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2-プロペン-1-スルフィノチオ酸S-(2-プロペニル)

2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 化学構造式
539-86-6
CAS番号.
539-86-6
化学名:
2-プロペン-1-スルフィノチオ酸S-(2-プロペニル)
别名:
2-プロペン-1-チオスルフィン酸S-アリル;2-プロペン-1-スルフィノチオ酸S-アリル;2-プロペン-1-チオスルフィン酸S-(2-プロペニル);アリル(アリルチオ)スルホキシド;チオスルフィン酸ジアリル;アリシン;2-プロペニル(2-プロペニルチオ)スルホキシド;アリシン【植物成分】;2-プロペン-1-スルフィノチオ酸S-(2-プロペニル);アリシン (IN SOLUTION);アリシン (〜90%)
英語化学名:
Allicin
英語别名:
ALLICIN;AlliMed;alliosan;Allitrid;C6H10S2O;Allisatin;ARICINE(P);ALLICIN(SH);garlic meal;Allicin 10%
CBNumber:
CB8466037
化学式:
C6H10OS2
分子量:
162.27
MOL File:
539-86-6.mol

2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 物理性質

融点 :
25°C
沸点 :
259°C (rough estimate)
比重(密度) :
d420 1.112
屈折率 :
nD20 1.561
外見 :
liquid
水溶解度 :
24g/L(10 ºC)

安全性情報

HSコード  29329990
毒性 LD50 in mice (mg/kg): 60 i.v.; 120 s.c. (Cavallito, Bailey)

2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 価格 もっと(6)

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) W01CHDASB-00001535 アリシン (In Solution)
Allicin (In Solution)
539-86-6 1mg ¥62000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01CHDASB-00001535 アリシン (In Solution)
Allicin (In Solution)
539-86-6 5mg ¥125600 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01LKTA4440 アリシン
Allicin
539-86-6 1mg ¥55400 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01TRCA543500 アリシン (〜90%)
Allicin (?90%)
539-86-6 25mg ¥330000 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01LKTA4440 アリシン
Allicin
539-86-6 5mg ¥194600 2021-03-23 購入

2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 化学特性,用途語,生産方法

解説

たまねぎやにんにくに含まれる特有の刺激臭(香気成分)や辛味成分。たまねぎやにんにくなどに含まれる含硫化合物であるアリインが傷つけられると、酵素アリナーゼの作用によってアリシンが生成される。にんにく、たまねぎ、長ねぎ、にら、らっきょうなどに多く含まれる。体内でビタミンB1と結合してアリチアミンとなり、ブドウ糖からのエネルギー産生に効果を発揮するほか、疲労回復、新陳代謝の活性化、血栓の予防、風邪の予防・改善、血中脂肪の燃焼促進、コレステロール値の抑制、がんの予防などの作用があるとされる。◇「硫化アリル」、「アリル化合物」とも呼ぶ。
講談社 漢方薬・生薬・栄養成分がわかる事典について 情報

用途

強化剤

説明

Allicin is one of the major allergens in garlic (Allium sativum L.). It is responsible of the characteristical fiavour of the bulbs.

説明

Allicin is a natural product originally isolated from A. sativum that has wide-ranging biological effects including antioxidative, anticancer, antimicrobial, and antifungal activities. It inhibits the cysteine proteases cathepsin B and L, facipain 2, and rhodesain with Ki values of 8.6 and 9.3, 1.04, and 5.31 μM, respectively. It shows antiparasitic activity against P. falciparum (IC50 = 5.2 μM) and T. b. brucei (IC50 = 13.8 μM), the parasites that cause malaria and African sleeping sickness, respectively. Allicin (5-10 μM) dose-dependently inhibits cell adhesion, invasion, and migration in various lung adenocarcinoma cell lines. It also alters the balance of tissue inhibitors of matrix metalloproteinases (TIMPs) and matrix metalloproteinases (MMPs), decreases phosphorylation of Akt, and decreases PI3K/Akt signaling.

化学的特性

Light yellow oily liquid

物理的性質

Appearance: Light yellow powder or light yellow oily liquid, with strong irritating odor. Unstable and light, heat, and organic solvents will easily degrade it into a variety of sulfur-containing organic compounds. Solubility: Its solubility is about 2.5% in the 10?°C water. Soluble in ethanol, ether, benzene, and other organic solvents. Boiling point: 80–85?°C (0.2?kPa). Relative density of d20?=?1.112; refractive index nD 20 ?=?1.561.

来歴

As the main active substance of garlic, garlic was separated by Cavallito and Bailey in 1944 from crushed garlic. Cavallito firstly clarified the physical properties and chemical structure of the scent of garlic.
Fresh garlic does not contain free allicin but only its precursor material alliin. When the garlic undergoes physical mechanical crushing, garlic alliinase is activated and catalyzes the breakdown of alliin into allicin.
The reported preparation methods of allicin contain extraction, biosynthesis, and chemical synthesis. Chemical synthesis starts from raw material of diallyldisulfides, m-chloroperoxy benzoic acid to get crude allicin. According to the United States patent report, biosynthesis preparation of allicin comes from natural sources or synthetic, after it is made into a certain concentration of aqueous solution, it is converted into allicin by reaction with alliinase. Extraction of allicin with low boiling nonpolar solvent can acquire pure allicin, but it must be stored at ?70?°C to prevent from decomposing.

使用

Allicin is naturally formed by the action of the enzyme allicinase on alliin when the tissue of the garlic bulb is disrupted. Allicin shows antibacterial activity.

定義

An antibacterial substance extracted from garlic (allium).

適応症

This product conforms to the national standards for chemical drugs. The current clinical used forms are allicin injection, garlic instant kelp capsule, etc. It is used clinically mainly for anti-pathogenic microbial infection, anti-tumor, and anti-dilation of blood vessels. It could also be used for the treatment of periodontitis and ulcerative colitis.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 8295, 1984 DOI: 10.1021/ja00338a049

接触アレルゲン

Allicin is one of the major allergens in garlic (Allium sativum L.). It is responsible for the characteristic flavor of the bulbs and has immunomodulating and antibacterial properties.

薬理学

Allicin has a broad spectrum of pharmacological activities, such as antibacterial, antiviral, anticancer, decreasing the blood pressure, and inhibition of platelet aggregation.
2. The Effect on Heart and Cerebral Vessels Allicin exerts a protective effect on the heart and cerebral vessels through reducing plasma total cholesterol, lowering blood pressure, inhibition of platelet activity, and reducing hematocrit and blood viscosity. Allicin increases the activity of inducible nitric oxide synthetase (iNOS) and boosts the NO level, which results in the vasodilation. In vitro study also found that allicin’s vasodilation is related to NO, and allicin can improve the level of iNOS and NO in platelet and placental villi as well as choriocarcinoma. In addition, allicin administration effectively reverses hyperlipidemia and atherosclerosis, inhibits lipid peroxidation, and reduces the level of glutathione decomposition and superoxide dismutase and peroxidase activity in high cholesterol-fed rats.
3. Anticancer Allyl sulfide, the active ingredient of allicin, shows anticancer effect. Epidemiological investigation and experimental studies have shown that allicin has a significant inhibitory effect on gastric, colon, liver, and lung cancers. Experimental results show that allicin improves the cellular immune function of cancer patients. Alliin is the precursor of allicin, which also has significant antitumor activity. In the 1980s, it was found that the growth of S180 tumor in mice was significantly inhibited by alliin injection or garlic thionine. Meanwhile, alliin could selectively inhibit the reduction synthesis of reduced glutathione (GSH)-dependent prostaglandin E2?in gland cells.

臨床応用

Allicin shows inhibitory effects on infections caused by bacteria, fungi, and virus. Clinical studies reported that allicin has cured 23 Candida albicans-infected patients . Combining allicin with surgery had cured ten patients with maxillary sinus aspergillosis. Good results for the treatment of chronic gastritis, peptic ulcer, chronic colitis, and fatty liver were achieved after allicin administration. Allicin is also capable of eliminating oxygen free radical ion. In addition, allicin can reduce the nitrite- and nitrate-reducing bacteria, and taking garlic could benefit chronic symptoms in stomach, such as stomach discomfort, fullness pain, acid reflux, heating, burning and loss of appetite, and so on.

抗がん研究

For allicin, a reduction of tumoral cell proliferation was reported by Misharina et al.(2013).

2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 上流と下流の製品情報

原材料

準備製品


2-プロペン-1-スルフィノチオ酸S-(2-プロペニル) 生産企業

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539-86-6(2-プロペン-1-スルフィノチオ酸S-(2-プロペニル))キーワード:


  • 539-86-6
  • 2-propene-1-sulfinothioicacid,s-2-propenylester
  • alliosan
  • ALLICIN
  • ALLICIN(SH)
  • ARICINE(P)
  • Dianyctrsnlgide
  • Allisatin
  • DIALLYLTHIOSULPHINATE
  • DIALLYLDISULPHIDE-OXIDE
  • Allantolin Allicin
  • S-Allyl acrylo-1-sulphinothioate
  • Allitrid
  • 2-Propene-1-sulfinothioic acid S-allyl ester
  • 2-Propene-1-thiosulfinic acid S-(2-propenyl) ester
  • 2-Propenyl(2-propenylthio) sulfoxide
  • Allyl(allylthio) sulfoxide
  • 3-(allylsulfinylthio)prop-1-ene
  • 3-prop-2-enylsulfinylsulfanylprop-1-ene
  • ALLICIN(IN SOLUTION)(SH)
  • 2-Propene-1-sulfinothioic Acid S-2-Propen-1-yl Ester
  • AlliMed
  • Allisure Liquid
  • Garlic P.E.(odorless)
  • ALLICIN [6.2Mg/ML](SH) (In Solution)
  • Allicin 539-86-6
  • garlic meal (Allicin)
  • 3-(prop-2-enylsulfinylthio)-1-propene
  • Allicin - Mixture of mainly diallyldisulfide and diallyl trisulfide
  • Allicin (90%)
  • S-allyl prop-2-ene-1-sulfinothioate (Allicin)
  • 2-プロペン-1-チオスルフィン酸S-アリル
  • 2-プロペン-1-スルフィノチオ酸S-アリル
  • 2-プロペン-1-チオスルフィン酸S-(2-プロペニル)
  • アリル(アリルチオ)スルホキシド
  • チオスルフィン酸ジアリル
  • アリシン
  • 2-プロペニル(2-プロペニルチオ)スルホキシド
  • アリシン【植物成分】
  • 2-プロペン-1-スルフィノチオ酸S-(2-プロペニル)
  • アリシン (IN SOLUTION)
  • アリシン (〜90%)
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