(S)-sulforaphane

Base Information

• Chemical Name: (S)-sulforaphane
• CAS No.: 155320-20-0
• Molecular Formula: C6H11NOS2
• Molecular Weight: 177.291
• UNII: 7J94TPZ10L
• Wikidata: Q27120805
• Metabolomics Workbench ID: 56801
• ChEMBL ID: CHEMBL1627201
• Mol file: 155320-20-0.mol

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

Chemical Property of (S)-sulforaphane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 368.164oC at 760 mmHg
• Flash Point: 176.459oC
• PSA: 80.73000
• Density: 1.177g/cm3
• LogP: 2.11360
• 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:

98%Min ^*data from raw suppliers

(S)-Sulforaphane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CS(=O)CCCCN=C=S
• Isomeric SMILES: C[S@](=O)CCCCN=C=S
• 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 agent.

Technology Process of (S)-sulforaphane

There total 3 articles about (S)-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:

D,L-sulforaphane (4478-93-7) → R-sulforaphane (142825-10-3) + (S)-Sulforaphane (155320-20-0)

Guidance literature:

With chiral column (Chiralpak AD-RH); In acetonitrile; at 35 ℃; Resolution of racemate;

DOI:10.1021/acs.jafc.6b04966

Reference yield:

erucin (4430-36-8) → R-sulforaphane (142825-10-3) + (S)-Sulforaphane (155320-20-0)

Guidance literature:

In ethanol; at 27 ℃; for 48h; Yield given. Title compound not separated from byproducts; Helminthosporium species NRRL 4671;

DOI:10.1016/0957-4166(95)00200-9

Reference yield:

thiophosgene (463-71-8) + 2-<2-(Methylthio)butyl>-1H-isoindole-1,3(2H)-dione (52096-68-1) → R-sulforaphane (142825-10-3) + (S)-Sulforaphane (155320-20-0)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/chem.19970030510

upstream raw materials:

erucin

thiophosgene

2-<2-(Methylthio)butyl>-1H-isoindole-1,3(2H)-dione

D,L-sulforaphane

Refernces

• 1、 Schenk, Wolfdieter A.,Duerr, Michael. "Synthesis of (R)-sulforaphane using [CpRu((R,R)-CHIRAPHOS)]+ as chiral auxiliary". . p. 713 - 716. Retrieved 2007/10/03.
• 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 2007/10/02.