Allyl methyl sulfide

CAS No. 10152-76-8

Formula: C4H8S
Basic Info

Allyl methyl sulfide (AMS) is an organosulfur compound with the chemical formula CH2=CHCH2SCH3. The molecule features two functional groups, an allyl (CH2=CHCH2) and a sulfide. It is a colourless liquid with a strong odor characteristic of alkyl sulfides. It is a metabolite of garlic, and "garlic breath" is attributed to its presence.
It is prepared by the reaction of allyl chloride with sodium hydroxide and methanethiol.
CH2=CHCH2Cl + NaOH(aq) + CH3SH → CH2=CHCH2SCH3 + NaCl + H2O

Formula
C4H8S
Molecular Weight
88.1713
Exact Mass
88.0347
LogP
1.5354
PSA
25.3
Synonyms

Allyl Methyl Sulfide

1-Propene, 3-(methylthio)-

3-Methylthio-1-propene

3-methylsulfanylprop-1-ene

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Properties
Appearance & Physical State
clear, colorless liquid
Density
0.803
Boiling Point
91-93ºC
Flash Point
18ºC
Refractive Index
1.4704-1.4724
Stability
Stable under normal temperatures and pressures.
Storage Condition
0-6ºC
Vapor Pressure
68.4mmHg at 25°C
Safety Info
Safety Statements
S15-S16
WGK Germany
3
Risk Statements
R11
RIDADR
UN 1993
Hazard Class
3
Packing Group
II
Hazard Codes
Spectrum
NMR Spectrum 1H NMR : Predict
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IR Spectrum IR : liquid film
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Mass Spectrum Mass spectrum (electron ionization)
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Analysis Methods
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
697.
Temperature Control
130.
Method
isothermal
Comments
He or N2, Chromosorb W, AW-DMCS; Column length: 2.1 m
Reference
Garbuzov, V.G.Misharina, T.A.Aerov, A.F.Golovnya, R.V.Gas chromatographic retention indices for sulphur(II)-containing organic substancesJ. Anal. Chem. USSR (Engl. Transl.)1985, 40, 4, 576-586.
Kovats' RI, non-polar column, isothermal
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Column Shape
Packed
Active Phase(℃)
Apiezon M
Retention index
697.
Temperature Control
130.
Method
isothermal
Comments
Chromosorb W, AW-DMCS; Column length: 2.1 m
Reference
Golovnya, R.V.Misharina, T.A.Garbuzov, V.G.Gas chromatographic characterization of sulfur-containing compounds. 4. The effect of unsaturated radicals on the retention indices of the vinyl, allyl, and propargyl alkyl sulfidesIzv. Akad. Nauk SSSR Ser. Khim.1978, 11, 2266-2270.
Van Den Dool and Kratz RI, non-polar column, temperature ramp
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Column Shape
Capillary
Active Phase(℃)
DB-1
Retention index
678.
Temperature Control
Method
temperature ramp
Comments
60. m/0.25 mm/1.0 μm, He, 40. C @ 5. min, 2. K/min, 260. C @ 60. min
Reference
Yu, T.-H.Lin, L.-Y.Ho, C.-T.Volatile compounds of blanched, fried blanched, and baked blanched garlic slicesJ. Agric. Food Chem.1994, 42, 6, 1342-1347.
Van Den Dool and Kratz RI, non-polar column, temperature ramp
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Column Shape
Capillary
Active Phase(℃)
OV-1
Retention index
678.
Temperature Control
Method
temperature ramp
Comments
N2, 1. K/min; Column length: 183. m; T<sub>start</sub>: 0. C; T<sub>end</sub>: 230. C
Reference
Schreyen, L.Dirinck, P.van Wassenhove, F.Schamp, N.Volatile flavor components of leekJ. Agric. Food Chem.1976, 24, 2, 336-341.
Van Den Dool and Kratz RI, non-polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
SPB-1
Retention index
684.
Temperature Control
Method
custom temperature program
Comments
30. m/0.32 mm/4.0 μm, N2; Program: 40 0C (10 min), 2 0C/min to 180 0C, 25 0C/min to 250 0C (5 min)
Reference
Mochizuki, E.Yamamoto, T.Komiyama, Y.Nakazawa, H.Identification of allium products using flame photometric detection gas chromatography and distribution patterns of volatile sulfur compoundsJ. Agric. Food Chem.1998, 46, 12, 5170-5176.

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