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75351

Oligomycin A

≥99% (HPLC)

Oligomycin A

Synonym(s):

MCH 32

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5 MG

$217.00

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About This Item

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

Key Documents

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InChI key

MNULEGDCPYONBU-VVXVDZGXSA-N

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

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

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

Quality Level

200

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Show Differences

1 of 4

This Item
O487649545559983
Oligomycin A ≥99% (HPLC)

Sigma-Aldrich

75351

Oligomycin A

Oligomycin from Streptomyces diastatochromogenes ≥90% total oligomycins basis (HPLC)

Sigma-Aldrich

O4876

Oligomycin from Streptomyces diastatochromogenes

Oligomycin A mixture of A, B, and C isomers.

Sigma-Aldrich

495455

Oligomycin

Josamycin ≥90% (HPLC)

Sigma-Aldrich

59983

Josamycin

mode of action

enzyme | inhibits

mode of action

enzyme | inhibits

mode of action

-

mode of action

protein synthesis | interferes

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-positive bacteria

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

assay

≥99% (HPLC)

assay

≥90% total oligomycins basis (HPLC)

assay

≥90% (mixture of A, B, and C isomers, HPLC)

assay

≥90% (HPLC)

form

powder

form

powder

form

powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

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.[1][2] Inhibits the growth of Rhodotorula glutinis, Aspergillus niger and other molds.[3]

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

11 - Combustible Solids

wgk

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
0000521836
0000521836
0000508842
0000508842
0000493828

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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
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)
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)
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)
Catherine G Burke et al.
Scientific reports, 9(1), 11489-11489 (2019-08-09)
Early life environmental exposures drive lasting changes to the function of the immune system and can contribute to disease later in life. One of the ways environmental factors act is through cellular receptors. The aryl hydrocarbon receptor (AHR) is expressed
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Questions

1–5 of 5 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. For how long does the product remain stable once dissolved, aliquoted and stored at -20°C?

    1 answer

    1. Storage of stock solutions at -20°C is stable for 1 month.

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  4. Does this product contain thimerosal or any mercury-containing preservatives?

    1 answer

    1. This is a pure product, not containing any preservative or thimerosal.

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  5. What's it's solubility in dmso

    1 answer

    1. This product is not tested for solubility in DMSO, however other Oligomycin products have been found to be soluble at in DMSO at 50 mg/ml.

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