E6383

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

crystalline

• Synonym(s): EDC, N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC hydrochloride, WSC hydrochloride
• Empirical Formula (Hill Notation): C₈H₁₇N₃ · HCl
• CAS Number: 25952-53-8
• Molecular Weight: 191.70
• Beilstein/REAXYS Number: 5764110
• EC Number: 247-361-2
• MDL number: MFCD00012503
• UNSPSC Code: 12161703
• PubChem Substance ID: 24894627
• NACRES: NA.28

Properties

• form: crystalline
• Quality Level: 200
• reaction suitability: reagent type: cross-linking reagent; reaction type: Peptide Synthesis
• color: white to off-white
• mp: 110-115 °C (lit.)
• solubility: H₂O: ≤100 mg/mL
• application(s): advanced drug delivery; general analytical
• storage temp.: −20°C
• SMILES string: Cl.CCN=C=NCCCN(C)C
• InChI: 1S/C8H17N3.ClH/c1-4-9-8-10-6-5-7-11(2)3;/h4-7H2,1-3H3;1H
• InChI key: FPQQSJJWHUJYPU-UHFFFAOYSA-N

Description

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, commonly known as EDAC HCl, is a potent and widely employed water-soluble reagent in chemical and biochemical research due to its pivotal role in facilitating amide bond formation. In peptide synthesis, EDC HCl demonstrates efficiency by coupling amino acids through their carboxyl and amine groups, thereby forming peptide backbones. This capability is particularly valuable for creating peptides with specific sequences and functionalities.

Beyond peptides, EDC HCl extends its influence to the construction of immunogens, where it covalently attaches haptens (small immune-response eliciting molecules) to carrier proteins, playing an instrumental role in vaccine research. The versatility of EDAC HCl further unfolds in its ability to modify nucleic acids, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This facilitates the visualization, tracking, and analysis of these essential molecules, contributing to advancements in nucleic acid research.

Additionally, EDAC HCl serves as a biomolecule bridge by acting as a crosslinker, connecting amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique proves valuable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism of EDAC HCl involves its reaction with a carboxyl group, forming an unstable intermediate that actively seeks an amine partner. The delicate balance of this reaction underscores the importance of optimizing conditions for efficient conjugation. The assistance of N-hydroxysuccinimide (NHS) further enhances EDAC HCl′s capabilities, stabilizing the intermediate and enabling two-step conjugation procedures. This additional feature provides greater flexibility and control, particularly in dealing with complex biomolecules.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used:

• for the immobilisation of trypsin onto self-assembled monolayers (SAMs)[1]
• as a component for the preparation of collagen matrices[2]
• for the preparation of phosphoethanolamine(PEt)-conjugated sepharose[3]

Biochem/physiol Actions

Water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. In addition, it will react with phosphate groups. EDAC has been used in peptide synthesis; crosslinking proteins to nucleic acids; and preparation of immunoconjugates as examples. Typically, EDAC is utilized in the pH range 4.0-6.0 without buffers. In particular, amine and carboxylate buffers should be avoided.

Features and Benefits

Versatile and adaptable for a wide variety of laboratory and research applications

Other Notes

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Safety Information

• pictograms: GHS06,GHS08,GHS09
• signalword: Danger
• hcodes: H302,H311,H315,H317,H373,H410
• pcodes: P260 - P273 - P280 - P301 + P312 - P302 + P352 + P312 - P314
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral
• target_organs: Stomach,large intestine,lymph node
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves