4-Mercapto-4-methyl-2-pentanone

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4-Mercapto-4-methyl-2-pentanone
4-mercapto-4-methyl-2-pentanone.svg
Names
Preferred IUPAC name
4-Methyl-4-sulfanylpentan-2-one
Other names
4-Mercapto-4-methylpentan-2-one; 4-Methyl-4-mercapto-2-pentanone; 4-Sulfanyl-4-methylpentan-2-one; 4-Sulphanyl-4-methylpentan-2-one; 2-Pentanone, 4-mercapto-4-methyl-; 4-Methyl-4-mercaptopentan-2-one; 4-Methyl-4-thiolpentan-2-one; 4-Methyl-4-sulfanyl-2-pentanone
Identifiers
3D model (JSmol)
ECHA InfoCard 100.039.427 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H12OS/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3
    Key: QRNZMFDCKKEPSX-UHFFFAOYSA-N
  • CC(=O)CC(C)(C)S
Properties
C6H12OS
Molar mass 132.22 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Mercapto-4-methyl-2-pentanone is an aroma compound with the chemical formula C6H12OS . [1] It has a tropical flavor. It is found in Sauvignon wines [2] and is a potent odorant of new-world hops. [3]

Related Research Articles

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2-Pentanone Chemical compound

2-Pentanone or methyl propyl ketone (MPK) is a ketone and solvent of minor importance. It is comparable to methyl ethyl ketone, but has a lower solvency and is more expensive. It occurs naturally in Nicotiana tabacum (Tobacco) and blue cheese as a metabolic product of Penicillium mold growth.

3-Pentanone Chemical compound

3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

Pentanone may refer to the following ketones containing five carbon atoms:

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Pomarose is a high-impact captive odorant patented by Givaudan. It is a double-unsaturated ketone that does not occur in nature. Pomarose has a powerful fruity rose odor with nuances of apples, plums and raisins, which is almost entirely due to the (2E,5Z)-stereoisomer, while its (2E,5E)-isomer is barely detectable for most people. Catalyzed by traces of acids, both isomers equilibrate however quickly upon standing in glass containers.

3-Methyl-3-penten-2-one Chemical compound

3-Methyl-3-penten-2-one is an unsaturated aliphatic ketone. It is an isomer of mesityl oxide and isomesityl oxide. It is a precursor of 3-methyl-2-pentanone and is obtained by acid-catalyzed dehydration of 4-hydroxy-3-methyl-2-pentanone. It is used as an intermediate in organic chemistry syntheses.

3-Methyl-2-pentanone Chemical compound

3-Methyl-2-pentanone is an aliphatic ketone and isomer of 2-hexanone. It is used as a solvent and as an intermediate for syntheses. Its industrial importance is low. It is produced by base-catalyzed aldol condensation of 2-butanone with acetaldehyde, forming 4-hydroxy-3-methyl-2-pentanone, which is dehydrated to 3-methyl-3-penten-2-one over an acid catalyst, followed by hydrogenation over a palladium catalyst.

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4-Methyl-α-ethylaminopentiophenone Chemical compound

4-Methyl-α-ethylaminopentiophenone (4-MEAP) is a designer drug of the cathinone class. It is a higher homolog of 4-methylpentedrone (4-MPD) with an ethyl group in place of the methyl group. 4-MEAP has been found in samples of drugs sold as 4-MPD.

Delta-3-Tetrahydrocannabinol Chemical compound

Delta-3-Tetrahydrocannabinol is a synthetic isomer of tetrahydrocannabinol, developed during the original research in the 1940s to develop synthetic routes to the natural products Δ8-THC and Δ9-THC found in the cannabis plant. While the normal trans configuration of THC is in this case flattened by the double bond, it still has two enantiomers as the 9-methyl group can exist in an (R) or (S) conformation. The (S) enantiomer has similar effects to Δ9-THC though with several times lower potency, while the (R) enantiomer is many times less active or inactive, depending on the assay used.

References

  1. National Institute of Standards and Technology. "4-mercapto-4-methyl-2-pentanone". webbook.nist.gov. Retrieved 2017-09-07.
  2. CID 88290 from PubChem
  3. Reglitz, Klaas; Lemke, Nadine; Steinhaus, Martin; Hanke, Stefan (2018). "On the Behavior of the Important Hop Odorant 4-Mercapto-4-methylpentan-2-one (4MMP) during Dry Hopping and during Storage of Dry Hopped Beer". Brewingscience. 71. doi:10.23763/BRSC18-13STEINHAUS.