155320-20-0

Basic information

• Product Name: (S)-Sulforaphane
• Synonyms: Butane, 1-isothiocyanato-4-[(S)-methylsulfinyl]-
• CAS NO: 155320-20-0
• Molecular Formula: C₆H₁₁NOS₂
• Molecular Weight: 177.28764
• Product Categories: Aliphatics;Chiral Reagents;Inhibitors;Sulfur & Selenium Compounds
• Mol File: 155320-20-0.mol

Chemical Properties

• Boiling Point: 368.164°C at 760 mmHg
• Flash Point: 176.459°C
• Appearance: /
• Density: 1.177g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: (S)-Sulforaphane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Sulforaphane(155320-20-0)
• EPA Substance Registry System: (S)-Sulforaphane(155320-20-0)

Safety Data

• Hazardous Substances Data: 155320-20-0(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
(S)-Sulforaphane is used as an anticancer agent for its ability to modulate the activity of phase II detoxification enzymes, which are crucial in the body's defense against cancer-causing substances. By enhancing the expression of these enzymes, (S)-Sulforaphane helps to neutralize and eliminate potential carcinogens, thereby reducing the risk of cancer development.
Used in Pharmaceutical Industry:
(S)-Sulforaphane is used as a pharmaceutical candidate for its potential in the development of cancer preventive and therapeutic agents. Its ability to inhibit tumor formation and modulate oncological signaling pathways makes it a promising compound for further research and drug development.
Used in Functional Foods and Supplements:
(S)-Sulforaphane is used as an ingredient in functional foods and dietary supplements for its health-promoting properties. Its inclusion in these products aims to provide consumers with the benefits of its anticarcinogenic and detoxification-enhancing effects, contributing to overall health and well-being.

InChI:InChI=1/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3/t10-/m0/s1

Upstream product

• 4478-93-7 D,L-sulforaphane 
• 463-71-8 thiophosgene 
• 52096-68-1 2-<2-(Methylthio)butyl>-1H-isoindole-1,3(2H)-dione 
• 4430-36-8 erucin 

Relevant articles and documents

HPLC separation of sulforaphane enantiomers in Broccoli & its sprouts by transformation into diastereoisomers using derivatization with (S)-Leucine

Racemic sulforaphane, which was derivatized with (S)-leucine (L-leucine), was resolved by reversed phase HPLC with UV detection. The optimum mobile phase conditions were found to be 10 mM citric acid (pH 2.8) containing 22% methanol at 35 °C using detection at 254 nm. Sulforaphane enantiomers in florets and stems of five brands of broccoli and leaves and stems of three brands of broccoli sprouts were analyzed by the proposed HPLC method. Both sulforaphane enantiomers were detected in all of the samples. The S/R ratios of sulforaphane in broccoli samples were 1.5-2.6/97.4-98.5% for florets and 5.0-12.1/87.9-95.0% for stems. The S/R ratios in broccoli sprout samples were higher than those in broccoli samples and were found to be 8.3-19.7/80.3-91.7% for leaves and 37.0-41.8/58.2-63.0% for stems. (S)-Sulforaphane detected in the broccoli and its sprout samples was positively identified by separately using an HPLC with a chiral column (Chiralpak AD-RH) and mass spectrometry.

Synthesis of (R)-sulforaphane using [CpRu((R,R)-CHIRAPHOS)]+ as chiral auxiliary

A new enantioselective (80% ee) synthesis of (R)-sulforaphane and its epimer (S)-sulforaphane is described, which makes use of the pseudotetrahedral complex fragment [CpRu(CHIRAPHOS)]+ as a chiral auxiliary. Reaction of the chloride complexes [CpRu(L-L)Cl] [L-L =1,2-bis(diphenylphosphino)ethane (dppe), (2S,3S) and (2R,3R)-bis(diphenylphosphino) butane ((S,S)- and (R,R)-CHIRAPHOS, respectively)] with phthalimidobutyl methyl sulfide gives the thioether complexes [CpRu(L-L)(MeSC4H8NPhth)]PF6. Oxygen transfer from dimethyldioxirane (DMD) produces the corresponding sulfoxide complexes in high yield and high diastereoselectivity. Cleavage of the phthaloyl group with aqueous hydrazine and subsequent reaction with thiophosgene yields the sulforaphane complexes [CpRu(L-L)(MeS(O)C4H8NCS)]PF6. Treatment of these with sodium iodide finally liberates the sulforaphane without noticeable racemization.

BIOTRANSFORMATION OF ORGANIC SULFIDES. PART 7. FORMATION OF CHIRAL ISOTHIOCYANATO SULFOXIDES AND RELATED COMPOUNDS BY MICROBIAL BIOTRANSFORMATION

The fungi Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613 have been used for the biotransformation of a series of isothiocyanatoalkyl methyl sulfides and their synthetic precursors, ω-(methylthio)alkylphthalimides.H. species gave predominantly (S) sulfoxides in all cases; M. isabellina gave (R) isothiocyanatoalkyl methyl sulfoxides, but in the case of two ω-(methylthio)alkylphthalimides substantial conversion of sulfoxide to sulfone resulted in the isolation of the former with predominant (S) configuration.A correction is made of the previously reported configurations of two biotransformation products (Tetrahedron: Asymmetry, 1994, 5, 1129).

PREPARATION OF (R)-SULFORAPHANE BY BIOTRANSFORMATION USING HELMINTHOSPORIUM SPECIES NRRL 4671

The fungus Helminthosporium species NRRL 4671 oxidizes 1-isothiocyanato-4-(methylthio)butane to (-)-1-isothiocyanato-(4R)-(methylsulfinyl)butane (sulforaphane).Helminthosporium also converts 1-methylthio-4-(N-phthalimidyl)butane to the (R) sulfoxide.