2503-13-1

Basic information

• Product Name: enniatin A
• Synonyms: enniatin A;N-Methylcyclo(L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-);Lateritin I;Cyclo[(2R)- 2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl- N-methyl-L- isoleucyl];(3S,6R,9S,12R,15S,18R)-3,9,15-tris[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CAS NO: 2503-13-1
• Molecular Formula: C36H63N3O9
• Molecular Weight: 681.906
• Mol File: 2503-13-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 122-124 °C
• Boiling Point: 847.4°Cat760mmHg
• Flash Point: 466.3°C
• Appearance: /
• Density: 1.022g/cm³
• Vapor Pressure: 5.53E-29mmHg at 25°C
• Refractive Index: 1.46
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble10mg/mL
• PKA: -0.96±0.70(Predicted)
• CAS DataBase Reference: enniatin A(CAS DataBase Reference)
• NIST Chemistry Reference: enniatin A(2503-13-1)
• EPA Substance Registry System: enniatin A(2503-13-1)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 45
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 2503-13-1(Hazardous Substances Data)

Usage

Description

Enniatin A is a cyclohexadepsipeptide commonly isolated from fungi, known for its antibiotic properties and ability to induce apoptosis in several cancer lines. It functions as an ionophore, forming pores in cellular membranes to allow selective ion transport. One of the four major analogues in the enniatin complex, Enniatin A has been shown to moderately inhibit acyl-CoA:cholesterol acyltransferase activity in rat liver microsomes with an IC50 value of 22 μM. Additionally, it demonstrates anthelmintic properties against N. brasiliensis, T. spiralis, and H. spumosa.

Uses

Used in Pharmaceutical Industry:
Enniatin A is used as an anticancer agent for its ability to induce apoptosis in several cancer lines and moderately inhibit acyl-CoA:cholesterol acyltransferase activity.
Used in Veterinary Medicine:
Enniatin A is used as an anthelmintic agent for its properties against various parasites, including N. brasiliensis, T. spiralis, and H. spumosa.
Used in Agricultural Industry:
Enniatin A is used as a biopesticide for its antibiotic properties, helping to control and eliminate harmful microorganisms in crops.

Biochem/physiol Actions

Enniatins are a group of cyclohexadepsipeptide mycotoxins produced by Gnomonia errabuda and several Fusaria species, with phytotoxic, antibiotic, and insecticidal activities. Enniatins function as ionophors by their incorporation into the cellular membrane to form dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. It has been demonstrated that enniatins have a cytotoxic effect on human cancer cells. Furthermore, incubation of H4IIE hepatoma cells with enniatins strongly diminished phosphorylation of the ERK (p44/p42).

InChI:InChI=1/C36H63N3O9/c1-16-22(10)25-34(43)46-29(20(6)7)32(41)38(14)27(24(12)18-3)36(45)48-30(21(8)9)33(42)39(15)26(23(11)17-2)35(44)47-28(19(4)5)31(40)37(25)13/h19-30H,16-18H2,1-15H3

Downstream Products

• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 4125-98-8 N-methyl-L-isoleucine