2-Octanamidoacetic acid

Base Information

• Chemical Name: 2-Octanamidoacetic acid
• CAS No.: 14246-53-8
• Molecular Formula: C10H19NO3
• Molecular Weight: 201.266
• European Community (EC) Number: 238-122-3
• UNII: 8TY5YO42NJ
• DSSTox Substance ID: DTXSID9065736
• Nikkaji Number: J216.923A
• Wikidata: Q27144409
• RXCUI: 1305600
• Metabolomics Workbench ID: 37454
• Mol file: 14246-53-8.mol

Synonyms:2-octanamidoacetic acid;Caprylylglycine;14246-53-8;capryloylglycine;Capryloyl glycine;N-(1-Oxooctyl)glycine;N-Octanoylglycine;2-(octanoylamino)acetic acid;Glycine, N-(1-oxooctyl)-;UNII-8TY5YO42NJ;8TY5YO42NJ;EINECS 238-122-3;EC 238-122-3;octanoylglycine;N-Capryloylglycine;N-octanoyl-Glycine;Lipacide C 8G;Octanoylamino-acetic acid;N-(1-oxooctyl)-Glycine;2-(octylamino)acetic acid;N- (1- oxooctyl)glycine;SCHEMBL125481;CAPRYLOYL GLYCINE [INCI];DTXSID9065736;CHEBI:74099;CAPRYLOYL GLYCINE [WHO-DD];AKOS009254081;AM806699;BS-24906;CS-0152288;FT-0765017;E75778;EN300-114896;N-Octanoylglycine, analytical reference material;Q27144409;Z362780008

Chemical Property of 2-Octanamidoacetic acid

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.000448mmHg at 25°C
• Melting Point: 102-103 °C
• Refractive Index: 1.455
• Boiling Point: 403.868 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 198.052 °C
• PSA: 66.40000
• Density: 1.037 g/cm³
• LogP: 1.93860
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 1.557g/L at 20℃
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 201.13649347
• Heavy Atom Count: 14
• Complexity: 180

Purity/Quality:

99% ^*data from raw suppliers

N-Octanoylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCC(=O)NCC(=O)O
• Uses: N-Octanoylglycine is a derivative of Glycine (G615990) and is an amphiphilic lipoamino acid commonly used in cosmetics for its antibacterial properties. N-Octanoylglycine is the active ingredient in products designed to treat seborrheic dermatitis on the scalp and acne prone skin.

Technology Process of 2-Octanamidoacetic acid

There total 9 articles about 2-Octanamidoacetic acid 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: 100.0%

C11H21NO3 → N-(1-oxooctyl)glycine (14246-53-8)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1039/c6tb02192a

Reference yield: 86.0%

glycine (56-40-6,18875-39-3,25718-94-9) + n-octanoic acid chloride (111-64-8) → N-(1-oxooctyl)glycine (14246-53-8)

Guidance literature:

With potassium carbonate; potassium hydroxide; In tetrahydrofuran; water; at 20 - 22 ℃; for 72h;

DOI:10.1039/c7ob01995e

Reference yield:

2-(palmitoylamino)ethanol (544-31-0) + N-stearoylethanolamine (111-57-9,8038-89-9) + N-(2-hydroxyethyl)dodecanamide (142-78-9) + myristic monoethanolamide (142-58-5) + N‐(2‐hydroxyethyl)octanamide (7112-02-9) + decanoic acid monoethanolamide (7726-08-1) → N-dodecanoylglycine (7596-88-5) + N-myristoylglycine (14246-55-0) + N-palmitoyl glycine (2441-41-0) + N-stearoylglycine (6333-54-6) + N-n-decanoylglycine (14305-32-9) + N-(1-oxooctyl)glycine (14246-53-8)

Guidance literature:

2-(palmitoylamino)ethanol; N-stearoylethanolamine; N-(2-hydroxyethyl)dodecanamide; myristic monoethanolamide; N‐(2‐hydroxyethyl)octanamide; decanoic acid monoethanolamide; With sodium hydroxide; sodium hypochlorite; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; potassium bromide; In water; toluene; at 31 - 38 ℃; for 5 - 6h; pH=6.9 - 8.9;

With hydrogenchloride; In tetrahydrofuran; water; toluene; pH=2.2; Product distribution / selectivity;

upstream raw materials:

glycine

n-octanoic acid chloride

2-(palmitoylamino)ethanol

N-stearoylethanolamine

Downstream raw materials:

C₁₈H₂₈N₂O₂

C₁₉H₃₀N₂O₂

C₁₈H₃₄N₂O₂

C₂₀H₃₂N₂O₂

Refernces

• 1、 Zhu, Mengyi,Wang, Lijuan,He, Jing. "Repurposing the 3-Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification". supporting information. p. 2030 - 2035. Retrieved 2020/11/30.
• 2、 -. "Antimicrobial Preservative Compositions for Personal Care Products". Paragraph 0061. . Retrieved 2014/10/29.