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ANISOMYCIN

CAS No.
22862-76-6
Chemical Name:
ANISOMYCIN
Synonyms
Nsc76712;Nsc147340;Aids031977;ANISOMYCIN;FLAGECIDIN;Aids-031977;Wuningmeisu C;4-beta))-alph;Anisomycin>(-)-anisomycin
CBNumber:
CB5363672
Molecular Formula:
C14H19NO4
Molecular Weight:
265.3
MDL Number:
MFCD00077650
MOL File:
22862-76-6.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 01:25:39

ANISOMYCIN Properties

Melting point 140-141 C
alpha D23 -30° (methanol)
Boiling point 408.52°C (rough estimate)
Density 1.1356 (rough estimate)
refractive index 1.5230 (estimate)
Flash point 87℃
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility methanol: 20 mg/mL, clear, colorless to faintly yellow
form solid
pka 7.9(at 25℃)
color white
Water Solubility Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
λmax 283nm(EtOH)(lit.)
Merck 14,670
BRN 20705
Stability Stable. Incompatible with strong oxidizing agents.
InChI 1S/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/t12-,13+,14+/m1/s1
InChIKey YKJYKKNCCRKFSL-RDBSUJKOSA-N
SMILES COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1
EWG's Food Scores 1
FDA UNII 6C74YM2NGI
UNSPSC Code 51102829
NACRES NA.85

SAFETY

Risk and Safety Statements

Symbol(GHS)  Skull and Crossbones (GHS06)
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
PPE Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes  T,Xn
Risk Statements  25-36/37/38-20/21/22
Safety Statements  45-36-26
RIDADR  UN 3462 6.1/PG 3
WGK Germany  3
RTECS  BZ9800000
3-10
HazardClass  6.1(b)
PackingGroup  III
HS Code  29419090
Storage Class 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard Classifications Acute Tox. 3 Oral
Toxicity LD50 orl-rat: 72 mg/kg ANTCAO 5,490,55
NFPA 704
0
2 0

ANISOMYCIN price More Price(97)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A9789 Anisomycin from Streptomyces griseolus ≥98% (HPLC), solid 22862-76-6 5mg $62 2026-04-30 Buy
Sigma-Aldrich A5862 Anisomycin, Ready Made Solution from Streptomyces griseolus 22862-76-6 0.5ml $230 2026-04-30 Buy
TCI Chemical A2613 Anisomycin >97.0%(GC) 22862-76-6 25mg $187 2026-04-30 Buy
TCI Chemical A2613 Anisomycin >97.0%(GC) 22862-76-6 100mg $549 2026-04-30 Buy
Cayman Chemical 11308 Anisomycin ≥98% 22862-76-6 5mg $38 2026-04-30 Buy
Product number Packaging Price Buy
A9789 5mg $62 Buy
A5862 0.5ml $230 Buy
A2613 25mg $187 Buy
A2613 100mg $549 Buy
11308 5mg $38 Buy

ANISOMYCIN Chemical Properties,Uses,Production

Description

Anisomycin (22862-76-6) activates JNK/SAPKs and reduces c-fos and c-jun. Protein synthesis inhibitor. Anisomycin induces apoptosis and sensitizes cells to anoikis. Cell permeable.

Chemical Properties

Crystalline

Uses

Anisomycin is a phenylmethylenepyrrolidine first isolated from Streptomyces griseolus in 1954 as an antiprotozoan with antifungal activity. Anisomycin is an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. Interestingly, anisomycin has found use for the induction of amnesia in animal models. More recently, anisomycin has been demonstrated to induce apoptosis, to be a selective signalling agonist, to activate mitogen-activated protein (MAP) kinases and to be immunomodulatory via its action on T cells.

Uses

It is applied as an antiparasitic agent and antineoplastic agent. It acts as a protein synthesis inhibitor (blocks translation), potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. It also scts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD). Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK).

Definition

ChEBI: An antibiotic isolated from various Streptomyces species. It interferes with protein and DNA synthesis by inhibiting peptidyl transferase or the 80S ribosome system.

Biological Activity

Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD).

Biochem/physiol Actions

Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.

Safety Profile

Poison by ingestion,intraperitoneal, subcutaneous, and intravenous routes.When heated to decomposition it emits toxic fumes ofNOx.

storage

+4°C

Background

Anisomycin, an antibiotic produced by Streptomyces griseolus and S. roseochromogenes, was originally described to inhibit protein-protein synthesis at the translational level. More recently, it is has been well characterized to strongly activate the stress kinases SAPK/JNK and p38 MAPK, as well as p70/85 S6 kinase in mammalian cells, which results in the rapid induction of immediate-early genes, such as c-fos, fosB, c-jun, JunB, and JunD. Investigators have demonstrated that anisomycin acts as a potent signaling agonist, synergizing with growth factors and phorbol esters to superinduce these IE genes. Research studies have demonstrated that anisomycin induces apoptosis in many cancer cell lines.

References

[1] C A HAZZALIN. Anisomycin selectively desensitizes signalling components involved in stress kinase activation and fos and jun induction.[J]. Molecular and Cellular Biology, 1998, 18 4: 1844-1854. DOI:10.1128/mcb.18.4.1844
[2] IMTIAZ A MAWJI. A chemical screen identifies anisomycin as an anoikis sensitizer that functions by decreasing FLIP protein synthesis.[J]. Cancer research, 2007, 67 17: 8307-8315. DOI:10.1158/0008-5472.can-07-1687

180081-83-8
22862-76-6
Synthesis of ANISOMYCIN from Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

ANISOMYCIN Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 344)Suppliers
Supplier Tel Email Country ProdList Advantage
Shanghaizehan biopharma technology co., Ltd. 021-61350663 13052117465 sales@zehanbiopharma.com China 989 55
Hubei widely chemical technology Co., Ltd. 027-83991130 18627774460 1718093273@QQ.COM China 1618 58
TargetMol Chemicals Inc. 021-021-33632979 15002134094 marketing@targetmol.com China 7993 58
Wuhan SynBioLily Biotechnology Co.,Ltd. 18971458902 yangsong@synbiolily.com China 482 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 3bsc@sina.com China 15813 69
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Taizhou Chemedir Biopharm-tech. Co., Ltd 0523-86200218 18994667082 sale1_cmd@chemedir.com China 58 64
VDM Biochemicals 0330-2528181 sales@vdmbio.com United States 510 64
Chemsky(shanghai)International Co.,Ltd. 021-50135380 shchemsky@sina.com China 32273 50

View Lastest Price from ANISOMYCIN manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Anisomycin pictures 2025-02-13 Anisomycin
22862-76-6
$1.00 1g 0.98 1000 Apeloa production Co.,Limited
ANISOMYCIN pictures 2021-11-27 ANISOMYCIN
22862-76-6
$8000.00 100g 99.99% 5ton/Month Qiuxian Baitai New Material Co., LTD
ANISOMYCIN pictures 2019-07-06 ANISOMYCIN
22862-76-6
$1.00 1kg 95%-99% 100kg Career Henan Chemical Co
  • Anisomycin pictures
  • Anisomycin
    22862-76-6
  • $1.00
  • 0.98
  • Apeloa production Co.,Limited
  • ANISOMYCIN pictures
  • ANISOMYCIN
    22862-76-6
  • $8000.00
  • 99.99%
  • Qiuxian Baitai New Material Co., LTD
  • ANISOMYCIN pictures
  • ANISOMYCIN
    22862-76-6
  • $1.00
  • 95%-99%
  • Career Henan Chemical Co

ANISOMYCIN Spectrum

(2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-PYRROLIDINEDOIL-3-ACETATE (2R,3S,4S)-2-[(4-METHOXYPHENYL)METHYL]-3,4-PYRROLIDINEDIOL 3-ACETATE 2-(P-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL-3-ACETATE 2-P-METHOXYPHENYLMETHYL-3-ACETOXY-4-HYDROXYPYRROLIDINE 1,4,5-trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate ANISOMYCIN FROM STREPTOMYCES GRISEOLUS 3,4-Pyrrolidinediol, 2-(4-methoxyphenyl)methyl-, 3-acetate, (2R,3S,4S)- (2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate (2R)-2α-(4-Methoxybenzyl)pyrrolidine-3α,4β-diol 3-acetate 1,4-Imino-5-(4-methoxyphenyl)1,4,5-trideoxy-D-xylo-pentitol 3-acetate Acetic acid (2R)-4β-hydroxy-2-(4-methoxybenzyl)pyrrolidin-3α-yl ester 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol-3-acetate D-xylo-Pentitol, 1,4,5-trideoxy-1,4-imino-5-(4-methoxyphenyl)-, 3-acetate Aids031977 Aids-031977 Nsc147340 Nsc76712 (2R,3S,4S)-4-hydroxy-2-(4-Methoxybenzyl)pyrrolidin-3-yl acetate Flagecidin, SA 3097C1, PA 106, Anhydroscopin A, NSC 76712 (2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine Wuningmeisu C (2S,3R,4R)-2-(4-methoxybenzyl)-4-hydroxypyrrolidin-3-yl acetate NSC 76712 Anisomycin Flagecidin Anisomycin, Streptomyces griseolus - CAS 22862-76-6 - Calbiochem FLAGECIDIN;WUNINGMEISU C Anisomycin (Flagecidin 2-((4-methoxyphenyl)methyl)-,3-acetate,(2r-(2-alpha,3-4-pyrrolidinediol 2-(p-methoxybenzyl)-,3-acetate,(2s,3r,4r)-4-pyrrolidinediol 4-beta))-alph antibioticpa-106 ANISOMYCIN ANISOMYCIN, STREPTOMYCES GRISEOLUS FLAGECIDIN (2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL-3-ACETATE Anisomycin, Ready Made Solution from Streptomyces griseolus Anisomycin (from Streptomyces griseolus)≥ 98% (HPLC) Anisomycin, 99%, from Streptomyces griseolus Anisomycin Anisomycin Anisomycin> ANISOMYCIN USP/EP/BP Anisomycin (NSC-76712, AI 3-50846, Flagecidin, Wuningmeisu C) Anisomycin, ≥98% (HPLC) (-)-anisomycin Anisomycin, Protein synthesis inhibitor Anisomycin, 10 mM in DMSO Anisomycin, Ready Made Solution from Streptomyces griseolus Anisomycin from Streptomyces griseolus Anisomycin, Streptomyces griseolus Anisomycin (Synonyms: Flagecidin fromStreptomycesgriseolus 22862-76-6 Antibiotics A to Z Antibiotics A-F Antibiotics BioChemical antibiotic Antibiotics Protein Kinase