2179-57-9 Usage
Description
Diallyldisulfide, an organic disulfide derived from the Allium genus, is a clear yellow liquid with a characteristic garlic odor. It is a major allergen found in garlic (Allium sativum) and onions, and is known for its chemopreventive properties. Diallyldisulfide is used in various applications due to its unique characteristics and benefits.
Uses
Used in Pharmaceutical Industry:
Diallyldisulfide is used as an antineoplastic, antibacterial, and apoptosis inducer. It exhibits chemopreventive characteristics and has been reported to have potential benefits in the treatment of various cancers.
Used in Food Industry:
Diallyldisulfide is used as a flavor enhancer, flavoring agent, or adjuvant in the food industry. It is commonly used in meat and condiments, providing a garlic-like taste with meaty nuances. The compound is also used in alcoholic and non-alcoholic beverages, baked goods, frozen dairy, gelatins, puddings, gravies, soft candy, and soups.
Used in Agriculture:
Diallyldisulfide is used as an insecticide in the agricultural industry, taking advantage of its antimicrobial properties to protect crops from pests.
Used in Flavor and Fragrance Industry:
Due to its distinct garlic-like aroma, Diallyldisulfide is utilized in the flavor and fragrance industry to create unique scents and enhance the taste of various products.
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
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).
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.).
Preparation
By oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with
potassium hydroxide.
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
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.
Trisulfides over disulfides: Highly selective synthetic strategies, anti-proliferative activities and sustained H2S release profiles
Bhattacherjee, Debojit,Sufian, Abu,Mahato, Sulendar K.,Begum, Samiyara,Banerjee, Kaustav,De, Sharmistha,Srivastava, Hemant Kumar,Bhabak, Krishna P.
supporting information, p. 13534 - 13537 (2019/11/14)
Temperature-and solvent-induced selective synthesis of trisulfides and disulfides is demonstrated. A remarkable selectivity was achieved using Na2S as a sulfur-Transfer agent under mild, greener, catalyst-free and additive-free conditions. This study reveals trisulfides as a better model than disulfides in general for a sustained release of H2S and potent anti-cancer activities.
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.