Heptadecanoic acid

Heptadecanoic acid, or margaric acid, is a saturated fatty acid. Its molecular formula is CH3(CH2)15CO2H. Classified as an odd-chain fatty acid, it occurs as a trace component of the fat and milkfat of ruminants,[2] but it does not occur in any natural animal or vegetable fat at high concentrations.[3] For example, it comprises only 2.2% of the fats from the fruit of the durian species Durio graveolens.[4] However, in the 19th and early 20th centuries, there were numerous reports of the acid being found in natural fats in significant amounts. Most likely, these were cases of misidentifying a eutectic mixture of palmitic and stearic acids.[5] Salts and esters of heptadecanoic acid are called heptadecanoates.

Heptadecanoic acid[1]
Names
IUPAC name
Heptadecanoic acid
Other names
Margaric acid
n-Margaric acid
n-Heptadecanoic acid
Heptadecylic acid
n-Heptadecylic acid
17:0 (Lipid numbers)
Identifiers
3D model (JSmol)
1781004
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.298
EC Number
  • 208-027-1
253195
UNII
Properties
C17H34O2
Molar mass 270.45 g/mol
Appearance White crystals
Density 0.853 g/cm3
Melting point 61.3 °C (142.3 °F; 334.4 K)
Boiling point 227 °C (441 °F; 500 K) 100 mmHg
insoluble
Hazards
GHS pictograms
GHS Signal word Warning
GHS hazard statements
 H315, H319, H335
P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Related compounds
Related fatty acids
 Palmitic acid
Stearic acid
Related compounds
 Heptadecanol
Heptadecanal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Semiochemistry

For many species, heptadecanoic acid plays a part as a semiochemical - specifically it possesses pheromonic and allomonic properties. Heptadecanoic acid has been identified in the subcaudal gland secretions of the European badger (Meles meles)[6] and in the occipital gland secretions of male bactrian camels (Camelus bactrianus) where it is one of the many pheromonic chemicals responsible for aiding in the finding and selection of mates.[7]

Heptadecanoic acid is an attractant of the khapra beetle (Trogoderma granarium)[8] and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito (Culex pipiens).[9]

Heptadecanoic acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius)[10] and the European viper (Vipera berus), where it is used for the identification of sexual partners.[11]

References
  1. Merck Index, 13th Edition, 5775
  2. R. P. Hansen, F. B. Shorland and N. June Cooke (1957). "Occurrence in Butterfat of n-Heptadecanoic Acid (Margaric Acid)". Nature. 179 (98): 98. Bibcode:1957Natur.179...98H. doi:10.1038/179098a0. PMID 13400103.
  3. Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685.
  4. Nasaruddin, Mohd hanif; Noor, Noor Qhairul Izzreen Mohd; Mamat, Hasmadi (2013). "Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah" [Proximate and Fatty Acid Composition of Sabah Yellow Durian (Durio graveolens)] (PDF). Sains Malaysiana (in Malay). 42 (9): 1283–1288. ISSN 0126-6039. OCLC 857479186. Retrieved 28 November 2017.
  5. Чёт или нечет? Занимательные очерки по химии, pages 116-120
  6. Sin, Yung Wa; Buesching, Christina D.; Burke, Terry; Macdonald, David W. (2012-05-30). "Molecular characterization of the microbial communities in the subcaudal gland secretion of the European badger (Meles meles)". FEMS Microbiology Ecology. 81 (3): 648–659. doi:10.1111/j.1574-6941.2012.01396.x. ISSN 0168-6496. PMID 22530962.
  7. Ayorinde, F.; Wheeler, J. W.; Wemmer, C.; Murtaugh, J. (January 1982). "Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus)". Journal of Chemical Ecology. 8 (1): 177–183. doi:10.1007/bf00984014. ISSN 0098-0331. PMID 24414593.
  8. Ayorinde, F.; Wheeler, J. W.; Wemmer, C.; Murtaugh, J. (January 1982). "Volatile components of the occipital gland secretion of the bactrian camel (Camelus bactrianus)". Journal of Chemical Ecology. 8 (1): 177–183. doi:10.1007/bf00984014. ISSN 0098-0331. PMID 24414593.
  9. Bernier, Ulrich R. (1995). Mass spectrometric investigations of mosquito attraction to human skin emanations /. [s.n.] doi:10.5962/bhl.title.49749.
  10. Mason, Robert T.; Gutzke, William H. N. (January 1990). "Sex recognition in the leopard gecko,Eublepharis macularius (Sauria: Gekkonidae) Possible mediation by skin-derived semiochemicals". Journal of Chemical Ecology. 16 (1): 27–36. doi:10.1007/bf01021265. ISSN 0098-0331. PMID 24264893.
  11. Razakov, R. R.; Sadykov, A. S. (July 1986). "Study of complex mixtures of natural substances by the defocusing and dadi methods. VI. Components of the secretion of the pre-anal gland of some poisonous snakes". Chemistry of Natural Compounds. 22 (4): 392–394. doi:10.1007/bf00579807. ISSN 0009-3130.


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