Diglucosyl Gallic Acid, also known as Trihydroxy Benzoic Acid Glucoside, is a cosmetic ingredient derived from gallic acid, a natural polyphenol, and glucose. This compound is primarily used in skincare products due to its skin-brightening, antioxidant, and anti-inflammatory properties.

Chemical Composition and Structure

Diglucosyl Gallic Acid is a glycosylated derivative of gallic acid. It involves attaching two glucose molecules to gallic acid, enhancing its stability and solubility in water. This modification increases the compound's ability to interact with skin cells, making it more effective in cosmetic formulations.

Physical Properties

As a cosmetic ingredient, Diglucosyl Gallic Acid typically appears as a white to off-white powder. It is highly soluble in water and has a stable shelf life, which makes it suitable for incorporation into various aqueous cosmetic formulations.

Production Process

• Synthesis: Diglucosyl Gallic Acid is synthesized through an enzymatic glycosylation process where gallic acid is reacted with glucose in the presence of specific enzymes to form the glycosylated product.
• Purification: The synthesized compound is then purified through filtration and crystallization to ensure its purity and quality.
• Quality Control: The final product undergoes various analytical tests, including high-performance liquid chromatography (HPLC), to verify its purity, stability, and composition.

Applications

Cosmetics: Diglucosyl Gallic Acid is used in skin care products such as serums, creams, and lotions. It is valued for its ability to brighten skin tone, reduce hyperpigmentation, and provide antioxidant protection against environmental stressors (1).

Anti-inflammatory Products: Due to its anti-inflammatory properties, it is also used in products aimed at soothing irritated skin (2).

INCI Functions

• Hair conditioning agent. A significant number of ingredients with specific and targeted purposes may co-exist in hair shampoo formulations: cleansers, conditioners, thickeners, matting agents, sequestering agents, fragrances, preservatives, special additives. However, the indispensable ingredients are the cleansers and conditioners as they are necessary and sufficient for hair cleansing and manageability. The others act as commercial and non-essential auxiliaries such as: appearance, fragrance, colouring, etc. Hair conditioning agents have the task of increasing shine, manageability and volume, and reducing static electricity, especially after treatments such as colouring, ironing, waving, drying and brushing. They are, in practice, dispersants that may contain cationic surfactants, thickeners, emollients, polymers. The typology of hair conditioning agents includes: intensive conditioners, instant conditioners, thickening conditioners, drying conditioners. They can perform their task generally accompanied by other different ingredients.

Environmental and Safety Considerations

Diglucosyl Gallic Acid is considered safe for cosmetic use and is generally well-tolerated by the skin. It is non-toxic and biodegradable, minimizing environmental impact. Cosmetic products containing Diglucosyl Gallic Acid are subject to rigorous safety assessments to ensure they meet regulatory standards for consumer use.

References__________________________________________________________________________

(1) Khmaladze I, Österlund C, Smiljanic S, Hrapovic N, Lafon-Kolb V, Amini N, Xi L, Fabre S. A novel multifunctional skin care formulation with a unique blend of antipollution, brightening and antiaging active complexes. J Cosmet Dermatol. 2020 Jun;19(6):1415-1425. doi: 10.1111/jocd.13176. Epub 2019 Oct 4. PMID: 31584241.

Zhang KQ, Lin LL, Xu HJ. Research on antioxidant performance of diglucosyl gallic acid and its application in emulsion cosmetics. Int J Cosmet Sci. 2022 Apr;44(2):177-188. doi: 10.1111/ics.12766. Epub 2022 Mar 15. PMID: 35211990.

(2) Monteiro E Silva SA, Calixto GMF, Cajado J, De Carvalho PCA, Rodero CF, Chorilli M, Leonardi GR. Gallic Acid-Loaded Gel Formulation Combats Skin Oxidative Stress: Development, Characterization and Ex Vivo Biological Assays. Polymers (Basel). 2017 Aug 24;9(9):391. doi: 10.3390/polym9090391. PMID: 30965694; PMCID: PMC6418529.

Abstract. Oxidative stress, which is a result of overproduction and accumulation of free radicals, is the main cause of several skin degenerative diseases, such as aging. Polyphenols, such as gallic acid, are an important class of naturally occurring antioxidants. They have emerged as strong antioxidants that can be used as active cosmetics. The purpose of this study was to develop a gallic acid-loaded cosmetic gel formulation and characterize it using rheological, mechanical, and bioadhesive tests. Its antioxidant effect in the stratum corneum was evaluated by a non-invasive method. According to the characterization tests, the formulation exhibited skin adhesiveness and pseudoplastic behavior without thixotropy, rendering it suitable for use as a cosmetic formulation. Furthermore, the non-invasive method indicated the antioxidant effect in the stratum corneum, with the global lipid peroxide reduction being 33.97 ± 11.66%. Thus, we were able to develop a promising gallic acid-loaded gel formulation that could reduce lipid peroxides and thus combat skin oxidative stress.

Ortega-Sánchez C, Pérez-Díaz MA, Martínez-López V, Zacaula-Juárez N, González-Torres M, Leyva-Gómez G, Hernandez-Valdepeña MA, Gimeno M, Sánchez-Sánchez R. Inhibition of proliferation, migration, and adhesion of skin fibroblasts by enzymatic poly(gallic acid) grafted with L-Arginine, migration, and adhesion of skin fibroblasts by enzymatic poly(gallic acid) grafted with L-Arginine. Cell Mol Biol (Noisy-le-grand). 2023 Jan 31;69(1):1-6. doi: 10.14715/cmb/2022.69.1.1. 

Abstract. Psoriasis and atopic dermatitis (AD) are characterized by enhanced skin inflammation, which results in hyperproliferation and the recruitment of immune cells into the skin. For that reason, it is needed a chemical capable to reduce cell proliferation and the recruitment of cells. The search for new molecules for therapeutic skin treatment mainly focuses on the antioxidant and anti-inflammatory properties, highlighting the rheological properties of polymeric polypeptides. We studied L-arginine (L-Arg) grafted (-g-) to enzymatic poly(gallic acid) (PGAL). The latter is a multiradical antioxidant with greater properties and thermal stability. The derivative was enzymatically polymerized in an innocuous procedure. The poly(gallic acid)-g-L-Arg molecule (PGAL-g-L-Arg) inhibits bacterial strains which also have been involved in the progression of psoriasis and AD. However, it is important to analyze their biological effect on skin cells. The cell viability was analyzed by calcein/ethidium homodimer assays and crystal violet. The proliferation and cell attachment were determined by a curve of time and quantitation of the optical density of crystal violet. To analyze the cell migration a wound-healing assay was performed. This synthesis demonstrates that it is not cytotoxic at high concentrations (250 μg/mL). We observed a decrease in the proliferation, migration, and adhesion of dermal fibroblasts in vitro but the compound could not avoid the increase of reactive oxygen species in the cell. Based on our findings, PGAL-g-L-Arg is a promising candidate for treating skin diseases such as psoriasis and AD where decreasing the proliferation and cell migration could help to avoid inflammation.