CAS No.22862-76-6,ANISOMYCIN Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	22862-76-6
Name:	ANISOMYCIN
Article Data:	8

Formula:	C₁₄H₁₉NO₄
Molecular Weight:	265.309
Synonyms:	3,4-Pyrrolidinediol,2-(p-methoxybenzyl)-, 3-acetate, (2R,3S,4S)- (8CI);3,4-Pyrrolidinediol,2-[(4-methoxyphenyl)methyl]-, 3-acetate, [2R-(2a,3a,4b)]-;Anisomycin (6CI,7CI);(-)-Anisomycin;(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate;(2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine;Anisomycin, (-)-;Flagecidin;NSC 76712;
EINECS:	245-269-7
Density:	1.21 g/cm³
Melting Point:	140-141 °C
Boiling Point:	398.7 °C at 760 mmHg
Flash Point:	194.9 °C
Solubility:	Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
Appearance:	White crystalline solid
Hazard Symbols:	T, Xn
Risk Codes:	25-36/37/38-20/21/22
Safety:	45-36-26
Transport Information:	UN 3462 6.1/PG 3
PSA:	67.79000
LogP:	0.83090

Synthetic route

: 27958-08-3
(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 0.25h;	95%

: 180081-83-8
(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 20℃;	88%

: 1262850-97-4
C19H27NO6

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogenchloride In methanol	78%

: 933992-79-1
(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; water for 3h; Yield given;

: 87796-48-3
(2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1.) MeOH, reflux, 2.) MeOH; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating 2: HCl, H2 / palladium-charcoal 10percent / methanol; H2O / 3 h View Scheme

: 173266-54-1
Acetic acid (1S,2R)-2-azido-1-((R)-2-bromo-1-hydroxy-ethyl)-3-(4-methoxy-phenyl)-propyl ester

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With sodium acetate In methanol for 10h; Heating; Yield given;

: C21H21NO5

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol; acetic acid at 20℃; under 3878.71 Torr; for 24h;	76 mg

: 951385-80-1
(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C 2: 98 percent / pyridine / CH2Cl2 3: O3; O2 / methanol / -78 °C 4: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr View Scheme

: 951385-97-0
C20H21NO3

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / pyridine / CH2Cl2 2: O3; O2 / methanol / -78 °C 3: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr View Scheme

: 951385-93-6
(4R,5S,6S)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazin-5-yl acetate

: 22862-76-6
(-)-anisomycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: O3; O2 / methanol / -78 °C 2: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr View Scheme

Raw Materials

19764-32-0

824-94-2

38769-92-5

922-65-6

556-02-5

17355-24-7

Total:76 Page 1 of 2 1 2 Next>>

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Chemistry

Molecular Formula: C₁₄H₁₉NO₄
Molar mass: 265.305 g/mol
EINECS: 245-269-7
Form: Solid
Color: White
Density: 1.21 g/cm³
Flash Point: 194.9 °C
Melting point: 140-141 °C
Storage temp: 2-8 °C
Appearance: Crystalline
Index of Refraction: 1.557
Boiling Point: 398.7 °C at 760 mmHg
Vapour Pressure: 4.5E-07 mmHg at 25 °C
Solubility: Methanol: 20 mg/mL, clear, colorless to faintly yellow
Stable: Stable. Incompatible with strong oxidizing agents.
Product categories of Anisomycin (CAS NO.22862-76-6): Antibiotics;Protein Kinase
Structure of Anisomycin (CAS NO.22862-76-6):

Uses

Anisomycin (CAS NO.22862-76-6) has wide usage as a protein biosynthesis inhibitor. It is used as a component of Martin Lewis Agar, an in- vitro diagnostic product which is used extensively in the United States for the selective isolation of Neisseria gonorrhoeae and Neisseria meningitidis. Mawji et al. showed that anisomycin can sensitize metastatic epithelial cells to anoikis and reduce circulating tumor cell implantation in vivo by using a novel high-throughput screening assay. Anisomycin achieved this anti-metastatic activity in part by decreasing the abundance of the death receptor inhibiting protein FLIP.

Production

Although pyrrolidine-based structure of Anisomycin (CAS NO.22862-76-6) suggests that it is derived from proline, the results from the experiments indicated that tyrosine, glycine, methionine, and acetate are the primary precursors for the biosynthesis of anisomycin. The methord is:

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD	oral	> 200mg/kg (200mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog	LD	intramuscular	> 100mg/kg (100mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog	LD	intravenous	> 100mg/kg (100mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog	LD	oral	> 300mg/kg (300mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
guinea pig	LDLo	oral	300mg/kg (300mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey	LD	intramuscular	> 50mg/kg (50mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey	LD	oral	> 300mg/kg (300mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey	LDLo	intravenous	200mg/kg (200mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse	LD50	intraperitoneal	400mg/kg (400mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse	LD50	intravenous	10mg/kg (10mg/kg)		"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 77, 1981.
mouse	LD50	oral	148mg/kg (148mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse	LD50	subcutaneous	600mg/kg (600mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rabbit	LD	oral	> 200mg/kg (200mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat	LD50	intraperitoneal	345mg/kg (345mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat	LD50	intravenous	167mg/kg (167mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat	LD50	oral	72mg/kg (72mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat	LD50	subcutaneous	230mg/kg (230mg/kg)		Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.

Safety Profile

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

Hazard Codes: Toxic T Harmful Xn
Risk Statements: 25-36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R25 :Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 45-36-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Specification

Anisomycin ,its cas register number is 22862-76-6. It also can be called Flagecidin ; 4-Hydroxy-2-(4-methoxybenzyl)-3-pyrrolidinylacetat ; Acétate de 4-hydroxy-2-(4-méthoxybenzyl)-3-pyrrolidinyle and 3,4-pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate . It is inactive against bacteria, and can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis.