Tridecanoic acid

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Structural formula
Structural formula of tridecanoic acid
General
Surname Tridecanoic acid
other names

n -Tridecanoic acid

Molecular formula C 13 H 26 O 2
Brief description

white solid with a waxy woody odor

External identifiers / databases
CAS number 638-53-9
EC number 211-341-1
ECHA InfoCard 100.010.311
PubChem 12530
ChemSpider 12013
DrugBank DB02448
Wikidata Q419857
properties
Molar mass 214.34 g mol −1
Physical state

firmly

density

0.8458 g cm −3 (80 ° C)

Melting point

41-42 ° C

boiling point

312-313 ° C

solubility
Refractive index

1.4286 (60 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 261-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

The tridecanoic acid is a saturated long-chain fatty acid having an odd carbon number and belongs to the substance group of alkanoic acids . Their salts and esters are called tridecanoates .

Occurrence

Like most long-chain fatty acids with an odd number of carbon atoms, tridecanoic acid occurs rarely and in low concentrations in nature.

For example, it was found with proportions of 0.24% to 0.64% of the total fatty acids in some freshwater species of cyanobacteria . Also, in some vegetable oils to low levels found at tridecanoic, so to 0.07% in the leaf oil of Cuban rue ( Ruta graveolens ) and 0.3% in the Cuban star fruit oil ( Averrhoa carambola ) u. a.

It is the main fatty acid with a share of almost 90% of the fatty acids in the seeds of the Australian plant Stackhousia tryonii .

Extraction and presentation

Tridecanoic acid can be made by oxidizing 1-tetradecene with potassium permanganate .

use

Tridecanoic acid is used in concentrations of up to 8% in perfume concentrates . Because of its rarity and its low occurrence in biological material, it is also often used as an internal standard in the gas chromatographic analysis of fatty acids .

Individual evidence

  1. ↑ a b c d data sheet of The Good Scents Company ; June 10, 2008 .
  2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 96th edition. (Internet Version :), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-524.
  3. ↑ a b c Data sheet Tridecanoic acid from Sigma-Aldrich , accessed on June 26, 2014 ( PDF ).
  4. ↑ SH Yalkowsky, RM Dannenfelser: Aquasol database of wässrige solubility . Version 5 .; College of Pharmacy, University of Arizona - Tucson, AZ. PC version. 1992.
  5. ↑ a b c David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-496.
  6. ↑ T. Rezanka, I. Dor, A. Prell, VM Dembitsky: Fatty acid composition of six wild freshwater cyanobacterial species. In: Folia Microbiol. 48 (1), 2003, pp. 71-75, doi : 10.1007 / BF02931279 .
  7. ↑ Tridecanoic acid at PlantFA Database, accessed November 7, 2017.
  8. ↑ Naveen P. Bhatia, Ani E. Nkang, Kerry B. Walsh, Alan JM Baker, Nanjappa Ashwath, David J. Midmore: Successful Seed Germination of the Nickel Hyperaccumulator Stackhousia tryonii. In: Annals of Botany . 96 (1), 2005, pp. 159-163, doi : 10.1093 / aob / mci151 .
  9. ↑ Donald G. Lee, Shannon E. Lamb, and Victor S. Chang: Carboxylic acids from the oxidation of terminal alkenes by permanganate: Nonadecanoic acid In: Organic Syntheses . 60, 1981, p. 11, doi : 10.15227 / orgsyn.060.0011 ; Coll. Vol. 7, 1990, p. 397 ( PDF ).
  10. ↑ Antonio Gonzalez Casado; Enrique J. Alonso Hernandez; Pedro Espinosa; Jose Luis Vílchez: Determination of total fatty acids (C8-C22) in sludges by gas chromatography-mass spectrometry. In: Journal of Chromatography A . 826 (1), 1998, pp. 49-56, doi : 10.1016 / S0021-9673 (98) 00725-0 .

Web links

Wiktionary: Tridecanoic acid  - explanations of meanings, word origins, synonyms, translations