Prenylthiol

Last updated
Prenylthiol
3-Methyl-2-buten-1-thiol V1.svg
Prenyl-mercaptan-3D-balls.png
Names
IUPAC name
3-methylbut-2-ene-1-thiol
Other names
Prenyl mercaptan; 3-Methyl-2-butene-1-thiol; MBT; Prenylthiol; UNII-FDG262156U; 2-Butene-1-thiol, 3-methyl-
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.118.632 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 610-907-9
PubChem CID
UNII
  • InChI=1S/C5H10S/c1-5(2)3-4-6/h3,6H,4H2,1-2H3
    Key: GYDPOKGOQFTYGW-UHFFFAOYSA-N
  • CC(=CCS)C
Properties
C5H10S
Molar mass 102.2 g/mol
Hazards [1]
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Warning
H226, H315, H319, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Prenylthiol or 3-methyl-2-butene-1-thiol is a chemical compound. It is one of a group of chemicals that give cannabis its characteristic "skunk-like" aroma. It is also present in lightstruck or "skunky" beer. [2] [3]

Related Research Articles

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In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond.

<span class="mw-page-title-main">Thiol</span> Any organic compound having a sulfanyl group (–SH)

In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".

<span class="mw-page-title-main">Methanethiol</span> Chemical compound

Methanethiol is an organosulfur compound with the chemical formula CH
3
SH
. It is a colorless gas with a distinctive putrid smell. It is a natural substance found in the blood, brain and feces of animals, as well as in plant tissues. It also occurs naturally in certain foods, such as some nuts and cheese. It is one of the chemical compounds responsible for bad breath and the smell of flatus. Methanethiol is the simplest thiol and is sometimes abbreviated as MeSH. It is very flammable.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character.

Butene, also known as butylene, is an alkene with the formula C4H8. The word butene may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for viable extraction. Butene is therefore obtained by catalytic cracking of long-chain hydrocarbons left during refining of crude oil. Cracking produces a mixture of products, and the butene is extracted from this by fractional distillation.

<span class="mw-page-title-main">Spotted skunk</span> Genus of carnivores

The genus Spilogale includes all skunks commonly known as spotted skunks. Currently, there are four accepted extant species: S. gracilis, S. putorius, S. pygmaea, and S. angustifrons. New research, however, proposes that there may be up to seven.

<i>Cannabis sativa</i> Plant species

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<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

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MBT may refer to:

<span class="mw-page-title-main">1-Butanethiol</span> Chemical compound

1-Butanethiol, also known as butyl mercaptan, is a volatile, clear to yellowish liquid with a fetid odor, commonly described as "skunk" odor. In fact, 1-butanethiol is structurally similar to several major constituents of a skunk's defensive spray but is not actually present in the spray. The scent of 1-butanethiol is so strong that the human nose can easily detect it in the air at concentrations as low as 10 parts per billion. The threshold level for 1-butanethiol is reported as 1.4 ppb

<span class="mw-page-title-main">Prilezhaev reaction</span>

The Prilezhaev reaction, also known as the Prileschajew reaction or Prilezhaev epoxidation, is the chemical reaction of an alkene with a peroxy acid to form epoxides. It is named after Nikolai Prilezhaev, who first reported this reaction in 1909. A widely used peroxy acid for this reaction is meta-chloroperoxybenzoic acid (m-CPBA), due to its stability and good solubility in most organic solvents. The reaction is performed in inert solvents between -10 and 60 °C with the yield of 60-80%.

An illustrative example is the epoxidation of trans-2-butene with m-CPBA to give trans-2,3-epoxybutane:
<span class="mw-page-title-main">Isohumulone</span> Chemical compound

Isohumulones are chemical compounds that contribute to the bitter taste of beer and are in the class of compounds known as iso-alpha acids. They are found in hops.

Zirconocene dichloride is an organozirconium compound composed of a zirconium central atom, with two cyclopentadienyl and two chloro ligands. It is a colourless diamagnetic solid that is somewhat stable in air.

The molecular formula C5H10S (molar mass: 102.20 g/mol, exact mass: 102.0503 u) may refer to:

<i>tert</i>-Butylthiol Chemical compound

tert-Butylthiol, also known as 2-methylpropane-2-thiol, 2-methyl-2-propanethiol, tert-butyl mercaptan (TBM), and t-BuSH, is an organosulfur compound with the formula (CH3)3CSH. This thiol is used as an odorant for natural gas, which is otherwise odorless. It may also have been used as a flavoring agent.

References

  1. "3-Methyl-2-butene-1-thiol". pubchem.ncbi.nlm.nih.gov.
  2. Oswald, Iain W. H.; Ojeda, Marcos A.; Pobanz, Ryan J.; Koby, Kevin A.; Buchanan, Anthony J.; Del Rosso, Josh; Guzman, Mario A.; Martin, Thomas J. (2021-11-30). "Identification of a New Family of Prenylated Volatile Sulfur Compounds in Cannabis Revealed by Comprehensive Two-Dimensional Gas Chromatography". ACS Omega. 6 (47): 31667–31676. doi:10.1021/acsomega.1c04196. PMC   8638000 . PMID   34869990.
  3. Remmel, Ariana (30 November 2021). "Here's the chemistry behind marijuana's skunky scent". ScienceNews.org. Retrieved 30 November 2021.