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Adding short description: "Organosulfur compound", overriding automatically generated description
 
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{{Short description|Organosulfur compound}}
{{chembox
{{Chembox
⚫
| Name = Allyl methyl sulfide
| Verifiedfields = changed
| ImageFileL1 =
| Watchedfields = changed
| IUPACName = Hydrogen sulfide, sulfane
| verifiedrevid = 477314172
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| OtherNames = 3-methylthio-1-propene; methyl propenyl sulfide; garlic sweat
| ImageFile = Allylmethyl sulfide Structural Formula V1.svg
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| Section1 = {{Chembox Identifiers
| ImageFile_Ref = {{chemboximage|correct|??}}
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| CASNo = 10152-76-8
| ImageSize = 244
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}}
| ImageName = XYZ
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| Section2 = {{Chembox Properties
| PIN = 3-(Methylsulfanyl)prop-1-ene
| Formula = C<sub>4</sub>H<sub>8</sub>S
⚫
| OtherNames = Methyl propenyl sulfide<br />
| MolarMass = 88.16752 g/mol
3-Methylthio-1-propene
| Denisty = 0.8g/L, gas
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|Section1={{Chembox Identifiers
| Boiling point = 91-93 °C (364-366 K)
| CASNo_Ref = {{cascite|changed|??}}
⚫
}}
⚫
| CASNo = 10152-76-8

| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = V7QI1R316C

| PubChem = 66282
| ChemSpiderID = 21159856
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 233-422-0
| UNNumber = 1993
⚫
| MeSHName = allyl+methyl+sulfide
| RTECS = UD1015000
| SMILES = CSCC=C
| StdInChI = 1S/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3
| StdInChIKey = NVLPQIPTCCLBEU-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = NVLPQIPTCCLBEU-UHFFFAOYAX
}}
}}
⚫
|Section2={{Chembox Properties
Allyl methyl sulfide commonly abbrevieted as AMS is a type of [[Thioether]] whose chemical formula is C<sub>4</sub>H<sub>8</sub>S. It is most commonly encountered as a byproduct of [[garlic]]'s digestion which causes bad breath and smell also referred to as [[Halitosis]].
| C=4 | H=8 | S=1
Eating garlic causes the production of several sulfur-containing gases in the digestion system, most of these are metabolized by the [[intestine]] or the [[liver]]. AMS however, is not, it is absorbed into the bloodstream from the [[gut]], from which it can pass to the: [[lung]]s and back up to the mouth causing bad breath hours after ingestion, urine <ref>http://www.webmd.com/news/19991127/garlic-bad-breath-king <ref/> and skin where is may be released along with sweat causing smelly sweat{{Fact|date=February 2009}}.
| Odor = Garlic
| Density = 0.803&nbsp;g&nbsp;cm<sup>−3</sup>
| BoilingPtK = 365
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}}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS flame}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225}}
| PPhrases = {{P-phrases|210}}
| FlashPtC = 18.0
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}}
}}

'''Allyl methyl sulfide''' is an [[organosulfur compound]] with the [[chemical formula]] CH<sub>2</sub>=CHCH<sub>2</sub>SCH<sub>3</sub>. The molecule features two [[functional group]]s, an [[allyl]] (CH<sub>2</sub>=CHCH<sub>2</sub>) and a [[thioether|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.<ref>{{cite book| author = Eric Block| title = Garlic and Other Alliums: The Lore and the Science| date = 2010-01-04| publisher = Royal Society of Chemistry| isbn = 978-0-85404-190-9 }}</ref>
It is prepared by the reaction of [[allyl chloride]] with [[sodium hydroxide]] and [[methanethiol]].
:CH<sub>2</sub>=CHCH<sub>2</sub>Cl + NaOH (aq) + CH<sub>3</sub>SH → CH<sub>2</sub>=CHCH<sub>2</sub>SCH<sub>3</sub> + NaCl + H<sub>2</sub>O

==References==
{{reflist}}

[[Category:Thioethers]]
[[Category:Allyl compounds]]

Latest revision as of 20:49, 2 August 2022

Allyl methyl sulfide
XYZ
Names
Preferred IUPAC name
3-(Methylsulfanyl)prop-1-ene
Other names
Methyl propenyl sulfide
3-Methylthio-1-propene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.030.371 Edit this at Wikidata
EC Number
  • 233-422-0
MeSH allyl+methyl+sulfide
RTECS number
  • UD1015000
UNII
UN number 1993
  • InChI=1S/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3 checkY
    Key: NVLPQIPTCCLBEU-UHFFFAOYSA-N checkY
  • InChI=1/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3
    Key: NVLPQIPTCCLBEU-UHFFFAOYAX
  • CSCC=C
Properties
C4H8S
Molar mass 88.17 g·mol−1
Odor Garlic
Density 0.803 g cm−3
Boiling point 92 °C; 197 °F; 365 K
Hazards
GHS labelling:
GHS02: Flammable
Danger
H225
P210
Flash point 18.0 °C (64.4 °F; 291.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Allyl methyl sulfide 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.[1]

It is prepared by the reaction of allyl chloride with sodium hydroxide and methanethiol.

CH2=CHCH2Cl + NaOH (aq) + CH3SH → CH2=CHCH2SCH3 + NaCl + H2O

References[edit]

  1. ^ Eric Block (2010-01-04). Garlic and Other Alliums: The Lore and the Science. Royal Society of Chemistry. ISBN 978-0-85404-190-9.
source: https://en.wikipedia.org/w/index.php?title=Allyl_methyl_sulfide&diff=1101990319&oldid=273682350

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