Basic information
- CAS
2179-57-9- Standard SMILES
C=CCSSCC=C- InChIKey
PFRGXCVKLLPLIP-UHFFFAOYSA-N- Molecular formula
- C6H10S2
- Average molar mass
- 146.3 g/mol
- Monoisotopic mass
- 146.02239232
Overview
Diallyl disulfide is an organic disulfide where the organic group specified is allyl. It has been isolated from garlic and other species of the genus Allium. It has a role as an antineoplastic agent, an antifungal agent and a plant metabolite.
Names & identifiers
- Preferred name
- Diallyl Disulfide
- IUPAC
- 3-(prop-2-enyldisulfanyl)prop-1-ene
- English name
- Diallyl disulfide
- Molecular formula
- C6H10S2
- Molecular weight
- 146.27
Names & synonyms
DIALLYL DISULFIDE2179-57-9DiallyldisulfideAllyl disulfideDiallyl disulphideDisulfide, di-2-propenylAllyl disulphide2-Propenyl disulphide4,5-Dithia-1,7-octadiene2-Propenyl disulfide3-(prop-2-enyldisulfanyl)prop-1-eneFEMA No. 2028
Show more names
DADSFEMA 2028Dially disulfide1,2-diallyldisulfaneDisulfide,di-2-propenylgarlicin oil
DTXSID90352063-(prop-2-en-1-yldisulfanyl)prop-1-ene5HI47O6OA7NSC-29228CHEBI:4488DTXCID7015206NSC29228allyll disulfide
Database identifiers
- CAS
2179-57-9- PubChem CID
- 16590
- DTXSID
DTXSID9035206- ChEMBL
CHEMBL366603- ChEBI
CHEBI:4488- UNII
- 5HI47O6OA7
- EC Number
- 218-548-6
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 50.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 5
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 58.9
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Sulfur Compounds
FragrancesFragrance Ingredient (Allyl disulfide) -> IFRA transparency List
OdorGARLIC ODOR
TasteSHARP, GARLIC FLAVOR
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density
1.010 @ 15 °C
0.998-1.015
Flavoring AgentsEU Flavoring substances
Color/FormLIQUID
Solubility
INSOL IN WATER; SOL IN MOST COMMON ORG SOLVENTS
insoluble in water; soluble in common organic solvents
(in ethanol)
Boiling Point
79 °C @ 16 MM HG
138.00 to 139.00 °C. @ 760.00 mm Hg
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (97.4%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1647 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Disulfide, di-2-propenyl
Regulation (EC) No 1831/2003 (amended)
Diallyl disulfide: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
One of the volatiles in onions responsible for lacrimation; Emergency treatment: Irritants; [HSDB] One of the major allergens in garlic and onions; [Kanerva, p. 1777] Diallyl disulfides (DADs): A moderate eye and strong skin irritant in rabbits; A skin sensitizer in guinea pigs using the Buehler method; Causes breathing abnormalities, wobbly gait, and decreased activity in oral lethal-dose studies of rats; Oral LD50 (rat) = 346 mg/kg; Dermal LD50 (rat) = 1,967 mg/kg; [EPA] Safe when used as a flavoring agent in food; [JECFA] A moderate skin and severe eye irritant; Causes hemolysis in oral lethal-dose study of rats; [RTECS] A skin and strong eye irritant; [Alfa Aesar MSDS]
FDA Requirements121.1164. /FROM TABLE/
Hazard Classes and CategoriesFlam. Liq. 3 (97.4%)
Toxicology
Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesDiallyl disulfide has known human metabolites that include DADSO and (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[(E)-3-(prop-2-enyldisulfanyl)prop-1-enyl]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Chemical substances that are destructive to spermatozoa used as topically administered vaginal contraceptives.
Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved.
Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved.
Cellular LocationsMembrane
Uses & manufacturing
Uses
Major constituent of garlic oil; [ChemIDplus] Used as synthetic flavoring ingredient; [HSDB] Constitutes 86.9% of diallyl disulfides (DADs) which is 90% active ingredient of biopesticide used to control white rot (fungal pathogen) in onions, garlic, and leeks; DADs are volatile sulfur compounds found in garlic, onions, and other members of Allium species; [EPA]
Farming (Pesticides) [Category: Industry]
SYNTHETIC FLAVORING ADJUVANT OR INGREDIENT
Methods of ManufacturingBY OXIDATION OF ALLYL MERCAPTAN WITH IODINE IN THE PRESENCE OF PYRIDINE & ETHANOL; FROM SODIUM ALLYL THIOSULFATE WITH POTASSIUM HYDROXIDE.
Use Classification
Related reactions
5 records
Compound notes
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