Margaric acid

Source: 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
 100.007.298 Edit 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-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 ?)

Margaric acid, or heptadecanoic acid, is a saturated

Salts and esters
of margaric acid are called heptadecanoates.

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

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.

stearic acids.[13]

See also

References

  1. ^ Merck Index, 13th Edition, 5775
  2. S2CID 4144443
    .
  3. PMID 22530962
    .
  4. S2CID 21202532
    .
  5. S2CID 21202532
    .
  6. doi:10.5962/bhl.title.49749
    .
  7. S2CID 28887051
    .
  8. S2CID 24684170
    .
  9. PMID 16357280
    .
  10. PMID 31174411
    .
  11. S2CID 84820785
    .
  12. 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

External links

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