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

commercial grade, powder

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Synonym(s):
N-Ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride, EDAC, EDC, EDC hydrochloride, WSC hydrochloride
Empirical Formula (Hill Notation):
C8H17N3 · HCl
CAS Number:
Molecular Weight:
191.70
Beilstein:
5764110
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.31

grade

commercial grade

Quality Level

form

powder

mp

110-115 °C (lit.)

solubility

H2O: ≤100 mg/mL

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

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This Item
E63838.00907341006
EDAC, Hydrochloride EDAC HCl is a water-soluble derivative of carbodiimide useful for conjugating haptens to proteins and polypeptides. Used to modify NMDA receptors and as a condensing agent in peptide synthesis.

Sigma-Aldrich

341006

EDAC, Hydrochloride

form

powder

form

crystalline

form

solid

form

solid

mp

110-115 °C (lit.)

mp

110-115 °C (lit.)

mp

110-115 °C

mp

-

solubility

H2O: ≤100 mg/mL

solubility

H2O: ≤100 mg/mL

solubility

-

solubility

aqueous buffer: 2-5 mg/mL, water: 2-5 mg/mL

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C (−15°C to −25°C)

storage temp.

−20°C

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

200

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC HCl), commonly referred to as EDAC, is a highly potent and extensively utilized water-soluble reagent in the realm of chemical and biochemical research, playing a crucial role in facilitating the formation of amide bonds. Within the domain of peptide synthesis, EDC HCl demonstrates notable efficiency by catalyzing the coupling of amino acids through their carboxyl and amine groups, thereby facilitating the creation of peptide backbones with specific sequences and functionalities. This particular attribute is highly valuable in the production of peptides for various research purposes. Expanding beyond peptides, EDC HCl′s influence extends to the construction of immunogens, where it actively participates in the covalent attachment of haptens (small molecules that elicit an immune response) to carrier proteins. This involvement proves instrumental in the research and development of vaccines.

The versatility of EDC HCl further manifests in its capacity to modify nucleic acids, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This functionality enhances the visualization, tracking, and analysis of these crucial molecules, contributing significantly to the progression of nucleic acid research. Moreover, EDC HCl serves as a vital biomolecule bridge, acting as a crosslinker that connects amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique is particularly valuable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism of EDC HCl involves its reaction with a carboxyl group, forming an unstable intermediate that actively seeks an amine partner. The delicate balance of this reaction emphasizes the need for optimizing conditions to ensure efficient conjugation. The assistance of N-hydroxysuccinimide (NHS) further enhances EDC HCl′s capabilities by stabilizing the intermediate and enabling two-step conjugation procedures, offering greater flexibility and control, especially when dealing with complex biomolecules.

Application

  • N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used for the formation of FND (fluorescent nanodiamonds)-transferrin bioconjugates.
  • It has been used for crosslinking polyethylenimine to gold particles.
  • It has been used as a carbodiimide linkage agent for coating of carboxylated polystyrene beads with biotinylated BSA (bovine serum albumin).

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

Signal Word

Danger

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

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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