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14487-05-9

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14487-05-9 Usage

Chemical Properties

Yellow Solid

Uses

Rifamycin O (Rifaximin EP Impurity F) is a Rifaximin intermediate.

Check Digit Verification of cas no

The CAS Registry Mumber 14487-05-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,4,8 and 7 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14487-05:
(7*1)+(6*4)+(5*4)+(4*8)+(3*7)+(2*0)+(1*5)=109
109 % 10 = 9
So 14487-05-9 is a valid CAS Registry Number.
InChI:InChI:1S/C39H47NO14/c1-17-11-10-12-18(2)37(48)40-24-15-39(51-16-26(42)53-39)29-27(33(24)46)32(45)22(6)35-28(29)36(47)38(8,54-35)50-14-13-25(49-9)19(3)34(52-23(7)41)21(5)31(44)20(4)30(17)43/h10-15,17,19-21,25,30-31,34,43-45H,16H2,1-9H3,(H,40,48)/b11-10-,14-13-,18-12-

14487-05-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name rifamycin O

1.2 Other means of identification

Product number -
Other names Rifomycin O

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:14487-05-9 SDS

14487-05-9Synthetic route

Rifamycin B
13929-35-6

Rifamycin B

rifamycin O
14487-05-9

rifamycin O

Conditions
ConditionsYield
With air Ambient temperature;80%
Conditions
ConditionsYield
With ammonium persulfate In methanol; aq. phosphate buffer at 60℃; for 4h; Solvent; Reagent/catalyst;
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

rifamycin O
14487-05-9

rifamycin O

4-(2-methoxy-phenylimino)-1-oxo-1,4-dihydro-1,4-dideoxy-rifamycin
51756-76-4

4-(2-methoxy-phenylimino)-1-oxo-1,4-dihydro-1,4-dideoxy-rifamycin

Conditions
ConditionsYield
In methanol
rifamycin O
14487-05-9

rifamycin O

(12S,3E,5S,13E,15Z)-7t-acetoxy-15,6,9c,11t-tetrahydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-11,17-dioxo-11,2-dihydro-2-oxa-18-aza-1(2,7)-naphtho[2,1-b]furana-cyclooctadecaphane-3,13,15-triene-19-diazonium betaine

(12S,3E,5S,13E,15Z)-7t-acetoxy-15,6,9c,11t-tetrahydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-11,17-dioxo-11,2-dihydro-2-oxa-18-aza-1(2,7)-naphtho[2,1-b]furana-cyclooctadecaphane-3,13,15-triene-19-diazonium betaine

Conditions
ConditionsYield
With toluene-4-sulfonic acid hydrazide In methanol
rifamycin O
14487-05-9

rifamycin O

(16ξH)-16,17,18,19-tetrahydro-4-deoxy-rifamycin
52137-32-3

(16ξH)-16,17,18,19-tetrahydro-4-deoxy-rifamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TsNHNH2 / methanol
2: H2 / Pd-C / ethyl acetate
View Scheme
2-Amino-4-methylpyridine
695-34-1

2-Amino-4-methylpyridine

rifamycin O
14487-05-9

rifamycin O

rifaximin

rifaximin

Conditions
ConditionsYield
Stage #1: 2-Amino-4-methylpyridine; rifamycin O In ethanol; water at 47℃; for 5h;
Stage #2: With ascorbic acid In ethanol; water at 20℃; for 1h;
Stage #3: With hydrogenchloride In ethanol; water at 20℃; for 0.5h; pH=2;
In ethanol; water at 20 - 47℃;
In water; isopropyl alcohol at 20℃; for 16h; Reagent/catalyst; Solvent;
Conditions
ConditionsYield
In aq. phosphate buffer; dimethyl sulfoxide at 60℃; for 1h; pH=7.5; pH-value; Temperature;
rifamycin O
14487-05-9

rifamycin O

C44H52N4O11

C44H52N4O11

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: trifluoroacetic acid / dichloromethane
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-[(4-methyl-1-piperazinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-[(4-methyl-1-piperazinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile / 1 h / 20 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-[(1-piperidinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-[(1-piperidinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile / 3.5 h / 20 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-[(N,N-dimethylamino)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-[(N,N-dimethylamino)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile / 3.5 h / 20 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-[(4-carboxyamidopyridyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-[(4-carboxyamidopyridyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile / 18 h / 20 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-[(4-methyl-1-piperazinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S

4'-[(4-methyl-1-piperazinyl)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile / 1 h / 20 °C
5: manganese(IV) oxide / dichloromethane / 0.5 h / 20 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-formyl-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-formyl-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
View Scheme
rifamycin O
14487-05-9

rifamycin O

4'-formyl-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S

4'-formyl-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
View Scheme
rifamycin O
14487-05-9

rifamycin O

C44H52N4O12

C44H52N4O12

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: ethanol / 4 h / 70 °C
2: manganese(IV) oxide / dichloromethane / 1 h / 40 °C
3: ascorbic acid / acetonitrile
4: acetonitrile
View Scheme
5-(N,N-dimethylamino)iminomethyl-2-aminopyridine

5-(N,N-dimethylamino)iminomethyl-2-aminopyridine

rifamycin O
14487-05-9

rifamycin O

5'-[(N,N-dimethylamino)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

5'-[(N,N-dimethylamino)iminomethyl]-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
In ethanol for 10h;0.13 g
rifamycin O
14487-05-9

rifamycin O

2-amino-4-hydroxymethylpyridine
105250-17-7

2-amino-4-hydroxymethylpyridine

4'-methylol-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

4'-methylol-4-desoxypyrido[1',2'-1,2]imidazo[5,4-c]rifamycin SV

Conditions
ConditionsYield
In ethanol at 70℃; for 4h;3.6 g

14487-05-9Relevant articles and documents

Comprehensive study on structure-activity relationships of rifamycins: Discussion of molecular and crystal structure and spectroscopic and thermochemical properties of rifamycin O

Bacchi, Alessia,Pelizzi, Giancarlo,Nebuloni, Marino,Ferrari, Pietro

, p. 2319 - 2332 (1998)

The mechanism of action of rifamycins against bacterial DNA-dependent RNA polymerase has been explained on the basis of the spatial arrangement of four oxygens which can form hydrogen bonds with the enzyme. Structural descriptors are derived from X-ray diffraction crystal structures of 25 active and nonactive rifamycins. Principal component analysis is used to find the combination of structural parameters which better discriminate between active and nonactive rifamycins. Two possible mechanisms of molecular rearrangement are described which can convert nonactive into active conformations. The energy involved for conformational rearrangements is studied by molecular modeling techniques. Methyl C34 is found to play a key role for determining the geometry of the pharmacophore. Rifamycin O, reported to be active, is obtained by oxidation of rifamycin B and is studied by X- ray single-crystal diffractometry, by solution IR and NMR spectroscopy, and by thermal analysis. Surprisingly the oxidation process is totally stereospecific, and an explanation is given based on solution spectroscopic evidence. The conformation found in the solid state is typical of nonactive compounds, and molecular mechanics calculations show that a molecular rearrangement to the active conformation would require about 15 kcal/mol. Thermal analysis confirms that rifamycin O has a sterically constrained conformation. Therefore, it is likely that the antibiotic activity of rifamycin O is due either to chemical modification prior to reaching the enzyme or to conformational activation.

A FACILE PREPARATION OF RIFAMYCIN DERIVATIVES BY USE OF MANGANESE DIOXIDE

Seong, Baik Lin,Han, Moon Hi

, p. 627 - 628 (2007/10/02)

Rifamycin O, rifamycin S and rifamycin SV were prepared in good yields (88-94percent) by the oxidation and hydrolytic cleavage of rifamycin B in the presence of manganese dioxide.

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