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A9789

Sigma-Aldrich

Anisomycin

from Streptomyces griseolus, ≥98% (HPLC), solid, protein synthesis inhibitor

Synonym(s):

(2R,3S,4S)-2-(4-Methoxybenzyl)-3,4-pyrrolidinediol-3-acetate, 2-[(4-Methoxyphenyl)methyl]-3,4-pyrrolidinediol 3-acetate, Flagecidin

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About This Item

Empirical Formula (Hill Notation):
C14H19NO4
CAS Number:
22862-76-6
Molecular Weight:
265.30
Beilstein:
20705
EC Number:
245-269-7
MDL number:
MFCD00077650
UNSPSC Code:
12352200
PubChem Substance ID:
24891496
NACRES:
NA.77

product name

Anisomycin from Streptomyces griseolus, ≥98% (HPLC), solid

Quality Level

300

Assay

≥98% (HPLC)

form

solid

color

white to faint yellow

solubility

H2O: 2 mg/mL (Aqueous solutions are stable over a wide range of pH at room temperature.)
DMSO: 20 mg/mL
methanol: 20 mg/mL

antibiotic activity spectrum

neoplastics

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

COc1ccc(C[C@H]2NC[C@H](O)[C@H]2OC(C)=O)cc1

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

InChI key

YKJYKKNCCRKFSL-RDBSUJKOSA-N

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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.

Caution

Hygroscopic

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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