Trans-3-Methyl-2-hexenoic acid

Last updated
trans-3-Methyl-2-hexenoic acid
Trans-3-methyl-2-hexenoic acid.svg
Names
Preferred IUPAC name
(2E)-3-Methylhex-2-enoic acid
Other names
E3M2H
3M2H
TMHA
MHA
C7:2 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.225.656 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H12O2/c1-3-4-6(2)5-7(8)9/h5H,3-4H2,1-2H3,(H,8,9)/b6-5+ Yes check.svgY
    Key: NTWSIWWJPQHFTO-AATRIKPKSA-N Yes check.svgY
  • InChI=1S/C7H12O2/c1-3-4-6(2)5-7(8)9/h5H,3-4H2,1-2H3,(H,8,9)/b6-5+
    Key: NTWSIWWJPQHFTO-AATRIKPKSA-N
  • CCCC(=CC(=O)O)C
Properties
C7H12O2
Molar mass 128.171 g·mol−1
Density 0.97 g/cm3
Melting point −3.4 °C (25.9 °F; 269.8 K)
Boiling point 225.2 °C (437.4 °F; 498.3 K)
Hazards
Flash point 132 °C (270 °F; 405 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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trans-3-Methyl-2-hexenoic acid (TMHA) is an unsaturated short-chain fatty acid that occurs in sweat secreted by the axillary (underarm) apocrine glands of Caucasians and some Asians. [1]

Hexanoic acids such as TMHA have a hircine odor. Of the fatty acids contributing to Caucasian men's underarm odor, TMHA has the most prominent odor. [2]

Schizophrenia odor

It has long been claimed that schizophrenia patients exhibit a particular peculiar body odor, and it has been postulated the odor may be caused by underlying metabolic abnormalities associated with the condition, among other factors. [3] [4] Initial studies identified the causal component as TMHA, [5] however, subsequent studies failed to reproduce such results, [3] [6] with subsequent researchers suggesting the initial research may have had misidentified impurities in samples as TMHA due to poor methodology. [3] However, a 2007 study found schizophrenia patients to have reduced olfactory sensitivity to TMHA, possibly indicating sensory habituation; the decreased ability to smell the substance due to the presence of the substance as a constant component of subjects' own sweat and body odor. Furthermore, the researchers noted a positive association between reduced ability to smell TMHA and greater severity of disorganised and negative symptoms. [4]

An allusion to TMHA and its purported link to the smell of the mentally ill is made in the 1996 David Foster Wallace novel, Infinite Jest , [7] and in the 1988 novel The Silence of the Lambs by Thomas Harris.

Related Research Articles

A deodorant is a substance applied to the body to prevent or mask body odor caused by bacterial breakdown of perspiration, for example in the armpits, groin, or feet. A subclass of deodorants, called antiperspirants, prevents sweating itself, typically by blocking sweat glands. Antiperspirants are used on a wider range of body parts, at any place where sweat would be inconvenient or unsafe, since unwanted sweating can interfere with comfort, vision, and grip. Other types of deodorant allow sweating but prevent bacterial action on sweat, since human sweat only has a noticeable smell when it is decomposed by bacteria.

<span class="mw-page-title-main">Olfactory system</span> Sensory system used for smelling

The olfactory system or sense of smell is the sensory system used for smelling (olfaction). Olfaction is one of the special senses, that have directly associated specific organs. Most mammals and reptiles have a main olfactory system and an accessory olfactory system. The main olfactory system detects airborne substances, while the accessory system senses fluid-phase stimuli.

Body odor or body odour (BO) is present in all animals and its intensity can be influenced by many factors. Body odor has a strong genetic basis, but can also be strongly influenced by various factors, such as sex, diet, health, and medication. The body odor of human males plays an important role in human sexual attraction, as a powerful indicator of MHC/HLA heterozygosity. Significant evidence suggests that women are attracted to men whose body odor is different from theirs, indicating that they have immune genes that are different from their own, which may produce healthier offspring.

Underarm hair, also known as axillary hair or armpit hair, is the hair in the underarm area (axilla).

<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.

Parosmia is a dysfunctional smell detection characterized by the inability of the brain to correctly identify an odor's "natural" smell. Instead, the natural odor is usually transformed into an unpleasant aroma, typically a "burned", "rotting", "fecal", or "chemical" smell. There can also be rare instances of a pleasant odor called euosmia. The condition was rare and little-researched until it became relatively more widespread since 2020 as a side effect of COVID-19.

The odor detection threshold is the lowest concentration of a certain odor compound that is perceivable by the human sense of smell. The threshold of a chemical compound is determined in part by its shape, polarity, partial charges, and molecular mass. The olfactory mechanisms responsible for a compound's different detection threshold is not well understood. As such, odor thresholds cannot be accurately predicted. Rather, they must be measured through extensive tests using human subjects in laboratory settings.

Phantosmia, also called an olfactory hallucination or a phantom odor, is smelling an odor that is not actually there. This is intrinsically suspicious as the formal evaluation and detection of relatively low levels of odour particles is itself a very tricky task in air epistemology. It can occur in one nostril or both. Unpleasant phantosmia, cacosmia, is more common and is often described as smelling something that is burned, foul, spoiled, or rotten. Experiencing occasional phantom smells is normal and usually goes away on its own in time. When hallucinations of this type do not seem to go away or when they keep coming back, it can be very upsetting and can disrupt an individual's quality of life.

Vaccenic acid is a naturally occurring trans fatty acid and an omega-7 fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food.

Olfactory reference syndrome (ORS) is a psychiatric condition in which there is a persistent false belief and preoccupation with the idea of emitting abnormal body odors which the patient thinks are foul and offensive to other individuals. People with this condition often misinterpret others' behaviors, e.g. sniffing, touching their nose or opening a window, as being referential to an unpleasant body odor which in reality is non-existent and cannot be detected by other people.

Dysosmia is a disorder described as any qualitative alteration or distortion of the perception of smell. Qualitative alterations differ from quantitative alterations, which include anosmia and hyposmia. Dysosmia can be classified as either parosmia or phantosmia. Parosmia is a distortion in the perception of an odorant. Odorants smell different from what one remembers. Phantosmia is the perception of an odor when no odorant is present. The cause of dysosmia still remains a theory. It is typically considered a neurological disorder and clinical associations with the disorder have been made. Most cases are described as idiopathic and the main antecedents related to parosmia are URTIs, head trauma, and nasal and paranasal sinus disease. Dysosmia tends to go away on its own but there are options for treatment for patients that want immediate relief.

<span class="mw-page-title-main">OR51E1</span> Protein-coding gene in the species Homo sapiens

Olfactory receptor 51E1 is a protein that in humans is encoded by the OR51E1 gene.

<span class="mw-page-title-main">Sense of smell</span> Sense that detects smells

The sense of smell, or olfaction, is the special sense through which smells are perceived. The sense of smell has many functions, including detecting desirable foods, hazards, and pheromones, and plays a role in taste.

Olfactory memory refers to the recollection of odors. Studies have found various characteristics of common memories of odor memory including persistence and high resistance to interference. Explicit memory is typically the form focused on in the studies of olfactory memory, though implicit forms of memory certainly supply distinct contributions to the understanding of odors and memories of them. Research has demonstrated that the changes to the olfactory bulb and main olfactory system following birth are extremely important and influential for maternal behavior. Mammalian olfactory cues play an important role in the coordination of the mother infant bond, and the following normal development of the offspring. Maternal breast odors are individually distinctive, and provide a basis for recognition of the mother by her offspring.

The University of Pennsylvania Smell Identification Test (UPSIT) is a test that is commercially available for smell identification to test the function of an individual's olfactory system.

Foot odor or bromodosis is a type of body odor that affects the feet of humans.

The biochemistry of body odor pertains to the chemical compounds in the body responsible for body odor and their kinetics.

Intestinal metabolic bromhidrosis syndrome (IMBS) is a disorder, that is characterized by bromhidrosis and halitosis symptoms that are caused by odorous intestinal metabolites passing through the intestinal wall and by the liver to be excreted by skin glands and the lung gas exchange.

Smell as evidence of disease has been long used, dating back to Hippocrates around 400 years BCE. It is still employed with a focus on volatile organic compounds (VOCs) found in body odor. VOCs are carbon-based molecular groups having a low molecular weight, secreted during cells' metabolic processes. Their profiles may be altered by diseases such as cancer, metabolic disorders, genetic disorders, infections, and among others. Abnormal changes in VOC composition can be identified through equipment such as gas chromatography-mass spectrometry(GC-MS), electronic nose (e-noses), and trained non-human olfaction.

<span class="mw-page-title-main">Olfactic communication</span> Social interaction through smell

Olfactic communication is a channel of nonverbal communication referring to the various ways people and animals communicate and engage in social interaction through their sense of smell. Our human olfactory sense is one of the most phylogenetically primitive and emotionally intimate of the five senses; the sensation of smell is thought to be the most matured and developed human sense.

References

  1. Akutsu, T.; Sekiguchi, K; Ohmori, T; Sakurada, K (2006). "Individual Comparisons of the Levels of (E)-3-Methyl-2-Hexenoic Acid, an Axillary Odor–Related Compound, in Japanese". Chemical Senses. 31 (6): 557–63. doi: 10.1093/chemse/bjj060 . PMID   16690870.
  2. Sun, Lixing; Williams, Wendy A.; Avalos, Corinna (2005). Human sweaty smell does not affect women's menstrual cycle. pp. 308–312. doi:10.1007/0-387-25160-X_34. ISBN   978-0-387-25159-2.
  3. 1 2 3 Perry, Thomas L.; Melançon, Serge B.; Lesk, Donna; Hansen, Shirley (December 1970). "Failure to detect trans-3-methyl-2-hexenoic acid in the sweat of schizophrenic patients". Clinica Chimica Acta. 30 (3): 721–725. doi:10.1016/0009-8981(70)90266-4. ISSN   0009-8981. PMID   5493894.
  4. 1 2 Brewer, Warrick J.; Wood, Stephen J.; Pantelis, Christos; Berger, Gregor E.; Copolov, David L.; McGorry, Patrick D. (January 2007). "Olfactory sensitivity through the course of psychosis: Relationships to olfactory identification, symptomatology and the schizophrenia odour". Psychiatry Research. 149 (1–3): 97–104. doi:10.1016/j.psychres.2006.03.005. ISSN   0165-1781. PMID   17156856. S2CID   37511465.
  5. Smith, K.; Thompson, G. F.; Koster, H. D. (1969-10-17). "Sweat in schizophrenic patients: identification of the odorous substance". Science. 166 (3903): 398–399. Bibcode:1969Sci...166..398S. doi:10.1126/science.166.3903.398. ISSN   0036-8075. PMID   5818039. S2CID   21377002.
  6. Gordon, S. G.; Smith, K.; Rabinowitz, J. L.; Vagelos, P. R. (July 1973). "Studies of trans-3-methyl-2-hexenoic acid in normal and schizophrenic humans". Journal of Lipid Research. 14 (4): 495–503. doi: 10.1016/S0022-2275(20)36883-8 . ISSN   0022-2275. PMID   4715330.
  7. Foster., Wallace David (1996). Infinite jest: a novel (1 ed.). Boston: Little, Brown and Co. pp. 748–749. ISBN   978-0-316-07385-1. OCLC   669069481.