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Rifamycin O
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Name

Rifamycin O

 EINECS 238-493-1
CAS No. 14487-05-9 Density 1.366 g/cm3
PSA 213.45000 LogP 3.50260
Solubility N/A Melting Point 171°C (dec.)
Formula C39H47NO14 Boiling Point 972.841 °C at 760 mmHg
Molecular Weight 753.8 Flash Point 542.155 °C
Transport Information N/A Appearance Yellow solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 14487-05-9 (Rifamycin O) Hazard Symbols N/A
Synonyms

Aceticacid, [(1,2,6,9-tetrahydro-5,9,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,11-trioxo-2,7-(epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-9-yl)oxy]-,g-lactone, 21-acetate (7CI);Rifomycin O (6CI);Spiro[1,3-dioxolane-2,9'(6'H)-[2,7](epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan]-1',4,6',11'(2'H)-tetrone,5',17',19',21'-tetrahydroxy-23'-methoxy-2',4',12',16',18',20',22'-heptamethyl-,21'-acetate (8CI);Spiro[1,3-dioxolane-2,9'(6'H)-[2,7](epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan],rifamycin deriv.;NSC 182391;Rifamycin O;

Article Data 3

Rifamycin O Synthetic route

13929-35-6

Rifamycin B

14487-05-9

rifamycin O

Conditions
ConditionsYield
With air Ambient temperature;80%
13929-35-6

Rifamycin B

A

62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2

rifamycin S

B

14487-05-9

rifamycin O

Conditions
ConditionsYield
With ammonium persulfate In methanol; aq. phosphate buffer at 60℃; for 4h; Solvent; Reagent/catalyst;
90-04-0

2-methoxy-phenylamine

14487-05-9

rifamycin O

51756-76-4

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

Conditions
ConditionsYield
In methanol
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

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

rifamycin O

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
695-34-1

2-Amino-4-methylpyridine

14487-05-9

rifamycin O

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;
14487-05-9

rifamycin O

62623-68-1, 76188-88-0, 81203-58-9, 101978-28-3, 13553-79-2

rifamycin S

Conditions
ConditionsYield
In aq. phosphate buffer; dimethyl sulfoxide at 60℃; for 1h; pH=7.5; pH-value; Temperature;
14487-05-9

rifamycin O

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
14487-05-9

rifamycin O

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
14487-05-9

rifamycin O

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 Specification

The Rifamycin O, with the CAS registry number 14487-05-9 and EINECS registry number 238-493-1, is also called Acetic acid, ((1,2,6,9-tetrahydro-5,9,17,19,21-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,11-trioxo-2,7-(epoxypentadeca(1,11,13)trienimino)naphtho(2,1-b)furan-9-yl)oxy)-, gamma-lactone, 21-acetate. Its classification codes are Drug/Therapeutic Agent and Natural Product. And the molecular formula of the chemical is C39H47NO14.

The physical properties of Rifamycin O are as following: (1)ACD/LogP: 1.38; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 0.6; (4)ACD/LogD (pH 7.4):  ; (5)ACD/BCF (pH 5.5): 1.09; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.18; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 15; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 213.45 Å2; (13)Index of Refraction: 1.607; (14)Molar Refractivity: 194.24 cm3; (15)Molar Volume: 561.9 cm3; (16)Polarizability: 77×10-24cm3; (17)Surface Tension: 63.2 dyne/cm; (18)Density: 1.36 g/cm3; (19)Flash Point: 542.2 °C; (20)Enthalpy of Vaporization: 148.48 kJ/mol; (21)Boiling Point: 972.8 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)O[C@@H]2[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)Oc4c(C1=O)c3C(/C=C(/NC(=O)C(/C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@H]2C)C(=O)c3c(O)c4C)C5OC(=O)CO5
(2)InChI: InChI=1/C40H49NO14/c1-17-11-10-12-18(2)38(49)41-25-15-24(39-51-16-27(43)54-39)28-29(34(25)47)33(46)22(6)36-30(28)37(48)40(8,55-36)52-14-13-26(50-9)19(3)35(53-23(7)42)21(5)32(45)20(4)31(17)44/h10-15,17,19-21,24,26,31-32,35,39,44-46H,16H2,1-9H3,(H,41,49)/b11-10+,14-13+,18-12-/t17-,19+,20+,21+,24?,26-,31-,32+,35+,39?,40-/m0/s1
(3)InChIKey: WNKSQFVXBVOSDN-NPQOYZKFBW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 2, Pg. 462, 1980.
mouse LD50 intravenous 1800mg/kg (1800mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 566, 1967.
mouse LD50 subcutaneous 3gm/kg (3000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 2, Pg. 462, 1980.

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