127183-02-2

Basic information

• Product Name: (Z)-phenylmethanethial S-oxide
• CAS NO: 127183-02-2
• Molecular Weight: 138.19
• Mol File: 127183-02-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (Z)-phenylmethanethial S-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-phenylmethanethial S-oxide(127183-02-2)
• EPA Substance Registry System: (Z)-phenylmethanethial S-oxide(127183-02-2)

Safety Data

• Hazardous Substances Data: 127183-02-2(Hazardous Substances Data)

Upstream product

• 16302-98-0 petivericin 
• 105584-71-2 (E)-Phenyltrimethylsilyl thioketone S-oxide 
• 79841-55-7 trimethylsilyl phenyl thioketone 
• 170100-68-2 α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol 
• 60668-81-7 petiveriin 

Downstream Products

• 132514-85-3 trans-6-phenyl-5,6-dihydro-2H-thiopyran S-oxide 
• 132514-85-3 cis-6-phenyl-5,6-dihydro-2H-thiopyran S-oxide 

Relevant articles and documents

A Novel Synthesis of Monosubstituted Sulfines via an Unusual β-Elimination of Chloroform from Allylic and Benzylic Trichloromethyl Sulfoxides.

A new method for the synthesis of thioaldehyde S-oxides by base-induced elimination of chloroform from allylic and benzylic trichloromethyl sulfoxides is described.The reaction proceeds smoothly under mild conditions.A mechanism for this remarkable sulfin

First insights into the mode of action of a "lachrymatory factor synthase" - Implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species

A study of an enzyme that reacts with the sulfenic acid produced by the alliinase in Petiveria alliacea L. (Phytolaccaceae) to yield the P. alliacea lachrymator (phenylmethanethial S-oxide) showed the protein to be a dehydrogenase. It functions by abstracting hydride from sulfenic acids of appropriate structure to form their corresponding sulfines. Successful hydride abstraction is dependent upon the presence of a benzyl group on the sulfur to stabilize the intermediate formed on abstraction of hydride. This dehydrogenase activity contrasts with that of the lachrymatory factor synthase (LFS) found in onion, which catalyzes the rearrangement of 1-propenesulfenic acid to (Z)-propanethial S-oxide, the onion lachrymator. Based on the type of reaction it catalyzes, the onion LFS should be classified as an isomerase and would be called a "sulfenic acid isomerase", whereas the P. alliacea LFS would be termed a "sulfenic acid dehydrogenase".

A NOVEL SYNTHESIS OF THIOALDEHYDE S-OXIDES VIA AN UNUSUAL β-ELIMINATION OF CHLOROFORM FROM ALLYLIC AND BENZYLIC TRICHLOROMETHYL SULFOXIDES

A new method for the synthesis of thioaldehyde S-oxides including α,β-unsaturated derivatives, by mild base-induced elimination of chloroform from readily available allylic and benzylic trichloromethyl sulfoxides is described.