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9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン

9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 化学構造式
78111-17-8
CAS番号.
78111-17-8
化学名:
9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン
别名:
オカダ酸;オカド酸;9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン;オカダ酸標準液;オカダ酸標準液 CRM6206‐A;オカダ酸, PROROCENTRUM CONCAVUM, HIGH PURITY;オカダ酸 渦鞭毛藻PROROCENTRUM CONCAVUM由来
英語化学名:
OKADAIC ACID
英語别名:
OA;CS-759;NSC 677083;Okadic acid;Ocadaic Acid;OKADAIC ACID;HALOCHONDRINE A;Okadaic acid,97%;35-Demethyl-DTX 1;OKADAIC ACID, 98+%
CBNumber:
CB0246204
化学式:
C44H68O13
分子量:
805
MOL File:
78111-17-8.mol

9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 物理性質

融点 :
164-166 °C
比旋光度 :
D20 +21° (c = 0.33 in CHCl3); D25 +25.4° (c = 0.24 in CHCl3)
沸点 :
672.95°C (rough estimate)
比重(密度) :
1.0795 (rough estimate)
屈折率 :
1.5940 (estimate)
貯蔵温度 :
-20°C
溶解性:
DMSO: ≥1 mg/mL
外見 :
translucent film
酸解離定数(Pka):
3.87±0.16(Predicted)
色:
translucent
水溶解度 :
It is soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), methanol (<1 mg/ml), chloroform, acetone, ethyl acetate, DMF, and dimethylsulfoxide. Insoluble in water, unless first dissolved in organic solvents, such as DMSO or ethanol.
Merck :
13,6891
安定性::
Stable. Light and heat-sensitive. Combustible. Incompatible with strong oxidizing agents.
CAS データベース:
78111-17-8
EPAの化学物質情報:
1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, .alpha,5-dihydroxy-.alpha.,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-, (.alpha.R,2S,5R,6R,8S)- (78111-17-8)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  T
Rフレーズ  23/24/25-38
Sフレーズ  26-36/37-45
RIDADR  UN 3462 6.1/PG 1
WGK Germany  3
RTECS 番号 AA8227800
10
国連危険物分類  6.1(a)
容器等級  II
HSコード  29321900
有毒物質データの 78111-17-8(Hazardous Substances Data)
毒性 LD50 i.p. in mice: 192 mg/kg (Shibata)
消防法 危-4-AL-S-II
安衛法 有機溶剤中毒予防規則:第2種有機溶剤,57,57-2
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H300 飲み込むと生命に危険 急性毒性、経口 1, 2 危険 P264, P270, P301+P310, P321, P330,P405, P501
H310 皮膚に接触すると生命に危険 急性毒性、経皮 1, 2 危険 P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H330 吸入すると生命に危険 急性毒性、吸入 1, 2 危険 P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P320 特別な治療が緊急に必要である(このラベ ルの...を見よ)。
P330 口をすすぐこと。
P403+P233 換気の良い場所で保管すること。容器を密閉 しておくこと。
P405 施錠して保管すること。

9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 価格 もっと(18)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01BVI1543-025
Okadaic acid
78111-17-8 25μg ¥16600 2020-09-21 購入
富士フイルム和光純薬株式会社(wako) W01FLCM02211 オカダ酸, Prorocentrum concavum, high purity
Okadaic acid, Prorocentrum concavum, high purity
78111-17-8 50g ¥39600 2018-12-26 購入
関東化学株式会社(KANTO) 49915-09 オカダ酸標準液
Okadaic acid standard solution
78111-17-8 0.5mL ¥29000 2021-03-23 購入
関東化学株式会社(KANTO) 32837-1A オカダ酸
Okadaic acid
78111-17-8 0.1mg ¥133800 2021-03-23 購入
Sigma-Aldrich Japan O9381 92-100% (HPLC)
Okadaic acid from Prorocentrum concavum 92-100% (HPLC)
78111-17-8 0.1 mg ¥167200 2021-03-23 購入

9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 化学特性,用途語,生産方法

外観

薄膜

溶解性

エーテル、アセトン、酢酸エチルに可溶。クロロホルム、メタノールにやや溶けにくく、水、n-ヘキサンにわずかに溶ける。

説明

Marine algal blooms, natural phenomena produced by the overgrowth of microscopic marine algae, have become a public health concern because of their increasing frequency and severity. About 300 phytoplanktonic species are known to have the ability to cause these blooms, and one-fourth of them are able to produce toxins, also called phycotoxins. Shellfish, mainly bivalve mollusks, and fish may accumulate these phycotoxins by direct filtration of the producer algal cells or by feeding on contaminated organisms. Human intoxications caused by phycotoxins occur worldwide through consumption of marine fishery products containing bioaccumulated toxins.
According to their toxic effects and chemical properties, phycotoxins are classified into different categories. Diarrheic shellfish poisoning (DSP) toxins are one of the most relevant groups of the phytoplanktonic toxins because its presence produces not only severe economic losses, but also health effects in human consumers. The first registered DSP episode after shellfish consumption occurred in 1961 in The Netherlands. However, no relationship with the phycotoxins was established at that time. It was in 1976 when the association between the frequent occurrence of gastroenteritis and the ingestion of phycotoxin-contaminated shellfish was proved the first time. Since then, a large number of DSP episodes have been documented worldwide. However, this number is believed to be much higher because these episodes are not often well documented for the reason that the acute symptoms are sometimes light and intoxicated people do not always require medical assistance. Okadaic acid (OA) and its analogs, the dinophysistoxins (DTX), are lipophilic marine toxins produced by several phytoplanktonic species and responsible for DSP in humans. OA, the main representative toxin of this group, was first isolated in 1981 from the black sponge Halichondria okadai as well as from H. melanodocia. It is usually accumulated by several marine organisms, mainly bivalve mollusks, by eating phytoplankton containing OA. This toxin is highly distributed all over the world, but is especially abundant in Japan in Europe. OA exposure can represent a severe threat to human health beyond its DSP effects, because it was demonstrated to be a specific inhibitor of several types of serine/threonine protein phosphatases and a tumor promoter in animal carcinogenesis experiments.

化学的特性

white crystals or powder

使用

Okadaic acid is a widely distributed marine toxin produced by several phytoplanktonic species and responsible for diarrheic shellfish poisoning in humans. At the molecular level, Okadaic acid is a pot ent and specific inhibitor of various types of serine/threonine protein phosphatases. Due to this enzymatic inhibition, Okadaic acid was reported to induce numerous alterations in relevant cellular ph ysiological processes, including metabolic pathways such as glucose uptake, lipolysis and glycolysis, heme metabolism and glycogen and protein synthesis.

使用

Biochemical tool as tumor promoter and probe of cellular regulation.

使用

OA is a natural marine toxin produced by different phytoplanktonic species mainly from the dynoflagellates group. It may pass through the food chain to humans who ingest OAcontaminated organisms. Thus, it does not have any commercial applications in medicine, food, construction, or similar industries. However, because of its well-known ability to selectively inhibit several types of serine/threonine protein phosphatases, it is often used in research as a useful tool for studying cellular processes regulated by reversible phosphorylation of proteins, including control of glycogen metabolism, coordination of the cell cycle and gene expression, and maintenance of cytoskeletal structure.
Furthermore, it was reported that other marine toxins, different from OA, can also act as specific protein phosphatase (mainly PP1 and PP2A) inhibitors. They are called OA class tumor promoters and were proved to be able to cause skin, stomach, and liver tumors in animals. This has led some authors to suggest a new concept of tumor promotion: the okadaic acid pathway. In this regard, studies with OA, as well as with other OA class tumor promoters, could deepen the knowledge of the mechanisms of cancer development in humans.

生物活性

Potent inhibitor of protein phosphatase 1 (IC 50 = 3 nM) and protein phosphatase 2A (IC 50 = 0.2-1 nM). Displays > 100,000,000-fold selectivity over PP2B and PP2C. Tumor promotor. Shown to activate atypical protein kinase C in adipocytes.

安全性プロファイル

A poison by intraperitoneal route.Questionable carcinogen. Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors

Toxicity evaluation

As the main representative DSP toxin, OA ingestion leads to the onset of acute gastrointestinal symptoms typical of this intoxication (e.g., diarrhea, nausea, vomiting, abdominal pain). It was suggested that diarrhea in humans is caused by hyperphosphorylation of ion channels in intestinal cells impairing the water balance, or by increased phosphorylation of cytoskeletal or junctional elements that regulate solute permeability, resulting in passive loss of fluids. It was also suggested that OA causes long-lasting contraction of smooth muscle from human and animal arteries.
At the molecular level, OA is a potent tumor promoter and a recognized inhibitor of serine/threonine protein phosphatases type 1 (PP1) and 2A (PP2A); PP2A is about 200 times more strongly inhibited than PP1. However, nowadays OA is also known to inhibit PP4, and less effi- ciently, PP5 and PP2B. This phosphatase activity inhibition causes a dramatic increase in the phosphorylation levels of numerous proteins that ultimately results in alterations of relevant cell processes.
Mostly because of this ability, OA was shown to induce severe cytotoxic effects that include cell cycle alterations, morphological changes, apoptosis, viability decreases, and cytoskeleton disruptions on different cell systems. Besides, genotoxicity after OA exposure was also reported (see Genotoxicity section), and it was also demonstrated to alter geneexpression patterns in OA-exposed cells. The existence of OA-binding proteins other than phosphatases has been demonstrated in several marine organisms but not in humans.
Although this toxin is not classified as a neurotoxin, it was shown to induce some neurotoxic effects both in vitro and in vivo. In vitro, OA induces apoptosis in a variety of human and animal neurons, generates redistribution of neuronal proteins, forces differentiated neuronal cells into the mitotic cycle, induces disintegration of neuritis, and generates changes in microtubule-associated proteins concomitant with early changes in neuronal cytoskeleton. In vivo, OA exposure was observed to produce inactivity and weakness in mice as well as hyperexcitation, spatial memory deficit, and neurodegeneration.

9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 上流と下流の製品情報

原材料

準備製品


9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン 生産企業

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78111-17-8(9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン)キーワード:


  • 78111-17-8
  • 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoicacid, a,5-dihydroxy-a,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(
  • Okadaic acid 35-Demethyl-DTX 1 NSC 677083 35-Demethyldinophysistoxin 1
  • OA
  • OKADAIC ACID, PROROCENTRUM CONCAVUM
  • 35-Demethyldinophysistoxin 1
  • 35-Demethyl-DTX 1
  • NSC 677083
  • 9,10-DEEPITHIO-9,10-DIDEHYDROACANTHIFOLICIN
  • 9,10-DEEPITHIO-9,10-DIDEHYDROACANTHIOFOLICIN
  • HALOCHONDRINE A
  • OKADAIC ACID >95% PROTEIN PHOSPHATASE I
  • OKADAIC ACID AMMONIUM SALT WATER-SOLUBLE ANALOG
  • OKADAIC ACID FREE ACID
  • OKADAIC ACID, 25 UG*
  • OKADAIC ACID FROM PROROCENTRUM SP.
  • OKADAIC ACID SODIUM SALT 98+%
  • 9,10-deepithio-9,10-didehydro-acanthifolici
  • OKADAIC ACID, 98+%
  • Okadaicacid,Prorocentrumconcavum,highpurity
  • 1,7-Dioxaspiro5.5undec-10-ene-2-propanoic acid, .alpha.,5-dihydroxy-.alpha.,10-dimethyl-8-(1R,2E)-1-methyl-3-(2R,4aR,5R,6S,8R,8aS)-octahydro-8-hydroxy-6-(1S,3S)-1-hydroxy-3-(2S,3R,6S)-3-methyl-1,7-dioxaspiro5.5undec-2-ylbutyl-7-methylenespirofuran-2(3H),2
  • OKADAICACID,HIGHPURITY
  • 9,45-Seco-10-demercapto-9,10-didehydroacanthifolicin
  • Ocadaic Acid
  • Okadic acid
  • Okadaic acid,97%
  • Blue mussel, homogenized (Okadaic acid)
  • Okadaic acid from Prorocentrum concavum,OA
  • Okadaic acid, free acid >98%
  • CS-759
  • OKADAIC ACID
  • オカダ酸
  • オカド酸
  • 9,45-セコ-10-デメルカプト-9,10-ジデヒドロアカンチホリシン
  • オカダ酸標準液
  • オカダ酸標準液 CRM6206‐A
  • オカダ酸, PROROCENTRUM CONCAVUM, HIGH PURITY
  • オカダ酸 渦鞭毛藻PROROCENTRUM CONCAVUM由来
  • イオノホア
  • 貝類毒
  • 発癌物質
  • 酵素阻害剤
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