Rifamycin S supplier | CasNO.13553-79-2

Name
1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
EINECS 236-938-4
CAS No. 13553-79-2
Article Data13
CAS DataBase
Density 1.338 g/cm³
Solubility
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
Appearance Yellow orange crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 194.99000
LogP 3.95910

Synthetic route

: 13929-35-6
rifamycin B

: 13553-79-2
rifamycin S

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In ethyl acetate at 70℃; for 4h; Product distribution;	A n/a B n/a C 49%

...Expand

: 54356-09-1
4-[(2R)-2-((S)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-4-deoxy-rifamycin

: 13553-79-2
rifamycin S

Conditions

Conditions	Yield
With cis-nitrous acid

: 14487-05-9
rifamycin O

: 13553-79-2
rifamycin S

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: HNO2 View Scheme

: 13553-79-2
rifamycin S

: 6998-60-3
rifamycin SV

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: 6462-50-6
sodium 4-methoxybenzenesulfinate

: 13553-79-2
rifamycin S

: C44H52NO15S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	80%

: 14752-66-0
sodium p-chlorobenzenesulphinate

: 13553-79-2
rifamycin S

: C43H49ClNO14S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	77%

: 16642-95-8
butanesulfinic acid sodium salt

: 13553-79-2
rifamycin S

: C41H54NO14S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	76%

: 873-55-2
sodium benzenesulfonate

: 13553-79-2
rifamycin S

: C43H50NO14S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	76%

: 15959-31-6
sodium 4-nitrobenzenesulfinate

: 13553-79-2
rifamycin S

: C43H49N2O16S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	76%

: 13553-79-2
rifamycin S

: 74-88-4
methyl iodide

: 98442-85-4
8-O-methyl-N-methylrifamycin

Conditions

Conditions	Yield
With silver(l) oxide In N,N-dimethyl-formamide for 12.5h; Ambient temperature;	73%

: 13553-79-2
rifamycin S

: sodium 4-hydroxybenzenesulfinate

: C43H50NO15S(1-)*Na(1+)

Conditions

Conditions	Yield
With dimethyl sulfoxide In water for 3h; Ambient temperature;	62%

: 13553-79-2
rifamycin S

: 74-88-4
methyl iodide

A: 98442-85-4
8-O-methyl-N-methylrifamycin

B: 98442-86-5
8-O-methylrifamycin S imino methylether

Conditions

Conditions	Yield
With silver(l) oxide In acetonitrile for 10h; Ambient temperature; work-up in the dark;	A 58% B n/a

...Expand

: 13553-79-2
rifamycin S

: 1,3,5-Tris-(1,1-dimethyl-propyl)-[1,3,5]triazinane

: C44H58N2O12

Conditions

Conditions	Yield
With pyridine at 40℃; for 3.5h;	48%

: 111-86-4
n-Octylamine

: 13553-79-2
rifamycin S

: 3,n-octylaminorifamycin S

Conditions

Conditions	Yield
at 4℃; for 1h;	42%

: 13553-79-2
rifamycin S

: 72975-88-3, 72975-89-4
sodium rifamycin SV-3-sulfonate

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium sulfite In 1,4-dioxane; water for 2h; Ambient temperature;	41%

: 13553-79-2
rifamycin S

: 10560-39-1
1,3,5-tri-tert-butyl-1,3,5-triazacyclohexane

: C43H56N2O12

Conditions

Conditions	Yield
With pyridine at 63℃; for 1.5h;	38%

: 873-55-2
sodium benzenesulfonate

: 13553-79-2
rifamycin S

: C43H51NO14S

Conditions

Conditions	Yield
With dimethyl sulfoxide In water Ambient temperature;	32%

: 14752-66-0
sodium p-chlorobenzenesulphinate

: 13553-79-2
rifamycin S

: C43H50ClNO14S

Conditions

Conditions	Yield
With dimethyl sulfoxide In water Ambient temperature;	31%

: 13553-79-2
rifamycin S

: sodium 4-hydroxybenzenesulfinate

: C43H51NO15S

Conditions

Conditions	Yield
With dimethyl sulfoxide In water Ambient temperature;	16%

: 824-79-3
sodium 4-methylbenzenesulfinate

: 13553-79-2
rifamycin S

: C44H53NO14S

Conditions

Conditions	Yield
With acetic acid In water for 12h; Ambient temperature;	9%

: 6281-14-7
1,3,5-tricyclohexyl-[1,3,5]triazinane

: 13553-79-2
rifamycin S

: C45H58N2O12

Conditions

Conditions	Yield
With pyridine for 3.5h; Ambient temperature;	4%

: 108-74-7
1,3,5-trimethyl-1,3,5-triazacyclohexane

: 13553-79-2
rifamycin S

: C40H50N2O12

Conditions

Conditions	Yield
With pyridine for 48h; Ambient temperature;	2%

: 7779-27-3
1,3,5-triethyl-1,3,5-triazacyclohexane

: 13553-79-2
rifamycin S

: C41H52N2O12

Conditions

Conditions	Yield
With pyridine for 48h; Ambient temperature;	2%

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)	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.

Product Name

1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin

Synthetic route

Rifamycin S Specification

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