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Kanamycin

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Name

Kanamycin

EINECS 200-411-7
CAS No. 59-01-8 Density 1.62g/cm3
PSA 282.61000 LogP -4.49020
Solubility N/A Melting Point N/A
Formula C18H36 N4 O11 Boiling Point 809.5°Cat760mmHg
Molecular Weight 484.504 Flash Point 443.4°C
Transport Information N/A Appearance N/A
Safety Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Risk Codes N/A
Molecular Structure Molecular Structure of 59-01-8 (KANAMYCIN) Hazard Symbols N/A
Synonyms

KanamycinA (7CI);4,6-Diamino-2-hydroxy-1,3-cyclohexane 3,6'-diamino-3,6'-dideoxydi-a-D-glucoside;KM;Kanacin;Kanamycin;

Article Data 14

Kanamycin Synthetic route

Conditions
ConditionsYield
With Amberlite IRA-400-OH In water91%
With Amberlite IRA-400 -OH In water
With Amberlite-IRA 400 (OH-)

C34H46N4O16

A

59-01-8

kanamycin A

B

1-deamino-1-dehydro-1-hydroxyiminokanamycin A

Conditions
ConditionsYield
With hydrogen; acetic acid; palladium In water under 760 Torr; for 2h; Ambient temperature;A 4.7%
B 83%
98084-09-4

6'-N-hydroxykanamicyn A (sulfate)

59-01-8

kanamycin A

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; platinum(IV) oxide In water under 2660 Torr; for 2h; Ambient temperature; Yield given;
80860-34-0

di-tert-butyl ((1S,3R,4S,5R,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,4S,5S,6R)-6-(((tert-butoxycarbonyl)amino)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

59-01-8

kanamycin A

Conditions
ConditionsYield
tetrafluoroboric acid at 20℃; for 0.1h;

1-deamino-1-dehydro-1-hydroxyiminokanamycin A

A

81076-65-5

1-epi-kanamycin A

B

59-01-8

kanamycin A

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen; nickel under 2280 Torr; for 5h; Ambient temperature;
74256-73-8

3,6'-bis(N-benzyloxycarbonyl)-3"-N-(trifluoroacetyl)kanamycin A

59-01-8

kanamycin A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent / sodium tungstate dihydrate, aq. H2O2 / various solvent(s) / Ambient temperature
2: aq. NH4OH / various solvent(s) / Ambient temperature
3: 4.7 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 4 steps
1: 86 percent / sodium tungstate dihydrate, aq. H2O2 / various solvent(s) / Ambient temperature
2: aq. NH4OH / various solvent(s) / Ambient temperature
3: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature
4: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature
View Scheme

C34H46N4O16

59-01-8

kanamycin A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature
2: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature
View Scheme

3,6'-bis(N-benzyloxycarbonyl)-1-deamino-1-dehydro-1-hydroxyimino-3"-N-(trifluoroacetyl)kanamycin A

59-01-8

kanamycin A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NH4OH / various solvent(s) / Ambient temperature
2: 4.7 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature
View Scheme
Multi-step reaction with 3 steps
1: aq. NH4OH / various solvent(s) / Ambient temperature
2: 83 percent / H2, AcOH / Pd black / H2O; various solvent(s) / 2 h / 760 Torr / Ambient temperature
3: H2, aq. NH4OH / Raney Ni / 5 h / 2280 Torr / Ambient temperature
View Scheme

2'-oxokanamycin

59-01-8

kanamycin A

Conditions
ConditionsYield
With His-tagged NADPH-dependent reductase; potassium chloride; glycerol; NADPH at 28℃; pH=7.5; Tris-HCl buffer; Enzymatic reaction; stereoselective reaction;

C22H43N5O13*2H2O4S

59-01-8

kanamycin A

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 20h; Reagent/catalyst; Solvent; Temperature;

Kanamycin Chemical Properties

Product Name: Kanamycin (CAS NO.59-01-8)


Molecular Formula: C18H36N4O11
Molecular Weight: 484.5g/mol
Mol File: 59-01-8.mol
Einecs: 200-411-7
Boiling point: 809.5 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 443.4 °C
Density: 1.62 g/cm3
Surface Tension: 104.4 dyne/cm
Enthalpy of Vaporization: 134 kJ/mol
Vapour Pressure: 2.47E-30 mmHg at 25°C
XLogP3-AA: -6.9
H-Bond Donor: 11
H-Bond Acceptor: 15

Kanamycin Uses

 Kanamycin (CAS NO.59-01-8) is for the production of sulfuric acid amikacin, kanamycin monosulfate, and pairs of kanamycin sulfate intermediates.
It is used in molecular biology as a selective agent most commonly to isolate bacteria (e.g., E. coli) which have taken up genes (e.g., of plasmids) coupled to a gene coding for kanamycin resistance (primarily Neomycin phosphotransferase II [NPT II/Neo]). Bacteria that have been transformed with a plasmid containing the kanamycin resistance gene are plated on kanamycin (50-100mg/L) containing agar plates or are grown in media containing kanamycin (50-100mg/L). Only the bacteria that have successfully taken up the kanamycin resistance gene become resistant and will grow under these conditions. As a powder kanamycin is white to off-white and is soluble in water (50mg/ml).
At least one such gene, Atwbc19 is native to a plant species, of comparatively large size and its coded protein acts in a manner which decreases the possibility of Horizontal Gene Transfer from the plant to bacteria; it may be incapable of giving resistance to kanamycin to bacteria even if gene transfer occurs.

Kanamycin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 1385mg/kg (1385mg/kg)   Antibiotiki. Vol. 19, Pg. 552, 1974.
human TDLo unreported 843mg/kg/17W- (843mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR

SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
American Review of Respiratory Disease. Vol. 82, Pg. 23, 1960.
mouse LD50 intracrebral 33750ug/kg (33.75mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Chemotherapy Vol. 17, Pg. 1664, 1969.
mouse LD50 intramuscular 54mg/kg (54mg/kg)   Bollettino Chimico Farmaceutico. Vol. 98, Pg. 224, 1959.
mouse LD50 intraperitoneal 794mg/kg (794mg/kg)   Chemotherapy Vol. 16, Pg. 371, 1971.
mouse LD50 intravenous 115mg/kg (115mg/kg)   Minerva Farmaceutica. Vol. 11, Pg. 108, 1962.
mouse LD50 oral 20700ug/kg (20.7mg/kg)   Antibiotiki. Vol. 19, Pg. 552, 1974.
mouse LD50 subcutaneous 1350mg/kg (1350mg/kg)   Antimicrobial Agents and Chemotherapy Vol. -, Pg. 341, 1967.
rabbit LD50 intravenous 150mg/kg (150mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 690, 1978.
rat LD50 intramuscular > 1014mg/kg (1014mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Chemotherapy Vol. 29(Suppl,
rat LD50 intraperitoneal 1515mg/kg (1515mg/kg)   Antibiotiki. Vol. 19, Pg. 552, 1974.
rat LD50 intravenous 437mg/kg (437mg/kg)   Chemotherapy Vol. 29(Suppl,
rat LD50 oral > 10gm/kg (10000mg/kg)   Chemotherapy Vol. 29(Suppl,
rat LD50 subcutaneous 4070mg/kg (4070mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 176, Pg. 59, 1968.

Kanamycin Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Kanamycin Safety Profile

Poison by intravenous and intramuscular routes. Moderately toxic by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Kanamycin Specification

 Kanamycin ,its CAS NO. is 59-01-8,the synonyms is Kanamycin a ; Kanamycin base ; 2-Deoxy-y-alpha-d-glucopyranosyl- ; 4,6-Diamino-2-hydroxy-1,3-cyclohexane3,6'diamino-3,6'-dideoxydi-alpha-d-gluc ; 4,6-Diamino-2-hydroxy-1,3-cyclohexane3,6'diamino-3,6'-dideoxydi-alpha-d-glucos ; D-deoxydi ; D-streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1.fwdarw.6)-o-6-amin .

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