Heneicosanoic acid
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| Surname | Heneicosanoic acid | |||||||||||||||
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| Molecular formula | C 21 H 42 O 2 | |||||||||||||||
| Brief description |
colorless needles |
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| properties | ||||||||||||||||
| Molar mass | 326.56 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
74-75 ° 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 . | ||||||||||||||||
The heneicosanoic acid is a saturated long-chain fatty acid having an odd number of carbon atoms and belongs to the substance group of alkanoic acids . Their salts and esters are called heneicosanoates .
Occurrence
Like most long-chain fatty acids with an odd carbon number, heneicosanoic acid occurs only rarely and in low concentrations in nature.
This fatty acid was found to be 0.24% of the fatty acids in human milk fat , 4–5% of the fatty acids in mushrooms of the genus Armillaria and in a few plants.
It occurs to 0.72% of the fatty acids in the oil from seeds of Azadirachta excelsa , a relative of the Indian neem tree, and 2.26% of the fatty acids in the seeds of Mucuna flagellipes , a legume that is used in India for its suitability was examined as animal feed. In the same investigation, no heneicosanoic acid could be found in another four Mucuna species.
In some microorganisms such as Rickettsia typhi and Rickettsia prowazekii it occurs chemically bound to a lipopolysaccharide .
Extraction and presentation
Heneicosanoic acid can be produced by the oxidation of 1-docose with potassium permanganate .
use
Because of its rarity and its low occurrence in biological material, it - like tridecanoic acid and nonadecanoic acid - is often used as an internal standard in the gas chromatographic analysis of fatty acids (e.g.).
Individual evidence
- ^ A b c Robert C. Weast (Editor): CRC Handbook of Chemistry and Physics . 58th edition, CRC Press, Cleveland, Ohio, USA, 1977.
- ↑ a b c data sheet Heneicosanoic acid from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).
- ↑ Heneicosanoic acid at PlantFA Database, accessed October 31, 2017.
- ↑ Maurı́cio HL Silva, Marco Túlio u. a .: Fatty acid composition of mature breast milk in Brazilian women. In: Food Chemistry . 93 (2), 2005, pp. 297-303, doi : 10.1016 / j.foodchem.2004.09.026 .
- ↑ KD Cox, H. Scherm, MB Riley: Characterization of Armillaria spp. from peach orchards in the southeastern United States using fatty acid methyl ester profiling. In: Mycological Research. 110 (4), 2006, pp. 414-422, doi : 10.1016 / j.mycres.2005.12.004 .
- ↑ P. Denrungruang, W. Subansenee, T. Ohira: The Composition of Fatty Acids from Azadirachta excelsa Seed ( Memento of the original from June 10, 2015 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. , IUFRO XX World Congress, Tampoere, Finland, 1995.
- ↑ KR Sridhar; Rajeev Bhat: Agrobotanical, nutritional and bioactive potential of unconventional legume - Mucuna. In: Livestock Research for Rural Development. 19 (9), 2007.
- ↑ Ken-ichi Amano, Jim C. Williams, Gregory A. Dasch: Structural Properties of Lipopolysaccharides from Rickettsia typhi and Rickettsia prowazekii and Their Chemical Similarity to the Lipopolysaccharide from Proteus vulgaris OX19 Used in the Weil-Felix Test. In: Infection and Immunity . 66 (3), 1998, pp. 923-926.
- ↑ Donald G. Lee, Shannon E. Lamb, 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 ).
- ↑ Stephen A. Buckley; Richard P. Evershed: Organic chemistry of embalming agents in Pharaonic and Graeco-Roman mummies. In: Nature . 413, 2001, pp. 837-841, doi : 10.1038 / 35101588 .
