Heptadecanoic acid

Margaric acid, or heptadecanoic acid, is a crystalline 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 margaric acid are called heptadecanoates.

Margaric acid[1]
Heptadecanoic acid
Heptadecanoic-acid-3D-balls.png
Names
Preferred IUPAC name
Heptadecanoic acid
Other names
Heptadecylic acid;
Daturic acid;
Margarinic acid;
17:0 (Lipid numbers)
Identifiers
CAS Number
  • 506-12-7 check
3D model (JSmol)
  • Interactive image
Beilstein Reference
1781004
ChEBI
  • CHEBI:32365 check
ChEMBL
  • ChEMBL1172910 check
ChemSpider
  • 10033 check
ECHA InfoCard100.007.298 Edit this at Wikidata
EC Number
  • 208-027-1
Gmelin Reference
253195
PubChem CID
  • 10465
UNII
  • V987Y9OZ8L
CompTox Dashboard (EPA)
  • DTXSID5021596 Edit this at Wikidata
InChI
  • 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) check
    Key: KEMQGTRYUADPNZ-UHFFFAOYSA-N check
  • 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
SMILES
  • O=C(O)CCCCCCCCCCCCCCCC
Properties
Chemical formula
C17H34O2
Molar mass270.45 g/mol
AppearanceWhite crystals
Density0.853 g/cm3
Melting point61.3 °C (142.3 °F; 334.4 K)
Boiling point227 °C (441 °F; 500 K) 100 mmHg
Solubility in water
insoluble
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319, H335
Precautionary statements
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).
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Infobox references

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

SemiochemistryEdit

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)[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]

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

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)[10] and the European viper (Vipera berus), where it is used for the identification of sexual partners.[11]

Unsaturated formsEdit

Unsaturated derivatives of margaric acid are found in nature, although rare. 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[12] and some varieties of olive oils.[13] Minor amounts (< 1%) of C17:1 cis-10 and C17:2 cis-8,11 were detected in seed oil of Portia tree (Thespesia populnea). 


This article uses material from the Wikipedia article
 Metasyntactic variable, which is released under the 
Creative Commons
Attribution-ShareAlike 3.0 Unported License.