ChemicalBook >> CAS DataBase List >>Cordycepin

Cordycepin

CAS No.
73-03-0
Chemical Name:
Cordycepin
Synonyms
Cipargamin;3'-dA;chongcaoduitang;Adenine cordyceposide;NSC 63984;CORDYCEPIN;NSC 401022;Cordycepine;Cordycepin-RM;Cordycepin >
CBNumber:
CB2190747
Molecular Formula:
C10H13N5O3
Molecular Weight:
251.24
MDL Number:
MFCD00037998
MOL File:
73-03-0.mol
MSDS File:
SDS
Last updated:2024-12-18 14:07:02

Cordycepin Properties

Melting point 225-229 °C
alpha D20 -47°; D27 -42°
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,Store in freezer, under -20°C
solubility Soluble in DMSO (up to 25 mg/ml).
form Powder
pka 13?+-.0.60(Predicted)
color White to Off-white
λmax 260nm(EtOH)(lit.)
Merck 14,2529
BRN 35194
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChIKey OFEZSBMBBKLLBJ-BAJZRUMYSA-N
CAS DataBase Reference 73-03-0(CAS DataBase Reference)
NCI Dictionary of Cancer Terms cordycepin
FDA UNII GZ8VF4M2J8
NCI Drug Dictionary cordycepin
EPA Substance Registry System Adenosine, 3'-deoxy- (73-03-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301+H311+H331
Precautionary statements  P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
Hazard Codes  Xn,T
Risk Statements  40-36/37/38-25-20/21/22
Safety Statements  22-36-45-26
RIDADR  UN 2811
WGK Germany  3
RTECS  AU7358610
10-21
HazardClass  6.1
HS Code  29349990
NFPA 704
0
2 0

Cordycepin price More Price(60)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich C3394 Cordycepin from Cordyceps militaris 73-03-0 10mg $144 2024-03-01 Buy
Sigma-Aldrich C3394 Cordycepin from Cordyceps militaris 73-03-0 25mg $282 2024-03-01 Buy
TCI Chemical C2689 Cordycepin from Cordyceps militaris >98.0%(HPLC) 73-03-0 25mg $158 2024-03-01 Buy
Alfa Aesar J65366 3'-Deoxyadenosine, 98% 73-03-0 25mg $160.65 2024-03-01 Buy
Alfa Aesar J65366 3'-Deoxyadenosine, 98% 73-03-0 100mg $437.65 2024-03-01 Buy
Product number Packaging Price Buy
C3394 10mg $144 Buy
C3394 25mg $282 Buy
C2689 25mg $158 Buy
J65366 25mg $160.65 Buy
J65366 100mg $437.65 Buy

Cordycepin Chemical Properties,Uses,Production

Plant extracts

In 1951, German scientist Cunningham had purified a crystal from the Cordyceps militaris and named it cordycepin. From then on, the crordycepin reported in published literature abroad regarding to its antitumor, antiviral efficacy as well as extraction and purification had been all obtained from Cordyceps instead of being from Cordyceps sinensis which contains only trace amount of Cordycepin.
Cordyceps is the major active ingredient contained in Cordyceps (especially nucleoside). It belongs to a kind of nucleoside drugs, purine alkaloids and is also the first kind of nuclear glycosides antibiotics isolated from fungus. Owing to its special efficacy in repairing cells and protection of the genetic code of life, it has become one of the leaders in modern biomedicine. Cordycepin is a drug of natural source with various kinds of pharmacological effects such as anti-tumor, antibacterial and antiviral, immunomodulatory as well as free radical-scavenging, etc., and has good prospects for clinical application. At present time, the research on cordycepin present study is becoming an extremely active area in the field of pharmaceutical chemistry.
As a structural analogue of adenosine, cordycepin can inhibit Bacillus subtilis, Mycobacterium tuberculosis of birds and Ehrlich ascites tumor cells with inhibitory effect on the RNA and DNA synthesis inhibition of cancer cells, therefore having very strong inhibitory effect on the human nose and pharynx cancer (KD) cells. The clinically applied cordycepin is mostly used for adjuvant treatment of malignant tumors with the cases of improved clinical symptoms accounting for more than 91.7%; it is mainly used for the treatment of patients of nasal cancer, throat cancer, lung cancer, leukemia, brain cancer and other malignant tumor.
Cordycepin is extracted from the Cordyceps and is the mostly nutritious active substance inside Cordyceps. Its major composition is Cordyceps polysaccharide, Cordyceps acid as well as Cordyceps SOD and is a kind of natural nutrients of high health function. It can activate dormant cells, repair diseased cells, propagate the new living cells, clean up dead cells and is of great value in improving immunity, anti-fatigue as well as improving the body's energy.

Pharmacological effects

Most currently known Cordyceps fungus contains Cordycepin, which obviously plays an important role in the anti-tumor effect. Jagger believes the cordycepin contained in Cordyceps fungus can inhibit tumorigenesis through three possible mechanisms:
1. The free alcoholic group contained in cordycepin can be incorporated into the DNA of cancer cells and takes effect.
2. Cordycepin can inhibit the phosphorylation of nucleoside or nucleotide to generate the derivatives of diphosphate and triphosphate, thereby inhibiting the synthesis of nucleic acids in tumor cell.
3. Cordycepin can block the amination of xanthylic acid into guanylate.
In 1977, Müller et al found that cordycepin had strong inhibitory effect against the proliferation of L5718Y cell with the ED50 being 0.27μg; this inhibitory effect can be eliminated by adenosine but not 2'-deoxy-nucleosides; The tritium marked Cordyceps trial have showed that cordycepin can be incorporated into RNA rather than DNA. The cordycepin, inside the cell, can be phosphorylated to 3'-ATP; 3'-ATP has no effect on the activity of the DNA-dependent DNA polymerase α and β in L5718Y cells, but has strong inhibitory effect on the nuclear Poly (a) polysaccharide which will inevitably lead to a maturation defect of mRNA, further negatively affecting the formation of mRNA and protein synthesis. The anti-tumor effects of Cordyceps may be related to this mechanism. In 1997, the United States has applied cordycepin to third-period clinical trials for the treatment of pre-B and pre-T acute lymphocytic leukemia, while cordycepin also exhibit strong anti-fungal, anti-HIV viral and selective inhibition activity on the activity of Clostridium genus.
In 1985, with in vitro experiments, Jiang ping et al observed the cytotoxicity of Cordyceps sinensis and cultured mycelium (Qinghai) on ECA cells. For the treatment of in vitro cell culture ECA, the result showed that when they two were at the lowest effective concentration 0.405mg/ml and 25mg/ml, the total infection rate was 100%, 80%, respectively, indicating that the drug has different strengths of ECA cytotoxicity. Comprehensive in vivo tests speculated that the anti-tumor effect is correlated with the certain amount of 3'-deoxy-nucleosides contained in the drug and Cordyceps polysaccharides as well as the relative balance between the overall immune regulatory function of the drugs and its effect of maintaining body immunity. Cordyceps sinensis has certain cytotoxic effect, which is consistent with the report regarding to the strong cytotoxicity of cordycepin-resistant L1210.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Uses

Cordycepin is known to have various kinds of effects of improving immune skill, anti-aging, anti-fatigue, anti-cancer, anti-bacterial, anti-virus, lowering blood glucose and lipid and male hormone.

Description

Cordycepin (73-03-0) is an adenosine analog lacking the hydroxyl at the 3’ position. Inhibits PARP1?and polyadenylation2. Displays anti-inflammatory effects1,3?and neuroprotective effects by inhibiting Aβ-induced apoptosis in hippocampal neurons4. Induces apoptosis in a variety of cancer cell lines5. Displays antiobesity effects.6?Inhibits cell senescence via activation of AMPK.7?Maintains stem cell pluripotency and increases iPS cell generation efficiency.8

Chemical Properties

Crystalline Solid

Uses

First reported nucleoside antibiotic.

Definition

ChEBI: Cordycepin is a 3'-deoxyribonucleoside and a member of adenosines. It has a role as an antimetabolite and a nucleoside antibiotic.

General Description

Chemical structure: nucleoside

Biological Activity

Nucleoside analog that acts as an anticancer and antifungal agent. Can be converted to 3'-deoxyadenosine triphosphate (3'-dATP), which inhibits ATP-dependent DNA synthesis. Inhibits growth of various tumor cells in vitro .

Biochem/physiol Actions

Cordycepin is an adenosine analogue that is readily converted to cordycepin 5′-triphosphate; can be used for 3′-end labeling of RNA.

storage

Store at +4°C

Purification Methods

3'-Deoxyadenosine forms needles from EtOH, n-BuOH and n-PrOH, and a monohydrate from H2O. It has max 260nm ( 14,600) in EtOH. The picrate has m 195o(dec, yellow crystals from H2O). [Kaczka et al. Biochim Biophys Acta 14 456 1964, Todd & Ulbricht J Chem Soc 3275 1960, Lee et al. J Am Chem Soc 83 1906 1961, Walton et al. J Am Chem Soc 86 2952 1964, Beilstein 26 III/IV 3594.]

References

1) Kim?et al. (2011),?Cordycepin blocks lung injury-associated inflammation and promotes BRCA1-deficient breast cancer cell killing by effectively inhibiting PARP; Mol. Med.?17?893 2) Kondrashov?et al.?(2012),?Inhibition of polyadenylation reduces inflammatory gene induction; RNA?18?2236 3)Yang?et al.?(2017),?Cordycepin inhibits LPS-induced inflammatory response by modulating NOD-Like Receptor Protein 3 inflammasome activation; Biomed. Pharmacother.?95?1777 4) Song?et al.?(2018),?Neuroprotective effects of cordycepin inhibit Aβ-induced apoptosis in hippocampal neurons; Neurotoxicology?68?73 5) Zhang?et al.?(2018),?Cordycepin induces apoptosis in human pancreatic cancer cells via the mitochondrial-mediated intrinsic pathway and suppresses tumor growth in vivo; OncoTargets Ther.?11?4479 6) Li?et al.?(2018),?Cordycepin modulates body weight by reducing prolactin via an adenosine A1 receptor; Curr. Pharm. Des.,?24?3240 7) Wang?et al?(2019)?Cordycepin prevents radiation ulcer by inhibiting cell senescence via NRF2 and SMPK in rodents;?Nat. Commun.?10?2538 8) Wang?et al.?(2020)?The novel application of cordycepin in maintaining stem cell pluripotency and increasing iPS cell generation efficiency; Sci. Rep.?10?2187

71196-28-6
73-03-0
Synthesis of Cordycepin from Adenosine, 3'-deoxy-, 2',5'-diacetate

Cordycepin Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 516)Suppliers
Supplier Tel Email Country ProdList Advantage
Chengdu Hepu Pharmaceutical Technology Co. , Ltd
+undefined13981809616 2041948498@qq.com China 5 58
Shaanxi Dideu Medichem Co. Ltd
+86-29-81148696 +86-15536356810 1022@dideu.com China 3882 58
Hebei Mojin Biotechnology Co., Ltd
+86 13288715578 +8613288715578 sales@hbmojin.com China 12834 58
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325 sales1@chuanghaibio.com China 5889 58
Wuhan Haorong Biotechnology Co.,ltd
+86-18565342920; +8618565342920 sales@chembj.net China 289 58
Hebei Zhuanglai Chemical Trading Co Ltd
+86-16264648883 +86-16264648883 niki@zlchemi.com China 2691 58
Capot Chemical Co.,Ltd.
+86-(0)57185586718 +86-13336195806 sales@capot.com China 29791 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21634 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 FandaChem@Gmail.com China 9087 55
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795 ivan@atkchemical.com China 32957 60

View Lastest Price from Cordycepin manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Cordycepin Powder pictures 2024-12-23 Cordycepin Powder
73-03-0
US $150.00 / kg 1kg 99% 500kg Hebei Zhuanglai Chemical Trading Co Ltd
Cordycepin pictures 2024-12-20 Cordycepin
73-03-0
US $0.00-0.00 / kg 1kg ≥98% HPLC 1000kg Changsha Staherb Natural Ingredients Co., Ltd.
Cordycepin pictures 2024-12-06 Cordycepin
73-03-0
US $0.00-0.00 / KG 1KG 99% 5000 Wuhan Haorong Biotechnology Co.,Ltd
  • Cordycepin pictures
  • Cordycepin
    73-03-0
  • US $0.00-0.00 / kg
  • ≥98% HPLC
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Cordycepin pictures
  • Cordycepin
    73-03-0
  • US $0.00-0.00 / KG
  • 99%
  • Wuhan Haorong Biotechnology Co.,Ltd

Cordycepin Spectrum

CORDYCEPIN 3’-deoxy-adenosin 9-cordyceposidoadenine 3'-DEOXYADENOSINE Cordycepin from Cordyceps militaris 9-(3-deoxypentofuranosyl)-9H-purin-6-amine cordycepin crystalline 9-(3-Deoxy-b-D-erythro-pentofuranosyl)-9H-purin-6-amine 9-(3-Deoxy-b-D-ribofuranosyl)adenine Cordycepine NSC 401022 NSC 63984 Adenosine, 3-deoxy- 3'-Deoxy-D-adenosine 3-Deoxyribosyl adenine 4-[3-(4-Hydroxy-2-methylphenyl)-1,1-dioxobenzo[c]oxathiol-3-yl]-3-methylphenol 9-[3-Deoxy-3-(hydroxymethyl)-b-D-erythrofuranosyl]adenine Adenosine 3'-deoxyriboside Cresolsulphonephthalein CORDYECEPIN (3''-DEOXYADENOSINE) β-D-erythro-Pentofuranoside,adenine-9 3-deoxy- 9-(3-Deoxy--D-erythro-pentofuranosyl)-9H-purin-6-amine 9-(3-Deoxy--D-ribofuranosyl)adenine 9-(.beta.-d-3'-deoxyribofuranosyl)adenine adenosine, 3'-deoxy- (8ci9ci) Cordyceps sinensis(Berk. )Sacc CORDYCEPIN [3''-DEOXYADENOSINE] 3'-Deoxyadenosine, 9CI,8CI 9-Cordyceposidoadenosine Cordycepin Hydrate (2R,3R,5S)-2-(6-aMino-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3-ol TIANFU-CHEM - Cordycepin Cordycepin USP/EP/BP Cordycepin powder USP/EP/BP 3’-Deoxyadenosine, Cordycepine Cordycepin,HPLC≥98% Cordycepin > Cordycepin Hydrate> CORDYCEPIN_73-03-0 3'-Deoxyadenosine(cordycepin) 3'-dA Cipargamin Adenine cordyceposide chongcaoduitang 2-ACETYL-5-CHLORO-112-METHYLTHIANAPHTHENE Cordyceps Mycelia powder Cordyceps Sinensis fruiting body 3'-Deoxyadenosine Cordycepin-RM Cordycepin in Water 73-03-0 73-03-3 BioChemical Antibiotics A-F Antibiotics A to Z Antibiotics Miscellaneous Natural Products Bases & Related Reagents