Panthenol

Last updated
Panthenol
Dexpanthenol.svg
D-panthenol
Names
Preferred IUPAC name
2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide [1]
Other names
  • Pantothenol
  • Pantothenyl alcohol
  • N-Pantoylpropanolamine
  • Bepanthen (trade name)
  • Dexpanthenol (D form)
Identifiers
3D model (JSmol)
3DMet
1724945, 1724947 R
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.036.839 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 240-540-6
KEGG
MeSH dexpanthenol
PubChem CID
RTECS number
  • ES4316500
UNII
  • InChI=1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14) Yes check.svgY
    Key: SNPLKNRPJHDVJA-UHFFFAOYSA-N Yes check.svgY
  • CC(C)(CO)C(O)C(=O)NCCCO
Properties
C9H19NO4
Molar mass 205.254 g·mol−1
AppearanceHighly viscous, colourless liquid
Density 1.2 g mL−1 (at 20 °C)
Melting point 66 to 69 °C (151 to 156 °F; 339 to 342 K) [ contradictory ]
Boiling point 118 to 120 °C (244 to 248 °F; 391 to 393 K) at 2.7 Pa
log P −0.989
Acidity (pKa)13.033
Basicity (pKb)0.964
+29° to +30°
1.499
Pharmacology
A11HA30 ( WHO ) D03AX03 ( WHO ), S01XA12 ( WHO )
Hazards
NFPA 704 (fire diamond)
1
1
0
Lethal dose or concentration (LD, LC):
10,100 mg kg−1 (intraperitoneal, mouse); 15,000 mg kg−1 (oral, mouse)
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.

Contents

Uses

Bepanthen eye and nose ointment (Germany) Bepanthen(r) -- BAYER -- Augen- und Nasensalbe (Dexpanthenol) mit Verpackung und Beipackzettel -- Deutschland.jpg
Bepanthen eye and nose ointment (Germany)

In pharmaceuticals, cosmetics, and personal-care products, panthenol is a moisturizer and humectant, used in ointments, lotions, shampoos, nasal sprays, eye drops, lozenges, and cleaning solutions for contact lenses.

In ointments it is used for the treatment of sunburns, mild burns, minor skin injuries, and disorders (in concentrations of up to 2–5%). [2] It improves hydration, reduces itching and inflammation of the skin, improves skin elasticity, and accelerates epidermal wounds' rate of healing. [3] For this purpose, it is sometimes combined with allantoin.

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,[ citation needed ] lubricating the hair shaft and giving it a shiny appearance.

It is also recommended by tattoo artists as a post-tattooing moisturising cream.

Adverse effects

Panthenol is generally well tolerated. In rare cases, skin irritation and contact allergies have been reported. [2] [3]

Pharmacology

Panthenol readily penetrates into the skin and mucous membranes (including the intestinal mucosa), where it is quickly oxidized to pantothenic acid. Pantothenic acid is extremely hygroscopic. [4] It is also used in the biosynthesis of coenzyme A, which plays a role in a wide range of enzymatic reactions and in cell growth. [2] [3]

Physical and chemical properties

Dexpanthenol Dexpanthenol viscosity.jpg
Dexpanthenol

Panthenol is an odourless, slightly bitter, highly viscous, transparent, and colourless liquid at room temperature, [5] but salts of pantothenic acid (for example sodium pantothenate) are powders that are typically white. It is easily soluble in water and alcohol, moderately soluble in diethyl ether, soluble in chloroform (1:100), [5] in propylene glycol, and slightly soluble in glycerin.

Panthenol's expanded chemical formula is HO–CH2–C(CH3)2–CH(OH)–CONH–CH2CH2CH2–OH.

Stereochemistry

Panthenol comes in two enantiomers: D, and L. Only D-panthenol (dexpanthenol) is biologically active, however both forms have moisturizing properties. For cosmetic use, panthenol comes either in D form, or as a racemic mixture of D and L (DL-panthenol).

Related Research Articles

<span class="mw-page-title-main">Pantothenic acid</span> Chemical compound

Pantothenic acid, also called vitamin B5 is a water-soluble B vitamin and therefore an essential nutrient. All animals require pantothenic acid in order to synthesize coenzyme A (CoA) – essential for fatty acid metabolism – as well as to, in general, synthesize and metabolize proteins, carbohydrates, and fats.

<span class="mw-page-title-main">Cosmetics</span> Substances applied to the body to change appearance or fragrance

Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protect the body or skin. Cosmetics designed to enhance or alter one's appearance (makeup) can be used to conceal blemishes, enhance one's natural features, add color to a person's face, or change the appearance of the face entirely to resemble a different person, creature or object. Cosmetics can also be designed to add fragrance to the body.

<span class="mw-page-title-main">Petroleum jelly</span> Chemical substance used as a lubricating agent and topical ointment

Petroleum jelly, petrolatum, white petrolatum, soft paraffin, or multi-hydrocarbon, CAS number 8009-03-8, is a semi-solid mixture of hydrocarbons, originally promoted as a topical ointment for its healing properties. The Vaseline brand is a well known American brand of petroleum jelly since 1870.

A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture in the food. Humectants are sometimes used as a component of antistatic coatings for plastics.

<span class="mw-page-title-main">Topical medication</span> Medication applied to body surfaces

A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes including creams, foams, gels, lotions, and ointments. Many topical medications are epicutaneous, meaning that they are applied directly to the skin. Topical medications may also be inhalational, such as asthma medications, or applied to the surface of tissues other than the skin, such as eye drops applied to the conjunctiva, or ear drops placed in the ear, or medications applied to the surface of a tooth. The word topical derives from Greek τοπικόςtopikos, "of a place".

<span class="mw-page-title-main">Hair conditioner</span> Hair care product

Hair conditioner is a hair care cosmetic product used to improve the feel, texture, appearance, and manageability of hair. Its main purpose is to reduce friction between strands of hair to allow smoother brushing or combing, which might otherwise cause damage to the scalp. Various other benefits are often advertised, such as hair repair, strengthening, or a reduction in split ends.

<span class="mw-page-title-main">Polydimethylsiloxane</span> Chemical compound

Polydimethylsiloxane (PDMS), also known as dimethylpolysiloxane or dimethicone, belongs to a group of polymeric organosilicon compounds that are commonly referred to as silicones and siloxane. PDMS is the most widely used silicon-based organic polymer, as its versatility and properties lead to many applications.

<span class="mw-page-title-main">Moisturizer</span> Type of cosmetics

A moisturizer, or emollient, is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb mollire, to soften.

Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form of white granules or flakes, which are insoluble in water. It has a wide range of uses as an ingredient in lubricants, resins, perfumes, and cosmetics. It is used as an emollient, emulsifier, and thickener in ointments, and is widely used as a hair coating in shampoos and hair conditioners. Stearyl heptanoate, the ester of stearyl alcohol and heptanoic acid (enanthic acid), is found in most cosmetic eyeliners. Stearyl alcohol has also found application as an evaporation suppressing monolayer when applied to the surface of water.

Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate, ammonium lauryl sulfate, and sodium laureth sulfate are all used in shampoos. Lauryl alcohol is tasteless and colorless with a floral odor.

<span class="mw-page-title-main">Diethanolamine</span> Chemical compound

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

<span class="mw-page-title-main">Cream (pharmacy)</span>

A cream is a preparation usually for application to the skin. Creams for application to mucous membranes such as those of the rectum or vagina are also used. Creams may be considered pharmaceutical products as even cosmetic creams are based on techniques developed by pharmacy and unmedicated creams are highly used in a variety of skin conditions (dermatoses). The use of the finger tip unit concept may be helpful in guiding how much topical cream is required to cover different areas.

Jojoba esters are the hydrogenation or transesterification product of Jojoba oil. Jojoba Esters are commonly used in cosmetic formulations as an emollient, due to its remarkable similarity to the natural oils produced by the human skin, and its high oxidative stability. Fully hydrogenated jojoba esters are most often small beads used to exfoliate the skin.

<span class="mw-page-title-main">Lotion</span> Skin treatment preparation

Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean cloth, or cotton wool.

Hydrolyzed jojoba esters are the hydrolysate of jojoba esters derived by acid, enzyme or other method of hydrolysis. Hydrolyzed jojoba esters are commonly used in cosmetic formulations.

<span class="mw-page-title-main">Octyl gallate</span> Chemical compound

Octyl gallate is the ester of 1-octanol and gallic acid. As a food additive, it is used under the E number E311 as an antioxidant and preservative.

<span class="mw-page-title-main">Shampoo</span> Hair care product

Shampoo is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the scalp, and then rinsing it out. Some users may follow a shampooing with the use of hair conditioner.

Silk amino acid (SAAs) also known as Sericin is a natural water-soluble glycoprotein extracted from raw silk. It is used as an additive in skin and hair care products due to its high levels of serine which has excellent moisture preservation characteristics. As a water-based additive it is used to provide a protective barrier and silky feel to lotions, soaps, personal lubricants, hair and skincare products. Silk amino acids are produced by hydrolyzing silk proteins into smaller peptide chains, typically 18 to 19 amino acids in length. Silk amino acids have a lower molecular weight than silk protein powders and are moisturizing to skin and hair.

<span class="mw-page-title-main">Aquaphor</span> Brand of skin care ointments

Aquaphor is a brand of over-the-counter (OTC) skin care ointments manufactured by Beiersdorf Inc., an affiliate of Beiersdorf AG. Aquaphor is offered in four product ranges: There are two skin protectant ointments. Aquaphor Original Ointment, used as a compounding agent and Aquaphor Advanced Therapy Healing Ointment, sold in mass retail outlets. The other product ranges include: Aquaphor Lip Repair and Lip Repair + Protect SPF 30, and Aquaphor Baby.

Phytantriol is an aliphatic alcohol used in cosmetic products and as a food additive. At room temperature it is a viscous liquid that is colourless to light yellow and with a sweetish odour.

References

  1. "Dexpanthenol – Compound summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification. Retrieved 29 June 2012.
  2. 1 2 3 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Bepanthen Creme.
  3. 1 2 3 Ebner F, Heller A, Rippke F, Tausch I (2002). "Topical use of dexpanthenol in skin disorders". American Journal of Clinical Dermatology. 3 (6): 427–33. doi:10.2165/00128071-200203060-00005. PMID   12113650. S2CID   35836478.
  4. Dinnendahl V, Fricke U, eds. (1991). Arzneistoff-Profile (in German). Vol. 7 (8 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. Pantothensäure. ISBN   978-3-7741-9846-3.
  5. 1 2 List PH, Hörhammer L, eds. (1969). Hagers Handbuch der pharmazeutischen Praxis (in German). Vol. 2. Springer. p. 699.