Diallyldisulfide

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

CLEAR YELLOW LIQUID

Chemical properties

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.).

The Uses of Diallyldisulfide

Diallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens.

The Uses of Diallyldisulfide

antineoplastic, antibacterial, apoptosis inducer, insecticide

The Uses of Diallyldisulfide

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 .

What are the applications of Application

Allyl disulfide is A sulfhydryl and carbonyl reactive heterobifunctional crosslinking reagent.

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/jo01340a520
Synthetic 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.]