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(1S)-2,3,6aα,9aα-テトラヒドロ-1β-ヒドロキシ-4-メトキシシクロペンタ[c]フロ[3',2':4,5]フロ[2,3-h][1]ベンゾピラン-11(1H)-オン

(1R,6aS,9aS)-1-Hydroxy-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-11(1H)-one

HCID 5284338
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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
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基本情報

CAS
29611-03-8
標準SMILES
COc1cc2c(c3oc(=O)c4c(c13)CC[C@H]4O)[C@@H]1C=CO[C@H]1O2
InChIKey
WYIWLDSPNDMZIT-BTKFHORUSA-N
分子式
C17H14O6
平均分子量
314.29 g/mol
単同位体質量
314.07903816

概要

Aflatoxicol is a metabolite of aflatoxin B1, one of the mycotoxins from Aspergillus flavus and A. parasiticus. Aflatoxins are toxic and probably among the most carcinogenic substances known. They are common and widespread in nature and can colonize and contaminate grain before harvest or during storage. (L1956)

名称と識別子

優先名称
(1R,6aS,9aS)-1-Hydroxy-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-11(1H)-one
IUPAC
(3S,7S,16R)-16-hydroxy-11-methoxy-6,8,19-trioxapentacyclo[10.7.0.02,9.03,7.013,17]nonadeca-1,4,9,11,13(17)-pentaen-18-one
現地名
(1S)-2,3,6aα,9aα-テトラヒドロ-1β-ヒドロキシ-4-メトキシシクロペンタ[c]フロ[3',2':4,5]フロ[2,3-h][1]ベンゾピラン-11(1H)-オン
英語名
AFLATOXICOL I NATURAL ISOMER*VACUUM DRIE D
分子式
C17H14O6
分子量
314.29

名称と別名

NS00028733(1R,6aS,9aS)-1-hydroxy-4-(methyloxy)-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h]chromen-11(1H)-one(1R,6aS,9aS)-1-Hydroxy-4-methoxy-2,3,6a,9a-tetrahydrocyclopenta[c]furo[3',2':4,5]furo[2,3-h][1]benzopyran-11(1H)-oneアフラトキシコールアフラトキシンR0(1S)-2,3,6aα,9aα-テトラヒドロ-1β-ヒドロキシ-4-メトキシシクロペンタ[c]フロ[3',2':4,5]フロ[2,3-h][1]ベンゾピラン-11(1H)-オン(1S)-2,3,6aα,9aα-テトラヒドロ-1β-ヒドロキシ-4-メトキシシクロペンタ[c]フロ[3′,2′:4,5]フロ[2,3-h][1]ベンゾピラン-11(1H)-オン1,2,3,6aα,9aα,11-ヘキサヒドロ-1β-ヒドロキシ-4-メトキシシクロペンタ[c]フロ[3′,2′:4,5]フロ[2,3-h][1]ベンゾピラン-11-オン(3S,7R,16S)-16-ヒドロキシ-11-メトキシ-6,8,19-トリオキサペンタシクロ[10.7.0.02,9.03,7.013,17]ノナデカ-1,4,9,11,13(17)-ペンタエン-18-オンaflatoxicolaflCcris 11
名称をさらに表示
flatoxicolAflatoxicol A[1S]-AflatoxicolEinecs 249-727-7aflatoxicolnaturalepimerahydro-1-hydroxy-4-methoxy-aflatoxin R0, natural isomer

データベース識別子

CAS
29611-03-8
PubChem CID
5284338
DTXSID
DTXSID4020034

物性

構造計算による物性

XLogP
1.2
極性表面積
74.2 Ų
水素結合供与体数
1
水素結合受容体数
6
回転可能結合数
1
重原子数
23
形式電荷
0
複雑度
610

実験および物理化学的性質

Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点
225 °C · 225°C
沸点
373.98 °C · 373.98°C (rough estimate)
比重(密度)
1.2564 · 1.2564 (rough estimate)
屈折率
1.48 · 1.4800 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
1 mg/ml · Methanol: 1 mg/ml
外見
白い粉。
色
White to off-white
安定性
Hygroscopic

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。

毒性情報

Treatment · 1 件

Administration of phonobarbital enhances hepatic transformation activities and also protects against AFB-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. Antioxidants such as ellagic acid and inducers of some cytochromes P450, such as indole-3-carbinol, may give a protective effect. (A704, L1879)

Health Effects · 1 件

The main target organ in mammals is the liver so aflatoxicosis is primarily a hepatic disease. Protracted exposure to aflatoxins may cause liver damage and necrosis, cholestasis, and hepatomas. Moreover, protracted exposure to aflatoxins has been associated with hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. However, aflatoxins accumulate in the presence of liver disease, and the association with hepatic cancer is confounded by the occurrence of hepatitis-B. Thus, it is not clear in these various instances whether aflatoxin is a primary cause of the disease, is an innocent bystander which accumulates secondary to the disease process, or is a contributing cause in conjunction with other factors. It is also mutagenic and teratogenic. Inhaled aflatoxins may produce pulmonary adenomatosis. Aflatoxins modify the immune system by affecting antibody formation, complement, cell-mediated immunity, and phagocytosis. (A704, L1956)

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

Aflatoxins produce singlet oxygen upon their exposure to UV (365-nm) light. Singlet oxygen in turn activates them to mutagens and DNA binding species. Aflatoxin metabolites can intercalate into DNA and alkylate the bases through their epoxide moiety, binding particularity to N7-guanine bases. In addition to randomly mutating DNA, this is thought to cause mutations in the p53 gene, an important gene in preventing cell cycle progression when there are DNA mutations, or signaling apoptosis. (L1877, A2859, A2972)

Signs and SymptomsA broad range of symptoms can be found depending upon dosage, including, vomiting, abdominal pain, hemorrhage, and pulmonary edema. (L1879)
Carcinogen ClassificationNot directly listed by IARC. Aflatoxin B1 is carcinogenic to humans (Group 1). (L135)

安全データ

ridadr
3172
hs_code
29419090
risk_code
45-46-61-26/27/28
hazard_code
T+
safety_code
53-22-36/37/39-45
hazard_class
6.1(a)
packing_group
I

化学と産業

薬理情報

Metabolism/MetabolitesAflatoxins are metabolized in the liver by the cytochrome P-450-dependent polysubstrate mono-oxygenase system to less toxic metabolites. The main reactions in aflatoxin metabolism are hydroxylation, oxidation, and demethylation. (A2973)

用途と製造

Uses · 1 件

The native habitat of Aspergillus is in soil, decaying vegetation, hay, and grains undergoing microbiological deterioration and it invades all types of organic substrates whenever conditions are favorable for its growth. Crops which are frequently affected include cereals (maize, sorghum, pearl millet, rice, wheat), oilseeds (peanut, soybean, sunflower, cotton), spices (chile peppers, black pepper, coriander, turmeric, ginger), and tree nuts (almond, pistachio, walnut, coconut, brazil nut). The toxin can also be found in the milk of animals which are fed contaminated feed. Thus, aflatoxins are usually encountered in thecontext of chronic exposure, via food intake or secondary to the handling of foodstuffs. (L1956)

応用分野 · 1 件

説明Aflatoxin R0 is a metabolite of the carcinogenic mycotoxin aflatoxin B1 . Aflatoxin R0 is produced by metabolism in animals as well as in fungi and can be reverted to the parent compound in fungi. Aflatoxin R0 is highly mutagenic when tested in the Ames'' in vitro microbial detection system for carcinogens.

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