Skip to Content
Merck
All Photos(1)

Documents

T511307

Sigma-Aldrich

5-Ethynyl-2′-deoxycytidine, (EdC)

AldrichCPR

Synonym(s):

2′-Deoxy-5-ethynylcytidine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C11H13N3O4
CAS Number:
69075-47-4
Molecular Weight:
251.24
MDL number:
MFCD22417249
UNSPSC Code:
12352200
PubChem Substance ID:
329826810

reaction suitability

reaction type: click chemistry

SMILES string

NC1=NC(=O)N(C=C1C#C)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

1S/C11H13N3O4/c1-2-6-4-14(11(17)13-10(6)12)9-3-7(16)8(5-15)18-9/h1,4,7-9,15-16H,3,5H2,(H2,12,13,17)/t7-,8+,9+/m0/s1

InChI key

HMJSYXIPNSASJY-DJLDLDEBSA-N

Application

A relatively nontoxic 2′-deoxycytidine analog for metabolic labeling of newly synthesized DNA in vivo. Especially suitable if the use of thymidine analogs is undesirable.

Other Notes

Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.

NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Dezhong Qu et al.
Analytical biochemistry, 417(1), 112-121 (2011-06-21)
The labeling of newly synthesized DNA in cells to identify cell proliferation is an important experimental technique. The most accurate methods incorporate [(3)H]thymidine or 5-bromo-2'-deoxyruidine (BrdU) into dividing cells during S phase, which is subsequently detected by autoradiography or immunohistochemistry
Lirui Guan et al.
Chembiochem : a European journal of chemical biology, 12(14), 2184-2190 (2011-08-02)
5-Ethynyl-2'-deoxycytidine triphosphate (EdCTP) was synthesized as a probe to be used in conjunction with fluorescent labeling to facilitate the analysis of the in vivo dynamics of DNA-centered processes (DNA replication, repair and cytosine demethylation). Kinetic analysis showed that EdCTP is
Yuan-Jhe Chang et al.
Archives of toxicology, 92(8), 2665-2680 (2018-06-27)
Adductomics is expected to be useful in the characterization of the exposome, which is a new paradigm for studying the sum of environmental causes of diseases. DNA adductomics is emerging as a powerful method for detecting DNA adducts, but reliable
Chenglong Sun et al.
Journal of immunology (Baltimore, Md. : 1950), 194(4), 1819-1831 (2015-01-18)
Herpesviruses are DNA viruses harboring the capacity to establish lifelong latent-recurrent infections. There is limited knowledge about viruses targeting the innate DNA-sensing pathway, as well as how the innate system impacts on the latent reservoir of herpesvirus infections. In this
Ramya Nandakumar et al.
Nature microbiology, 4(4), 701-713 (2019-02-26)
The innate immune system is crucial for eventual control of infections, but may also contribute to pathology. Listeria monocytogenes is an intracellular Gram-positive bacteria and a major cause of food-borne disease. However, important knowledge on the interactions between L. monocytogenes
View All Related Papers

Related Content

Luedtke Group – Professor Product Portal

Metabolic incorporation of a bioorthogonal functional group (e.g. alkyne, azide, alkene, etc.) into cellular DNA can be achieved by simply adding a synthetic nucleoside to the nutritional media of cells or whole animals.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service