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A9789

Sigma-Aldrich

Anisomycin from Streptomyces griseolus

≥98% (HPLC), solid

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

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)

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