15-ACETOXY-3ALPHA,7ALPHA-DIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE Chemical Properties

Boiling point:

538.6±50.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

Flash point:

2 °C

storage temp. 

2-8°C

solubility 

Chloroform: soluble; Ethanol: soluble

form 

Solid

pka

11.83±0.70(Predicted)

color 

White to off-white

Major Application

cleaning products
cosmetics
food and beverages
personal care

InChI

1S/C17H22O7/c1-8-4-11-16(6-22-9(2)18,13(21)12(8)20)15(3)5-10(19)14(24-11)17(15)7-23-17/h4,10-11,13-14,19,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1

InChIKey

IDGRYIRJIFKTAN-HTJQZXIKSA-N

SMILES

[H][C@]12O[C@]3([H])[C@H](O)C[C@@](C)([C@]34CO4)[C@@]1(COC(C)=O)[C@H](O)C(=O)C(C)=C2

LogP

-0.400 (est)

Safety Information

Hazard Codes 

T,Xn,F

Risk Statements 

23/24/25-36-20/21/22-11

Safety Statements 

36/37-45-26-16

RIDADR 

UN 2811 6.1/PG 2

WGK Germany 

3

RTECS 

YD0155000

HazardClass 

6.1(a)

PackingGroup 

I

HS Code 

29329990

Storage Class

3 - Flammable liquids

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2

MSDS

• Language:English Provider:SigmaAldrich

15-ACETOXY-3ALPHA,7ALPHA-DIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE Usage And Synthesis

Chemical Properties

Solid

Uses

A mycotoxin produced by the fungi Fusarium culmorum and Fusarium graminearum, inhibits protein synthesis.

Definition

ChEBI: 15-acetyldeoxynivalenol is a trichothecene mycotoxin that is deoxynivalenol acetylated on the oxygen at C-15. A skin and eye irritant, along with its 3-acetyl regioisomer and its parent deoxynivalenol it is considered among the most commonly and widely distributed cereal contaminants. It has a role as an epitope and a mycotoxin. It is functionally related to a deoxynivalenol.

Biological Activity

15-O-Acetyl-4-deoxynivalenol (15-ADON) can be harmful for the consumption of humans and livestock.

Synthesis

DON (79.0 mg, 0.27 mmol) was dissolved in 50 mL of anhydrous dichloromethane, pyridine (1 mL) and 4-DMAP (ca. 10 mg) were added, then acetic anhydride (27.2 mg, 0.27 mmol) was added dropwise. The reaction was stirred overnight, treated with 20 mL of HCl (2N) and extracted three times with 50 mL of dichloromethane. After drying with sodium sulfate, it was filtered and the solvent evaporated. The remaining residue was separated by column chromatography (CHCl3: MeOH = 95:5) to give 15-ADON, i.e., 15-O-acetoxydeoxyguaifenesin (42.0 mg, 47%,).

15-ACETOXY-3ALPHA,7ALPHA-DIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE(88337-96-6)Related Product Information

• 2-Ethylhexyl glycidyl ether
• 2-(TETRAHYDRO-PYRAN-4-YL)-ETHANOL
• 2-TERT-BUTYLPROPANE-1,3-DIOL
• 1,3-cyclopentanediol
• (R)-(+)-1,2-EPOXYDECANE
• 1-METHYL-3-CYCLOHEXENE-1-METHANOL
• 4-Methyl-2-(2-methyl-1-propenyl)tetrahydropyran (cis- and trans- mixture)
• (R)-(+)-1,2-EPOXY-9-DECENE
• 15-ACETOXY-3ALPHA,7ALPHA-DIHYDROXY-12,13-EPOXYTRICHOTHEC-9-EN-8-ONE
• (S)-(+)-Methyl glycidyl ether
• Allyl glycidyl ether
• (TETRAHYDRO-PYRAN-3-YL)-METHANOL
• DEOXYNIVALENOL
• (R)-(+)-1 2-EPOXYUNDECANE 97
• 3-METHYL-2-CYCLOHEXEN-1-OL
• ACETOPROPYLACETATE
• 1,2-epoxy-2,4,4-trimethylpentane
• 2,2-DIMETHYL-5-HEXEN-3-OL