55021-77-7Relevant academic research and scientific papers
Antioxidant activity of two edible isothiocyanates: Sulforaphane and erucin is due to their thermal decomposition to sulfenic acids and methylsulfinyl radicals
Cedrowski, Jakub,D?browa, Kajetan,Przybylski, Pawe?,Krogul-Sobczak, Agnieszka,Litwinienko, Grzegorz
, (2021/03/30)
Sulforaphane (SFN) and erucin (ERN) are isothiocyanates (ITCs) bearing, respectively, methylsulfinyl and methylsulfanyl groups. Their chemopreventive and anticancer activity is attributed to ability to modulate cellular redox status due to induction of Phase 2 cytoprotective enzymes (indirect antioxidant action) but many attempts to connect the bioactivity of ITCs with their radical trapping activity failed. Both ITCs are evolved from their glucosinolates during food processing of Cruciferous vegetables, therefore, we studied antioxidant behaviour of SFN/ERN at elevated temperature in two lipid systems. Neither ERN nor SFN inhibit the oxidation of bulk linolenic acid (below 100 °C) but both ITCs increase oxidative stability of soy lecithin (above 150 °C). On the basis of GC-MS analysis we verified our preliminary hypothesis (Antioxidants 2020, 9, 1090) about participation of sulfenic acids and methylsulfinyl radicals as radical trapping agents responsible for the antioxidant effect of edible ITCs during thermal oxidation of lipids at elevated temperatures (above 140 °C).
4 - methanesulfonyl-butyl isothiocyanate synthetic method (by machine translation)
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, (2017/06/28)
The invention relates to a 4 - methanesulfonyl-butyl isothiocyanate (Erysolin) chemical synthesis method, the method to 1 - bromo - 4 - chlorobutane, aqueous methyl mercaptan sodium as initial material to synthetic chlorinated thioether, then with the phthalimide potassium salt reaction, to form the tertiary amine combination, continue to hydrazinolysis by thioether primary amine, primary amine in the sulfur phosgene formed under action of the isothiocyanate, final oxidation to obtain Erysolin. The invention provides a method for synthesizing the operation is simple, less dangerous reagent consumption, both cost and yield, is suitable for industrial production of Erysolin synthetic method. (by machine translation)
ISOTHIOCYNATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIONS CONTAINING SAME
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Paragraph 0090, (2013/05/21)
The present invention provides glucosinolate and isothiocyanate compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.
Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents
Hu, Kun,Qi, Yan-Jie,Zhao, Juan,Jiang, He-Fei,Chen, Xin,Ren, Jie
, p. 529 - 539 (2013/07/11)
A series of sulforaphane derivatives were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacological results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative 85 could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and 85 exhibited time- and dose-dependent activation on Nrf2 transcription factor, and 85 acted as a more potent Nrf2 inducer than SFN.
PROCESS FOR THE SYNTHESIS OF ISOTHIOCYANATES AND DERIVATIVES THEREOF AND USES OF SAME
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Paragraph 0089-0110, (2013/06/26)
A method for synthesizing an isothiocyanate of general formula (I) [in-line-formulae]SCN—R1—R4—R2??(I)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl-aryl or aryl group, R4 represents a carbonyl, sulfinyl, sulfonyl group or a sulfide group and of its derivatives comprising a step for reacting an alkylalkylamine having the general formula (II) [in-line-formulae]NH2—R1—R4—R2??(II)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl, aryl or alkylaryl group, R4 represents a carbonyl, sulfinyl, sulfonyl or sulfide group, in the presence of carbon sulfide and of di-tert-butyl dicarbonate with formation of the corresponding aforesaid isothiocyanate, compounds obtained by this method as well as their uses.
Analysis and anti- helicobacter activity of sulforaphane and related compounds present in Broccoli (Brassica oleracea L.) sprouts
Moon, Joon-Kwan,Kim, Jun-Ran,Ahn, Young-Joon,Shibamoto, Takayuki
experimental part, p. 6672 - 6677 (2011/08/06)
A crude methanol extract prepared from fresh broccoli sprouts was extracted with hexane, chloroform, ethyl acetate, and butanol sequentially. Residual water fraction was obtained from the residual aqueous layer. The greatest inhibition zones (>5 cm) were noted for Helicobacter pylori strain by the chloroform extract, followed by the hexane extract (5.03 cm), the ethyl acetate extract (4.90 cm), the butanol extract (3.10 cm), and the crude methanol extract (2.80 cm), whereas the residual water fraction did not show any inhibition zone. Including sulforaphane, five sulforaphane-related compounds were positively identified in the chloroform extract, of which 5- methylsulfinylpentylnitrile was found in the greatest concentration (475.7 mg/kg of fresh sprouts), followed by sulforaphane (222.6 mg/kg) and 4-methylsulfinylbutylnitrile (63.0 mg/kg). Among 18 sulforaphane and related compounds synthesized (6 amines, 6 isothiocyanates, and 6 nitriles), 2 amines, 6 isothiocyanates, and 1 nitrile exhibited >5 cm inhibitory zones for H. pylori strain. The results indicate that broccoli sprouts can be an excellent food source for medicinal substances.
ISOTHIOCYANATES AND GLUCOSINOLATE COMPOUNDS AND ANTI-TUMOR COMPOSITIOS CONTAINING SAME
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Page/Page column 23, (2008/06/13)
The present invention provides glucosinolate and isothiocyante compounds and related methods for synthesizing these compounds and analogs. In certain embodiments, these glucosinolate and isothiocyanate compounds are useful and chemopreventive and or chemotherapeutic agents.
Medicine comprising a thiourea for use as depigmenting agent or anti-mutagenic and anti-carcinogenic agent
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Page/Page column 4, (2008/06/13)
The invention concerns a medicine or a cosmetic composition comprising at least one thiourea of general formula (I), or at least one of its monooxide or dioxide derivatives of general formulae (IIa), (IIb) and (III), or mixtures thereof. This medicine is advantageously used for inhibiting tyrosinase, inhibiting melanin synthesis, for lightening or depigmenting the skin or for eliminating age spots and as antimutagenic and anti-carcinogenic agent.
Synthesis of isothiocyanate-derived mercapturic acids
Vermeulen, Martijn,Zwanenburg, Binne,Chittenden, Gordon J.F.,Verhagen, Hans
, p. 729 - 737 (2007/10/03)
Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-L-cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which subsequently was reacted with thiophosgene yielding the isothiocyanate with an overall yield of 16%. Mercapturic acids in urine can serve as a biomarker of intake to determine the health promoting potential of isothiocyanates present in cruciferous vegetables.
A facile and efficient synthesis of 14C-labelled sulforaphane
D'Souza, Christopher A.,Amin, Shantu,Desai, Dhimant
, p. 851 - 859 (2007/10/03)
Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3-(methylthio)-1-propanol (2). Reacting 2 with tosyl chloride in the presence of Et3N yielded the tosylate 3. Gently refluxing 3 with K 14CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH3-THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1-14C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K 14CN. Copyright
