Nivalenol

Names

[ Name ]:
Nivalenol

[Synonym ]:
Nivalenol from Fusarium nivale
Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-, (2α,3α,4β,6β,7β,11β,12ξ)-
MFCD10567355
12,13-epoxy-3,4,7,15-tetrahydroxytrichothec-9-en-8-one
Nivalenol hydrate
fusarenon-X
NIV
Nivalenol in acetonitrile
(3β,4α,7α,12ξ)-3,4,7,15-Tetrahydroxy-12,13-epoxytrichothec-9-en-8-one
nivalenol solution

Biological Activity

[Description]:

Nivalenol, classified as type B trichotecenes toxins produced by Fusarium graminearum, is a fungal metabolite present in agricultural product[1]. Nivalenol induces cell death through caspase-dependent mechanisms and via the intrinsic apoptotic pathway. Nivalenol affects the immune system, causes emesis, growth retardation, reproductive disorders and has a haematotoxic/myelotoxic effect[2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Apoptosis >> Caspase

Research Areas >> Inflammation/Immunology

[Target]

Caspase

[References]

[1]. Bryła M, et al. Natural Occurrence of Nivalenol, Deoxynivalenol, and Deoxynivalenol-3-Glucoside in Polish Winter Wheat. Toxins (Basel). 2018 Feb 13;10(2).

[2]. Aupanun S, et al. Individual and combined mycotoxins deoxynivalenol, nivalenol, and fusarenon-X induced apoptosis in lymphoid tissues of mice after oral exposure. Toxicon. 2019 Jul;165:83-94.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
585.1±50.0 °C at 760 mmHg

[ Melting Point ]:
222-223ºC

[ Molecular Formula ]:
C₁₅H₂₀O₇

[ Molecular Weight ]:
312.315

[ Flash Point ]:
221.9±23.6 °C

[ Exact Mass ]:
312.120911

[ PSA ]:
119.75000

[ LogP ]:
-0.75

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.658

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YD0165000

CHEMICAL NAME :: Trichothec-9-en-8-one, 12,13-epoxy-3,4,7,15-tetrahydroxy-, (3-alpha,4-beta,7-alpha)-

CAS REGISTRY NUMBER :: 23282-20-4

LAST UPDATED :: 199703

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C15-H20-O7

MOLECULAR WEIGHT :: 312.35

WISWESSER LINE NOTATION :: T C665 A AX EV IO FUTJ B1 C1Q DQ F1 KQ LQ 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 - rat

DOSE/DURATION :: 19500 ug/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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4100 ug/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 - rat

DOSE/DURATION :: 900 ug/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 :: Rodent - mouse

DOSE/DURATION :: 5 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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes Endocrine - other changes Blood - changes in bone marrow (not otherwise specified)

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5200 ug/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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6300 ug/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 42 mg/kg/4W-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 126 mg/kg/12W-C

TOXIC EFFECTS :: Endocrine - changes in thymus weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 131 mg/kg/26W-C

TOXIC EFFECTS :: Behavioral - food intake (animal) 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 :: 262 mg/kg/1Y-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - leukopenia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 3500 ug/kg/7D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure) Skin and Appendages - hair

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Ascites tumor

DOSE/DURATION :: 1 mg/L

REFERENCE :: EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 24,1032,1968 *** 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 TOXICOLOGY REVIEW MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 26,225,1974 TOXICOLOGY REVIEW NUREA8 Nutrition Reviews. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1942- Volume(issue)/page/year: 31,169,1973

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302 + H332-H319

[ Precautionary Statements ]:
P210-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
T+: Very toxic;Xn: Harmful;F: Flammable;

[ Risk Phrases ]:
R26/27/28

[ Safety Phrases ]:
S22;S26;S28;S45;S36/S37;S36/S37/S39

[ RIDADR ]:
UN 2811 6

[ WGK Germany ]:
3

[ RTECS ]:
YD0165000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
38220090

Synthetic Route

Click to get detail synthetic route

Preparation

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...

Toxicity induced by F. poae-contaminated feed and the protective effect of Montmorillonite supplementation in broilers.

Food Chem. Toxicol. 74 , 120-30, (2014)

The T-2 and HT-2 toxins, the main metabolites of Fusarium poae, induce toxicity in broilers and accumulate in tissues. Consequently, during the breeding process of broilers, diets are frequently suppl...

Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet.

Phytopathology 101(11) , 1338-45, (2011)

Crop rotations with putative non-host crops such as sugar beet are often recommended to reduce Fusarium head blight (FHB) in cereals. However, recent observations have shown pathogenic, endophytic, an...