Ldao

• CAS: 1643-20-5
• Catalog Number: ACM1643205-4
• Category: Main Products
• Molecular Weight: 229.4
• Molecular Formula: C14H31NO
• Synonyms: N,N-dimethyl-1-dodecanamine, N-oxide; Dimethyldodecylamine N-oxide; Lauramine oxide; Lauryldimethylamine oxide; N-Lauryldimethylamine N-oxide
• IUPAC Name: N,N-dimethyldodecan-1-amine oxide
• Canonical SMILES: CCCCCCCCCCCC[N+](C)(C)[O-]
• InChI: InChI=1S/C14H31NO/c1-4-5-6-7-8-9-10-11-12-13-14-15(2,3)16/h4-14H2,1-3H3
• InChI Key: SYELZBGXAIXKHU-UHFFFAOYSA-N
• Boiling Point: 100ºC
• Melting Point: 132-133 °C (lit.)
• Flash Point: 94ºC
• Density: 0.996 g/mL at 20 °C
• Solubility: DMF: 0.3 mg/mL; DMSO: 0.1 mg/mL; Ethanol: 15 mg/mL; PBS (pH 7.2): 0.1 mg/mL
• Appearance: A crystalline solid
• Complexity: 146
• EC Number: 216-700-6
• Exact Mass: 229.240564612
• Formal Charge: 0
• Hazard Statements: H315-H319-H335
• Heavy Atom Count: 16
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 0
• Isomeric SMILES: CCCCCCCCCCCC[N+](C)(C)[O-]
• Monoisotopic Mass: 229.240564612
• Packing Group: III
• pH: 5-9 (1% solution in water)
• pKa: 4.79±0.40 (Predicted)
• RIDADR: NONH for all modes of transport
• Rotatable Bond Count: 11
• Safety Description: 26-36/37/39-45-27
• Shipping: Room temperature
• Stability: ≥2 years
• Storage Conditions: -20 °C
• Symbol: GHS07
• Topological Polar Surface Area: 18.1 Ų
• UN Number: 3249
• XLogP3-AA: 5.3

Case Study

Endotoxin Masking by Dodecyldimethylamine Oxide in Bacterial Endotoxin Testing

Bech Ørving, René, et al. Microorganisms, 2020, 8(11), 1728.

Bacterial endotoxin testing is one of a set of mandatory tests for the release of parenteral drug products. In this study, the quality control (QC) sample holding times of different process controls during the manufacturing of biopharmaceutical products were analyzed. It was found that dodecyldimethylamine oxide (LDAO) causes strong endotoxin masking via a one-step mechanism.
Mechanism of LDAO Masking Effect
· The positively charged head of LDAO can intercalate with lipopolysaccharides (LPS) molecules, binding to the negatively charged lipid A and core region through ionic interactions. As a result, the cations in the salt bridges connecting LPS molecules can be gradually replaced by the positively charged head of LDAO, which may reduce the overall rigidity between the LPS molecules.
· The stabilization of this intercalation is further enhanced by the hydrophobic tail of LDAO, allowing the C12 alkyl chain and fatty acid residues of lipid A to interact through hydrophobic forces, thereby destabilizing LPS aggregates. LDAO features a simple amine oxide and a straight C-chain, similar in length to the fatty acids of lipid A. This makes it more favorable for LDAO to intercalate through ionic interactions and binding with the fatty acids.
· Furthermore, at elevated concentrations, LDAO tends to form micelles in aqueous solutions. Consequently, it is likely that LPS and LDAO will create mixed aggregates and potentially mixed micelles under these conditions, altering the supramolecular structure of the endotoxin. In this modified conformation, the endotoxin may become inaccessible to factor C, rendering it undetectable.

Surfactants Such as Lauramine Oxide Used to Prepare Organoclays for the Removal of Lead Cations

Gertsen, Maria, et al. Toxics, 2024, 12(10), 713.

In this study, organoclays based on bentonite and various amphoteric and nonionic surfactants were synthesized and tested for their effectiveness as effective adsorbents for lead ions. The results show that the prepared organoclays present an increasing sequence calculated according to the adsorption limit of the Langmuir equation: organoclay with cocamide diethanolamine < bentonite < organoclay with lauramine oxide (LDAO) < organoclay with sodium cocoiminodipropionate < organoclay with disodium cocoamphodiacetate < organoclay with alkyl polyglucoside.
Synthesis of organoclay
· Organoclays were synthesized using monoionic sodium bentonite. This involved treating purified, <75 µm crushed natural phyllosilicate with 0.2 N NaCl (1:50 weight:volume ratio) for 6 hours, followed by another 18 hours. The resulting mineral was repeatedly washed with deionized water until a chloride-free condition was confirmed using AgNO3. After centrifugation at 10,000 rpm for 10 minutes, the solid was dried at 60 ± 2 °C to constant weight and then pulverized.
· The surfactant solution comprised 1 g of surfactant in 95 mL deionized water before combining it with 5 g of prepared mineral inside a flask. The mixture underwent stirring and shaking at 180 strokes per minute for 24 hours within a temperature range of 22-23 °C. After 10 minutes of centrifugation at 10,000 rpm the organoclay was separated and the supernatant liquid was removed. The sediment underwent three wash cycles with 40 mL of deionized water and was stirred and centrifuged (10,000 rpm, 10 minutes) after each cycle while the supernatant was discarded. Then dried the combined sediment to a constant weight at 60 ± 2 °C.

Custom Q&A

What is the molecular formula of lauramine oxide?

The molecular formula of lauramine oxide is C14H31NO.

What are the synonyms of lauramine oxide?

The synonyms of lauramine oxide are Lauryldimethylamine oxide, Dodecyldimethylamine oxide, and Lauryldimethylamine N-oxide.

What is the molecular weight of lauramine oxide?

The molecular weight of lauramine oxide is 229.40 g/mol.

When was lauramine oxide created?

Lauramine oxide was created on June 1, 2005.

What is the role of lauramine oxide?

Lauramine oxide has a role as a plant metabolite and a detergent.

Where is lauramine oxide found naturally?

Lauramine oxide is a natural product found in Euglena gracilis.

What is the IUPAC name of lauramine oxide?

The IUPAC name of lauramine oxide is N,N-dimethyldodecan-1-amine oxide.

What is the InChIKey of lauramine oxide?

The InChIKey of lauramine oxide is SYELZBGXAIXKHU-UHFFFAOYSA-N.

What is the canonical SMILES of lauramine oxide?

The canonical SMILES of lauramine oxide is CCCCCCCCCCCC[N+](C)(C)[O-].

What is the UN Number of lauramine oxide?

The UN Number of lauramine oxide is 3249.