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Key Documents

R0950000

Rifamycin S

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin

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About This Item

Empirical Formula (Hill Notation):
C37H45NO12
CAS Number:
13553-79-2
Molecular Weight:
695.75
UNSPSC Code:
41116107
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

rifamycin, rifampicin

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

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

InChI key

BTVYFIMKUHNOBZ-ODRIEIDWSA-N

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Rifamycin S EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Warning

Hazard Statements

H371,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - STOT SE 2

Target Organs

Liver

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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S BouzBouz et al.
Organic letters, 3(25), 3995-3998 (2001-12-12)
[reaction: see text] An efficient, simple method has been developed for the stereocontrolled synthesis of polypropionate stereopentads in high enantio- and diastereomeric purities.
Chemical modification of the amide group of rifamycin S.
M Taguchi et al.
Chemical & pharmaceutical bulletin, 33(5), 2133-2136 (1985-05-01)
O Ghisalba et al.
The Journal of antibiotics, 35(1), 74-80 (1982-01-01)
The transformation of rifamycin S into rifamycins B and L was reinvestigated in order to establish more detailed pathways. Our results exclude rifamycin O as a common progenitor in the biosyntheses of rifamycins B and L. Rifamycins B and L
Māris Turks et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 11(2), 465-476 (2004-11-20)
In the presence of sulfur dioxide and an acid promoter, (-)-(1E,3Z)-2-methyl-1-((1S)-1-phenylethoxy)penta-1,3-dien-3-yl isobutyrate reacts with (Z)-3-(trimethylsilyloxy)pent-2-ene giving a silyl sulfinate intermediate that undergoes, in the presence of palladium catalyst, a desilylation and retro-ene elimination of SO(2) with formation of (-)-(1Z,2S,3R,4S)-1-ethylidene-2,4-dimethyl-5-oxo-3-((1S)-1-phenylethoxy)-heptyl isobutyrate
R Chênevert et al.
The Journal of organic chemistry, 65(6), 1707-1709 (2000-04-06)
The stereoselective acylation of meso polyol 2 by vinyl acetate (solvent and acyl donor) in the presence of porcine pancreas lipase gave the corresponding monoester 5 in good yield (76%) and high enantiomeric purity (ee > 98%). The enzymatic reaction
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