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D5782

2′,3′-Dideoxycytidine

≥98% (HPLC), synthetic (organic), powder

Synonym(s):

ddC

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D5782-100MG

CZK 4,330.00

D5782-250MG

CZK 9,550.00

D5782-500MG

CZK 17,300.00

CZK 4,330.00

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About This Item

Empirical Formula (Hill Notation):
C9H13N3O3
CAS Number:
7481-89-2
Molecular Weight:
211.22
NACRES:
NA.52
PubChem Substance ID:
24278377
UNSPSC Code:
41106305
MDL number:
MFCD00012188
Beilstein/REAXYS Number:
654956
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless to faintly yellow
Storage temp.:
−20°C

Key Documents

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Product Name

2′,3′-Dideoxycytidine, ≥98% (HPLC)

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (HPLC)

form

powder

feature

PCR Additives

technique(s)

PCR: suitable

color

colorless

input

crude DNA

mp

217-218 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

−20°C

SMILES string

NC1=NC(=O)N(C=C1)[C@H]2CC[C@@H](CO)O2

InChI

1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1

InChI key

WREGKURFCTUGRC-POYBYMJQSA-N

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1 of 4

This Item
E9386D1285D3897
2′,3′-Dideoxycytidine ≥98% (HPLC)

Sigma-Aldrich

D5782

2′,3′-Dideoxycytidine

5-Ethyl-2′-deoxyuridine

Sigma-Aldrich

E9386

5-Ethyl-2′-deoxyuridine

2′,3′-Dideoxyadenosine ≥97% (HPLC)

Sigma-Aldrich

D1285

2′,3′-Dideoxyadenosine

2′-Deoxycytidine ≥99% (HPLC)

D3897

2′-Deoxycytidine

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

-

biological source

synthetic (organic)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

≥97% (HPLC)

assay

≥99% (HPLC)

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

solubility

water: 50 mg/mL, clear, colorless to yellow

solubility

water: 100 mg/mL, clear, colorless

solubility

water: 50 mg/mL, clear, colorless to very faintly yellow

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

Application

2′,3′-Dideoxycytidine is used:
  • as a DNA chain-terminating nucleotide for DNA sequencing methods based on the Sanger chain-termination method
  • as a nucleoside reverse transcriptase inhibitor (NRTI) to study its effects on the development of mechanical allodynia in aging mice[1]
  • as a mitochondrial DNA (mtDNA) replication inhibitor to inhibit the activation of cGAS-STING pathway and study its effects on signaling protein-stimulator of interferon genes (STING), cyclic GMP-AMP synthase (cGAS), and phospho-interferon regulator factor 3 (p-IRF3) expression in mouse hippocampal and microglial cells[2]
  • as an NRTI inhibitor to study its effects on the drug induced-mitochondrial toxicity in Caenorhabditis elegans[3]

Biochem/physiol Actions

2′,3′-Dideoxycytidine (ddC), is an ionic compound and a nucleoside analog.[4] [5]It acts as a nucleoside reverse transcriptase inhibitor and exhibits therapeutic effects against human immunodeficiency virus (HIV) infection.[5] 2′,3′-Dideoxycytidine possesses anti-adenovirus activity and inhibits the adenovirus polymerase.[6]

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H351

pcodes

P281

Hazard Classifications

Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF7173V
WXBF6509V
WXBF5210V
WXBF4536V
WXBF4775V

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Anindya Roy Chowdhury et al.
iScience, 23(8), 101370-101370 (2020-08-02)
This study shows that multiple modes of mitochondrial stress generated by partial mtDNA depletion or cytochrome c oxidase disruption cause ryanodine receptor channel (RyR) dysregulation, which instigates the release of Ca2+ in the cytoplasm of C2C12 myoblasts and HCT116 carcinoma
R Mentel et al.
Antiviral research, 47(2), 79-87 (2000-09-21)
The antiviral activity of 2',3'-dideoxycytidine (ddC) has been investigated in a mouse pneumonia model. Consolidation of lung, histopathological changes, DNA synthesis as well as levels of TNFalpha were assayed. In this in vivo model, the oral administration of ddC twice
Jun Xiang et al.
International journal of pharmaceutics, 231(1), 57-66 (2001-11-24)
Permeation of 2',3'-dideoxycytidine (ddC), an ionic compound, through buccal mucosa was investigated in this in vitro study to identify the major permeation barrier within the epithelium of buccal mucosa and explore the feasibility of transbuccal delivery of ddC. In vitro
Guo-Liang Jiang et al.
Brain research bulletin, 171, 183-195 (2021-03-23)
Inflammation plays a pivotal role in promoting the pathophysiology of ischemic stroke (IS). Microglia is the major immunocompetent cells involved in different neuropathologies. The activation of cyclic GMP-AMP synthase (cGAS) and its downstream signaling protein-stimulator of interferon genes (STING) is
Shuang-Xi Gu et al.
Bioorganic & medicinal chemistry, 19(17), 5117-5124 (2011-08-10)
A series of 26 diarylpyrimidines, characterized by the hydroxymethyl linker between the left wing benzene ring and the central pyrimidine, were synthesized and evaluated for in vitro anti-HIV activity. Most of the compounds exhibited moderate to excellent activities against wild-type
View All Related Papers

Questions

  1. iS THIS TOXIN?

    1 answer

    1. This product is classified in the Globally Harmonized System as GHS08, which is a Health Hazard. Please see the link below to access the SDS:
      https://www.sigmaaldrich.com/documents-search?tab=sds

      To review the Hazard and Precautionary Statement, please see the link below:
      https://www.sigmaaldrich.com/life-science/safety/hazard-and-precautionary-statements#pictogram

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