(S)-2-Tetradecanamidopropanoic acid

Name: (S)-2-Tetradecanamidopropanoic acid
Brand: ChemScene
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CAS No. 71448-29-8
Cat. No. CS-0163236
Purity≥98%
MDL No.MFCD00417781

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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(S)-2-Tetradecanamidopropanoic acid|CS-0163236

Structure of 71448-29-8

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General Information

CAS No. 71448-29-8
Cat. No. CS-0163236
Purity ≥98%
MDL No. MFCD00417781
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₃₃NO₃
Molecular Weight 299.45
Synonym(s) N-Tetradecanoyl-L-alanine
SMILES C[C@H](NC(CCCCCCCCCCCCC)=O)C(O)=O

Description

(S)-2-Tetradecanamidopropanoic acid features a chiral propanoic acid backbone functionalized with a long-chain tetradecanamide group, delivering enhanced lipophilicity and stereochemical control. This configuration enables precise integration into peptide mimetics and lipid-based delivery systems, where its stable amide linkage resists hydrolysis under physiological conditions.

Application

(S)-2-Tetradecanamidopropanoic acid serves as a chiral building block for peptide-based scaffolds and bioactive lipid analogs, leveraging its amide-functionalized aliphatic chain for enhanced membrane affinity. The stereochemistry at the alpha carbon ensures predictable conformational behavior in synthetic peptides, while the long C14 alkyl tail supports hydrophobic interactions in receptor binding studies. Its bench-stable nature facilitates handling and purification via standard chromatographic methods, enabling reliable incorporation into complex molecular architectures.

Synthesis

Route1
- 56-41-7
- 112-64-1
- ~%
- In-stock
  
  71448-29-8
References
- Chemical Communications, , # 17 p. 1556 - 1557
Route2
- 112-64-1
- ~%
- In-stock
  
  71448-29-8
References
- Tetrahedron, , vol. 63, # 31 p. 7334 - 7348
Route3
- In-stock
  
  338-69-2
- In-stock
  
  2425-54-9
- ~%
- In-stock
  
  71448-29-8
References
- Biochemische Zeitschrift, , vol. 40, p. 402

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 66.4
LogP 4.2768
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 14

Other Classifications

Life Science Amino Acids and their Derivatives Alanine and derivatives

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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(S)-2-Tetradecanamidopropanoic acid

CAS No. 71448-29-8

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