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HCID 5284433作成日：2026年10月30日

12,13-エポキシ-3α,4β,7β,15-テトラヒドロキシトリコテカ-9-エン-8-オン

12,13-エポキシ-3α,4β,7β,15-テトラヒドロキシトリコテカ-9-エン-8-オン · ニバレノール · 3α,4β,7α,15-テトラヒドロキシ-12,13-エポキシトリコテカ-9-エン-8-オン · 12,13-エポキシ-3α,4β,7α,15-テトラヒドロキシトリコテカ-9-エン-8-オン · ニバレノール標準液 · ニバレノール水和物標準品 · ニバレノール 100ΜG/ML · ニバレノール 水和物

https://huagongshe.com/ja/chemical/5284433

12,13-エポキシ-3α,4β,7β,15-テトラヒドロキシトリコテカ-9-エン-8-オン の分子構造式

識別子と物理属性

CAS No.23282-20-4
分子式C15H20O7
平均分子量312.31 g/mol
単同位体質量312.12090297 g/mol
SMILESCC1=C[C@H]2O[C@@H]3[C@H](O)[C@@H](O)[C@](C)([C@@]2(CO)[C@H](O)C1=O)[C@]31CO1
InChIKeyUKOTXHQERFPCBU-XBXCNEFVSA-N
PubChem CID5284433
ChEMBLCHEMBL509655
EC No.621-749-5
DTXSIDDTXSID3021067
現地名12,13-エポキシ-3α,4β,7β,15-テトラヒドロキシトリコテカ-9-エン-8-オン

化学・物理的性質

XLogP-1.7
極性表面積120
水素結合供与体数4
水素結合受容体数7
回転可能結合数1
重原子数22
形式電荷0
複雑度588
物質分類Biological Agents -> Mycotoxins
Color/FormCrystals from methanol
溶解度Soluble in polar organic solventsDMF: 30 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
DecompositionHazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)
融点222-223 °C, decomposes222-223℃
Optical RotationSpecific optical rotation: +21.54 deg at 20 °C/D
Physical DescriptionSolid[Merck Index]
Stability/Shelf LifeStable under recommended storage conditions.
Collision Cross Section180 Ų [M+H3C2O2]- [CCS Type: TWMethod: calibrated with polyalanine]
Other Experimental PropertiesColorless, mostly crystalline solids that have been well characterized by physical and spectroscopic techniques. ... require higher polarity solvents, such as aqueous methanol or aqueous acetonitrile. /Trichothecenes/The trichothecenes are generally stablefor example, DON (deoxynivalenol) can be stored in organic solvents, such as ethyl acetate, for a long time without any significant deterioration ... They remain unaffected when refluxed with various organic solvents and also under mildly acidic conditions.
比旋光度24D +21.54° (c = 1.3 in ethanol)
沸点372.24°C (rough estimate)
密度1.2307 (rough estimate)
屈折率1.4790 (estimate)
引火点2 °C
貯蔵条件2-8°C
pKa（酸解離定数）11.78±0.70(Predicted)
外観・状態Solid
色MeOHからの結晶
ヘンリー定数1.4×1010 mol/(m3Pa) at 25℃, HSDB (2015)
主な用途洗浄剤化粧品食品および飲料パーソナルケア
InChI1S/C15H20O7/c1-6-3-7-14(4-16,11(20)8(6)17)13(2)10(19)9(18)12(22-7)15(13)5-21-15/h3,7,9-12,16,18-20H,4-5H2,1-2H3/t7-,9-,10-,11-,12-,13-,14-,15+/m1/s1
InChIKeyUKOTXHQERFPCBU-XBXCNEFVSA-N
SMILES[H][C@]12O[C@]3([H])[C@H](O)[C@@H](O)[C@@](C)([C@]34CO4)[C@@]1(CO)[C@H](O)C(=O)C(C)=C2
LogP（分配係数）-1.558 (est)

化学的特性

Solid

安全性と法規制

GHS 分類DangerH300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Regulation (EC) No 178/2002 (amended)
火災の可能性Vapors may form explosive mixture with air.Flammable in the presence of a source of ignition when the temperature is above the flash point. Keep away from heat/sparks/open flame/hot surface. No smoking.
有害性の概要Trichothecene mycotoxins causes bone marrow suppression, leukopenia, immunosuppression, and secondary sepsis[HSDB] May cause necrotic lesions to skin and mucosa[Merck Index] A vesicant to skin, can cause irritation to severe tissue destruction[MSDSonline] See Deoxynivalenol.
Special ReportsSaito M, Tatsuno TToxins of Fusarium nivaleMicrobial toxins 7: 293 (1971). A review with 75 ref. The toxic effects of nivalenol produced by F nivale and related species on livestock and humans, and the phys, chem, and carcinogenic properties of these compd are discussed.WHOEnvironmental Health Criteria 105: Selected Mycotoxins: Ochratoxins, Trichothecenes, Ergot (1990)WHO ENVIRONMENTAL HEALTH CRITERIA 11: MYCOTOXINS WHO GENEVA SWITZERLAND ILLUS PAPER ISBN 92-4-154071-0 0(0) 127 PAGES (1979) A review on toxicity of mycotoxins to humans and animals, incl nivalenol.Hascheh WM and Beasley VRp. 353-369 in Handbook of Toxicology of Chemical Warfare AgentsGupta RC, ed (2009)
History and IncidentsHuman toxicosis related to ingestion of Fusarium infected grain (Scabby grain diseases) was previously reported in several countries, including Japan and Korea during the period of 1946-1963, and India ...nausea, vomiting, diarrhea and abdominal pain were common symptoms associated with the toxicosis, recovery usually occurred within a few days and no lethal cases were reported. Typically mixtures of trichothecenes were detected but no single toxin could be identified as being solely responsible for the toxicosis. In the outbreaks in Japan and Korea, F. graminearum was isolated from suspected cereals suggesting a possibility of deoxynivalenol and/or nivalenol contamination. The number of cases involved was over 100 in both the two Chinese and the two Indian outbreaks, although none was lethal. In 1987, an acute outbreak in India affecting approximately 50 000 people was due to consumption of bread made from rain-damaged wheat. The wheat contained deoxynivalenol (0.34-8.4 mg/kg in 11 of 24 samples), acetyldeoxynivalenol (0.6-2.4 mg/kg in 4 of 24 samples), nivalenol (0.03-0.1 mg/kg in 2 of 24 samples) and T-2 toxin (0.55-4.0 mg/kg in 3 of 24 samples). Cases exhibited mainly minor gastrointestinal symptoms (abdominal pain, diarrhea, bloody stool and vomiting) for approximately two days.

用途

使用

Nivalenol is a mycotoxin found in wheat and maize which is produced by different Fusarium species that inhibit eukaryotic biosynthesis of protein.Environmental contaminants; Food contaminants

The Soviet Union was alleged to have provided mycotoxins to the armies of Vietnam and Laos for use against resistance forces in Laos and Cambodia and to have used mycotoxins in combat operations in Afghanistan. Confirmation of this use of mycotoxins has been difficult and controversial. T-2 toxin, nivalenol, and dexynivalenol were identified in vegetation at affected sites and both T-2 toxin and HT-2 toxin, a metabolite of T-2 toxin, were found in urine and blood samples from victims of alleged attacks. T-2 toxin was also reportedly found in high concentrations in spots found on rocks and gas masks. While mycotoxins are considered impractical as a tactical weapons, crude preparations could be readily produced and used by terrorist organizations to contaminate food or water supplies, or be released as an aerosol in small crowded areas.
Toxic Combustion ProductsHazardous decomposition products formed under fire conditions. - Carbon oxides, nitrogen oxides (NOx)
Hazard Classes and CategoriesAcute Tox. 1 (100%)
Skin, Eye, and Respiratory IrritationsTrichothecenes are well known skin irritants and nivalenol has been shown in some early studies to have weak skin irritancy properties.
Hazardous Reactivities and Incompatibilities/Avoid/ Heat, flames and sparks. Extremes of temperature and direct sunlight.
消火手順Wear self contained breathing apparatus for fire fighting if necessary.Use water spray to cool unopened containers.Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
保管条件Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: -20 °C Handle and store under inert gas.
清掃方法Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations
処分方法SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive MeasuresUse personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.
TreatmentThere are no known antidotes to trichothecene mycotoxins. Treatments are directed at supporting hemopoietic abnormalities, gastrointestinal damage, and skin damage. Administer charcoal as a slurry in case of acute oral exposure. In case of inhalation: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (A704)
相互作用A feeding trial was conducted in order to determine the effects of a Fusarium poae extract on the health and performances of broiler chickens and the possible protective effect of a natural zeolite. The F. poae extract contained nivalenol, T-2 toxin and diacetoxyscirpenol and demonstrated high toxicity when administered i.p. to rats. One-day-old broiler chickens were fed ad libitum over a period of 28 days with the following diets: group I - controlgroup II - 0.5% zeolitegroup III -F. poae extractgroup IV-0.5% zeolite andF. poae extract. Broilers were sacrificed at 28 days for the measurement of relative organs weights, leukocyte counts and serum biochemical values. No mortality was recorded over the experiment. Body weight gains, feed intake, feed utilization and water consumption were depressed by the F. poae extract (p<0.05). A decrease of these parameters was also observed in group IV which received the diet with zeolite and the F. poae extract. No significant differences were seen in group II when compared to control. In groups III and IV the relative weights of liver, kidney, heart and gizzard were significantly increased (p<0.05), while in group II only the relative liver weight was increased. F. poae extract, administered singly or in combination with zeolite, significantly decreased leukocytes count, serum total protein and serum albumin. Zeolite and F. poae extract, singly or combined, increased serum creatinine and uric acid concentrations (p<0.05). These findings indicate that sublethal doses of F. poae extract can affect adversely the performances and the health in broiler chickens. By adding zeolite these impairments could not be diminished and for some parameters the zeolite additive increased the adverse effects of the F. poae extract.Deoxynivalenol (DON) and nivalenol (NIV) are toxic Fusarium secondary trichothecene metabolites that often co-occur regularly in cereal grains. These compounds were compared for their toxicity towards C57BL/6 mice on several parameters including alteration in plasma biochemistry, immune system reactivity and hepatic drug metabolism capacity. Mice received individual or combined oral doses of each toxin: 0.071 or 0.355 mg/kg of body weight, administrated three days a week for 4 weeks. Food consumption was altered by the single administration of 0.355 mg/kg of NIV, although no noticeable change of body and organ weights or liver protein contents was detected. NIV administration did cause also significant changes in total CO2 and uric acid concentrations in plasma. Individual toxin exposures led to increases in plasma IgA without no detectable change in the ex vivo production of cytokine by splenocytes. The liver ethoxyresorufin O-deealkylase, pentoxyresorufin O-depenthylase and glutathione S-transferase activities were increased in concert with cytochrome P4501a and P4502b subfamily expression. Administration of combinations of DON and NIV resulted in responses similar to that observed using individual doses of each toxin. However, depending on the ratio of toxin doses and biochemical parameters, some responses could be also additive (plasma IgA and hepatic DCNB conjugation) or synergistic (plasma uric acid).Deoxynivalenol (DON) is the most prevalent trichothecene mycotoxin in crops in Europe and North America. DON is often present with other type B trichothecenes such as 3-acetyldeoxynivalenol (3-ADON), 15-acetyldeoxynivalenol (15-ADON), nivalenol (NIV) and fusarenon-X (FX). Although the cytotoxicity of individual mycotoxins has been widely studied, data on the toxicity of mycotoxin mixtures are limited. The aim of this study was to assess interactions caused by co-exposure to Type B trichothecenes on intestinal epithelial cells. Proliferating Caco-2 cells were exposed to increasing doses of Type B trichothecenes, alone or in binary or ternary mixtures. The MTT test and neutral red uptake, respectively linked to mitochondrial and lysosomal functions, were used to measure intestinal epithelial cytotoxicity. The five tested mycotoxins had a dose-dependent effect on proliferating enterocytes and could be classified in increasing order of toxicity: 3-ADON<15-ADON =~ DON<NIV << FX. Binary or ternary mixtures also showed a dose-dependent effect. At low concentrations (cytotoxic effect between 10 and 30-40%), mycotoxin combinations were synergistichowever DON-NIV-FX mixture showed antagonism. At higher concentrations (cytotoxic effect around 50%), the combinations had an additive or nearly additive effect. These results indicate that the simultaneous presence of low doses of mycotoxins in food commodities and diet may be more toxic than predicted from the mycotoxins alone. Considering the frequent co-occurrence of trichothecenes in the diet and the concentrations of toxins to which consumers are exposed, this synergy should be taken into account.Molded and mycotoxin containing barley was incorporated into the diets for laying hens to study the effects on performance and health. Health indicators were different blood plasma parameters and liver vitamin A and E levels. A total of 30 hens were fed 3 diets, one supplemented with 30% of toxin-free and two with differently molded barley from 1997 and 1998 for 7 weeks. The molded diets contained low to moderate concentrations of ochratoxin A, zearalenone, deoxynivalenol and nivalenol. Inclusion of moldy barley in the diets had an adverse effect on feed intake, feed conversion, digestibility of nutrients, egg production and egg quality. Plasma alkaline phosphatase was increased and certain biochemical blood parameters (bilirubin, uric acid, chloride, protein, albumin, vitamin A) were also higher or changed compared to control. The ochratoxin A contamination although relatively low could have contributed to some of these effects as well as reduced intake of feed. The higher mold contamination and an unidentified cell-toxic constituent in the diet containing barley from 1998 can probably also explain the more marked effects from this diet./ALTERNATIVE and IN VITRO TESTS/ Nivalenol (NIV) and Deoxynivalenol (DON), mycotoxins of the trichothecene family are considered very common food contaminants. In this work, /the authors/ investigated whether the immunotoxic effects ascribed to these trichothecenes may be mediated by perturbations in the activity of dendritic cells (DCs). Murine bone marrow-derived DCs were used to evaluate the effects of NIV and DON on the LPS-induced maturation process. /The authors/ found that the expression of the class II MHC and of the accessory CD11c molecules, but not of the costimulatory CD86 marker, was down-regulated by NIV and DON exposure in LPS-treated DCs, as well as nitric oxide (NO) production. Interestingly, NIV, but not DON, induced DC necrosis. Moreover, the analysis of the cytokine pattern showed that IL-12 and IL-10 expressions induced by LPS exposure were suppressed by both trichothecenes in a dose-dependent fashion. On the other hand, the secretion of the proinflammatory cytokine TNF-alpha was increased as a direct consequence of DON and NIV exposure. Taken together, /this/ data indicated that the immunotoxicity of NIV and DON was related to the capacity of both trichothecenes to interfere with phenotypic and functional features of maturing DCs.
健康影響Trichothecenes have multiorgan effects including anoerxia and weight loss, growth retardation, nervous disorders, cardiovascular alterations, immunodepression, hemostatic derangements, skin toxicity, decreased reproductive capacity, bone marrow damage, and alimentary toxic aleukia. (L1948, L1949, A2964)
環境中動態TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that nivalenol is expected to have very high mobility in soil(SRC). Volatilization of nivalenol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 7.3X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Nivalenol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.9X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2013).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that nivalenol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 7.3X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -2.24(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2013).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nivalenol, which has an estimated vapor pressure of 6.9X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase nivalenol may be removed from the air by wet and dry deposition(SRC). Trichothecenes, such as nivalenol, are stable to UV light(4) and, therefore, may not be susceptible to direct photolysis by sunlight(SRC).
食品調査値Nivalenol was not detected in four cassava flour, fifteen peanut cake nor four maize samples from local markets in the Republic of Benin, sub-Saharan Africa. Limit of detection in maize, cassava (Manihot esculata), and peanut cake was 35, 31, and 25 ug/kg, respectively(1).In the present study, the occurrence of eighteen mycotoxins, nine trichothecenes (deoxynivalenol, 3-acetyl-deoxynivalenol, 15-acetyl-deoxynivalenol, nivalenol, neosolaniol, diacetoxyscirpenol, fusarenon-X, T-2 toxin and HT-2 toxin), three zearalenones (zearalenone, alpha-zearalenol and beta-zearalenol), and six emergent mycotoxins, beauvericin and five enniatins (A, A1, B, B1 and B4), was monitored in different Italian organic cereals and cereal products by using a liquid chromatography coupled to triple quadrupole mass spectrometry method. A total of 93 organic cereal samples (wheat, barley, rye and oat) were collected from Italy. Limits of quantification ranged from 5 to 15 ug/kg. 80% of analyzed samples contained mycotoxins. The occurrence was 33%, 6.5%, 2%, 27%, 7%, 10% and 43% for deoxynivalenol, HT-2, T-2, nivalenol, zearalenone, beauvericin and enniatins, respectively. The major mycotoxin found was enniatin B4it was detected in 40% of all analyzed samples and its levels ranged from 5.7 to 284.2 ug/kg. Risk assessment was evaluated by EDI calculations which were lower than TDI for all legislated Fusarium mycotoxins.Natural occurrence of nivalenol in cereals and foods sampled worldwide from 1980-1985(1).[Table#4622]
有害作用Dermatotoxin - Skin burns.
暴露経路Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
毒性の概要Unlike many other mycotoxins, trichothecenes do not require metabolic activation to exert their biological activity, instead directly reacting with cellular components. Trichothecenes are cytotoxic to most eukaryotic cells due to their powerful ability to inhibit protein synthesis. They do this by freely moving across the plasma membrane and binding specifically to ribosomes with high-affinity. Specifically, they interfere with the active site of peptidyl transferase at the 3'-end of large 28S ribosomal RNA and inhibit the initiation, elongation or termination step of protein synthesis, as well as cause polyribosomal disaggregation. Protein synthesis is an essential function in all tissues, but tissues where cells are actively and rapidly growing and dividing are very susceptible to the toxins. Additionally, binding to ribosomes is thought to activate proteins in downstream signalling events related to immune response and apoptosis, such as mitogen-activated protein kinases. This is known as ribotoxic stress response. Trichothecenes may also induce some alterations in membrane structure, leading to increased lipid peroxidation and inhibition of electron transport activity in the mitochondria. They can further induce apoptosis through generation of reactive oxygen species. Further secondary effects of trichothecenes include inhibition of RNA and DNA synthesis, and also inhibition of mitosis. (L1948, L1949, A2962, A2963, A2964, A2980)
Average Daily IntakeMycotoxins are harmful substances produced by fungi in several commodities with a widespread presence in foodstuffs. Human exposure to mycotoxins occurs mainly by contaminated food. The quantitation of mycotoxins in cereal-based food, highly consumed by different age population, is of concern. In this survey, 159 cereal-based samples classified as wheat, maize and rice-based, have been evaluated for the occurrence of patulin, deoxynivalenol, 3-acetyl-deoxynivalenol, fusarenon-X, diacetoxyscirpenol, nivalenol, neosolaniol, HT-2, T-2 and zearalenone by gas chromatography-tandem mass spectrometry. Intakes were calculated for average consumers among adults, children and infants and compared with the tolerable daily intakes (TDI). Data obtained were used to estimate the potential exposure levels. 65.4% of the samples were contaminated with at least one mycotoxin and 15.7% of the analyzed samples showed co-occurrence of mycotoxin. The dietary exposure to HT-2 and T-2 toxins was estimated as 0.010 and 0.086 ugkg-1bwd-1, amounting to 10% and 86% of the TDI, for adults and infants respectively. These results back up the necessity to take a vigilant attitude in order to minimize human intake of mycotoxins.
Plant ConcentrationsFreshly harvested wheat and barley of the 1977 harvest in Saitama Prefecture, Japan were examined for trichothecene mycotoxin contamination and for the presence of Fusarium species. Trichothecenes, such as nivalenol, were not detected in these samples. The incidence of Fusarium contamination ranged from 0-32.7%. The most common species was F. graminearum. Among 57 isolates of F. graminearum, 43 produced nivalenol.
Signs and SymptomsAfter direct dermal application or oral ingestion, the trichothecene mycotoxins can cause rapid irritation to the skin or intestinal mucosa, including skin irritation, burning and itching, rash or blisters, and bleeding. Eye contact can cause tearing, eye pain, conjunctivitis, burning sensations about the eyes, and blurred vision for up to 1 week. Symptoms also include nausea, vomiting, fatigue, dyspnea, and acute vascular effects leading to hypotension and shock. (L1948, L1949, A737)
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of nivalenol can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that nivalenol is expected to have very high mobility in soil.
水環境危害等級（WGK）3
RTECS 番号YD0165000
輸送番号（UN）UN 2811 6.1/PG 1
毒性LD50 i.p. in mice: 40 mg/10 g (Tatsuno)
PRTR法1-13
税関コード38220090
危険文句（R）26/27/28-36-20/21/22-11
安衛法57-2
消防法危-4-1-S-II
危険表示T+,Xn,F
安全措置（S）22-36/37/39-45-36/37-26-28-16
危険等級6.1(a)Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
包装等級I
毒劇物取締法II
貯蔵分類3 - Flammable liquids
有害物質データ23282-20-4(Hazardous Substances Data)