2-Heptanone

Last updated
2-Heptanone [1]
Skeletal formula of 2-heptanone.svg
2-Heptanone-3D-balls.png
Names
Preferred IUPAC name
Heptan-2-one
Other names
Amyl methyl ketone
Butyl acetone
Methyl n-amyl ketone
Methyl pentyl ketone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.426 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 Yes check.svgY
    Key: CATSNJVOTSVZJV-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
    Key: CATSNJVOTSVZJV-UHFFFAOYAO
  • O=C(C)CCCCC
Properties
C7H14O
Molar mass 114.18 g/mol
AppearanceClear liquid
Odor banana-like, fruity [2]
Density 0.8 g/mL
Melting point −35.5 °C (−31.9 °F; 237.7 K)
Boiling point 151 °C (304 °F; 424 K)
0.4% by wt
Vapor pressure 3 mmHg (20°C) [2]
-80.50·10−6 cm3/mol
Hazards
Flash point 39 °C (102 °F; 312 K)
393 °C (739 °F; 666 K)
Explosive limits 1.1% at 151 °F (66 °C) - 7.9% at 250 °F (121 °C) [2]
Lethal dose or concentration (LD, LC):
1670 mg/kg (rat, oral)
750 mg/kg (mouse, oral) [3]
4000 ppm (rat, 4 hr)
2000 ppm (guinea pig, 14.8 hr) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (465 mg/m3) [2]
REL (Recommended)
TWA 100 ppm (465 mg/m3) [2]
IDLH (Immediate danger)
800 ppm [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

2-Heptanone, also known as methyl n-amyl ketone, or Heptan-2-one, is a ketone with the molecular formula C7H14O. It is a colorless, water-like liquid with a banana-like, fruity odor. 2-Heptanone has a neutral formal charge, and is only slightly soluble in water. [4] It is one of several compounds that contributes to the odor of sweaty clothing. [5]

The typical smell of gorgonzola is related to 2-heptanone. Gorgonzola 1.jpg
The typical smell of gorgonzola is related to 2-heptanone.

2-Heptanone is listed by the FDA as a "food additive permitted for direct addition to food for human consumption" (21 CFR 172.515), and it occurs naturally in certain foods (e.g., beer, white bread, butter, various cheeses and potato chips). [6]

The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated. [7] [8] [9] 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats. [9] [10] Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of pathogenesis. [11] 2-Heptanone has also been found to be excreted by honey bees when they bite small pests within the colony such as wax moth larvae and Varroa mites. Though it was historically believed to be an alarm pheromone, 2-heptanone has been shown to act as an anaesthetic on the pests, enabling the honey bee to stun the pest and eject it from the hive. The work could lead to the use of 2-heptanone as an alternative local anaesthetic to lidocaine, which although well established for clinical use, has the disadvantage of provoking allergic reactions in some people. [12]

2-Heptanone was one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. [13] This commonly occurs from exposure to plasticisers. [14] 2-Heptanone can be absorbed through the skin, inhaled and consumed. [15] Exposure to 2-Heptanone can cause irritation of skin/eyes, respiratory system, headaches, vomiting, and nausea. [15]

In mice 2-H is a urinary component and pheromone. It has a high affinity for the main olfactory epithelium. Gaillard et al 2002 found that it agonizes one specific olfactory receptor, and that that OR only binds 2-H. [16]

Related Research Articles

<span class="mw-page-title-main">Pheromone</span> Secreted or excreted chemical factor that triggers a social response in members of the same species

A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used by many organisms, from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones. The ecological functions and evolution of pheromones are a major topic of research in the field of chemical ecology.

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

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

<span class="mw-page-title-main">Vomeronasal organ</span> Smell sense organ above the roof of the mouth

The vomeronasal organ (VNO), or Jacobson's organ, is the paired auxiliary olfactory (smell) sense organ located in the soft tissue of the nasal septum, in the nasal cavity just above the roof of the mouth in various tetrapods. The name is derived from the fact that it lies adjacent to the unpaired vomer bone in the nasal septum. It is present and functional in all snakes and lizards, and in many mammals, including cats, dogs, cattle, pigs, and some primates. Some humans may have physical remnants of a VNO, but it is vestigial and non-functional.

<span class="mw-page-title-main">Aroma compound</span> Chemical compound that has a smell or odor

An aroma compound, also known as an odorant, aroma, fragrance or flavoring, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficiently volatile for transmission via the air to the olfactory system in the upper part of the nose. As examples, various fragrant fruits have diverse aroma compounds, particularly strawberries which are commercially cultivated to have appealing aromas, and contain several hundred aroma compounds.

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

Enflurane is a halogenated ether. Developed by Ross Terrell in 1963, it was first used clinically in 1966. It was increasingly used for inhalational anesthesia during the 1970s and 1980s but is no longer in common use.

Demeton-S-methyl is an organic compound with the molecular formula C6H15O3PS2. It was used as an organothiophosphate acaricide and organothiophosphate insecticide. It is flammable. With prolonged storage, Demeton-S-methyl becomes more toxic due to formation of a sulfonium derivative which has greater affinity to the human form of the acetylcholinesterase enzyme, and this may present a hazard in agricultural use.

<span class="mw-page-title-main">Trimethylamine</span> Chemical compound responsible for rotten fish odor

Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes on contact. At lower concentrations, it has a "fishy" odor, the odor associated with rotting fish.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

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

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

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

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

<i>p</i>-Cresol Chemical compound

para-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula C7H14O2. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

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

Azinphos-methyl (Guthion) is a broad spectrum organophosphate insecticide manufactured by Bayer CropScience, Gowan Co., and Makhteshim Agan. Like other pesticides in this class, it owes its insecticidal properties to the fact that it is an acetylcholinesterase inhibitor. It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act, and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Trace amine-associated receptors (TAARs), sometimes referred to as trace amine receptors, are a class of G protein-coupled receptors that were discovered in 2001. TAAR1, the first of six functional human TAARs, has gained considerable interest in academic and proprietary pharmaceutical research due to its role as the endogenous receptor for the trace amines phenethylamine, tyramine, and tryptamine – metabolic derivatives of the amino acids phenylalanine, tyrosine and tryptophan, respectively – ephedrine, as well as the synthetic psychostimulants, amphetamine, methamphetamine and methylenedioxymethamphetamine. In 2004, it was shown that mammalian TAAR1 is also a receptor for thyronamines, decarboxylated and deiodinated relatives of thyroid hormones. TAAR2–TAAR9 function as olfactory receptors for volatile amine odorants in vertebrates.

<span class="mw-page-title-main">Dichlorvos</span> Insect killing chemical, organophosphate

Dichlorvos is an organophosphate widely used as an insecticide to control household pests, in public health, and protecting stored products from insects. The compound has been commercially available since 1961. It has become controversial because of its prevalence in urban waterways and the fact that its toxicity extends well beyond insects. Since 1988, dichlorvos cannot be used as a plant protection product in the EU.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<span class="mw-page-title-main">Major urinary proteins</span> Proteins found in the urine and other secretions of many animals

Major urinary proteins (Mups), also known as α2u-globulins, are a subfamily of proteins found in abundance in the urine and other secretions of many animals. Mups provide a small range of identifying information about the donor animal, when detected by the vomeronasal organ of the receiving animal. They belong to a larger family of proteins known as lipocalins. Mups are encoded by a cluster of genes, located adjacent to each other on a single stretch of DNA, that varies greatly in number between species: from at least 21 functional genes in mice to none in humans. Mup proteins form a characteristic glove shape, encompassing a ligand-binding pocket that accommodates specific small organic chemicals.

<span class="mw-page-title-main">Mammalian reproduction</span> Most mammals are viviparous, giving birth to live young

Most mammals are viviparous, giving birth to live young. However, the five species of monotreme, the platypuses and the echidnas, lay eggs. The monotremes have a sex determination system different from that of most other mammals. In particular, the sex chromosomes of a platypus are more like those of a chicken than those of a therian mammal.

<span class="mw-page-title-main">3-Heptanone</span> Chemical compound


3-Heptanone, is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules.

<span class="mw-page-title-main">Copulation (zoology)</span> Animal sexual reproductive act in which a male introduces sperm into the females body

In zoology, copulation is animal sexual behavior in which a male introduces sperm into the female's body, especially directly into her reproductive tract. This is an aspect of mating. Many animals that live in water use external fertilization, whereas internal fertilization may have developed from a need to maintain gametes in a liquid medium in the Late Ordovician epoch. Internal fertilization with many vertebrates occurs via cloacal copulation, known as cloacal kiss, while most mammals copulate vaginally, and many basal vertebrates reproduce sexually with external fertilization.

References

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  2. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0399". National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 "Methyl (n-amyl) ketone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. "2-Heptanone". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2019-03-07.
  5. Denawaka CJ, Fowlis IA, Dean JR (2016). "Source, impact and removal of malodour from soiled clothing". Journal of Chromatography A. 1438: 216–225. doi: 10.1016/j.chroma.2016.02.037 . PMID   26898151.
  6. Methyl (n-amyl) ketone, Chemical Sampling Information, Occupational Safety & Health Administration
  7. Wang Z, Balet Sindreu C, Li V, Nudelman A, Chan GC, Storm DR (July 2006). "Pheromone detection in male mice depends on signaling through the type 3 adenylyl cyclase in the main olfactory epithelium". The Journal of Neuroscience. 26 (28): 7375–9. doi: 10.1523/JNEUROSCI.1967-06.2006 . PMC   6674185 . PMID   16837584.
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