Sulforaphane

Base Information

• Chemical Name: Sulforaphane
• CAS No.: 4478-93-7
• Molecular Formula: C6H11NOS2
• Molecular Weight: 177.291
• Hs Code.: 29309090
• European Community (EC) Number: 878-934-0
• NSC Number: 749790
• UNII: 41684WL1GL
• DSSTox Substance ID: DTXSID8036732
• Nikkaji Number: J13.479A
• Wikipedia: Sulforaphane
• Wikidata: Q424489
• NCI Thesaurus Code: C1424
• Pharos Ligand ID: 4A3C5XHZY84X
• Metabolomics Workbench ID: 138660
• ChEMBL ID: CHEMBL48802
• Mol file: 4478-93-7.mol

Synonyms:(+-)-sulforaphane;(R)-sulforaphane;(S)-sulforaphane;1-isothiocyanato-4-methylsulphinylbutane;4-methylsulfoxybutylisothiocyanate;sulforafan;sulforaphane;sulforaphane, (R)-;sulphoraphane

Chemical Property of Sulforaphane

Chemical Property:

• Appearance/Colour: Light yellow liquid
• Boiling Point: 368.2 °C at 760 mmHg
• Flash Point: 176.5 °C
• PSA: 80.73000
• Density: 1.17 g/cm³
• LogP: 2.11360
• Storage Temp.: −20°C
• Solubility.: DMSO: 40 mg/mL, soluble
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 177.02820632
• Heavy Atom Count: 10
• Complexity: 152

Purity/Quality:

1%, ^*data from raw suppliers

D,L-Sulforaphane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)CCCCN=C=S
• Recent ClinicalTrials: Safety, Feasibility and Efficacy of Sulforaphane (Avmacol Extra Strength) in Chronic Kidney Disease
• Recent NIPH Clinical Trials: Investigation on the anti-inflammatory and antioxidant effects of sulforaphane to exercise
• Description: 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).
• Uses: 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

Technology Process of Sulforaphane

There total 25 articles about Sulforaphane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

erucin (4430-36-8) → D,L-sulforaphane (4478-93-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 0.5h;

DOI:10.1016/S0223-5234(03)00141-7

Reference yield: 85.7%

thiophosgene (463-71-8) + (+/-)-1-amino-4-(methylsulfinyl)butane (84104-30-3,187587-70-8) → D,L-sulforaphane (4478-93-7)

Guidance literature:

With sodium hydroxide; In chloroform; water; for 1h;

Reference yield: 79.0%

carbon disulfide (75-15-0,12122-00-8) + (+/-)-1-amino-4-(methylsulfinyl)butane (84104-30-3,187587-70-8) → D,L-sulforaphane (4478-93-7)

Guidance literature:

carbon disulfide; (+/-)-1-amino-4-(methylsulfinyl)butane; With triethylamine; In ethanol; at 20 ℃; for 0.5h; Inert atmosphere;

With dmap; di-tert-butyl dicarbonate; In ethanol; at 0 - 20 ℃; for 2.25h;

upstream raw materials:

sulforaphane-cysteine

(11R,16S)-16-amino-11-((carboxymethyl)carbamoyl)-13-oxo-8-methylsulfinyl-2,9-dithia-7,12-diazaheptadecan-17-oic acid

thiophosgene

(+/-)-1-amino-4-(methylsulfinyl)butane

Downstream raw materials:

4-isothiocyanato-1-butene

methanethiosulfonic acid S-methyl ester

Refernces

• 1、 Papi, Alessio,Orlandi, Marina,Bartolini, Giovanna,Barillari, Jessica,Iori, Renato,Paolini, Moreno,Ferroni, Fiammetta,Fumo, Maria Grazia,Pedulli, Gian Franco,Valgimigli, Luca. "Cytotoxic and antioxidant activity of 4-methylthio-3-butenyl isothiocyanate from Raphanus sativus L. (Kaiware Daikon) sprouts". . p. 875 - 883. Retrieved 2008.
• 2、 Barillari, Jessica,Canistro, Donatella,Paolini, Moreno,Ferroni, Fiammetta,Pedulli, Gian Franco,Iori, Renato,Valgimigli, Luca. "Direct antioxidant activity of purified glucoerucin, the dietary secondary metabolite contained in rocket (Eruca sativa Mill.) seeds and sprouts". . p. 2475 - 2482. Retrieved 2005.
• 3、 Li, Yiming,Rizvi, S. Aal-e-Ali,Hu, Deqing,Sun, Danwen,Gao, Anhui,Zhou, Yubo,Li, Jia,Jiang, Xuefeng. "Selective Late-Stage Oxygenation of Sulfides with Ground-State Oxygen by Uranyl Photocatalysis". supporting information. p. 13499 - 13506. Retrieved 2019/08/21.
• 4、 -. "Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof". Paragraph 0045-0048; 0201-0204. . Retrieved 2019/12/02.