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03449

Sigma-Aldrich

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

≥99.0% (AT)

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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/REAXYS Number:
5764110
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

assay

≥99.0% (AT)

form

powder

technique(s)

bioconjugation: suitable

mp

110-115 °C (lit.)
112-116 °C

solubility

H2O: soluble 0.2 g/L

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
03450E7750E1769
form

powder

form

powder

form

powder

form

powder

technique(s)

bioconjugation: suitable

technique(s)

-

technique(s)

Northern blotting: suitable, bioconjugation: suitable

technique(s)

-

mp

110-115 °C (lit.)

mp

110-115 °C (lit.)

mp

110-115 °C (lit.)

mp

110-115 °C (lit.)

solubility

H2O: soluble 0.2 g/L

solubility

H2O: soluble 1 gm/10 ml, clear to very slightly hazy, colorless to very faintly yellow

solubility

H2O: ≤100 mg/mL

solubility

H2O: 0.5 M, clear to very slightly hazy, colorless to very faintly yellow

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride, commonly referred to as EDAC HCl, plays a pivotal role as a potent and widely utilized water-soluble reagent in chemical and biochemical research, primarily facilitating the formation of amide bonds. In the realm of peptide synthesis, EDAC HCl showcases efficiency by coupling amino acids through their carboxyl and amine groups, crucial for the creation of peptides with specific sequences and functionalities. Expanding its influence beyond peptides, EDAC HCl contributes to the construction of immunogens by covalently attaching haptens—small molecules that elicit an immune response—to carrier proteins, playing a key role in vaccine research.The versatility of EDAC HCl extends to nucleic acid modification, allowing for the labeling of DNA and RNA through their 5′ phosphate groups. This capability facilitates the visualization, tracking, and analysis of these crucial molecules, contributing significantly to advancements in nucleic acid research.

Furthermore, EDAC HCl serves as a biomolecule bridge, acting as a crosslinker that connects amine-reactive NHS-esters of biomolecules to carboxyl groups. This technique proves invaluable in protein conjugation, enabling the creation of hybrid molecules with novel properties and functions. The underlying mechanism involves EDAC HCl′s 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 by stabilizing the intermediate and enabling two-step conjugation procedures. This additional feature provides greater flexibility and control, particularly when dealing with complex biomolecules.

Application

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride ≥99.0% (AT) has been used as an activator to covalently immobilize tyrosinase to prepare enzyme electrodes. It has also been used as a prefixative for histamine immunolabeling.
N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride has been used for amine coupling reaction during self-assembly of the tethered bilayer lipid membrane. It has also been used for derivatizing antibody against COX5b to carboxylated polystyrene microspheres.

Biochem/physiol Actions

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide is a water soluble condensing reagent. EDAC is generally utilized as a carboxyl activating agent for amide bonding with primary amines. Additionally, it will react with phosphate groups. It has been utilized in peptide synthesis, crosslinking proteins to nucleic acids as well as preparation of immunoconjugates.
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 wide variety of laboratory and research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Water soluble peptide coupling reagent; Modification of carboxyl groups in proteins, review; Synthesis of esters.

signalword

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

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


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A flight sensory-motor to olfactory processing circuit in the moth Manduca sexta
Bradley SP, et al.
Frontiers in Neural Circuits, 10(6), 5-5 (2016)
Total synthesis of a monocyclic peptide lactone antibiotic, etamycin.
J C Sheehan et al.
Journal of the American Chemical Society, 95(3), 875-879 (1973-02-07)
Xuchen Hu et al.
eLife, 8 (2019-09-06)
Cultured mouse peritoneal macrophages release large numbers of ~30-nm cholesterol-rich particles. Here, we show that those particles represent fragments of the plasma membrane that are pulled away and left behind during the projection and retraction of filopodia and lamellipodia. Consistent
R.L. Lundblad et al.
Chemical Reagents for Protein Modification, 2, 105-105 (1984)
Synthesis of esters.
Dhaon, M.K.
The Journal of Organic Chemistry, 47, 1962-1962 (1982)

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