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12,13-エポキシ-3α,7α,15-トリヒドロキシトリコテカ-9-エン-8-オン3-アセタート

3-Acetyldeoxynivalenol

HCID 5458510
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基本情報

CAS
50722-38-8
標準SMILES
CC(=O)O[C@@H]1C[C@]2(C)[C@@]3(CO)[C@H](O)C(=O)C(C)=C[C@H]3O[C@H]1[C@@]21CO1
InChIKey
ADFIQZBYNGPCGY-HTJQZXIKSA-N
分子式
C17H22O7
平均分子量
338.4 g/mol
単同位体質量
338.13655304

概要

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

名称と識別子

優先名称
3-Acetyldeoxynivalenol
IUPAC
[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate
現地名
12,13-エポキシ-3α,7α,15-トリヒドロキシトリコテカ-9-エン-8-オン3-アセタート
英語名
3-Acetyldeoxynivalenol
分子式
C17H22O7
分子量
338.35

名称と別名

3-Acetyldeoxynivalenol50722-38-83-Acetyl dondeoxynivalenol 3-acetateDeoxynivalenol monoacetate3-ADONDehydronivalenol monoacetateDTXSID60891850CHEBI:146195838JJ2425YNSC-267036acetylDON
名称をさらに表示
3-アセチル-4-デオキシニバレノール3α-アセトキシ-7α,15-ジヒドロキシ-12,13-エポキシトリコテカ-9-エン-8-オン3α-アセトキシ-12,13-エポキシ-7α,15-ジヒドロキシトリコテカ-9-エン-8-オン12,13-エポキシ-3α-アセトキシ-7α,15-ジヒドロキシトリコテカ-9-エン-8-オン3α-アセトキシ-7α,15-ジヒドロキシ-トリコテカ-9-エン-8-オン12,13-エポキシ-3α,7α,15-トリヒドロキシトリコテカ-9-エン-8-オン3-アセタート3-アセチルデオキシニバレノールDON-3-アセタート3‐アセチルデオキシニバレノール標準品3‐アセチルデオキシニバレノール標準液3-アセチルデオキシニバレノール 100ΜG/ML3-アセチル-デオキシニバレノール溶液(100ΜG/ML アセトニトリル溶液)3-アセチルデオキシニバレノール標準品3-アセチルデオキシニバレノール 溶液(1S,2R,3S,7R,9S,10R,12S)-3-ヒドロキシ-2-(ヒドロキシメチル)-1,5,12-トリメチル-4-オキソ-8-オキサトリシクロ[7.2.1.02,7]ドデカ-5-エン-10-イル アセタート3-アセチルデオキシニバレノール標準液標準物質3-ACDON3-olNSC 2670363-acetyldonDON-3-acetate3α-Acetylvomitoxinreference material3ALPHA-ACETYLVOMITOXIN
[(1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-10-yl] acetate((1R,2R,3S,7R,9R,10R,12S)-3-hydroxy-2-(hydroxymethyl)-1,5-dimethyl-4-oxospiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-10-yl) acetateRefChem:92824DTXCID3010312713-Acetyl Deoxynivalenol3-Acetyl-deoxynivalenol3-acetyl-DON7alpha,15-dihydroxy-8-oxo-12,13-epoxytrichothec-9-en-3alpha-yl acetate

データベース識別子

CAS
50722-38-8
PubChem CID
5458510
DTXSID
DTXSID60891850
ChEMBL
CHEMBL468652
ChEBI
CHEBI:146195
UNII
838JJ2425Y
EC Number
621-771-5
Nikkaji
J275.534C

物性

構造計算による物性

XLogP
-0.1
極性表面積
106 Ų
水素結合供与体数
2
水素結合受容体数
7
回転可能結合数
3
重原子数
24
形式電荷
0
複雑度
657

実験および物理化学的性質

Collision Cross Section · 2 件

196 Ų [M+H3C2O2]- [CCS Type: TW; Method: calibrated with polyalanine]

183.83 Ų [M+Na]+

物理化学的性質

融点
185.75 °C · 185.75°C
沸点
394.5 °C · 394.5°C (rough estimate)
比重(密度)
1.2179 · 1.2179 (rough estimate)
屈折率
1.479 · 1.4790 (estimate)
闪点
2 °C · 2 °C
貯蔵温度
-20 °C · -20°C
溶解性
30 mg/ml; · DMF: 30 mg/ml; DMSO: 25 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml
酸解離定数(Pka)
11.84 · 11.84±0.70(Predicted)
外見
powder
由来生物
Fusarium roseum
主な用途
洗浄剤化粧品食品および飲料パーソナルケア
InChI
1S/C17H22O7/c1-8-4-11-16(6-18,13(21)12(8)20)15(3)5-10(23-9(2)19)14(24-11)17(15)7-22-17/h4,10-11,13-14,18,21H,5-7H2,1-3H3/t10-,11-,13-,14-,15-,16-,17+/m1/s1
InChIKey
ADFIQZBYNGPCGY-HTJQZXIKSA-N
SMILES
CC(=O)O[C@@H]1C[C@@]2(C)[C@]3(CO3)[C@@H]1O[C@@H]4C=C(C)C(=O)[C@@H](O)[C@]24CO
LogP
-0.448 · -0.448 (est)

化学的性質

化学的特性Solid

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and CategoriesAcute Tox. 2 (100%)

毒性情報

Treatment · 1 件

There 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)

Health Effects · 1 件

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)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 件

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)

Signs and Symptoms · 1 件

After 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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

wgk
3
rtecs
YD0150000
ridadr
UN 2811 6.1/PG 2
PRTR法
1-13
hs_code
29329990
risk_code
23/24/25-36-20/21/22-11
安衛法
57-2
消防法
危-4-1-S-II
hazard_code
T,Xn,F
safety_code
36/37-45-26-16
hazard_class
6.1(a)
packing_group
I
毒劇物取締法
II
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
ストレージクラス
3 - Flammable liquids

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

Trichothecenes are lipophilic and thus easily absorbed through the skin, gut, and pulmonary mucosa. They are metabolized mainly by cytochrome P-450 and trichothecene-specific carboxylesterase activity in the liver, although other tissues such as the kidney, spleen, and intestine also show some metabolic activity. Trichothecenes are metabolically transformed to less toxic metabolites by such reactions as hydrolysis, hydroxylation, de-epoxidation, and glucuronidation. Metabolites are excreted in the urine and feces. (L1910, L1949)

用途と製造

Uses · 1 件

Trichothecenes are a very large family of chemically related mycotoxins produced by various species of Fusarium, Myrothecium, Trichoderma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. They are produced on many different grains like wheat, oats or maize by various Fusarium species such as F. graminearum, F. sporotrichioides, F. poae and F. equiseti. Some molds that produce trichothecene mycotoxins, such as Stachybotrys chartarum, can grow in damp indoor environments and may contribute to health problems among building occupants. (L1948)

応用分野 · 3 件

解説JIS Q0030(ISO GUIDE30)で定められている.測定装置の校正,測定方法の評価または材料に値を付与することに用いるために一つ以上の特性値が十分に均一で適切に確定されている材料または物質.さらに値が保証されたものを認証標準物質という.

使用3-Acetyldeoxynivalenol is a trichothecene mycotoxin that is produced in a plant-pathogenic fungus, Fusarium graminearum Schwabe.

一般的な説明3-Acetyldeoxynivalenol is a trichothecene mycotoxin, secreted by Fusarium species. It stimulates the activation of c-Jun N-terminal kinase (JNK)/ p38 mitogen-activated protein kinases and prevents protein synthesis. 3-Acetyldeoxynivalenol is a weak inducer of apoptosis.

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