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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.

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Micah Steffek et al.
Biochemistry, 42(41), 12067-12076 (2003-10-15)
Mycothiol is comprised of N-acetylcysteine (AcCys) amide linked to 1D-myo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside (GlcN-Ins) and is the predominant thiol found in most actinomycetes. Mycothiol S-conjugate amidase (Mca) cleaves the amide bond of mycothiol S-conjugates of a variety of alkylating agents and xenobiotics
Molecular structure and conformation of rifamycin S, a potent inhibitor of DNA-dependent RNA polymerase.
S K Arora et al.
The Journal of antibiotics, 45(3), 428-431 (1992-03-01)
Ming Chen et al.
The Journal of organic chemistry, 78(1), 3-8 (2012-06-19)
Syntheses of the C(15)-C(27) fragments of chaxamycins A/D, rifamycin S, and the C(12)-C(24) fragment of salinisporamycin have been accomplished in 10 steps from commercially available starting materials. Three crotylboron reagents were utilized to construct the seven contiguous stereocenters in these
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.
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
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