Nigericin (free)

Molecular Formula

C40H68O11

M.W.

724.96

CAS number

28380-24-7

Details

Source

Streptomyces hygroscopicus

Fermentek product Code

NIG-002

Brand/grade

For research

Specifications

Appearance

White powder

Purity by HPLC

≥98% ; refer to CoA for more data

Purity By TLC

≥98% ; refer to CoA for more data

Melting point

180-190°C

Solubility test

Clear colorless solution at 10mg/ml of
Dichloromethane
or Methanol
or Ethyl acetate
or Water

Chemical identification

Names and identifiers

Synonyms:

Polyetherin A; Azalomycin M; Helexin C ; Antibiotic K178; Antibiotic X-464

Chemical names:

IUPAC:

(2R)-2-[(2R,3S,6R)-6-[[(2S,4R,5R,6R,7R,9R)-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-7-methoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-3-methyloxan-2-yl]propanoic acid

RTECS# QT6825000

EU number

686-881-8

Chemical name

Polyetherin A; Azalomycin M; Helexin C ; Antibiotic K178; Antibiotic X-464

Description

Nigericin is a polyether antibiotic which affects ion transport and ATPase activity in mitochondria.

Nigericin is produced by Streptomyces hygroscopicus. Nigericin, an ionophore and antibiotic, is supplied as a free acid. It is also available as a Na salt.sodium salt.

Nigericin is one of the compounds successfully tested as a feed additive, displaying a significant effect on milk production in cattle. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumor cell lines and some viruses, including HIV.

InChl Key

DANUORFCFTYTSZ-SJSJOXFOSA-N

Isomeric SMILES

C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC

Further Information

Solubility ( literature )

DMSO, Ethanol, petrol ether. Not soluble in water

Storage, handling

Store in a freezer upon arrival, at -10°C to -25°C

Open carefully.

Use the original container to store the product.

Keep the lid tightly closed.

Retest time

3 Years

Applications

Disrupts the membrane potential and stimulates ATPase activity in mitochondria.