592-88-1 Usage
Description
Diallyl sulfide, a volatile flavor compound naturally found in Allium species such as garlic and onion, is a colorless liquid with a characteristic garlic odor. It consists of four ingredients: diallyl monosulfide, diallyl disulfide, diallyl trisulfide, and diallyl tetrasulfide. As the main component of garlic extract, it is known for its strong anti-cancer, anti-virus, and antibacterial activities, as well as its ability to inhibit platelet aggregation and improve immunity.
Uses
Used in Medical and Health Industry:
Diallyl sulfide is used as a modulator of the drug metabolizing enzyme P450 system and an inducer of the phase II detoxifying enzyme GST. It acts as an inhibitor of CYP2E1 and is believed to prevent chemically-induced carcinogenesis in various tissues. It is also used as an antibacterial, antifungal, antineoplastic, antihypercholesterolaemic, and hepatoprotectant agent.
Used in Fodder Industry:
Diallyl sulfide is used in the fodder industry due to its various beneficial properties, such as its antibacterial and antifungal activities, which can help improve animal health and productivity.
Used in Food Industry:
Diallyl sulfide is used as a food additive, particularly as a flavoring agent in meat and condiments. It is also used in the manufacture of flavors, contributing to the characteristic garlic odor and taste.
Used in Organic Synthesis, Pharmaceuticals, Agrochemicals, and Dye Industry:
Diallyl sulfide serves as an important raw material and intermediate in organic synthesis, pharmaceuticals, agrochemicals, and the dye industry, thanks to its versatile chemical properties and potential applications.
Taste and Aroma Characteristics:
Diallyl sulfide has a taste threshold value of 2 ppm, with a sulfureous, onion-garlic, and vegetative radish-like flavor with a slightly hot nuance. Its aroma threshold value is 0.05 ppb, indicating its strong and distinctive garlic odor.
Occurrence:
Diallyl sulfide is reported to be found in various plants, including garlic (Allium sativum L.), onion (Allium cepa L.), nira (Allium tuberosum Rottl.), caucas (Allium victoralis L.), mustard (Brassica species), and cooked/boiled beef.
Physical & Chemical Properties
It is an oily substance scented with garlic. Boiling point: 139 ° C (101.056Pa), relative density: 0.8876, refractive index: 1.4877. Soluble in organic solvents such as ether and the like, insoluble in water. Also it can be oxidized to diallyl sulfone.
Figure 1: Diallyl Disulfide
Figure 2: Diallyl trisulfide
Preparation Method
The two main methods for preparation of diallyl sulfide are: biological extraction and chemical synthesis.
Biological extraction
The more common biological extraction methods are steam distillation, organic solvent extraction and supercritical CO2 extraction. Steam distillation is to use water as a solvent, then heat under a certain pressure to extract the soluble active ingredients from the natural products. The advantage of this method is that it is simple to operate and suitable for the extraction of active ingredients that are generally easier to extract. Its disadvantages include the greater loss of the active ingredients in the thermosensitives, lower yield, and that the active ingredients in the extract are not easily separated.
Process for allicin extraction: fermentation temperature: ?50 ~ 55 ℃, fermentation duration: 2h ~ 3h, add water into the garlic with the proportion of 1: 4 water, distilled for the duration of 1.5h ~ 2h.
Organic solvent extraction method is to use organic solvent as extraction agent, and extract the active ingredients of natural products at a certain temperature and extraction duration. ?Usually methanol, ethanol, acetone, ethyl ether or the mixture of these solvents are used as the organic solvents. Compared withthe steam distillation extraction, the advantage of the organic solvent extraction is that the extract has higher purity. Also it is one of the traditional extraction methods.
Use ethanol with volume fraction of 95% as the extraction solvent, and add the extractant in proportion of 1g: 4mL. First the enzymolysis time was 0.5h when the temperature is set to 40 ℃; then have the extraction for 1.5h when the temperature is set to 30 ℃; finally set the temperature at 50 ℃, and have it concentrated under reduced pressure in a steamer rotating at a speed of 4500r / min to extract allicin. The extraction rate can reach 0.24%.
Chemical synthesis
Mix Na2S2O3?5H2O62g (0.25mol) and 3-bromopropene 24g (0.20mol) in ethanol - water (V ethanol: V water = 60:40) evenly and reflux to homogeneity. Add 30mL of concentrated hydrochloric acid, reflux for 5h, standing still, then separate the upper layer and put it into 100mL10% NaOH solution placed in an ice bath, add 80mL of 25% K3Fe (CN) 6 (6mmol) aqueous solution while stirring and stop after 2.5h. Separate the organic layer and dry it over anhydrous sodium sulfate. Then filter off the desiccant, recover the solvent, and finally 6.6 g of pale yellow oily substance will be obtained.?
Figure 3: Synthetic route
Toxicity
GRAS(FEMA)。
Maximum limits
FEMA (mg / kg): Drinks 0.04; Cold Drink 0.06; Confectionery 0.07; Bakery Products 0.05; Seasoning 13; Meat 3.7.
FDA, § 172.515: Appropriate amount.
Preparation
From allyl iodide plus potassium sulfide in alcoho
Biochem/physiol Actions
Organosulfur compound from garlic that inhibits chemically-induced carcinogenesis in experimental animals. Competitive inhibitor of Cytochrome P450 2E1 (CYP2E1) that, in turn, blocks the activation of several chemcal carcinogens.
Anticancer Research
It is a thioether, found in garlic, inhibits cytochrome P450 IIE1 isoform, and therebysuppresses carcinogenesis (Aggarwal and Shishodia 2004). The consumption ofgarlic provides protection from gastrointestinal cancers and also suppresses theprogression of colorectal adenomas (Hosseini and Ghorbani 2015).
Check Digit Verification of cas no
The CAS Registry Mumber 592-88-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 2 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 592-88:
(5*5)+(4*9)+(3*2)+(2*8)+(1*8)=91
91 % 10 = 1
So 592-88-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2
592-88-1Relevant articles and documents
Regioselective reactions of sulfur, selenium and tellurium chlorides with allyl trimethyl silane
Martynov, Alexander V.,Makhaeva, Natalia A.,Larina, Lyudmila I.,Amosova, Svetlana V.
, p. 1964 - 1968 (2011)
Electrophilic addition of SCl2, SeCl2 and SeCl 4 to 2 equivalents of allyl trimethyl silane proceeds regioselectively to give bis[2-chloro-3-(trimethylsilyl)propyl] sulfide, selenide and selenium dichloride, respectively. The reaction with TeCl 4 affords only diallyl tellurium dichloride. The structures of the compounds were confirmed by 1H, 13C, 77Se and 125Te NMR techniques.
Yb(iii)-catalysedsyn-thioallylation of ynamides
Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 7521 - 7524 (2021/08/05)
Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
Diallyl Trisulfide Is a Fast H2S Donor, but Diallyl Disulfide Is a Slow One: The Reaction Pathways and Intermediates of Glutathione with Polysulfides
Liang, Dong,Wu, Haixia,Wong, Ming Wah,Huang, Dejian
supporting information, p. 4196 - 4199 (2015/09/15)
Diallyl trisulfide (DATS) reacts rapidly with glutathione (GSH) to release H2S through thiol-disulfide exchange followed by allyl perthiol reduction by GSH. Yet diallyl disulfide (DADS) only releases a minute amount of H2S via a sluggish reaction with GSH through an α-carbon nucleophilic substitution pathway. The results clarify the misunderstanding of DADS as a rapid H2S donor, which is attributed to its DATS impurity.
NaI/silica sulfuric acid as an efficient reducing system for deoxygenation of sulfoxides in poly ethylene glycol (PEG-200)
Zarei, Morteza,Ameri, Mohammad Aghil,Jamaleddini, Azar
, p. 259 - 263 (2013/08/26)
Deoxygenation of structurally diverse sulfoxides including dialkyl, diaryl, aryl alkyl and allyl sulfoxides to the corresponding sulfides were carried out using a NaI/silica sulfuric acid reducing system at room temperature in poly ethylene glycol (PEG-200) in excellent yields.