17795-26-5

Basic information

• Product Name: 3-(allylsulphinyl)-L-alanine
• Synonyms: 3-(allylsulphinyl)-L-alanine;Einecs 241-773-6;L-Alanine, 3-(2-propenylsulfinyl)-;Alliin (Mixture of DiastereoMers);rac-Alliin;ACSO;(+/-)-L-ALLIIN, >=90% (HPLC)
• CAS NO: 17795-26-5
• Molecular Formula: C₆H₁₁NO₃S
• Molecular Weight: 177.22144
• EINECS: 241-773-6
• Product Categories: Amino Acids & Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals, Sulfur & Selenium Compounds
• Mol File: 17795-26-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 416.132oC at 760 mmHg
• Flash Point: 205.469oC
• Appearance: /
• Density: 1.354g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: ?20°C
• PKA: 1.88±0.10(Predicted)
• BRN: 1724805
• CAS DataBase Reference: 3-(allylsulphinyl)-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(allylsulphinyl)-L-alanine(17795-26-5)
• EPA Substance Registry System: 3-(allylsulphinyl)-L-alanine(17795-26-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 17795-26-5(Hazardous Substances Data)

Usage

Description

3-(Allylsulphinyl)-L-alanine is an organic compound derived from L-alanine, an essential amino acid, with an allyl sulphinyl group attached to it. 3-(Allylsulphinyl)-L-alanine is known for its various biological activities and potential applications in the pharmaceutical and food industries.

Uses

Used in Pharmaceutical Applications:
3-(Allylsulphinyl)-L-alanine is used as a therapeutic agent for its potential anticancer properties. It has been shown to exhibit anti-cancer activities, which can be beneficial in the development of new cancer treatments.
Used in Food Industry:
3-(Allylsulphinyl)-L-alanine is used as a flavor enhancer due to its allyl sulphinyl group, which contributes to the characteristic aroma and taste of certain foods.
Used in Antimicrobial Applications:
3-(Allylsulphinyl)-L-alanine is used as an antimicrobial agent, particularly against Clostridium jejuni, a bacterium that can cause food poisoning. It has been used in nutrient broth No. 2 (NB2) for determining the concentrations of garlic-derived products active against this bacterium.
Used in Cardioprotective Applications:
3-(Allylsulphinyl)-L-alanine is used as a cardioprotective agent, showing potential preventive effects on cardiac marker enzymes and lipids in isoproterenol-induced myocardial injury.
Used in Antihypertensive Applications:
3-(Allylsulphinyl)-L-alanine is used as an antihypertensive agent, which can help in the regulation of blood pressure.
Used in Antioxidant Applications:
3-(Allylsulphinyl)-L-alanine is used as an antioxidant, which can help in neutralizing free radicals and reducing oxidative stress in the body.

Biochem/physiol Actions

S-Allyl-L-cysteine ((±)-L-Alliin) (SAC) may be used to study its potential as an anti-Alzheimer′s factor. SAC has been shown to increase cell proliferation and neuroblast differentiation by increasing 5-HT(1A) and provide antioxidative benefit to neurons and synapses.

InChI:InChI=1/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11-/m0/s1

Upstream product

• 21593-77-1 S-allyl cysteine 
• 770742-93-3 (S)-3-(allylthio)-2-aminopropanoic acid 
• 49621-03-6 S-propenyl-L-cysteine 
• 52467-58-0 S-allyl-N-formyl-DL-cysteine 

Downstream Products

• 23127-41-5 (2R)-2-(acetylamino)-3-(prop-2-en-1-ylsulfanyl)propanoic acid 
• 21593-77-1 S-allyl cysteine 
• 17795-24-3 (+/-)-S-propyl-L-cysteine sulfoxide 
• 539-86-6 allicin 
• 127-17-3 2-oxo-propionic acid 

Relevant articles and documents

Type of complex-BSA binding forces affected by different coordination modes of alliin in novel water-soluble ruthenium complexes

Three novel water-soluble ruthenium complexes having differently bound alliin ligands were prepared by solution synthesis and characterized by chemical analysis, and infrared, mass, nuclear magnetic resonance and electron paramagnetic resonance spectrosco

Changes of S-Allylmercaptocysteine and γ-Glutamyl- S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process

γ-Glutamyl-S-allylmercaptocysteine (GSAMC), a putative precursor compound of S-allylmercaptocysteine (SAMC), was isolated and identified from aged garlic extract (AGE). We analyzed the change of their contents in AGE during the aging process, chronologica

IMPROVEMENTS IN OR RELATING TO ALLIUM EXTRACTS

The present invention relates to improvements in or relating to Allium extracts. In particular, it relates to improvements in or relating to extending the therapeutic half- life or duration of Allium extracts. The invention also relates to the synthesis of certain thiosulfinate compounds, especially to the synthesis of methyl allyl thiosulfinate and allyl methyl thiosulfinate, in particular from either methiin or alliin alone or a mixture of both. The invention further relates to the synthesis of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allicin, and methyl methyl thiosulfinate in a mixture with varying molar or mass ratios depending on the reaction conditions, in particular from either methiin or alliin alone or a mixture of both. A high yielding, optimized synthesis of allicin starts from alliin, whereas methyl methyl thiosulfinate is advantageously obtained from methiin. Also provided is a kit comprising methiin in a first container and/or alliin in a second container and an allinase source, in particular garlic powder in a third container. Finally, the invention provides a method of preparing a mixture of methyl allyl thiosulfinate, allyl methyl thiosulfinate, allyl allyl thiosulfinate (allicin) and methyl methyl thiosulfinate from methiin and pieces of an Allium species.