Diallyldisulfide Chemical Properties,Usage,Production
Identification
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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
Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant.
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)
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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.).
Description
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.
Chemical Properties
Allyl disulfide has a characteristic garlic odor. It is used as a flavor enhancer, flavoring agent or adjuvant
Chemical Properties
CLEAR YELLOW LIQUID
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
Diallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens.
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 .
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
Allyl disulfide is naturally found in Allium species such as garlic and onion. It is used as a flavoring agent in meat and condiments.
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.
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.
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.]
