing the skin barrier through a source of exogenous lipids that adhere to the skin, improving barrier properties by filling gaps in intercorneocyte clusters to improve hydration while protecting against inflammation. In practice, they have the ability to create a barrier that prevents transepidermal water loss.  Emollients are described as degreasing or refreshing additives that improve the lipid content of the upper layers of the skin by preventing degreasing and drying of the skin. The problem with emollients is that many have a strong lipophilic character and are identified as occlusive ingredients; they are oily and fatty materials that remain on the skin surface and reduce transepidermal water loss. In cosmetics, emollients and moisturisers are often considered synonymous with humectants and occlusives.

Commercial applications

Emollient. Oleyl Erucate is used in skin care products to soften and smooth the skin.

Skin Conditioning Agent. Used in skin care products to improve the appearance and feel of the skin.

Spreading Agent. Enhances the spreadability of cosmetic products, allowing for better application to the skin.

Ingredient in Hair Products. Used to condition the hair, making it soft and manageable.

Hair care products - Acts as a conditioner and a shine-enhancing agent for hair.

Lip products - Used in lip balms and lipsticks for its ability to provide shine and a smooth feel.

Sometimes used as a food additive, though its applications in this area are less common.

• Molecular Formula    C₄₀H₇₆O₂
• Molecular Weight   589.0 g/mol
• CAS   17673-56-2  143485-69-2 
• UNII 753W099NQ6
• EC Number: 241-654-9 

Synonyms: 

• (Z)-Octadec-9-enyl (Z)-docos-13-enoate
• 13-Docosenoic acid, 9-octadecenyl ester

References_________________________________________________________________________

Berkey, C., Kanno, D., Mehling, A., Koch, J.P., Eisfeld, W., Dierker, M., Bhattacharya, S. and Dauskardt, R.H., 2020. Emollient structure and chemical functionality effects on the biomechanical function of human stratum corneum. International Journal of Cosmetic Science, 42(6), pp.605-614.

Goossens, A., Verbruggen, K., Cattaert, N. and Boey, L., 2008. New cosmetic allergens: isononyl isononanoate and trioleyl phosphate. Contact Dermatitis, 59(5), pp.320-321.

BEKTAŞ, Ç. and KAFADAR, B., 2020. SENSORY MAPPING FOR COMMON SPECIAL ESTERS IN CREAM PRODUCTS. The Online Journal of Science and Technology-October, 10(4).