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165344

Sigma-Aldrich

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide methiodide

for peptide synthesis

Synonym(s):

EDC methiodide

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About This Item

Linear Formula:
C2H5N=C=N(CH2)3N(CH3)3I
CAS Number:
Molecular Weight:
297.18
EC Number:
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Product Name

1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimide methiodide,

form

powder

reaction suitability

reaction type: Coupling Reactions

mp

97-99 °C (lit.)

application(s)

peptide synthesis

functional group

amine

storage temp.

2-8°C

SMILES string

[I-].CCN=C=NCCC[N+](C)(C)C

InChI

1S/C9H20N3.HI/c1-5-10-9-11-7-6-8-12(2,3)4;/h5-8H2,1-4H3;1H/q+1;/p-1

InChI key

AGSKWMRPXWHSPF-UHFFFAOYSA-M

Application

  • Crosslinking agent

Reactant for:
  • Amide bond forming (amidation) crosslinking reactions
Water-soluble carboxyl modifying reagent for proteins.[1]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Zainub Khan et al.
Drug delivery, 10(3), 213-220 (2003-08-29)
Low density lipoproteins (LDL) have been cationized using the water-soluble carbodiimide, N-ethyl-N'-(3-trimethylpropylammonium) carbodiimide iodide at a reagent: lipoprotein mole ratio of 10 000:1. This was shown to increase the innate DNA-binding capacity of LDL 10-fold. [125I]-labeled carbodiimide-modified LDL ([125I])-labeled ECDI-LDL)
I Iu Ponedel'kina et al.
Bioorganicheskaia khimiia, 32(5), 524-529 (2006-10-18)
Heparin was modified at carboxyl groups by reaction with several pharmacologically important amino-containing compounds in aqueous medium in the presence of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide. In dependence on the nature of the amine and the ratio of reagents, conjugates containing 36-100% amide and
Mou-Chieh Kao et al.
Biochemistry, 43(12), 3750-3755 (2004-03-24)
The proton-translocating NADH-quinone oxidoreductase (NDH-1) of Paracoccus denitrificans is composed of 14 different subunits (designated Nqo1-14), seven of which are located in the membrane domain and the other seven in the peripheral domain. It has been previously reported that membrane
P E Row et al.
Journal of experimental botany, 52(354), 57-66 (2001-02-22)
In order to identify functionally important amino acid residues in the chloroplast protein import machinery, chloroplasts were preincubated with amino-acid-modifying reagents and then allowed to import or form early import intermediates with precursor proteins. Incubation of chloroplasts with N-ethyl maleimide
Edit Csapó et al.
Carbohydrate polymers, 195, 99-106 (2018-05-29)
This work demonstrates the preparation, structural characterization, and the kinetics of the drug release of hyaluronic acid (HyA)-based colloidal drug delivery systems which contain hydrophobic ketoprofen (KP) as model molecule. Because of the highly hydrophilic character of HyA the cross-linked

Questions

1–3 of 3 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. Is it possible to have EDC conjugated with a fluorophore such that it can still target Carboxyl groups on the cellular proteins

    1 answer
    1. To target a carboxyl group on cellular proteins, the carbodiimide group of EDC must be unbound so the carbonyl from the carboxylic acid can initiate an attack. This interaction results in the formation of an O-acylisourea intermediate that can react with amines, with an urea by-product being released as a part of the process. Should a fluorophore be pre-conjugated to EDC, it is likely to be released as this by-product and thus would not attach to the carboxyl groups of the cells.

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