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2'-Deoxyadenosine

CAS No.
958-09-8
Chemical Name:
2'-Deoxyadenosine
Synonyms
DA;DEOXYADENOSINE;IFN-α;(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol;2'-dA;-dA CEP;2'-dA·H2O;DESOXYADENOSINE;8-Bromo-2’8-Amino-2&rsquo
CBNumber:
CB7162318
Molecular Formula:
C10H13N5O3
Molecular Weight:
251.24
MDL Number:
MFCD00005754
MOL File:
958-09-8.mol
MSDS File:
SDS
Last updated:2024-10-31 20:01:59

2'-Deoxyadenosine Properties

Melting point 187-189 °C
Boiling point 394.4°C (rough estimate)
Density 1.2938 (rough estimate)
refractive index 1.7610 (estimate)
storage temp. Keep in dark place,Inert atmosphere,2-8°C
solubility DMSO (Slightly), Methanol (Slightly), Water (Slightly)
pka pK1:3.8(+1) (25°C,μ=0.1)
form powder
color White
PH 3.8
Water Solubility Soluble in water and caustic soda.
λmax 258 (pH 2);260 (pH 7)
Stability Hygroscopic
InChI InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1
InChIKey OLXZPDWKRNYJJZ-RRKCRQDMSA-N
SMILES OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)C[C@@H]1O
CAS DataBase Reference 958-09-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII P582C98ULC
NIST Chemistry Reference Deoxyadenosine(958-09-8)
EPA Substance Registry System Adenosine, 2'-deoxy- (958-09-8)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310
RIDADR  2811
WGK Germany  3
RTECS  AU7358600
10-23
TSCA  Yes
HazardClass  6.1
PackingGroup 
HS Code  2934999090
NFPA 704
1
1 0

2'-Deoxyadenosine price More Price(34)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical D4137 2'-Deoxyadenosine Anhydrous >98.0%(HPLC)(T) 958-09-8 5g $131 2024-03-01 Buy
Alfa Aesar J63886 2'-Deoxyadenosine, 99% 958-09-8 50g $275 2024-03-01 Buy
Alfa Aesar J63886 2'-Deoxyadenosine, 99% 958-09-8 100g $515 2024-03-01 Buy
Alfa Aesar J63886 2'-Deoxyadenosine 99% 958-09-8 5g $28.65 2024-03-01 Buy
Alfa Aesar J63886 2'-Deoxyadenosine 99% 958-09-8 25g $151 2024-03-01 Buy
Product number Packaging Price Buy
D4137 5g $131 Buy
J63886 50g $275 Buy
J63886 100g $515 Buy
J63886 5g $28.65 Buy
J63886 25g $151 Buy

2'-Deoxyadenosine Chemical Properties,Uses,Production

Description

2'-Deoxyadenosine is a natural deoxyribonucleoside, which is a structural fragment of deoxyribonucleic acid DNA. It is a purine nucleoside component of DNA comprised of adenosine linked by its N9 nitrogen to the C1 carbon of deoxyribose. Like other natural nucleosides, it is involved in the transmission of genetic information in almost all biological cells, affecting protein synthesis and polysaccharide. It plays a very important role in regulating the growth, proliferation, differentiation and inhibition of cells in vivo.

Uses

2'-Deoxyadenosine is used in paradoxical stimulation study of human sperm motility. It plays an essential role as sperm motility stimulants used in sperm micro-injection on mouse and human embryo development. It finds an application in some cells as an energy source under energy stress conditions. It is involved in various biological processes to compare the functions of adenosine analogues.

Definition

ChEBI: 2'-deoxyadenosine is a purine 2'-deoxyribonucleoside having adenine as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines 2'-deoxy-D-ribonucleoside and a purine 2'-deoxyribonucleoside.

Preparation

2'-deoxyadenosine synthesis: esterification of adenosine, acylation of an acylating agent and an acid binding agent to obtain an acylate; the obtained acylate is then subjected to reduction and purification to obtain 2'-deoxyadenosine. The esterification agent used in the esterification process is dialkyl tin oxide, 2'-O-p-toluenesulfonyladenosine is synthesized from adenosine, and 2'-deoxyadenosine is synthesized from 2'-O-p-toluenesulfonyladenosine glycosides.

Biological Functions

2'-Deoxyadenosine (Deoxyadenosine) is a critical component of DNA. When present in sufficiently high levels, deoxyadensoine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels.

Biological Activity

2'-Deoxyadenosine is a deoxyribonucleoside and an intermediate in the purine nucleotide degradation pathway. It is transported into cells via facilitated diffusion or formed within cells by degradation of S-adenosylhomocysteine or AMP and is removed from cells by purine metabolism or is converted into adenine nucleotides. 2'-Deoxyadenosine has been used in the characterization of DNA conformations and the synthesis of nucleoside analogs as antiviral agents.

Source

2'-Deoxyadenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). 2'-Deoxyadenosine is a natural product found in Streptomyces jiujiangensis, Fritillaria przewalskii, and other organisms with data available.

258529-66-7
958-09-8
Synthesis of 2'-Deoxyadenosine from 9H-Purin-6-amine, 9-[2-deoxy-3,5-O-[1,1,3,3-tetrakis(1-methylethyl)-1,3-disiloxanediyl]-β-L-erythro-pentofuranosyl]-
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View Lastest Price from 2'-Deoxyadenosine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2'-Deoxyadenosine pictures 2024-11-03 2'-Deoxyadenosine
958-09-8
US $0.00-0.00 / g 10g 99% HPLC 10000 HangZhou RunYan Pharma Technology Co.,LTD.
2'-Deoxyadenosine pictures 2024-11-02 2'-Deoxyadenosine
958-09-8
US $1.00 / g 10g ≥98% 10kgs/month WUHAN FORTUNA CHEMICAL CO., LTD
2'-Deoxyadenosine pictures 2024-10-31 2'-Deoxyadenosine
958-09-8
US $55.00-39.00 / mg 99.85% 10g TargetMol Chemicals Inc.
  • 2'-Deoxyadenosine pictures
  • 2'-Deoxyadenosine
    958-09-8
  • US $0.00-0.00 / g
  • 99% HPLC
  • HangZhou RunYan Pharma Technology Co.,LTD.
(2R,3S,5R)-5-(6-AMINO-PURIN-9-YL)-2-HYDROXYMETHYL-TETRAHYDRO-FURAN-3-OL 2'-DEOXYADENOSINE 2'-DEOXY-D-ADENOSINE 2'-Deoxyadenosineanhydrous 2'-dA·H2O 2'-Deoxy-a-adenosine 2’-deoxy-adenosin 9-(2-Deoxy-beta-D-erythro-pentofuranosyl)adenine 9H-Purin-6-amine, 9-(2-deoxy-beta-D-erythro-pentofuranosyl)- 9H-Purin-6-amine, 9-(2-deoxy-beta-D-ribofuranosyl)- Adenine deoxy nucleoside Adenine deoxyribonucleoside 2''-DEOXYADENOSINE (isolated from DNA) adeninedeoxyribonucleoside adeninedeoxyribose Adenosine, 2'-deoxy- Adenyldeoxyriboside beta-D-Erythro-Pentofuranoside, adenine-9 2-deoxy- beta-D-Ribofuranose, 1-(6-amino-9H-purin-9-yl)-1,2-dideoxy- ADENINE DESOXYRIBOSIDE DEOXYADENOSINE-2' DESOXYADENOSINE 9-(2'-DEOXY-BETA-D-RIBOFURANOSYL)ADENINE 2-Methoxy 2&rsquo N6-Benzoyl-8-benzyloxy-2&rsquo 3-Deaza-3-methyl-2&rsquo -dA CEP 2'-Deoxyadenosine(Da) N6-(6-Aminohexyl)-2&rsquo -deoxyadenosine-13C2,15N 6-N-Acyl-6-N-methyl-2&rsquo 8-Bromo-2&rsquo N6-Benzoyl-8-oxo-2&rsquo 8-Amino-2&rsquo 2-Amino-N2-isobutyryl-2&rsquo 2-Amino-5&rsquo -O-(dimethoxytrityl)-N6-(dimethylaminomethylidene)-N2-isobutyryl-2&rsquo 8-Bromo-N6-(dimethylaminomethylidene)-2&rsquo N6-Benzoyl-5&rsquo -O-(dimethoxytrityl)-8-oxo-2&rsquo 2-Fluoro-2&rsquo 8-Azido-2&rsquo 7-(3-Nitrophenyl)-7-deaza-2&rsquo 2'-Deoxyadenosine anhydrate 2'-DeoxyadenosineAnhydrous> 2'-Deoxyadenosine USP/EP/BP 2'-Deoxyadenosine-WIDELY (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol DA DEOXYADENOSINE IFN-α 2'-Deoxyadenosine(2'-dA) Rabbit Interferon Alpha (IFNa)ELISA Kit Monkey Interferon Alpha (IFNa)ELISA Kit 2'-Deoxyadenosine Anhydrous, ≥ 98.0% 2'-Deoxyadenosine 2'-Deoxyadenosine(2'-dA) 2'-Deoxyadenosine Anhydrous