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Dexpanthenol

CAS：81-13-0
MW:205.25146
MF：C9H19NO4

Dexpanthenol belongs to a derivative of pantothenic acid (vitamin B5). It can penetrate the skin and mucous membrane to be quickly oxidized to pantothenic acid. The later one is extremely hygroscopic and binds water effectively. Therefore, Dexpanthenol can be used as a moisturizer. It is added to pharmaceutical and cosmetic products to relieve itching and improve wound healing. In ointments, it can be used for the treatment of sunburns, mild burns, minor skin injuries and disorders. It is also immediately applied after major abdominal surgery to minimize the possibility of paralytic ileus. In addition, it can also be supplemented into the commercial shampoos and hair conditioners to lubricate the hair shaft and give the hair a shiny appearance. The exact mechanism of action of Dexpanthenol is still unclear, perhaps through its enhancing effect on acetylcholine. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Dexpanthenol

1.2 Synonyms: 4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-(theta)-butanamid; 4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-d-(+)-butyramid; Alcopan-250; Bepanthen; Bepanthene; Bepantol; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-; Butanamide, 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-, (R)-; Cozyme; D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide; D-panthenol; D-pantothenyl alcohol; EINECS 201-327-3; Ilopan; Intrapan; MFCD00065006; Motilyn; Panadon; Pantol; Proleus; synapan; Urupan; Vitamin B5;

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1.3 CAS No.: 81-13-0

1.4 CID: 131204

1.5 EINECS: 201-327-3

1.6 Molecular Formula: C9H19NO4

1.7 Inchi: 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)/t7-/m0/s1

1.8 InChkey: SNPLKNRPJHDVJA-ZETCQYMHSA-N

1.9 Canonical Smiles: CC(C)(CO)C(C(=O)NCCCO)O

1.10 Isomers Smiles: CC(C)(CO)[C@H](C(=O)NCCCO)O

2. Properties

2.1 Appearance: clear colorless to slightly yellow viscous liquid

2.2 Storage: Keep Cold. Hygroscopic.

2.3 Chemical Properties: clear colorless to slightly yellow viscous liquid

2.4 Color/Form: Hygroscopic oil
Viscous liquid
Clear viscous, somewhat hygroscopic liquid ... Some crystallization may occur on standing

2.5 Contact Allergens: Pan(to)thenol is the alcohol corresponding to pantothenicacid, of the vitamin B5 group. It is used as a food additive,and in skin and hair products as a conditioning agent.Contact dermatitis and urticaria have been reported.

2.6 Decomposition: When heated to decomposition it emits toxic fumes of /nitric oxide/.

2.7 HenrysLawConstant: Henry's Law constant = 2.8X10-11 cu cm/molec-sec at 25 °C (est)

2.8 PH: pH 9.5

2.9 pKa: 13.03±0.20(Predicted)

2.10 Water Solubility: 4.87 M

2.11 Spectral Properties: Index of refraction: 1.497 at 20 deg C/D
Specific optical rotation: +29.5 deg at 20 deg C/D (water, 5%)
SADTLER REFERENCE NUMBER: 17635 (IR, PRISM)
Intense mass spectral peaks: 102 m/z, 133 m/z, 157 m/z, 175 m/z, 205, m/z
IR: 17635 (Sadtler Research Laboratories IR Prism collection)

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2.12 Stability: Reasonably stable to usual sterilization time and temp in aqueous solution at pH 3.0-4.0; long heating causes racemization.

2.13 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Description: Dexpanthenol (CAS 81-13-0) is a clear, viscous liquid that is commonly used in various industries. Its chemical structure consists of a pantothenic acid derivative with an alcohol group, making it a stable and water-soluble compound. Dexpanthenol is highly soluble in water and has a slightly sweet taste. It is also known as provitamin B5, as it can be converted into vitamin B5 (pantothenic acid) in the body.

Applicable Fields
Pharmaceutical Industry: Dexpanthenol is widely used in the pharmaceutical industry for its therapeutic properties. It is commonly used in topical formulations such as creams, ointments, and lotions, as it has moisturizing and soothing effects on the skin. Dexpanthenol is also used in oral medications and supplements for its role in promoting skin health and wound healing.

Cosmetics Industry: In the cosmetics industry, dexpanthenol is a popular ingredient in skincare and haircare products. It is known for its moisturizing and hydrating properties, making it suitable for products such as moisturizers, serums, shampoos, and conditioners. Dexpanthenol helps to improve the skin's barrier function, reduce transepidermal water loss, and enhance the appearance and texture of hair.

Mechanism of Action
Dexpanthenol functions as a prodrug, meaning it is converted into its active form (pantothenic acid) in the body. Pantothenic acid is an essential nutrient that plays a crucial role in various biological processes, including the synthesis of coenzyme A (CoA). CoA is involved in numerous metabolic reactions, such as the production of energy from carbohydrates, fats, and proteins. Dexpanthenol's moisturizing and wound healing effects are attributed to its ability to enhance the skin's natural barrier function and promote tissue repair.

Storage Conditions
Store in a cool, dry place.

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3.2 Usage: cholinergic

4. Safety and Handling

4.1 Exposure Standards and Regulations: Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: dexpanthenol is included in poison ivy, poison oak and poison sumac drug products.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including dexpanthenol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
d-Pantothenyl alcohol used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

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4.2 Octanol/Water Partition Coefficient: log Kow = -1.92 (est)

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

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4.4 DisposalMethods: SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

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4.5 Safety Profile: Moderately toxic by intravenous route. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.

4.6 Formulations/Preparations: USEPA/OPP Pesticide Code 068801; Trade Names: Piprotal and Tropital. /Former trade names/
Aqueous solution can be stabilized with pantolactone.
Injection: 250 mg/mL, In 10 ML and 2 mL vials (various manufacturers); 250 mg/mL, In UD Stat-Pak 2mL disposal syringes (Syringes contain no more than 0.5% chlorobutanol) Ilopan (Adria).
Pantothenic acid is included in multiple vitamin preparations as calcium or sodium salt or alcohol, panthenol.
Aqueous emulsions containing pantothenol with a light-protective substance were prepared and proposed for prevention and treatment of sunburns.
IV hyperalimentation infusion solution containing panthenol and other vitamins are presented.
A composition for treating dental gum diseases consists of a gel in which inflammation inhibitors and antimicrobial substances are added, it is applied directly on tooth gum and contained pantothenyl alc.
A nontoxic, nonirritant composition for prevention of hair loss and for the control of seborrhea was prepared containing D-panthenol.
A mixture suitable for skin protection against polluting agents, water, salt water, air, sunrays, etc, contained 30 parts panthenol.
A perfumed friction tonic for treatment of dry, delicate skin is described. It is nonalcoholic and consists of a solution of poly(vinylpyrrolidone) and panthenol in water.
Oral compositions for prophylaxis and treatment of inflammatory diseases of the periodontium contained D-panthenol 0.25% wt.
A stable aqueous multivitamin preparation in sterile, storage-stable injection form in a 2 compartment hypodermic syringe contained dexpanthenol.
/Used in formulation/ gingival; med-tech: /a comforting antiseptic for gums and mouth/.

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4.7 Protective Equipment and Clothing: A skin and eye irritant.

4.8 Reactivities and Incompatibilities: Dexpanthenol is incompatible with alkalis & strong acids.

4.9 Report: Reported in EPA TSCA Inventory.

4.10 Skin, Eye, and Respiratory Irritations: A skin and eye irritant.

4.11 Safety: Hazard Codes:?Xn
Risk Statements: 36/37/38-48-41-37/38-20/21/22?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R48:Danger of serious damage to health by prolonged exposure.?
R41:Risk of serious damage to the eyes.?
R37/38:Irritating to respiratory system and skin.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 23-24/25-45-36/37/39-26-22?
S23:Do not breathe vapour.?
S24/25:Avoid contact with skin and eyes.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S22:Do not breathe dust.
WGK Germany: 1
RTECS: ES4316000
F: 3-10
Moderately toxic by intravenous route. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NO_x. See also AMIDES.

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4.12 Sensitive: Hygroscopic

4.13 Specification: ?Dexpanthenol (CAS NO.81-13-0) is also named as (+)-Panthenol ; (R)-2,4-Dihydroxy-N-(3-hydroxy-propyl)-3,3-
dimethylbutanamide ;?2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide ;?(R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide, D-(+)- ; 4-04-00-01652 (Beilstein Handbook Reference) ; Alcopan-250 ; BAY 81-2996 ; BRN 1724947 ; Bepanthen ; Bepanthene ; D(+)-Pantothenyl alcohol ; D(+)-alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide ; D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide ; D-P-A Injection ; Intrapan ; Motilyn ; NSC 302962 ; Panadon ; Pantenyl ; Thenalton ; UNII-1O6C93RI7Z ; Urupan ; Varitan ; Zentinic ; alpha,gamma-Dihydroxy-N-(3-hydroxypropyl)-beta,beta-dimethylbutyramide, D-(+)- ; d(+)-Panthenol ; d-Pantothenol ; d-Pantothenyl alcohol .?Dexpanthenol (CAS NO.81-13-0) is clear colorless to slightly yellow viscous liquid.?It is soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin.

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4.14 Toxicity

1.	???	skn-rbt 500?mg/4H MLD	???	JACTDZ ?? Journal of the American College of Toxicology. 6 (1)(1987),139.
2.	???	eye-rbt 500?μg MLD	???	JACTDZ ?? Journal of the American College of Toxicology. 6 (1)(1987),139.
3.	???	orl-mus LD50:15?g/kg	???	JACTDZ ?? Journal of the American College of Toxicology. 6 (1)(1987),139.
4.	???	ipr-mus LD50:9?g/kg	???	FRPSAX ?? Farmaco, Edizione Scientifica. 14 (1959),43.
5.	???	ivn-mus LD50:7000?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),599.
6.	???	ivn-rbt LD50:4000?mg/kg	???	NIIRDN ?? “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),599.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

IR : liquid film

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

81-13-0Total: 1 Synthesis Route

156-87-6 162 Suppliers

599-04-2 77 Suppliers

81-13-0 242 Suppliers

8. Precursor and Product

precursor:

599-04-2

156-87-6

product:

1211493-82-1

79-83-4

558-43-0

9. Computed Properties

Molecular Weight：205.25146g/mol
Molecular Formula：C₉H₁₉NO₄
Compound Is Canonicalized：True
Exact Mass：-0.9
XLogP3-AA：205.13140809
Monoisotopic Mass：205.13140809
Complexity：182
Rotatable Bond Count：6
Hydrogen Bond Donor Count：4
Hydrogen Bond Acceptor Count：4
Topological Polar Surface Area：89.8
Heavy Atom Count：：14
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceByOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAADhThgAYCAALAAgAIAAEQEAIAAAAAAAAAAIFIAAACEBAAgAAEQAAHFgCQAAAiAAAJAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10.Other Information

水溶性: soluble

蒸汽压: 2.21E-11mmHg at 25°C

Usage: D-Panthenol is used as precursors in the biosynthesis of coenzyme A. D-Panthenol and D-Pantothenic acid are used in a variety of skin protection products. D-pantothenic acid have a role in controlling keratinocyte proliferation and differentiation. D-Panthenol is used for studies of skin protection emulsions from UV irradiation and as a humectant. It is also used in creams, lotions, shampoos, conditioners and body washes.

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Merck: 14,2947

BRN: 1724947

毒性: GRAS(FDA，§182．5580，2000).

Description: Dexpanthenol belongs to a derivative of pantothenic acid (vitamin B5). It can penetrate the skin and mucous membrane to be quickly oxidized to pantothenic acid. The later one is extremely hygroscopic and binds water effectively. Therefore, Dexpanthenol can be used as a moisturizer. It is added to pharmaceutical and cosmetic products to relieve itching and improve wound healing. In ointments, it can be used for the treatment of sunburns, mild burns, minor skin injuries and disorders. It is also immediately applied after major abdominal surgery to minimize the possibility of paralytic ileus. In addition, it can also be supplemented into the commercial shampoos and hair conditioners to lubricate the hair shaft and give the hair a shiny appearance. The exact mechanism of action of Dexpanthenol is still unclear, perhaps through its enhancing effect on acetylcholine.

View all

References: https://pubchem.ncbi.nlm.nih.gov/compound/Dexpanthenol#section=Top
https://www.drugs.com/pro/dexpanthenol.html
https://de.wikipedia.org/wiki/Dexpanthenol

Chemical Properties: clear colorless to slightly yellow viscous liquid

Originator: Bepanthene,Roche,France,1951

Uses: Dexpanthenol may be used as an analytical reference standard for the determination of the analyte in pharmaceutical formulations by various chromatography techniques as well as partial least-squares multivariate calibration.

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12. Related Questions

: What Makes Dexpanthenol a "Sweet Guardian" in Cosmetics?Introduction Discover the hidden gem in the world of cosmetics known as dexpanthenol. This unique ingredient plays a crucial role in various industries like skincare, medicine, and food. Let's delve i..; What is Dexpanthenol and its Benefits in Skincare?In the world of vitamins, Vitamin B complex is often overlooked. However, in our everyday skincare products, we frequently encounter the presence of Vitamin B complex. Today, let's get acquainted with..; What are the benefits of Dexpanthenol in skincare?Dexpanthenol, also known as provitamin B5, is a B-complex vitamin and the dextrorotatory isomer of panthenol. When absorbed into the body, Dexpanthenol is converted into pantothenic acid, which then s..; What are the basic information about Dexpanthenol?There are various chemicals in our daily life. Some chemicals can be used in the pharmaceutical and cosmetics industries, while others can be applied in the food industry to produce a variety of food ..

13. Realated Product Infomation