Panthenol

General Description

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used as a moisturizer and to improve wound healing in pharmaceutical and cosmetic products.
Panthenol is a multi-functional active ingredient that would be useful in most skin care formulations. Its efficacy has been substantiated in numerous peer-reviewed journals. The biologically active form of Panthenol, D-panthenol (EU), is the stable alcohol analogue of vitamin B5, pantothenic acid (EU), and is quickly converted to vitamin B5 (pantothenate) in the body. Pantothenic acid is present in all living cells and acts as an essential nutritional component due to its role in the formation of acetyl-co-enzyme A in the early stages of metabolism. The main role of acetyl-co-enzyme A is to provide activated acetic acid into the citric acid cycle (Krebs Cycle). This produces carbon dioxide, water, and energy. Co-enzyme A also transfers to other molecules such as Nacetyl-glucosamine (EU) and acetylcholine (EU) to help in the production of steroids and the synthesis of fatty acids. Coenzyme A also helps the body detoxify foreign substances.

Uses

Panthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium.
Due to its good penetration and high local concentrations, dexpanthanol 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 re-epithelialization in wound healing. Furthermore, it acts as a topical protectant, moisturizer, and has demonstrated anti-inflammatory properties. The vitamin ingredient Panthenol is valued in skin and hair care applications for its moisturizing properties. It has anti-inflammatory effects and soothes irritated and sensitive skin. For hair care application it is known for its humectant properties and its ability to improve the resistance of hair to mechanical stress.

Mechanism of action

Pantothenic acid is a precursor of coenzyme A, which serves as a cofactor for a variety of enzyme-catalyzed reactions involving transfer of acetyl groups. The final step in the synthesis of acetylcholine consists of the choline acetylase transfer of acetyl group from acetylcoenzyme A to choline. Acetylcholine is the neurohumoral transmitter in the parasympathetic system and as such maintains the normal functions of the intestine. Decrease in acetylcholine content would result in decreased peristalsis and in extreme cases adynamic ileus.
Panthenol is well absorbed into the skin and quickly converted into Pantothenic acid by oxidation. Pantothenic acid is distributed into the cells and is converted to Acetyl Coenzyme-A (Acetyl CoA) in the cells of the epidermis. Human being require Vitamin B5 to synthesize Acetyl CoA which is an essential mediator to many biochemical reactions that sustain life (maintenance and repair of all cells) and which breaks down fats, carbohydrates and proteins for carbon dioxide, water, and energy generation. Furthermore, it synthesis fatty acids and sphingolipids, for stratum corneum lipid layers and cell membrane integrity & fluidity.

Side effects

Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported. Generally, topical panthenol formulations were well tolerated with minimal risk of skin irritation or sensitization.

Uses

vitamin B5 precursor, radioprotectant, antimalarial

Uses

panthenol (pro-vitamin B5) acts as a penetrating moisturizer. Panthenol appears to stimulate cellular proliferation and aid in tissue repair. Studies indicate that when topically applied, panthenol penetrates the skin and gets converted into pantothenic acid, a B complex vitamin. Such action could possibly influence the skin’s natural resources of pantothenic acid. It imparts a nonirritant, non-sensitizing, moisturizing, and conditioning feel and promotes normal keratinization and wound-healing. Panthenol protects the skin against sunburn, provides relief for existing sunburn, and enhances the natural tanning process. Panthenol’s humectant character enables it to hold water in the product or attract water from the environment, resulting in a moisturizing effect. It enhances skin suppleness, and claims are that it also acts as an anti-inflammatory agent. It is considered a non-comedogenic raw material.

Uses

DL-Panthenol is used in the topical treatment of skin disorders, such as minor irritations and skin burns. Also used in the strengthening and treatment of hair.

Application

Panthenol is used as a moisturizer, soothing and softening agent.

• Skin care: It improves hydration and elasticity of the skin, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates the rate of healing of wounds. In topical creams, it is found to be in a concentration of 1-5%.
• Hair care: It binds to the hair shaft readily, so, it is a common component of commercial shampoos and hair conditioners (in concentrations of 0.1-1%). It coats the hair and seals its surface, lubricating the hair shaft and giving it a shiny appearance. It can also help protect your hair from styling or environmental damage by locking in moisture.

General Description

Panthenol is an alcohol derivative of pantothenic acid, a component of the B complex vitamins and an essential component of a normally functioning epithelium. Panthenol exists in two optically active forms, both of which are used in pharmaceutical preparations. While pantothenic acid is optically active, only the dextrorotatory form is biologically active. Dexpanthenol, the active form of panthenol, is enzymatically cleaved to form pantothenic acid (Vitamin B5), which is an essential component of Coenzyme A that acts as a cofactor in many enzymatic reactions that are important for protein metabolism in the epithelium.

Flammability and Explosibility

Non flammable

Synthesis

Panthenol [D(+)-panthenol, α,γ-dihydroxy-N-(3-hydroxypropyl)-β,β-dimethylbutyramide] is synthesized by condensation of D-pantolactone (II) with 3-aminopropyl alcohol (III) in a medium of the lowest aliphatic alcohol: 3-aminopropyl alcohol (4.61 g, 0.062 mol, ca. 5% excess) was added to a solution of D-pantolactone (7.61 g, 0.058 mol) in ethanol (30 ml) and stirred at 78–80°C for 2 h (second-order reaction); after cooling to 20°C, KU-23 sulfonate-type cation-exchange resin (1.5 g) was added and stirred for 30 min to remove residual amino alcohol, the resin was filtered off and washed with ethanol (15 ml), and the combined filtrate was evaporated to dryness at 60–65°C to give chromatographically pure D-panthenol in 98.6% yield. Optimization studies showed that with equimolar reactants, 90.17% of 3-aminopropanol reacted after 2 h at 70°C in methanol and 94.7% of panthenol formed after 2 h at 80°C in ethanol; with a 5% excess of 3-aminopropanol, 99.6% D-panthenol was formed after 2 h at 80°C [1].

References

[1] KOZLOVA, G. S., EROKHINA, T. I., & GUNAR, V. I. (1977). ChemInform Abstract: SYNTHESIS OF D(+)-PANTHENOL. ChemInform, 8 38. https://doi.org/10.1002/chin.197738363