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R2636

Sigma-Aldrich

Rosamicin

from Micromonospora rosaria, ~98%

Synonym(s):

Juvenimicin A3, Rosaramicin

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About This Item

Empirical Formula (Hill Notation):
C31H51NO9
CAS Number:
35834-26-5
Molecular Weight:
581.74
Beilstein/REAXYS Number:
1633003
EC Number:
252-742-1
MDL number:
MFCD00133803
UNSPSC Code:
12352202
PubChem Substance ID:
24899357

biological source

Micromonospora rosaria

assay

~98%

form

solid

storage temp.

2-8°C

SMILES string

[H]C(=O)C[C@H]1C[C@@H](C)C(=O)\C=C\[C@]2(C)O[C@@]2([H])[C@H](C)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C

InChI

1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1

InChI key

IUPCWCLVECYZRV-JZMZINANSA-N

Biochem/physiol Actions

Macrolide antibiotic similar to erythromycin, and with a similar spectrum of bactericidal activity.[1] Against a wide variety of anaerobes, rosamicin is at least as potent as, and in some cases more potent than, erythromycin.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
067K2617
052H4072
052H4070
052H4071

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Yohei Iizaka et al.
Applied microbiology and biotechnology, 104(8), 3403-3415 (2020-02-28)
The cytochrome P450 monooxygenase RosC catalyzes the three-step oxidation reactions, which leads to the formation of a hydroxy, formyl, and carboxy group at C-20 during rosamicin biosynthesis in Micromonospora rosaria IFO13697. To determine if amino acid substitutions in RosC could
Isolation and characterization of 23-O-mycinosyl-20-dihydro-rosamicin: a new rosamicin analogue derived from engineered Micromonospora rosaria.
Yojiro Anzai et al.
The Journal of antibiotics, 63(6), 325-328 (2010-04-24)
Yojiro Anzai et al.
Journal of industrial microbiology & biotechnology, 36(8), 1013-1021 (2009-05-02)
Some of the polyketide-derived bioactive compounds contain sugars attached to the aglycone core, and these sugars often impart specific biological activity to the molecule or enhance this activity. Mycinamicin II, a 16-member macrolide antibiotic produced by Micromonospora griseorubida A11725, contains
A new Micromonospora-produced macrolide antibiotic, rosamicin.
G H Wagman et al.
The Journal of antibiotics, 25(11), 641-646 (1972-11-01)
C Vilches et al.
Journal of bacteriology, 174(1), 161-165 (1992-01-01)
Cell extracts of Streptomyces antibioticus, an oleandomycin producer, can inactivate oleandomycin in the presence of UDP-glucose. The inactivation can be detected through the loss of biological activity or by alteration in the chromatographic mobility of the antibiotic. This enzyme activity
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