(7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate

Basic Information

$(7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate$

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CAS Number

13553-79-2

Molecular Formula

C37H45NO12

Molecular Weight

695.76 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ketones

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Melting Point

179-181 ºC (dec.)

Boiling Point

700.89°C (rough estimate)

Flash Point

508.6 °C

Refractive Index

1.6630 (estimate)

Specific Rotation

+476° (c=0.1, MeOH)

SMILES

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CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c4C(=O)C=C(NC(=O)/C(=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(=O)C)[C@@H]1C)/C)C(=O)c4c(O)c3C

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

InChIKey

BTVYFIMKUHNOBZ-ODRIEIDWSA-N

LogP

3.630320000000002

Topological Polar Surface Area

194.98999999999998 Å²

Hydrogen Bond Donor/Acceptor

4 / 13

Complexity

1480

Safety Information

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GHS Hazard Pictograms

H371

Hazard Statement

H371 May cause damage to organs
Specific target organ toxicity, single exposure

Toxicity

LD50 in mice (mg/kg): 122 i.v.; 258 i.p.; 3000 orally (Sensi, 1964)

Synonyms & References

English

Rifamycin S
1,4-Dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
Rifampicin S
rifomycin S
(12S,3E,5S,13E,15Z)-7t-acetoxy-15,9c,11t-trihydroxy-5r-methoxy-12,4,6t,8c,10c,12t,16-heptamethyl-2-oxa-18-aza-1(2,7)-naphtho[2,1-b]furana-cyclooctadecaphane-3,13,15-triene-11,6,9,17-tetraone
1,4-Dideoxy-1,4-dihydro-1,4-dioxorifamycin
EINECS 236-938-4
NCI 144-130
O1,O4-didehydro-rifamycin
Rifamycin,1,4-dideoxy-1,4-dihydro-1,4-dioxo
rifamycin-S
rifaximin S
rifomycin-S
UNII-PI53N820JV
Rifaximin EP Impurity E
Rifaximin impurity E (EP)
4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin
Rifamycin, 1,4-dideoxy-1,4-dihydro-1,4-dioxo-
5,17,19,21-tetrahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-21-aceta
rifomycins
nci144-130
RIFAMYCIN S
RIFAMPICIN S
1,4-dideoxy-1,4-dihydro-1,4-dioxo-rifamycin

MDL Number

MFCD06198807

FAQ

What are the physical and chemical properties of (7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate (CAS: 13553-79-2)?

This compound is a complex organic molecule with a high molecular weight. It crystallizes in a stable form and has a high melting point. Its solubility is low in water but better in organic solvents. It is chemically reactive, particularly towards nucleophiles and electrophiles. It is used in synthesizing other compounds due to its functional groups and stereochemistry.

How is (7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate (CAS: 13553-79-2) typically synthesized?

This compound is synthesized via multi-step reactions involving the introduction of functional groups and ring formation. Common synthetic routes include the use of metal catalysts and organocatalysts to achieve high selectivity and yield. The exact synthesis method depends on the desired stereochemistry and functional groups.

What industries use (7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate (CAS: 13553-79-2)?

This compound is primarily used in pharmaceutical and research industries for the development of new drugs and in organic synthesis. It is also used in industries requiring highly specific organic molecules, such as polymer science and materials science for creating novel materials with specific properties.

What precautions should be taken when handling (7S,11S,12R,13S,14R,15R,16R,17S,18S,19Z,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.1^{4,7}.0^{5,28}]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl acetate (CAS: 13553-79-2)?

Proper handling of this compound requires the use of personal protective equipment (PPE) such as gloves, goggles, and a lab coat. It should be handled in a well-ventilated environment or a fume hood. Spills should be cleaned up using appropriate absorbent materials and disposed of according to local regulations. Safety data sheets (SDS) should be consulted for detailed information on handling and emergency procedures.