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Rifamycin S
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Name

Rifamycin S

 EINECS 236-938-4
CAS No. 13553-79-2 Density 1.338 g/cm3
PSA 194.99000 LogP 3.95910
Solubility N/A Melting Point 179-181 °C (dec.)
Formula C37H45NO12 Boiling Point 917.4 °C at 760 mmHg
Molecular Weight 695.764 Flash Point 508.615 °C
Transport Information N/A Appearance Yellow orange crystalline powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 13553-79-2 (1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin) Hazard Symbols N/A
Synonyms

2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone,5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, 21-acetate(7CI,8CI);Rifomycin S (6CI);NSC 144130;

Article Data 13

Rifamycin S Synthetic route

13929-35-6

rifamycin B

13553-79-2

rifamycin S

Conditions
ConditionsYield
With hydrogenchloride In methanol 1.) 5 min; 2.) room temperature, 5 h;91%

C45H52NO15S(1-)*Na(1+)

A

13553-79-2

rifamycin S

B

1-[4-(sodiosulfonyl)phenyl]ethan-1-one

Conditions
ConditionsYield
In ethyl acetate at 70℃; for 4.75h; Product distribution;A 70%
B 80%

C44H52NO14S(1-)*Na(1+)

A

657-84-1

sodium tosylate

B

13553-79-2

rifamycin S

Conditions
ConditionsYield
In ethyl acetate at 70℃; for 5.75h; Product distribution;A 71%
B 46%

C44H52NO15S(1-)*Na(1+)

A

6140-09-6

sodium 4-methoxy-benzenesulfonate

B

13553-79-2

rifamycin S

Conditions
ConditionsYield
In ethyl acetate at 70℃; for 6.25h; Product distribution;A 67%
B 37%

C43H49ClNO14S(1-)*Na(1+)

A

14752-66-0

sodium p-chlorobenzenesulphinate

B

5138-90-9

sodium 4-chlorobenzenesulfonate

C

13553-79-2

rifamycin S

Conditions
ConditionsYield
In ethyl acetate at 70℃; for 4h; Product distribution;A n/a
B n/a
C 49%
54356-09-1

4-[(2R)-2-((S)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-4-deoxy-rifamycin

13553-79-2

rifamycin S

Conditions
ConditionsYield
With cis-nitrous acid
14487-05-9

rifamycin O

13553-79-2

rifamycin S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: HNO2
View Scheme
13553-79-2

rifamycin S

6998-60-3

rifamycin SV

Conditions
ConditionsYield
With ascorbic acid 1.) phosphate buffer, pH 7.0, 50 deg C; 2.) 4 deg C, 1 day;88%
13553-79-2

rifamycin S

1-[4-(sodiosulfonyl)phenyl]ethan-1-one

C45H52NO15S(1-)*Na(1+)

Conditions
ConditionsYield
With dimethyl sulfoxide In water for 3h; Ambient temperature;87%
824-79-3

sodium 4-methylbenzenesulfinate

13553-79-2

rifamycin S

C44H52NO14S(1-)*Na(1+)

Conditions
ConditionsYield
With dimethyl sulfoxide In water for 3h; Ambient temperature;85%

Rifamycin S Specification

The Rifamycin S is an organic compound with the formula C37H45NO12. The systematic name of this chemical is (2S, 12Z, 14E, 16S, 17S, 18R, 19R, 20R, 21S, 22R, 23S, 24E)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-1,6,9,11-tetraoxo-1,2,6,9-tetrahydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b ]furan-21-yl acetate. With the CAS registry number 13553-79-2, it is also named as 2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,6,9,11(2H)-tetrone, 21-(acetyloxy)-5,17,19-trihydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-, (2S, 12Z, 14E, 16S, 17S, 18R, 19R, 20R, 21S, 22R, 23S, 24E)-. The product's classification codes are Drug / Therapeutic Agent; Natural Product. Besides, it can be used as pharmaceutical intermediate.

Physical properties about Rifamycin S are: (1)ACD/LogP: 5.01; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 1; (4)ACD/BCF (pH 5.5): 2; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 23; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 13; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 6; (11)Polar Surface Area: 194.99 Å2; (12)Index of Refraction: 1.605; (13)Molar Refractivity: 178.956 cm3; (14)Molar Volume: 519.843 cm3; (15)Polarizability: 70.944×10-24cm3; (16)Surface Tension: 61.847 dyne/cm; (17)Density: 1.338 g/cm3; (18)Flash Point: 508.615 °C; (19)Enthalpy of Vaporization: 139.754 kJ/mol; (20)Boiling Point: 917.383 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)O[C@H]1[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)N\C4=C\C(=O)c3c2C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]1C)Oc2c(C)c(O)c3C4=O
(2)InChI: InChI=1/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
(3)InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWBD
(4)Std. InChI: InChI=1S/C37H45NO12/c1-16-11-10-12-17(2)36(46)38-23-15-24(40)26-27(32(23)44)31(43)21(6)34-28(26)35(45)37(8,50-34)48-14-13-25(47-9)18(3)33(49-22(7)39)20(5)30(42)19(4)29(16)41/h10-16,18-20,25,29-30,33,41-43H,1-9H3,(H,38,46)/b11-10+,14-13+,17-12-/t16-,18+,19+,20+,25-,29-,30+,33+,37-/m0/s1
(5)Std. InChIKey: BTVYFIMKUHNOBZ-ODRIEIDWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 258mg/kg (258mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 865, 1978.
mouse LD50 intravenous 122mg/kg (122mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 1, Pg. 865, 1978.
mouse LD50 oral > 3gm/kg (3000mg/kg)   Experientia. Vol. 16, Pg. 412, 1960.

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