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メチル(4-イソチオシアナトブチル)スルホキシド

Sulforaphane

HCID 5350
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
142825-10-3
標準SMILES
CS(=O)CCCCN=C=S
InChIKey
SUVMJBTUFCVSAD-UHFFFAOYSA-N
分子式
C6H11NOS2
平均分子量
177.3 g/mol
単同位体質量
177.02820632

概要

Sulforaphane is an isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen. It has a role as an antioxidant, an antineoplastic agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and a plant metabolite. It is a sulfoxide and an isothiocyanate.

名称と識別子

優先名称
Sulforaphane
IUPAC
1-isothiocyanato-4-methylsulfinylbutane
現地名
メチル(4-イソチオシアナトブチル)スルホキシド
英語名
DL-Sulforaphane
分子式
C6H11NOS2
分子量
177.29

名称と別名

sulforaphane4478-93-71-Isothiocyanato-4-(methylsulfinyl)butaneSulforafanSulphoraphane1-isothiocyanato-4-methylsulfinylbutaneButane, 1-isothiocyanato-4-(methylsulfinyl)-SulfaforaphaneDTXSID8036732CHEBI:4780741684WL1GL1-isothiocyanato-4-methylsulphinylbutane
名称をさらに表示
スルホラファンスルフォラファン1-イソチオシアナト-4-(メチルスルフィニル)ブタン4-(メチルスルフィニル)ブチルイソチオシアナートメチル(4-イソチオシアナトブチル)スルホキシドD,L-スルホラファンR,S-スルホラファンスルホラファン, D-R,S-スルホラファン, RESEARCH GRADEスルホラファン, DL-DL-スルホラファンR-スルホラファン4-メチルスルフィニルブチルイソチオシアナート1-イソチオシアナト-4-メタンスルフィニルブタンsulforaphanSulforaphen-SuLforaphaneDetoxophanesulforphaneR-SULFORAPHANE
1-isothiocyanato-4-methylsulfinyl-butane4-methylsulfoxybutylisothiocyanate(+-)-sulforaphaneRefChem:889698DTXCID6016732GA49J4310UDL-SulforaphaneD,L-Sulforaphane

物性

構造計算による物性

XLogP
1.4
極性表面積
80.7 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
5
重原子数
10
形式電荷
0
複雑度
152

実験および物理化学的性質

Physical DescriptionSolid

物理化学的性質

沸点
125 · 125-135°C
比重(密度)
1.17 · 1.17±0.1 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
40 mg/mL、可溶 · DMSO: 40 mg/mL、可溶
外見
液体
色
わずかに黄色
由来生物
synthetic
安定性
光に敏感
化粧品成分の機能
漂白肌を保護する
InChI
InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3
InChIKey
SUVMJBTUFCVSAD-UHFFFAOYSA-N
SMILES
C(N=C=S)CCCS(C)=O
LogP
0.407 · 0.407 (est)
CAS データベース
4478 · 4478-93-7(CAS DataBase Reference)
化学的性質 · 1 件

DL-Sulforaphane (SFN) is a slightly yellow liquid. soluble in DMSO, methanol, or water-like solvents. SFN exists in food in its food-bound form known as Glucoraphanin. It is present in a wide range of vegetables such as cabbage, cauliflower, bok choy, kale, chinese broccoli, mustard, turnip, radish, and watercress.

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

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

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

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

安全データ

wgk
3
hs_code
29309090
safety_code
23-24/25
ストレージクラス
10 - Combustible liquids

化学と産業

薬理情報

MeSH Pharmacological ClassificationAgents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
応用分野 · 4 件

用途スルフォラファン (sulforaphane) とは、ブロッコリーに微量含まれるフィトケミカルの一種。体内の解毒酵素や抗酸化酵素の生成を促進し、体の抗酸化力や解毒力を高める。 通常、植物細胞内では前駆物質であるスルフォラファングルコシノレート (SGS) の状態で存在する。

説明Sulforaphane is a compound within the isothiocyanate group of organosulfur compounds and mainly found in cruciferous vegetables. It is produced when the enzyme myrosinase transforms glucoraphanin,a prodrug or storage form of SFN, into SFN upon damage to the plant (such as from chewing),which allows the two compounds to mix and react. Glucoraphanin is one of a few molecules known as isothiocyanates, existing alongside Sinigrin (metabolized into allylisothiocyanate).

使用Potent, selective inducer of phase II detoxification enzymes with anticarcinogenic properties. Occurs naturally in broccoli. It was found to inhibit chemically induced mammary tumor formation in rats. Antitumor agentLNCaP prostate cancer cells were treated with DL-Sulforaphane to study the effect on androgen receptor. Effects on malathion toxicity was studied in rats by treating them with DL-Sulforaphane.Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.Sulforaphane is an isothiocyanate derived from cruciferous vegetables, including broccoli, that potently induces chemopreventative enzymes via Keap1-Nrf2 signaling and ARE-driven gene expression.At 15 μM, sulforaphane inhibits class I and II HDAC activity and suppresses tumor growth by inducing cell cycle arrest and apoptosis selectively in various cancerous prostate epithelial cells without affecting normal cells.Differential effects of sulforaphane on histone deacetylases, cell cycle arrest and apoptosis in normal prostate cells versus hyperplastic and cancerous prostate cells

一般的な説明An isothiocyanate isolated from broccoli that acts as a potent inducer of phase II detoxifying enzymes in mouse tissues and murine hepatoma cells in culture. It has been shown to be an effective agent in prevention of chemically-induced mammary tumors in rats. It also inhibits the phase I cytochrome P450 isoenzymes 2E1 and IA2 which have been associated with the activation of carcinogens. The induction of phase II enzymes is mediated by mitogen-activated protein kinase (MAPK) pathway.

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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

データベース識別子

CAS
142825-10-3、4478-93-7
PubChem CID
5350
DTXSID
DTXSID8036732
ChEMBL
CHEMBL48802
ChEBI
CHEBI:47807
UNII
41684WL1GL
EC Number
878-934-0
Nikkaji
J13.479A
化学的特性

上流・下流製品情報

上流原料

エルシン(R)-4-(メチルスルフィニル)-1-ブチルアミン二塩化チオカルボニル

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補足説明 · 1 件

定義ChEBI: Sulforaphane is an isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen. It has a role as an antineoplastic agent, a plant metabolite, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a sulfoxide and an isothiocyanate.