Pentadecanoic acid
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| General | ||||||||||||||||
| Surname | Pentadecanoic acid | |||||||||||||||
| other names |
n -pentadecanoic acid |
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| Molecular formula | C 15 H 30 O 2 | |||||||||||||||
| Brief description |
colorless slat-shaped or rod-shaped crystals |
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| properties | ||||||||||||||||
| Molar mass | 242.3975 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| density |
1.02 g cm −3 |
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| Melting point |
52.3 ° C |
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| boiling point |
339 ° C |
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| solubility |
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| Refractive index |
1.4254 (80 ° C) |
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| 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 pentadecanoic belongs to the group of alkanoic acids . It is a saturated fatty acid with an odd number of carbon atoms, namely 15. Its salts and esters are called pentadecanoates .
Occurrence
Like most long-chain fatty acids with an odd carbon number, pentadecanoic acid occurs only rarely in nature and in lower concentrations than fatty acids with an even carbon number. It can be in the cod liver oil of codfish to 0.1%, the fat of the eel prove to 1.6%, in beef and lamb to about 0.6% of the total fatty acids.
They are also found in milk fat at 1.05% and in body fat of ruminants at approx. 0.43%.
It is rare in plants, a relatively high proportion of this fatty acid in the leaf fatty acids of the Milky Mangrove (Blind-Your-Eye Mangrove) Excoecaria agallocha was found to be 2.65%.
Fatty acids of odd carbon number are found in the membrane lipids of bacteria . Their proportion can be significantly higher than that of fatty acids with an even carbon number, which is used as a diagnostic feature , e.g. B. in some orders of Actinobacteria . Pentadecanoic acid occurs, for example, in Micrococcus species as a branched fatty acid chain, which is referred to as anteiso -C 15: 0 ( anteiso- pentadecanoic acid, systematic name : 12-methyltetradecanoic acid ) and iso -C 15: 0 ( iso- pentadecanoic acid, 13-methyltetradecanoic acid) .
properties
Pentadecanoic acid crystallizes in different forms, depending on the solvent used for the crystallization.
use
Pentadecanoic acid is used industrially as a solvent in the manufacture of paints.
pharmacology
Since the human body cannot produce this fatty acid itself, conclusions can be drawn about the intake of milk and / or milk products from the proportion of pentadecanoic acid in blood lipids.
Fats containing pentadecanoic acid, like those containing margaric acid, are associated with a protective effect against type 2 diabetes mellitus .
Individual evidence
- ^ A b c Erik von Sydow: "On the Structure of the Crystal Form B 'of n- Pentadecanoic Acid", Acta Cryst. , 1954 , 7 , pp. 823-826; doi : 10.1107 / S0365110X54002538 .
- ↑ a b c d 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. 3-412.
- ↑ Data sheet pentadecanoic acid from Acros, accessed on June 8, 2008.
- ↑ SH Yalkowsky, RM Dannenfelser: Aquasol database of wässrige solubility . Version 5 .; College of Pharmacy, University of Arizona, Tucson, AZ. PC version. 1992.
- ↑ a b Datasheet Pentadecanoic acid from Sigma-Aldrich , accessed on April 18, 2011 ( PDF ).
- ↑ C. Lentner (ed.): Geigy Scientific Tables Volume 1 - Units of Measurement, Body Fluids, Composition of the Body, Nutrition , CIBA-GEIGY, Basel, 8th edition, 1981; ISBN 0-914168-50-9 .
- ↑ Entry on Pentadecanoic acid in the Human Metabolome Database (HMDB) , accessed on June 8, 2008.
- ↑ G. Agoramoorthy, M. Chandrasekaran, V. Venkatesalu, MJ Hsu: "Antibacterial and antifungal activities of fatty acid methyl esters of the blind-your-eye mangrove from India", Brazilian Journal of Microbiology , 2007 , 38 , p. 739 -742; doi : 10.1590 / S1517-83822007000400028 .
- ↑ E. Stackebrandt, C. Koch, O. Gvozdiak, P. Schumann: Taxonomic dissection of the genus Micrococcus: Kocuria gen. Nov., Nesterenkonia gen. Nov., Kytococcus gen. Nov., Dermacoccus gen. Nov., And Micrococcus Cohn 1872 called emend. In: International journal of systematic bacteriology. Volume 45, Number 4, October 1995, pp. 682-692, PMID 7547287 .
- ^ Scorecard - The pollution information site ; June 8, 2008.
- ↑ A. Smedman, I.-B. Gustafsson, L. Berglund, B. Vessby: "Pentadecanoic acid in serum as a marker for intake of milk fat: relations between intake of milk fat and metabolic risk factors", American Journal of Clinical Nutrition , 1999 , 69 , p. 22– 29; PMID 9925119 .
- ↑ NZ Herald News: Slice of good news for cheese lovers , August 7, 2014.
