DEOXYNIVALENOL

Names

[ Name ]:
DEOXYNIVALENOL

[Synonym ]:
(3β,7α)-3,7,15-Trihydroxy-12,13-epoxytrichothec-9-en-8-one
(3beta,7alpha,12R)-3,7,15-trihydroxy-12,13-epoxytrichothec-9-en-8-one
4-Desoxynivalenol
Desoxynivalenol
MFCD09039270
Vomitoxin
Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (2α,3α,6β,7β,11β,12α)-
Deoxynivalenol
Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3α,7α)-
4-Deoxynivalenol

Biological Activity

[Description]:

Deoxynivalenol, a mycotoxin of the trichothecenes family, crosses the intestinal mucosa by a paracellular pathway through the tight junctions. The Deoxynivalenol transport is not affected by P-glycoprotein (PgP) or multidrug resistance-associated proteins (MRPs) inhibitors[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[References]

[1]. Sergent T, et al. Deoxynivalenol transport across human intestinal Caco-2 cells and its effects on cellularmetabolism at realistic intestinal concentrations. Toxicol Lett. 2006 Jul 1;164(2):167-76.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
543.9±50.0 °C at 760 mmHg

[ Melting Point ]:
151-153ºC

[ Molecular Formula ]:
C₁₅H₂₀O₆

[ Molecular Weight ]:
296.316

[ Flash Point ]:
206.9±23.6 °C

[ Exact Mass ]:
296.125977

[ PSA ]:
99.52000

[ LogP ]:
-1.41

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.632

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YD0167000

CHEMICAL NAME :: Trichothec-9-en-8-one, 12,13-epoxy-3,7,15-trihydroxy-, (3-alpha,7-alpha)-

CAS REGISTRY NUMBER :: 51481-10-8

LAST UPDATED :: 199801

DATA ITEMS CITED :: 25

MOLECULAR FORMULA :: C15-H20-O6

MOLECULAR WEIGHT :: 296.35

WISWESSER LINE NOTATION :: T C665 A AX EV IO FUTJ B1 C1Q DQ F1 KQ A-& BT3OX CHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - guinea pig

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 46 mg/kg

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 27 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 63 mg/kg/9W-C

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - changes in chlorine Biochemical - Metabolism (Intermediary) - other proteins

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 51375 ug/kg/19W-C

TOXIC EFFECTS :: Blood - changes in other cell count (unspecified) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 123 mg/kg/8W-C

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg/5W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 103 mg/kg/19W-C

TOXIC EFFECTS :: Blood - changes in other cell count (unspecified) Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg/1W-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - changes in thymus weight Immunological Including Allergic - decreased immune response

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg/1W-I

TOXIC EFFECTS :: Endocrine - changes in thymus weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 82500 ug/kg

SEX/DURATION :: male 60 day(s) pre-mating female 15 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - other measures of fertility

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 10 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 20 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 mg/kg

SEX/DURATION :: female 8-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 31 mg/kg

SEX/DURATION :: female 1-30 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 49600 ug/kg

SEX/DURATION :: female 1-30 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 55800 ug/kg

SEX/DURATION :: female 1-30 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 1 mg/L

REFERENCE :: FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 32,617,1994 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 56,397,1993

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Supplemental HS ]:
Repeated exposure may cause skin dryness or cracking.

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T,Xn,F,Xi

[ Risk Phrases ]:
25-68/20/21/22-67-66-36-20/21/22-11-36/37/38

[ Safety Phrases ]:
36/37/39-45-36-26-16-36/37-37/39

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
YD0167000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
29329990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Low toxicity of deoxynivalenol-3-glucoside in microbial cells.

Toxins (Basel.) 7(1) , 187-200, (2015)

Host plants excrete a glucosylation enzyme onto the plant surface that changes mycotoxins derived from fungal secondary metabolites to glucosylated products. Deoxynivalenol-3-glucoside (DON3G) is synt...

Deoxynivalenol-mimic nanobody isolated from a naïve phage display nanobody library and its application in immunoassay.

Anal. Chim. Acta 887 , 201-8, (2015)

In this study, using mycotoxin deoxynivalenol (DON) as a model hapten, we developed a nanobody-based environmental friendly immunoassay for sensitive detection of DON. Two nanobodies (N-28 and N-31) w...

Neurological sequelae induced by alphavirus infection of the CNS are attenuated by treatment with the glutamine antagonist 6-diazo-5-oxo-l-norleucine.

J. Neurovirol. 21(2) , 159-73, (2015)

Recovery from encephalomyelitis induced by infection with mosquito-borne alphaviruses is associated with a high risk of lifelong debilitating neurological deficits. Infection of mice with the prototyp...