Dexpanthenol

Base Information

• Chemical Name: Dexpanthenol
• CAS No.: 81-13-0
• Deprecated CAS: 1113-70-8,17307-32-3,50584-68-4,17307-32-3
• Molecular Formula: C9H19NO4
• Molecular Weight: 205.254
• Hs Code.: 29241990
• European Community (EC) Number: 201-327-3
• UNII: 1O6C93RI7Z
• DSSTox Substance ID: DTXSID3022906
• Nikkaji Number: J4.605A
• Wikidata: Q47495755
• NCI Thesaurus Code: C47481
• RXCUI: 22701
• Metabolomics Workbench ID: 51291
• ChEMBL ID: CHEMBL1200979
• Mol file: 81-13-0.mol

Synonyms:(+)-2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide;2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide;Bepanthen;butanamide, 2,4-dihydroxy-n-(3-hydroxypropyl)-3,3-dimethyl-, (+--)-;Corneregel;D-panthenol;dexpanthenol;Dexpanthenol Heumann;DL-panthenol;Ilopan;Marolderm;NasenSpray ratiopharm Panthenol;Nasicur;Otriven Dexpanthenol;Pan Rhinol;Pan-Ophtal;panthenol;Panthenol Braun;Panthenol Jenapharm;Panthenol LAW;Panthenol Lichtenstein;panthenol von ct;Panthenol-ratiopharm;Panthoderm;Panthogenat;pantothenol;Repa-Ophtal;Rhinoclir;Siozwo SANA;Ucee D;Urupan;Wund- und Heilsalbe LAW

Chemical Property of Dexpanthenol

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow viscous liquid
• Vapor Pressure: 2.21E-11mmHg at 25°C
• Melting Point: 64～69℃
• Refractive Index: 1.495 - 1.502
• Boiling Point: 483.6 °C at 760 mmHg
• PKA: 13.03±0.20(Predicted)
• Flash Point: 246.3 °C
• PSA: 89.79000
• Density: 1.166 g/cm³
• LogP: -0.74470
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: DMSO (Sparingly), Methanol (Slightly), Water (Sparingly)
• Water Solubility.: soluble
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 205.13140809
• Heavy Atom Count: 14
• Complexity: 182

Purity/Quality:

99% ^*data from raw suppliers

D-Panthenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-48-41-37/38-20/21/22
• Safety Statements: 23-24/25-45-36/37/39-26-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(CO)C(C(=O)NCCCO)O
• Isomeric SMILES: CC(C)(CO)[C@H](C(=O)NCCCO)O
• Recent ClinicalTrials: Topical Application of Imiquimod Gel at Different Concentrations in Actinic Cheilitis
• Recent EU Clinical Trials: Selective local anesthesia versus a combined medication injection with corticosteroids in degenerartive spine
• 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.
• 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. D-Panthenol is an analogue of pantothenic acid (P190300), a member of the B complex vitamins. D-Panthenol is the biologically active enantiomer of Panthenol. immunosuppressant, mitoxantrone analogue less toxic on cardiac tissue antineoplastic
• Therapeutic Function: Gastrointestinal drug

Technology Process of Dexpanthenol

There total 2 articles about Dexpanthenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

propan-1-ol-3-amine (156-87-6) + (R)-Pantolacton (599-04-2) → pantothenol (81-13-0,1113-70-8)

Guidance literature:

With triethylamine; In ethanol; at 160 ℃; for 3h; Microwave irradiation;

Reference yield:

panthenol (50584-68-4,16485-10-2,1113-70-8) → dexpanthenol (74561-18-5,1113-70-8) + pantothenol (81-13-0,1113-70-8)

Guidance literature:

With LUX i-Amylose-1; In ethanol; hexane; at 25 ℃; Temperature; Resolution of racemate;

DOI:10.1002/chir.23152

Reference yield: 93.2%

pantothenol (81-13-0,1113-70-8) + acetic anhydride (108-24-7) → D-panthenol triacetate (94089-18-6)

Guidance literature:

pantothenol; acetic anhydride; With dmap; at 60 - 90 ℃; for 2h;

With acetic acid; In ethyl acetate; at 80 - 110 ℃; under 7.60051 Torr;

upstream raw materials:

propan-1-ol-3-amine

(R)-Pantolacton

panthenol

Downstream raw materials:

pantothenic acid

2-Methyl-1,2-propanediol

[3-hydroxypropylamino]oxoacetic acid

D-panthenol triacetate

Refernces

A first approach to asymmetric protonation via a polymer supported chiral proton donor

10.1016/S0040-4039(00)76652-4

The research focuses on the asymmetric protonation of silyl enol ethers using a chiral proton donor supported on a polymer, aiming to address challenges in asymmetric synthesis. The purpose was to achieve improved asymmetric induction by supporting the proton donor on a polymeric chain, which could potentially allow for the recovery and recycling of the chiral inductor, reducing synthesis costs, and enabling reactions at more convenient temperatures without compromising enantiomeric excess. The study concluded that this approach resulted in higher chemical yields, significantly reduced reaction times, and a considerably higher optimum enantiomeric excess (up to 94%) compared to the 21% achieved in homogeneous solutions. The chemicals used in the process included silyl enol ethers, lithium enolates, pantothenic acid bound on Merrifield resin as the polymer-supported chiral proton donor, and various chiral alcohols such as pantothenol and methyl marzipate. The research demonstrated the advantages of using a polymer-supported chiral proton donor over its analogues, including the ability to recycle the chiral resin without a decrease in the degree of asymmetric induction.