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12,13-エポキシトリコテカ-9-エン-4β,15-ジオール

Verrucarol

HCID 10038552
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
2198-92-7
標準SMILES
CC1=C[C@H]2O[C@@H]3C[C@@H](O)[C@](C)([C@@]2(CO)CC1)[C@]31CO1
InChIKey
ZSRVBNXAPSQDFY-OJVARPOJSA-N
分子式
C15H22O4
平均分子量
266.33 g/mol
単同位体質量
266.15180918

概要

Verrucarol is a trichothecene.

名称と識別子

優先名称
Verrucarol
IUPAC
(1S,2R,7R,9R,11R,12S)-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-ol
現地名
12,13-エポキシトリコテカ-9-エン-4β,15-ジオール
英語名
VERRUCAROL
分子式
C15H22O4
分子量
266.33

名称と別名

Verrucarol2198-92-716Z45187LG(1S,2R,7R,9R,11R,12S)-2-(hydroxymethyl)-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-11-ol(4beta)-12,13-Epoxytrichothec-9-ene-4,15-diolTrichothec-9-ene-4,15-diol, 12,13-epoxy-, (4beta)-DTXSID00891793(1S,2R,7R,9R,11R,12S)-2-(hydroxymethyl)-1,5-dimethylspiro(8-oxatricyclo(7.2.1.02,7)dodec-5-ene-12,2'-oxirane)-11-olRefChem:901814(4 beta)-12,13-epoxytrichothec-9-ene-4,15-diolDTXCID8010312882'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro(oxirane-2,12'-tricyclo(7.2.1.02,7)dodecan)-5'-en-11'-ol
名称をさらに表示
12,13-エポキシトリコテカ-9-エン-4β,15-ジオールベルカロール(2S,5R)-12,13-エポキシトリコテカ-9-エン-4β,15-ジオール(1'S,2S,2'R,7'R,9'R,11'R)-2'-(ヒドロキシメチル)-1',5'-ジメチル-8'-オキサスピロ[オキシラン-2,12'-トリシクロ[7.2.1.02,7]ドデカン]-5'-エン-11'-オール(-)-ベルカロール(1'R,2S,2'R,7'R,9'S,11'R)-2'-(ヒドロキシメチル)-1',5'-ジメチル-8'-オキサスピロ[オキシラン-2,12'-トリシクロ[7.2.1.02,7]ドデカン]-5'-エン-11'-オールVerrucarol StandardVerrucarol in acetonitrile

物性

構造計算による物性

XLogP
0
極性表面積
62.2 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
1
重原子数
19
形式電荷
0
複雑度
461

物理化学的性質

融点
155 · 155-156 °C
沸点
422 · 422.0±45.0 °C(Predicted)
比重(密度)
1.3 · 1.30±0.1 g/cm3(Predicted)
貯蔵温度
20 °C · −20°C
酸解離定数(Pka)
14.35 · 14.35±0.70(Predicted)

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]

P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

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 Routes

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)

サプライヤー3 社

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
12,13-Epoxytrichothec-9-ene-4β,15-diol
4β,15-dihydroxy-12,13-epoxytrichothec-9-ene
4BETA,15-DIHYDROXY-12,13-EPOXY-TRICHOTHEC-9-ENE
Trichothec-9-ene-4,15-diol, 12,13-epoxy-, (4β)-
633-621-6Verrucarol, (+/-)-(-)-VERRUCAROL4FAZ232G4J80514-49-4Trichothec-9-ene-4,15-diol, 12,13-epoxy-, (4.beta.)-UNII-4FAZ232G4J(+/-)-VERRUCAROL

データベース識別子

CAS
2198-92-7、80514-49-4
PubChem CID
10038552
ChEMBL
CHEMBL504718
ChEBI
CHEBI:228528
UNII
16Z45187LG、4FAZ232G4J
EC Number
633-621-6
Nikkaji
J34.207F
Oral, 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
ridadr
UN 2811 6.1/PG 1
risk_code
26/27/28-36/37/38
hazard_code
T+
safety_code
22-26-36/37/39-45