| 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 |
| Mol File: | 2179-57-9.mol |
| 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) |
| refractive index | n |
| FEMA | 2028 | ALLYL DISULFIDE |
| Fp | 144 °F |
| storage temp. | 2-8°C |
| Water Solubility | Insoluble in water |
| form | oil |
| color | colorless to yellow |
| Odor | Diallyl disulfide is an essential odor component of garlic oil. |
| Odor Threshold | 0.00022ppm |
| JECFA Number | 572 |
| BRN | 1699241 |
| InChIKey | PFRGXCVKLLPLIP-UHFFFAOYSA-N |
| CAS DataBase Reference | 2179-57-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Diallyl disulphide(2179-57-9) |
| EPA Substance Registry System | Diallyl 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 |
| F | 13 |
| TSCA | Yes |
| HazardClass | 6.1 |
| PackingGroup | II |
| HS Code | 29309090 |
| Hazardous Substances Data | 2179-57-9(Hazardous Substances Data) |
| MSDS Information |
| Provider | Language |
|---|---|
| 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
|
| 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)
▼ ▲ 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 | 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.). |
| Uses | antineoplastic, antibacterial, apoptosis inducer, insecticide |
| Uses | 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 . |
| Uses | Diallyl disulfide is one of the three principallow-molecular-weight allergens of garlic. Allylpropyl disulfide and allicin are the other allergens. |
| 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/jo01340a520Synthetic 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.] |
| Diallyldisulfide Preparation Products And Raw materials |
| Raw materials | Allyl mercaptan-->DIALLYLSELENIDE-->diallyl tetrasulphide-->Diallyl trisulfide-->Diallyl sulfide-->3-METHYLBUTYL ISOTHIOCYANATE-->ALLYL IODIDE |
| Preparation Products | ETHYL METHYL DISULFIDE |
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