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Shinkolobwe (talk | contribs) Adding short description: "Organosulfur compound", overriding automatically generated description Tag: Shortdesc helper |
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{{Short description|Organosulfur compound}} |
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|Reference=<ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=A34201|ALDRICH&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Allyl methyl sulfide] at [[Sigma-Aldrich]]</ref> |
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|ImageFile=Allyl methyl sulfide.png |
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| verifiedrevid = 477314172 |
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|IUPACName=3-Methylsulfanylprop-1-ene |
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| ImageFile = Allylmethyl sulfide Structural Formula V1.svg |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageName = XYZ |
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| PIN = 3-(Methylsulfanyl)prop-1-ene |
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3-Methylthio-1-propene |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = 10152-76-8 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = V7QI1R316C |
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| ChemSpiderID = 21159856 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| EINECS = 233-422-0 |
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| UNNumber = 1993 |
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| MeSHName = allyl+methyl+sulfide |
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| RTECS = UD1015000 |
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| StdInChI = 1S/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C4H8S/c1-3-4-5-2/h3H,1,4H2,2H3 |
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| StdInChIKey = NVLPQIPTCCLBEU-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChIKey = NVLPQIPTCCLBEU-UHFFFAOYAX |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| C=4 | H=8 | S=1 |
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| Formula=C<sub>4</sub>H<sub>8</sub>S |
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| Odor = Garlic |
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| MolarMass=88.17 g/mol |
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| Density = 0.803 g cm<sup>−3</sup> |
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| Appearance= |
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| BoilingPtK = 365 |
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| Density=0.803 g/mL |
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| MeltingPt= |
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| BoilingPt=91-93 °C |
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| Solubility= |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS flame}} |
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| MainHazards= |
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| GHSSignalWord = '''DANGER''' |
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| FlashPt=18 °C (65 °F) |
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| HPhrases = {{H-phrases|225}} |
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| Autoignition= |
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| PPhrases = {{P-phrases|210}} |
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| FlashPtC = 18.0 |
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| SPhrases={{S16}} {{S29}} {{S33}} |
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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> |
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'''Allyl methyl sulfide''' (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 ([[halitosis]]). Eating garlic causes the production of several sulfur-containing gases in the digestion system, most of these are metabolized in the [[intestine]] or the [[liver]]. AMS however, is not, and 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, the urine, and the skin where is may be released causing smelly sweat.<ref>[http://www.webmd.com/news/19991127/garlic-bad-breath-king Why Garlic Is the Bad Breath King], Andrea M. Braslavsky, WebMD Health News</ref> |
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It is prepared by the reaction of [[allyl chloride]] with [[sodium hydroxide]] and [[methanethiol]]. |
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: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 |
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==References== |
==References== |
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[[Category:Thioethers]] |
[[Category:Thioethers]] |
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[[Category: |
[[Category:Allyl compounds]] |
Latest revision as of 20:49, 2 August 2022
Names | |
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Preferred IUPAC name
3-(Methylsulfanyl)prop-1-ene | |
Other names
Methyl propenyl sulfide
3-Methylthio-1-propene | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.030.371 |
EC Number |
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MeSH | allyl+methyl+sulfide |
PubChem CID
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RTECS number |
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UNII | |
UN number | 1993 |
CompTox Dashboard (EPA)
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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: | |
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).
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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