Allyl propyl disulfide

Allyl propyl disulfide

Names
Preferred IUPAC name 3-(Propyldisulfanyl)prop-1-ene
Other names 2-Propenyl propyl disulphide 4,5-Dithia-1-octene[1] Onion oil[1] 2-Propenyl propyl disulfide[1] Propyl allyl disulfide[1] 1-Allyl-2-propyldisulfane (not recommended)
Identifiers
CAS Number	2179-59-1
3D model (Jmol)	Interactive image
ChemSpider	15731
ECHA InfoCard	100.016.864
InChI InChI=1S/C6H12S2/c1-3-5-7-8-6-4-2/h3H,1,4-6H2,2H3 Key: FCSSPCOFDUKHPV-UHFFFAOYSA-N InChI=1/C6H12S2/c1-3-5-7-8-6-4-2/h3H,1,4-6H2,2H3 Key: FCSSPCOFDUKHPV-UHFFFAOYAQ
SMILES S(SCCC)CC=C
Properties
Chemical formula	C6H12S2
Appearance	Pale-yellow liquid
Odor	strong onion-like odor[1]
Density	0.984 g/cm^3
Melting point	−15 °C; 5 °F; 258 K
Solubility in water	Insoluble[1]
Hazards
Flash point	54.4 °C (129.9 °F; 327.5 K)
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 2 ppm (12 mg/m^3)[1]
REL (Recommended)	TWA 2 ppm (12 mg/m^3) ST 3 ppm (18 mg/m^3)[1]
IDLH (Immediate danger)	N.D. [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Allyl propyl disulfide is an organosulfur compound with the chemical formula C₃H₅S₂C₃H₇. It is a volatile pale-yellow liquid with a strong odor. It is a major component of onion oil and is used in food additives and flavors.^[2] This substance is present in garlic and onion. When onion or garlic is sliced, the substance evaporates and causes eyes to irritate.^[3] When garlic or onion is cooked, it also evaporates, ridding them of the spicy taste, and leaving a sweet taste in them.

References

1. "NIOSH Pocket Guide to Chemical Hazards #0020". National Institute for Occupational Safety and Health (NIOSH).
2. Lawson, Larry D.; Wang, Zhen Yu J.; Hughes, Bronwyn G. "Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products" Planta Medica 1991, vol. 57, pp. 363-70. doi:10.1055/s-2006-960119
3. CDC - NIOSH Pocket Guide to Chemical Hazards