Margaric acid

Margaric acid, or heptadecanoic 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] Salts and esters of margaric acid are called heptadecanoates.

Margaric acid[1]
Heptadecanoic acid
Names
Preferred IUPAC name
Heptadecanoic acid
Other names
Heptadecylic acid;
Daturic acid;
Margarinic 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
  • InChI=1S/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19) checkY
    Key: KEMQGTRYUADPNZ-UHFFFAOYSA-N checkY
  • InChI=1/C17H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-16H2,1H3,(H,18,19)
    Key: KEMQGTRYUADPNZ-UHFFFAOYAT
  • O=C(O)CCCCCCCCCCCCCCCC
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 labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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).
checkY verify (what is checkY☒N ?)
Infobox references

Its name is derived from the Ancient Greek μάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.

Semiochemistry

For many species, margaric acid plays a role as a semiochemical - specifically it possesses pheromonic and allomonic properties. Margaric acid has been identified in the subcaudal gland secretions of the European badger (Meles meles)[3] 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.[4]

Margaric acid is an attractant of the khapra beetle (Trogoderma granarium)[5] and the yellow fever mosquito (Aedes aegypti) but is a repellent of the common house mosquito (Culex pipiens).[6]

Margaric acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius)[7] and the European viper (Vipera berus), where it is used for the identification of sexual partners.[8]

Unsaturated forms

Unsaturated derivatives of margaric acid are found in nature, although rarely. Unsaturation occurs at position 9 or both at 9 and 12 positions of the fatty chain giving heptadecenoic (C17:1) and heptadecadienoic (C17:2) acids, respectively. C17:1 cis-9 (ω-8) is found at trace amounts in ruminant fats[9] and some varieties of olive oils.[10] Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of Portia tree (Thespesia populnea).[11]

Rarity in vegetable and animal fats

Margaric acid is rare in animals and vegetables.[12] In the 19th and early 20th centuries, however, the acid was often identified as a significant component of natural fats. Most likely, these were cases of misidentifying a eutectic mixture of palmitic and stearic acids.[13]

See also

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. S2CID 4144443.
  3. 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.
  4. 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. S2CID 21202532.
  5. 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. S2CID 21202532.
  6. Bernier, Ulrich R. (1995). Mass spectrometric investigations of mosquito attraction to human skin emanations /. [s.n.] doi:10.5962/bhl.title.49749.
  7. 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. S2CID 28887051.
  8. 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. S2CID 24684170.
  9. Alves, S.P.; Marcelino, C.; Portugal, P.V.; Bessa, R.J.B. (2006-01-01). "Short Communication: The Nature of Heptadecenoic Acid in Ruminant Fats". Journal of Dairy Science. 89 (1): 170–173. doi:10.3168/jds.S0022-0302(06)72081-1. ISSN 0022-0302. PMID 16357280.
  10. Sánchez-Rodríguez, Lucía; Kranjac, Marina; Marijanović, Zvonimir; Jerković, Igor; Corell, Mireia; Moriana, Alfonso; Carbonell-Barrachina, Ángel A.; Sendra, Esther; Hernández, Francisca (2019-06-06). "Quality Attributes and Fatty Acid, Volatile and Sensory Profiles of "Arbequina" hydroSOStainable Olive Oil". Molecules. 24 (11): 2148. doi:10.3390/molecules24112148. ISSN 1420-3049. PMC 6600446. PMID 31174411.
  11. Dowd, Michael K. (2012). "Identification of the Unsaturated Heptadecyl Fatty Acids in the Seed Oils of Thespesia populnea and Gossypium hirsutum". Journal of the American Oil Chemists' Society. 89 (9): 1599–1609. doi:10.1007/s11746-012-2071-5. ISSN 1558-9331. S2CID 84820785.
  12. 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. S2CID 84492006.
  13. Leenson, Ilia Abramovitch (1987). Tchiot ili netchet? Zanimatelnye otcherki po chimii [Odd or Even? Entertaining Essays on Chemistry] (in Russian). Moskva: Chimia. pp. 116–120. or djv format
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