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 

n20/D 1.541(lit.)

FEMA 

2028 | ALLYL DISULFIDE

Flash point:

144 °F

storage temp. 

2-8°C

Water Solubility 

Insoluble in water

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

oil

color 

colorless to yellow

Odor

Diallyl disulfide is an essential odor component of garlic oil.

Odor Threshold

0.00022ppm

Odor Type

alliaceous

JECFA Number

572

BRN 

1699241

InChIKey

PFRGXCVKLLPLIP-UHFFFAOYSA-N

LogP

3.26

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

• Language:English Provider:Allyl disulfide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Diallyldisulfide Usage And Synthesis

Identification

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)

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

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

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 .

Preparation

By oxidation of allyl mercaptan with iodine in the presence of pyridine and ethanol; from sodium allyl thiosulfate with potassium hydroxide.

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.

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.]

Diallyldisulfide(2179-57-9)Related Product Information

• Allyl ether
• 1,5-HEXADIENE
• Allyloxypolyethyleneglycol
• Allyl hexanoate
• Propyl disulfide
• Dimethyl disulfide
• Allyl chloride
• Diallylamine
• Allyl glycidyl ether
• Allyl bromide
• N,N-Dimethylallylamine
• 2,2'-DIFURFURYL ETHER
• ETHYL METHYL DISULFIDE
• Methyl allyl disulfide
• Allyl mercaptan
• Diethyl disulfide
• Diallyl sulfide
• Allicin