Available forms:clear yellow liquid
pd_proNo:514622-81b07cf6-3473-497a-8e99-a036e0f0ab7b
pd_productuse:
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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 |
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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). |
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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.). |
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Preparation |
By oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with potassium hydroxide. |
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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 |
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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. |
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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. |
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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.] |
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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 |
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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. |
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Aroma threshold values |
Detection: 4.3 to 30 ppb; Recognition: 80 ppb |
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Taste threshold values |
Taste characteristics at 2 ppm: green onion and garlic-like with meaty nuances |
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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. |
InChI:InChI=1/C8H12O4/c9-5-1-2-6(10)7-4(5)3-12-8(7)11/h4-7,9-10H,1-3H2
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allicin
3-vinyl-4H-<1,2>-dithiin
diallyl disulphide
diallyl trisulfide
2‐ethenyl‐4H‐1,3‐dithiine
(Z)-ajoene
(E)-ajoene
| Conditions | Yield |
|---|---|
|
at 37 ℃;
for 48h;
Product distribution;
other temperatures, other times;
|
S-allyl cysteine
diallyl disulphide
allicin
bis-2-propenyl thiosulfonate
sodium pyruvate
| Conditions | Yield |
|---|---|
|
With
nitrogen(II) oxide;
In
water;
for 24h;
Yield given. Yields of byproduct given;
Ambient temperature;
|
prop-2-ene-1-thiol
allyl iodid
allyl bromide
S-allyl cysteine
allicin
diallyl sulphide
3-vinyl-4H-<1,2>-dithiin
diallyl trisulfide
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