3312-96-7

Basic information

• Product Name: 3-(phenyldisulfanyl)propanoic acid
• CAS NO: 3312-96-7
• Molecular Formula: C₉H₁₀O₂S₂
• Molecular Weight: 214.3045
• Mol File: 3312-96-7.mol

Chemical Properties

• Boiling Point: 361.4°C at 760 mmHg
• Flash Point: 172.3°C
• Density: 1.32g/cm³
• Vapor Pressure: 7.47E-06mmHg at 25°C
• Refractive Index: 1.638
• CAS DataBase Reference: 3-(phenyldisulfanyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(phenyldisulfanyl)propanoic acid(3312-96-7)
• EPA Substance Registry System: 3-(phenyldisulfanyl)propanoic acid(3312-96-7)

Safety Data

• Hazardous Substances Data: 3312-96-7(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 107-96-0 3-mercaptopropionic acid 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 3312-97-8 N-(2-Tritylthio-ethyl)-5-phenyl-4,5-dithiapentansaeureamid 
• 1119-62-6 3,3'-dithiobis(propionic acid) 
• 15515-60-3 N-(2-Benzhydrylthio-ethyl)-(5-phenyl-4,5-dithia-pentan)-saeureamid 
• 123861-58-5 NHS-DTP 
• 382599-34-0 N-methyl-N-(3-phenyldithio-propanoyl)-L-alanine 
• 3313-01-7 N-(6-Carboxy-3.4-dithiahexyl)-5-phenyl-4.5-dithiapentan-saeureamid 
• 3313-02-8 N-[2-(4-Nitro-benzyldisulfanyl)-ethyl]-3-phenyldisulfanyl-propionamide 
• 3312-99-0 N-<3-Thiapropyl>-5-phenyl-4,5-dithiapentanamid-disulfid 

Relevant articles and documents

Photochemical metal-free aerobic oxidation of thiols to disulfides

Thiol oxidation to disulfides is an area of great importance in organic synthesis, both for synthetic and biological purposes. Herein, we report a mild, inexpensive and green photochemical approach for the synthesis of both symmetrical and non-symmetrical disulfides, using metal-free and environmentally friendly conditions. Utilizing phenylglyoxylic acid as the photoinitiator, common household bulbs as the light source and a simple inorganic salt as the additive, a versatile oxidation of thiols leading to products in excellent yields is described. This journal is

Semisynthetic Maytansine analogues for the targeted treatment of cancer

Maytansine, a highly cytotoxic natural product, failed as an anticancer agent in human clinical trials because of unacceptable systemic toxicity. The potent cell killing ability of maytansine can be used in a targeted delivery approach for the selective destruction of cancer cells. A series of new maytansinoids, bearing a disulfide or thiol substituent were synthesized. The chain length of the ester side chain and the degree of steric hindrance on the carbon atom bearing the thiol substituent were varied. Several of these maytansinoids were found to be even more potent in vitro than maytansine. The targeted delivery of these maytansinoids, using monoclonal antibodies, resulted in a high, specific killing of the targeted cells in vitro and remarkable antitumor activity in vivo.

Process for the preparation and purification of thiol-containing maytansinoids

The present invention provides a process for the preparation and purification of thiol-containing maytansinoids comprising the steps of: (1) reductive hydrolysis of a maytansinoid C-3 ester with a reducing agent selected from the group consisting lithium trimethoxyaluminum hydride (LiAl(OMe)3H), lithium triethoxyaluminum hydride (LiAl(OEt)3H), lithium tripropoxyaluminum hydride (LiAl(OPr)3H), sodium trimethoxyaluminum hydride (NaAl(OMe)3H), sodium triethoxyaluminum hydride (NaAl(OEt)3H) and sodium tripropoxyaluminum hydride (NaAl(OPr)3H) to yield a maytansinol; (2) purifying the maytansinol to remove side products when present; (3) esterifying the purified maytansinol with a carboxylic acid to yield a mixture of an L- and a D-aminoacyl ester of maytansinol; (4) separating the L-aminoacyl ester of maytansinol from the reaction mixture in (3); (5) reducing the L-aminoacyl ester of maytansinol to yield a thiol-containing maytansinoid; and (6) purifying the thiol-containing maytansinoid.

Cytotoxic agents comprising maytansinoids and their therapeutic use

A cytotoxic agent comprising one or more maytansinoids linked to a cell binding agent. A therapeutic agent for killing selected cell populations comprising: (a) a cytotoxic amount of one or more maytansinoids linked to a cell binding agent, and (b) a pharmaceutically acceptable carrier diluent or excipient. A method for killing selected cell populations comprising contacting a cell population or tissue suspected of containing cells from said selected cell population with a cytotoxic amount of a cytotoxic agent comprising one or more maytansinoids linked to a cell binding agent. An N-methyl-alanine-containing ester of maytansinol or an analogue of maytansinol, said N-methyl-alanine-containing ester comprising a linking group capable of linking an N-methyl-alanine-containing maytansinoid ester to a chemical moiety. N-methyl-cysteine-containing ester of maytansinol or an analogue of maytansinol.

Conversion of Thiols into Disulfides with Diethyl Bromomalonate

Reaction of aliphatic, aromatic and heterocyclic thiols (2 and 5a-h) with diethyl bromomalonate (1a) gave the corresponding symmetrical disulfides (3 and 6a-h) in high yields.In the case of L-cysteine (5i), glutathione (5j) or thiamine (5k), the reaction also gave L-cystine (6i), oxidized glutathione (6j) or thiamine disulfide (6k) in high yields regardless of the presence of other functional groups.Dithiols (11) were converted into cyclic disulfides (12) by this method.In particular, N-(2-mercapto-2-methylpropionyl)-L-cysteine (9) was converted into (4R)-tetrahydro-7,7-dimethyl-6-oxo-3H-1,2,5-dithiazepine-4-carboxylic acid (10) (obtained in poor yields by general oxidation methods) in good yields.The intermediate in the reaction was considered to be sulfenyl bromide (8).Keywords-diethyl bromomalonate; thiol; dithiol; disulfide; cyclic disulfide; thiol oxidation; disulfide formation; N-(2-mercapto-2-methylpropionyl)-L-cysteine; (4R)-tetrahydro-7,7-dimethyl-6-oxo-3H-1,2,5-dithiazepine-4-carboxylic acid