Uses and Preparation of D-panthenol

General description 

D-panthenol, also known as Provitamin B5, Dexpanthenol, Alcopan-250, Bepanthen and Cozyme, is a stereoisomer of panthenol with optical activity. D-panthenol is a monocarboxylic acid amide that is 3,3-dimethylbutanamide substituted by hydroxy groups at positions 2 and 4 and a 3-hydroxypropyl group at the carbomyl nitrogen, which can soluble in water, ethanol, methanol and propylene glycol [1]. It is a colorless viscous liquid or colorless transparent liquid with a slight specific odor. Its chemical name is (D)-N-(2,4-dihydroxy-β,β-dimethylbutyryl)-β-aminopropanol, and the chemical formula is C9H19NO4 (Figure 1). D-panthenol is widely used in medicine, food, cosmetics and liquid preparations. After entering the human body, it can be converted into pantothenic acid, which can then synthesize coenzyme A, promote the metabolism of human protein, fat and sugar, protect skin and mucous membrane, improve hair luster, and prevent disease. D-panthenol can prevent small wrinkles, inflammation, sunlight and erosion, prevent hair loss, promote hair growth, keep hair moist, reduce hair bifurcations, prevent hair from cracking, and protect, repair and care hair [2].

Figure 1. The molecular formula of D-panthenol

Uses

D-panthenol is widely used in medicine, cosmetics, food, feed and other fields, and has been listed as a routine additive by the international advanced health organization and nutrition authority. It is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. D-panthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium [3]. Due to its good penetration and high local concentrations, D-panthenol is used in many topical products, such as ointments and lotions for treatment of dermatological conditions to relieve itching or promote healing. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated reepithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties. D-panthenol is also available as a racemic mixture containing both the dextrorotatory form (dexpanthenol) and the levorotatory form (levopanthenol) as [DB11204]. While pantothenic acid is optically active, only the dextrorotatory form (dexpanthenol) is biologically active [4].

Preparation

The synthesis of D-panthenol is mainly prepared by the condensation reaction of D-pantolactone and 3-aminopropanol, or by the condensation reaction of DL-pantolactone and 3-aminopropanol to prepare the racemic DL-pantothenol, which is then resolved to obtain D-panthenol.

Figure 2. Synthesis of DL panthenol

Due to the fact that panthenol is not easy to crystallize, it is difficult to obtain high-quality products by the usual physical resolution method, so the first method is rarely reported; The second method is to prepare diastereomeric DL guanidine lactone through the reaction of DL panthenolide and guanidine, and then separate it to obtain d-guanidine lactone. D-guanidine lactone is hydrolyzed to obtain d-panthenolide under acidic conditions, and then synthesize D-panthenol with 3-aminopropanol. This process is relatively simple and easy to obtain high quality [5].

Physiological Mechanism of Action ^[6-7]

D-panthenol is more easily absorbed by the body than pantothenic acid, which is rapidly transformed into pantothenic acid in the body, and pantothenic acid is finally transformed into Coenzyme A in the tissue (Figure 3).

Figure 3. The process of pantothenic acid synthesis of Coenzyme A

D-panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Dexpanthenol is enzymatically cleaved to form pantothenic acid, which is an essential component of Coenzyme A, which acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium. Dermatological effects of the topical use of dexpanthenol include increased fibroblast proliferation and accelerated re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties. D-panthenol is readily converted to pantothenic acid which is widely distributed into body tissues, mainly as coenzyme A. Moreover, coenzyme A exists in most tissues and is necessary for important reactions in material metabolism.

References

1. Xuan M J, Zhang J Z, Yuan H Y, et al.Optimization of process for optical resolution of DL-pantolactone using immobilized D-lactonohydrolase[J].Lecture Notes in Electrical Engineering.2018: 459-467.

2. Sun Z H, Lei H. Progress on Production of D-calcium Pantothenate and D-panthenol by Biotechnology[J]. Fine and Specialty Chemicals, 2004.

3. Bhrle-Rapp M . D-Panthenol[J]. Springer Berlin Heidelberg, 2007.

4. National Center for Biotechnology Information. "PubChem Compound Summary for CID 131204, Dexpanthenol" PubChem.

5. Kozlova G S, Erokhina T I, Gunar V I. Synthesis of D(+)-panthenol[J]. Pharmaceutical Chemistry Journal, 1977, 11(4):505-507.

6. Sampedro A, Rodriguezgranger J, Ceballos J , et al. PANTOTHENIC ACID: AN OVERVIEW FOCUSED ON MEDICAL ASPECTS[J]. Journal of Experimental Zoology, India, 2015 Vol. 18 No. 1 pp. 203-206, 2015.

7. Combs G F, Mcclung J P. Pantothenic Acid - ScienceDirect[J]. The Vitamins (Fifth Edition), 2017:387-398.

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