L-Sulforaphane

Base Information

• Chemical Name: L-Sulforaphane
• CAS No.: 142825-10-3
• Molecular Formula: C6H11NOS2
• Molecular Weight: 177.291
• Hs Code.: 29309090
• UNII: GA49J4310U
• DSSTox Substance ID: DTXSID40162196
• Wikidata: Q27120804
• NCI Thesaurus Code: C1424
• Pharos Ligand ID: 4A3C5XHZY84X
• Metabolomics Workbench ID: 56800
• ChEMBL ID: CHEMBL128136
• Mol file: 142825-10-3.mol

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

Chemical Property of L-Sulforaphane

Chemical Property:

• Appearance/Colour: Clear pale yellow oil
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• Boiling Point: 368.164 °C at 760 mmHg
• Flash Point: 176.459 °C
• PSA: 80.73000
• Density: 1.177 /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:

5%, 10%, 90%, 98% ^*data from raw suppliers

(R)-Sulforaphane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)CCCCN=C=S
• Isomeric SMILES: C[S@@](=O)CCCCN=C=S
• Description: Sulforaphane is a naturally-occurring phytochemical belonging to the class of isothiocyanates. As the aglycone metabolite of glucosinolate glucoraphanin (sulforaphane glucosinolate), sulforaphane acts as an antioxidant and potent stimulator of endogenous detoxifying enzymes. This agent displays anticarcinogenic properties due to its ability to induce phase II detoxification enzymes, such as glutathione S-transferase and quinone reductase, thereby providing protection against certain carcinogens and toxic, reactive oxygen species. Broccoli sprouts contain large amounts of sulforaphane, which is also found in other cruciferous vegetables including cabbage and kale.
• Uses: L-sulforaphane is an Antitumor agent and has antioxidant, anti-cancer, anti-ultraviolet, help clear lung bacteria, and prevent gout. It was found to inhibit chemically induced mammary tumor formation in rats. L-Sulforaphane has been reported to prevent NFκB binding, which results in downregulation of apoptosis inhibitors therefore inducing apoptosis. It also displays a capacity to inhibit intracellular, extracellular, and antibiotic-resistant strains of Helicobacter pylori. Additionally, L-Sulforaphane has been found to prevent clonogenicity. This Sulforaphane is sold in the L-enantiomer form.

Technology Process of L-Sulforaphane

There total 13 articles about L-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: 99.0%

glucoraphanin potassium salt → R-sulforaphane (142825-10-3)

Guidance literature:

With myrosinase; In aq. phosphate buffer; dichloromethane; at 37 ℃; pH=7; Enzymatic reaction;

DOI:10.3390/molecules19066975

Reference yield:

(S)-4-Hydroxybutyl methyl sulfoxide (155184-98-8) → R-sulforaphane (142825-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: NaN₃ / dimethylformamide / 12 h / Ambient temperature

3: 1.) Ph₃P / 1.) Et₂O, reflux, 3 h, 2.) reflux, 1 h

With sodium azide; triethylamine; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00082a016

Reference yield:

(S)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide (155184-96-6) → R-sulforaphane (142825-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / HF / acetonitrile / 0.5 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: NaN₃ / dimethylformamide / 12 h / Ambient temperature

4: 1.) Ph₃P / 1.) Et₂O, reflux, 3 h, 2.) reflux, 1 h

With sodium azide; hydrogen fluoride; triethylamine; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00082a016

upstream raw materials:

(R)-4-methanesulfinyl-butylamine

carbon disulfide

(S)-4-Azidobutyl methyl sulfoxide

erucin

Downstream raw materials:

AIIGLMVGGVV

Aβ_1?5

Refernces

• 1、 De Nicola, Gina Rosalinda,Rollin, Patrick,Mazzon, Emanuela,Iori, Renato. "Novel gram-scale production of enantiopure R-Sulforaphane from tuscan black kale seeds". . p. 6975 - 6986. Retrieved 2014.
• 2、 Holland, Herbert L.,Brown, Frances M.,Larsen, Brett G.. "PREPARATION OF (R)-SULFORAPHANE BY BIOTRANSFORMATION USING HELMINTHOSPORIUM SPECIES NRRL 4671". . p. 1129 - 1130. Retrieved 1994.
• 3、 Giacoppo, Sabrina,Galuppo, Maria,Iori, Renato,De Nicola, Gina Rosalinda,Bramanti, Placido,Mazzon, Emanuela. "(RS)-glucoraphanin purified from Tuscan black kale and bioactivated with myrosinase enzyme protects against cerebral ischemia/reperfusion injury in rats". . p. 166 - 177. Retrieved 2014.