Glucuronic Acid is an organic compound belonging to the family of sugar acids, derived from glucose. It plays a crucial role in the detoxification processes of the body by binding to toxins, drugs, and other harmful substances, facilitating their elimination. In the cosmetics industry, glucuronic acid is valued for its hydrating and regenerating properties, and it is often used in anti-aging and moisturizing products.

Chemical Composition and Structure

Glucuronic acid is a six-carbon monosaccharide formed by the oxidation of glucose. Its chemical structure allows it to form bonds with various substances in a process known as glucuronidation, which primarily occurs in the liver to aid in the elimination of toxins. This mechanism is essential for detoxification.

Physical Properties

It appears as a white or crystalline powder and is water-soluble. It has a slight acidity, making it useful as a hydrating agent in cosmetic formulations, where it helps improve skin elasticity and hydration.

Production Process
Glucuronic acid can be extracted from natural sources or synthesized chemically. Industrially, it is produced through fermentation or chemical synthesis from glucose. This ensures a pure and safe ingredient for use in cosmetics and skincare products.

Applications

• Skincare: Glucuronic acid is used in moisturizers, serums, and anti-aging treatments for its hydrating and regenerating abilities. It helps improve the skin barrier by retaining moisture and enhancing skin elasticity.

INCI Functions:

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.

• Detox and Purification: It is also used in products designed to promote skin detoxification, thanks to its ability to help eliminate toxins.

• Pharmaceuticals: In medicine, it plays a key role in some drugs to assist liver detoxification.

Health and Safety Considerations

Safety in Use
Glucuronic acid is considered safe for use in cosmetic products. It is not known to cause skin irritation or sensitization and is generally well tolerated even by sensitive skin.

Allergic Reactions
Allergic reactions to glucuronic acid are very rare. However, as with any ingredient, individuals with extremely sensitive skin may experience mild irritation.

Toxicity and Carcinogenicity
It is considered safe by major regulatory authorities and is widely used in both cosmetics and pharmaceuticals.

Environmental Considerations
Glucuronic acid is biodegradable, and since it is naturally present in the human body and many plants, it poses no significant environmental risks when used in cosmetics.

Regulatory Status
Glucuronic acid is approved for use in cosmetics by major regulatory authorities, including the European Union and the Food and Drug Administration (FDA) in the United States.

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Glucuronic Acid and D-Glucuronic Acid refer to the same molecule, but with a distinction in their chemical description and stereochemical orientation. Here’s the breakdown:

Glucuronic Acid

• Description: Glucuronic acid is a carboxylic acid derived from glucose. It plays a crucial role in the structure of glycosaminoglycans, such as hyaluronic acid, and is essential in the detoxification processes in the liver.
• Chemical Composition: Glucuronic acid is an oxidized form of glucose, where the terminal hydroxyl group on carbon 6 is converted into a carboxyl group (-COOH).
• Function: It is involved in glucuronidation, a process where toxic substances or metabolites are conjugated with glucuronic acid to be excreted from the body.

D-Glucuronic Acid

• Description: D-Glucuronic acid is the specific stereochemical form of glucuronic acid, referring to the spatial orientation of the hydroxyl group on carbon 5.
• Chirality: The "D" prefix indicates the configuration of the molecule, which is the naturally occurring stereoisomeric form in biological systems. In D-glucuronic acid, the hydroxyl group on carbon 5 is positioned in a specific orientation relative to the molecule.
• Function: As the biologically active form of glucuronic acid, D-glucuronic acid performs the same functions, including its role in glucuronidation and detoxification.

Key Difference:

• Glucuronic Acid is a general term for a molecule derived from glucose with a carboxyl group.
• D-Glucuronic Acid specifies the "D" stereochemical configuration of the molecule, which is the form naturally active in the body.

D-Glucuronic Acid

Molecular Formula  C₆H₁₀O₇

Molecular Weight   194.14 g/mol

CAS     528-16-5   576-37-4

DTXSID50894097

EC Number  209-401-7   229-486-4

Synonyms:

Glucopyranuronic acid

D-Glucuronic Acid

Glucuronic Acid

D-GlcA

Bibliografia__________________________________________________________________________

Rees SG, Hughes W, Embery G. Interaction of glucuronic acid and iduronic acid-rich glycosaminoglycans and their modified forms with hydroxyapatite. Biomaterials. 2002 Jan;23(2):481-9. doi: 10.1016/s0142-9612(01)00130-2.

Abstract. Proteoglycans and their spatial arms, glycosaminoglycans (GAGs), are known to interact with hydroxyapatite (HAP) and have been implicated as important modulators of mineralisation. In the present study isotherm data (0.02 M sodium acetate, pH 6.8) revealed that the iduronic-rich GAGs heparan sulphate, heparin and dermatan sulphate showed greater binding onto HAP with higher adsorption maxima compared with the glucuronic acid-rich GAGs chondroitin-4-sulphate, chondroitin-6-sulphate and hyaluronan. Chemically desulphated chondroitin showed no adsorption onto HAP. With the exception of hyaluronan, the GAGs studied showed no desorbability in sodium acetate buffer only, whereas in di-sodium orthophosphate, desorption occurred much more readily. The data indicates that GAG chemistry and conformation in solution greatly influence the interaction of these molecules with HAP. The conformational flexibility of iduronic acid residues may be an important determinant in the strong binding of iduronic acid-rich GAGs to HAP, increasing the possibility of the appended anionic groups matching calcium sites on the HAP surface, compared with more rigid glucuronic acid residues. This work provides important information concerning interfacial adsorption phenomena between the organic-inorganic phases of mineralised systems.

de Jong AR, Hagen B, van der Ark V, Overkleeft HS, Codée JD, Van der Marel GA. Exploring and exploiting the reactivity of glucuronic acid donors. J Org Chem. 2012 Jan 6;77(1):108-25. doi: 10.1021/jo201586r. 

Abstract. The relative reactivity of glucuronic acid esters was established in a series of competition experiments, in which two thioglucoside and/or thioglucuronic acid ester donors competed for a limited amount of activator (NIS-TfOH). Although glucuronic acid esters are often considered to be of very low reactivity, the series of competition reactions revealed that the reactivity of the glucuronic acid esters studied is sufficient to provide productive glycosylation reactions. The latter is illustrated in the synthesis of two Streptococcus pneumoniae trisaccharides, in which the applicability of the two similarly protected frame-shifted thiodisaccharide donors, Glc-GlcA and GlcA-Glc, were compared. The Glc-GlcA disaccharide, featuring the glucuronic acid donor moiety, proved to be the most productive in the assembly of a protected S. pneumoniae trisaccharide.

el-Nezhawy AO, Adly FG, Eweas AF, Hanna AG, el-Kholy YM, el-Syed SH, el-Naggar TB. Design, synthesis and antitumor activity of novel D-glucuronic acid derivatives. Med Chem. 2011 Nov;7(6):624-38. doi: 10.2174/157340611797928398. 

Abstract. A series of D-glucuronic acid derivatives were chemically synthesized including acetylated and deacetylated glucuronamides, as well as N-glucuronides starting from the D-glucuronic acid itself by means of protection/deprotection, activation and condensation protocols. Structure elucidation of all products along with optimization of the synthetic steps is described. The synthesized compounds were evaluated for their in vitro antitumor activity against MCF-7, TK-10 and UACC-62 cell lines. The compounds 4, 5, 7, 8, 14, 16 and 18 were the most active against TK-10 cell line. On the other hand, the most active compounds against the MCF-7 cell line were 9, 18 and 20. However, compounds 7-10 13-15 and 17 were the most active against the UACC-62 cell line.