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75351

Sigma-Aldrich

Oligomycin A

≥99% (HPLC)

Synonym(s):

MCH 32

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About This Item

Empirical Formula (Hill Notation):
C45H74O11
CAS Number:
579-13-5
Molecular Weight:
791.06
Beilstein:
5702132
EC Number:
209-437-3
MDL number:
MFCD00065705
UNSPSC Code:
51102829
PubChem Substance ID:
57652563
NACRES:
NA.76

Assay

≥99% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: soluble

antibiotic activity spectrum

fungi

Mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CCC1CCC2OC3(CC[C@@H](C)C(C[C@H](C)O)O3)[C@H](C)C(OC(=O)\C=C\[C@@H](C)[C@H](O)[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H](C)C(=O)[C@@](C)(O)[C@H](O)[C@@H](C)C\C=C\C=C\1)[C@H]2C

InChI

1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3/b14-13+,17-15+,21-18+/t25-,26-,27+,28+,29+,30-,31+,32+,33-,34?,35?,36?,38+,40-,41?,42-,44+,45?/m1/s1

InChI key

MNULEGDCPYONBU-VVXVDZGXSA-N

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General description

Chemical structure: macrolide

Application

Oligomycin was used to inhibit sucrose synthesis and 14C translocation in sunflower leaves, to study antibiotic resistance, and to study carotid chemoreceptor responses to O2 and CO2 in the cat. Inhibits the growth of Rhodotorula glutinis, Aspergillus niger and other molds.

Biochem/physiol Actions

Oligomycin blocks oxidative phosphorylation and the electron transport chain by inhibiting membrane bound mitochondrial ATP synthase (ATPase) and proton channel (pump, FO subunit) blocker.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place. Keep in a dry place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hidetaka Kioka et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(1), 273-278 (2013-12-18)
The oxidative phosphorylation (OXPHOS) system generates most of the ATP in respiring cells. ATP-depleting conditions, such as hypoxia, trigger responses that promote ATP production. However, how OXPHOS is regulated during hypoxia has yet to be elucidated. In this study, selective
Differential effects of oligomycin on carotid chemoreceptor responses to O2 and CO2 in the cat.
M. Shirahata, S. Andronikou, et. Al
Journal of Applied Physics, 63, 2084-2092 (1987)
Isolation of oligomycin A as a result of screening for antagonists of lipids.
Y Nakakita et al.
The Journal of antibiotics, 33(5), 514-516 (1980-05-01)
Translocation of organic compounds in sunflower III. Effect of oligomycin, ouabain and phlorizin on translocation of sugars.
Michi Shiroya and Mariko Kura
Plant & Cell Physiology, 20, 369-374 (1979)
Mauro Gaya et al.
Cell, 172(3), 517-533 (2017-12-19)
B cells constitute an essential line of defense from pathogenic infections through the generation of class-switched antibody-secreting cells (ASCs) in germinal centers. Although this process is known to be regulated by follicular helper T (TfH) cells, the mechanism by which
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