2-Heptanone, also known as methyl ''n''-amyl ketone, or Heptan-2-one, is a

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

with the

molecular formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as paren ...

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. It is one of several compounds that contributes to the odor of sweaty clothing. Gorgonzola 1

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). The mechanism of action of 2-heptanone as a pheromone at odorant receptors in rodents has been investigated. 2-Heptanone is present in the urine of stressed rats and believe that it is used as a means to alert other rats. Certain species of worms are attracted to 2-heptanone and bacteria can use this as a means of

pathogenesis In pathology, pathogenesis is the process by which a disease or disorder develops. It can include factors which contribute not only to the onset of the disease or disorder, but also to its progression and maintenance. The word comes . Descript ...

. 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. 2-Heptanone was one of the metabolites of ''n''-

heptane 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 poi ...

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

mice A mouse (: mice) is a small rodent. Characteristically, mice are known to have a pointed snout, small rounded ears, a body-length scaly tail, and a high breeding rate. The best known mouse species is the common house mouse (''Mus musculus' ...

2-H is a

urinary The human urinary system, also known as the urinary tract or renal system, consists of the kidneys, ureters, bladder, and the urethra. The purpose of the urinary system is to eliminate waste from the body, regulate blood volume and blood pressu ...

component and

pheromone 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 behavio ...

. It has a high

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

for the main

olfactory epithelium The olfactory epithelium is a specialized epithelium, epithelial tissue inside the nasal cavity that is involved in olfaction, smell. In humans, it measures and lies on the roof of the nasal cavity about above and behind the nostrils. The olfact ...

. Gaillard et al 2002 found that it agonizes one specific

olfactory receptor Olfactory receptors (ORs), also known as odorant receptors, are chemoreceptors expressed in the cell membranes of olfactory receptor neurons and are responsible for the detection of odorants (for example, compounds that have an odor) which give ...

, and that that OR only binds 2-H.

References

External links

MSDS for 2-heptanone

NIOSH Pocket Guide to Chemical Hazards {{DEFAULTSORT:Heptanone, 2- Heptanones