Diallyldisulfide

Diallyldisulfide Basic information
Identification Description Regulatory Status Usage Natural occurrence
Product Name:Diallyldisulfide
Synonyms:dialkyldisulfide;Disulfide, di-2-propenyl;Disulfide,di-2-propenyl;DADS;Diallyldisulfide, remainder mainly diallyl sulfide;ALLYL DISULFIDE 80+%;ALLYL DISULFIDE, TECH., 80%;DIALLYL DISULPHIDE 90%(GC)
CAS:2179-57-9
MF:C6H10S2
MW:146.27
EINECS:218-548-6
Product Categories:sulfide Flavor;2179-57-9
Mol File:2179-57-9.mol
Diallyldisulfide Structure
Diallyldisulfide Chemical Properties
Boiling point 180-195 °C(lit.)
density 1.008 g/mL at 25 °C(lit.)
vapor density >5 (vs air)
vapor pressure 1 mm Hg ( 20 °C)
FEMA 2028 | ALLYL DISULFIDE
refractive index n20/D 1.541(lit.)
Fp 144 °F
storage temp. 2-8°C
solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Water Solubility Insoluble in water
form oil
color colorless to yellow
OdorDiallyl disulfide is an essential odor component of garlic oil.
Odor Threshold0.00022ppm
Odor Typealliaceous
JECFA Number572
BRN 1699241
InChIKeyPFRGXCVKLLPLIP-UHFFFAOYSA-N
LogP3.26
CAS DataBase Reference2179-57-9(CAS DataBase Reference)
NIST Chemistry ReferenceDiallyl disulphide(2179-57-9)
EPA Substance Registry SystemDiallyl disulfide (2179-57-9)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-10
Safety Statements 26-36/37/39-37/39-16-36
RIDADR UN 2810 6.1/PG 3
WGK Germany 3
RTECS BB1000000
13
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29309090
Hazardous Substances Data2179-57-9(Hazardous Substances Data)
MSDS Information
ProviderLanguage
Allyl disulfide English
SigmaAldrich English
ACROS English
ALFA English
Diallyldisulfide Usage And Synthesis
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
 
 
DescriptionAllyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant.
Regulatory StatusCoE: 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).


UsageReported 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 occurrenceMain 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.).
DescriptionDiallyl 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.
Chemical PropertiesCLEAR YELLOW LIQUID
Chemical PropertiesAllyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant
OccurrenceMain 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.).
Usesantineoplastic, antibacterial, apoptosis inducer, insecticide
UsesDiallyldisulfide 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 .
UsesDiallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens.
DefinitionChEBI: An organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium.
PreparationBy oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with potassium hydroxide.
Aroma threshold valuesDetection: 4.3 to 30 ppb; Recognition: 80 ppb
Taste threshold valuesTaste 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/jo01340a520
Synthetic Communications, 25, p. 3573, 1995 DOI: 10.1080/00397919508015492
General DescriptionAllyl 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 ActionsOrganosulfur 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 allergensDiallyldisulfide 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 MethodsPurify 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.]
Diallyldisulfide Preparation Products And Raw materials
Raw materialsAllyl mercaptan-->DIALLYLSELENIDE-->diallyl tetrasulphide-->Diallyl trisulfide-->Diallyl sulfide-->3-METHYLBUTYL ISOTHIOCYANATE-->ALLYL IODIDE
Preparation ProductsETHYL METHYL DISULFIDE
Methyl allyl disulfide Diallyldisulfide Allyl glycidyl ether Allyloxypolyethyleneglycol 1,5-HEXADIENE Propyl disulfide GGKPDLRPCHPPCHYIPRPKPR RADICININ FROM ALTERNARIA CHRYSANTHEMI N,N-Dimethylallylamine Allyl bromide Dimethyl disulfide Allyl ether Allyl hexanoate Bisphenol S diallyl ether Allyl chloride Diethyl disulfide Diallylamine Allyl mercaptan

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