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Margaric acid

From Wikipedia, the free encyclopedia
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 100.007.298Edit this at Wikidata
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-NcheckY
  • 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
GHSlabelling:
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
Palmitic acid
Stearic acid
Related compounds
 Heptadecanol
Heptadecanal
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Margaric acid,orheptadecanoic acid,is a saturatedfatty acid.Its molecular formula isCH3(CH2)15CO2H.Classified as anodd-chain fatty acid,it occurs as a trace component of the fat and milkfat ofruminants.[2]Saltsandestersof margaric acid are calledheptadecanoates.

Its name is derived from theAncient Greekμάργαρος (márgar(on)), meaning "pearl(y)", due to its appearance.

Semiochemistry

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For many species, margaric acid plays a role as asemiochemical- specifically it possessespheromonicandallomonicproperties. Margaric acid has been identified in the subcaudal gland secretions of theEuropean badger(Meles meles)[3]and in the occipital gland secretions of maleBactrian 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 thekhapra beetle(Trogoderma granarium)[5]and theyellow fever mosquito(Aedes aegypti) but is a repellent of thecommon house mosquito(Culex pipiens).[6]

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

Unsaturated forms

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Unsaturatedderivatives 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 inruminantfats[9]and some varieties ofolive oils.[10]Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil ofPortia tree(Thespesia populnea).[11]

Rarity in vegetable and animal fats

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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 aeutectic mixtureofpalmiticandstearicacids.[13]

See also

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References

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  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.PMID13400103.S2CID4144443.
  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.ISSN0168-6496.PMID22530962.
  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.ISSN0098-0331.PMID24414593.S2CID21202532.
  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.ISSN0098-0331.PMID24414593.S2CID21202532.
  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.ISSN0098-0331.PMID24264893.S2CID28887051.
  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.ISSN0009-3130.S2CID24684170.
  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.ISSN0022-0302.PMID16357280.
  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.ISSN1420-3049.PMC6600446.PMID31174411.
  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.ISSN1558-9331.S2CID84820785.
  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.S2CID84492006.
  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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