2179-57-9 Usage
Identification
▼▲
CAS.No.:?
2179-57-9?
FL.No.:?
12.008
FEMA.No.:?
2028
NAS.No.:?
2028
CoE.No.:?
485
EINECS.No.:?
218-548-6?
JECFA.No.:?
572
Description
Different sources of media describe the Description of 2179-57-9 differently. You can refer to the following data:
1. Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant.
2. Diallyl disulfide is one of the major allergens in garlic
(Al/ium sativum) and onions. Among patients who are
patch-test positive to garlic, all 13 who were tested had
positive reactions to diallyl sulfide 5% petrolatum.
Regulatory Status
CoE: Used provisionally. Food: 5 ppm
FDA: 21 CFR 172.515
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1999).
Usage
Reported uses (ppm): (FEMA, 1994)
▼▲
Food Category?
Usual?
Max.?
Alcoholic beverages?
0.1
1
Baked goods?
9.09
13.16
Condiments, relishes?
13.82
15.21
Frozen dairy?
0.1
1
Gelatins, puddings?
0.5
1
Gravies?
2
6.5
Meat products?
9.4
13.1
Nonalcoholic beverages?
0.07
0.68
Soft candy?
0.5
1
Soups?
1
10
Natural occurrence
Main constituent of Allium sativum essential oil. Reported found in onion (Allium cipa, L.), garlic (Allium sativum L.), chive (Allium schoenoprasum L.), nira (Allium tuberosum rottl.), raw cabbage and caucas (Allium victoralis L.).
Chemical Properties
Different sources of media describe the Chemical Properties of 2179-57-9 differently. You can refer to the following data:
1. CLEAR YELLOW LIQUID
2. Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant
Occurrence
Main constituent of Allium sativum essential oil. Reported found in onion (Allium cipa, L.), garlic (Allium
sativum L.), chive (Allium schoenoprasum L.), nira (Allium tuberosum rottl.), raw cabbage and caucas (Allium victoralis L.).
Uses
Different sources of media describe the Uses of 2179-57-9 differently. You can refer to the following data:
1. antineoplastic, antibacterial, apoptosis inducer, insecticide
2. Diallyldisulfide has a range of uses varying from a Cytocrome P450 inhibitor to vasorelaxant and hypotensive. Being in the class of organosulfur compounds, it carries chemopreventive characteristics .
3. Diallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens.
Definition
ChEBI: An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.
Preparation
By oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with
potassium hydroxide.
Aroma threshold values
Detection: 4.3 to 30 ppb; Recognition: 80 ppb
Taste threshold values
Taste characteristics at 2 ppm: green onion and garlic-like with meaty nuances
Synthesis Reference(s)
The Journal of Organic Chemistry, 31, p. 615, 1966 DOI: 10.1021/jo01340a520Synthetic Communications, 25, p. 3573, 1995 DOI: 10.1080/00397919508015492
General Description
Allyl disulfide is naturally found in Allium species such as garlic and onion. It is used as a flavoring agent in meat and condiments.
Biochem/physiol Actions
Organosulfur compound that is naturally found in garlic. Contributes to the pungent odor of crushed garlic. Anticancer agent and may provide protection against cardiovascular disease.
Contact allergens
Diallyldisulfide is one of the major allergens in garlic (Allium sativum) and onions. Among patients patch-testpositive to garlic, all 13 who were tested had positive reactions to diallyl sulfide 5% pet.
Purification Methods
Purify the disulfide by fractional distillation until the molar refractivity is in uniformly good agreement with the calculated value [Small et al. J Am Chem Soc 69 1710 1947]. It has also been purified by gas chromatography [retention times: Carson & Wong J Org Chem 24 175 1959, UV: Koch J Chem Soc 395 1949]. It is present in garlic. [Beilstein 1 IV 2098.]
Check Digit Verification of cas no
The CAS Registry Mumber 2179-57-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,7 and 9 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2179-57:
(6*2)+(5*1)+(4*7)+(3*9)+(2*5)+(1*7)=89
89 % 10 = 9
So 2179-57-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H12O4/c9-5-1-2-6(10)7-4(5)3-12-8(7)11/h4-7,9-10H,1-3H2
2179-57-9Relevant articles and documents
Synthesis and preliminary evaluation of the anti-cancer activity on A549 lung cancer cells of a series of unsaturated disulfides
Olivito, Fabrizio,Amodio, Nicola,Di Gioia, Maria Luisa,Nardi, Monica,Oliverio, Manuela,Juli, Giada,Tassone, Pierfrancesco,Procopio, Antonio
, p. 116 - 119 (2019)
We synthesized a series of small symmetrical unsaturated disulfides by a multi-step reaction starting from organic alcohols, and we performed a preliminary test to evaluate the effect of these compounds on the viability of A549 lung cancer cells. The garlic-derived natural compound diallyl disulfide, known for its anticancer activity, was used as the lead compound in this study. We synthesized five DADS analogues having different carbon chain lengths and different positions of the double bonds. Two analogues exhibited a promising antitumor activity in vitro, and the allylic double bond did not seem to be the main driving force.
Oxidation of some organic thiols with tetramethylammonium fluorochromate(VI)
Imanieh,Ghamami,Mohammadi,Jangjoo
, p. 282 - 284 (2007)
Tetramethylammonium fluorochromate oxidizes alcohols to the corresponding aldehydes and ketones without polymerization of double bonds, overoxidation, and other side reactions. This reagent is effective for oxidation of thiols to disulfides.
Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus
Saima,Soni, Isha,Lavekar, Aditya G.,Shukla, Manjulika,Equbal, Danish,Sinha, Arun K.,Chopra, Sidharth
, p. 171 - 178 (2019/01/04)
Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.
A rapid, efficient and green procedure for transformation of alkyl halides/ tosylates to organochalcogens in water
Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
supporting information, p. 41 - 44 (2017/09/25)
A one-pot and efficient synthesis of dialkyl dichalcogenides (S, Se) in aqueous media under catalyst-free conditions using benzylic, allylic and primary halides with elemental sulfur and selenium has been developed. Also, this procedure was extended to preparation of trisulfides and triselenides from secondary and tertiary halides in same condition. In all cases, products can be obtained in good to excellent yield in short reactions time.