Names | |
---|---|
Preferred IUPAC name
(2E)-3-Methylhex-2-enoic acid | |
Other names | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.225.656 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
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.
Names | |
---|---|
Preferred IUPAC name
(2E)-3-Methylhex-2-enoic acid | |
Other names | |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.225.656 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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]
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.