Pentadecylic acid, also known as pentadecanoic acid or C15:0, is an odd-chain saturated fatty acid. Its molecular formula is CH3(CH2)13CO2H. It is a colorless solid.
A laboratory preparation involves permanganate oxidation of 1-hexadecene (CH3(CH2)13CH=CH2).
It is one of the most common odd-chain fatty acids, although it is rare in nature. Pentadecylic acid is found primarily in dairy fat, as well as in ruminant meat and some fish and plants. The butterfat in cow milk is its major dietary source, comprising 1.2% of cow milk fat.
Rare genetic disorders causing unusually high concentrations of C15:0 and C17:0, including Refsum disease, Zellweger Syndrome, and propionic acidemia, confirmed endogenous synthesis of these odd-chain FAs in humans, involving alpha-oxidation.
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InChI=1S/C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(16)17/h2-14H2,1H3,(H,16,17) |
WQEPLUUGTLDZJY-UHFFFAOYSA-N |
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Hypericum roeperianum
(NCBI:txid269018)
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See:
PubMed
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Chlamydomonas reinhardtii
(NCBI:txid3055)
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See:
PubMed
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Daphnia magna
(NCBI:txid35525)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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Found in
blood serum
(BTO:0000133).
See:
MetaboLights Study
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Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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Daphnia magna metabolite
A Daphnia metabolite produced by the species Daphnia magna.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
food component
A physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
human blood serum metabolite
Any metabolite (endogenous or exogenous) found in human blood serum samples.
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View more via ChEBI Ontology
15:00
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ChEBI
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C15
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ChEBI
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C15:0
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ChEBI
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n-pentadecanoic acid
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NIST Chemistry WebBook
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n-Pentadecanoic acid
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KEGG COMPOUND
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PENTADECANOIC ACID
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PDBeChem
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pentadecylic acid
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NIST Chemistry WebBook
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Pentadecylic acid
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KEGG COMPOUND
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1002-84-2
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CAS Registry Number
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NIST Chemistry WebBook
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1002-84-2
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CAS Registry Number
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ChemIDplus
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1773831
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Reaxys Registry Number
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Reaxys
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Tanemossu SA, Franke K, Arnold N, Schmidt J, Wabo HK, Tane P, Wessjohann LA (2014) Rare biscoumarin derivatives and flavonoids from Hypericum riparium. Phytochemistry 105, 171-177 [PubMed:24930002] [show Abstract] Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae. Chemical investigation of the methanol extract of the stem bark of H. riparium led to the isolation of four natural products, 7,7'-dihydroxy-6,6'-biscoumarin (1), 7,7'-dihydroxy-8,8'-biscoumarin (2), 7-methoxy-6,7'-dicoumarinyl ether (3), 2'-hydroxy-5'-(7″-methoxycoumarin-6″-yl)-4'-methoxyphenylpropanoic acid (4), together with one known 7,7'-dimethoxy-6,6'-biscoumarin (5), two flavones, 2'-methoxyflavone (6) and 3'-methoxy flavone (7), and two steroids, stigmast-4-en-3-one (8) and ergosta-4,6,8,22-tetraen-3-one (9). In addition, tetradecanoic acid (10), n-pentadecanoic acid (11), hexadecanoic acid (12), cis-10-heptadecenoic acid (13), octadecanoic acid (14) campesterol (15), stigmasterol (16), β-sitosterol (17), stigmastanol (18), β-eudesmol (19), 1-hexadecanol (20), and 1-octadecanol (21) were identified by GC-MS analysis. Compound 4 consists of a phenylpropanoic acid derivative fused with a coumarin unit, while compounds 2 and 3 are rare members of C8-C8' and C7-O-C6 linked biscoumarins. Their structures were elucidated by UV, IR, extensive 1D- and 2D-NMR experiments and electrospray (ESI) high resolution mass spectrometry (MS) including detailed MS/MS studies. This is the first report on the isolation of biscoumarins from the genus Hypericum, although simple coumarin derivatives have been reported from this genus in the literature. The cytotoxic activities of compounds 2-5 were evaluated against the human prostate cancer cell line PC-3 and the colon cancer cell line HT-29. They do not exhibit any significant cytotoxic activity. | Coroian A, Erler S, Matea CT, Mireșan V, Răducu C, Bele C, Coroian CO (2013) Seasonal changes of buffalo colostrum: physicochemical parameters, fatty acids and cholesterol variation. Chemistry Central journal 7, 40 [PubMed:23442377] [show Abstract]
BackgroundColostrum has many beneficial effects on newborns due to its main compounds (proteins, fats, lactose, essential fatty acids, amino acids) as well as protective antibodies that confer to the body. The buffaloes are the second important species for milk production in the world after cows. The importance of the species is also conferred by a longer longevity, high dry content of milk and a strong organic resistance when compared with cows. The purpose of this study was to investigate the changes of buffalo colostrum compounds such as fatty acids, cholesterol and physicochemical parameters during the first seven days postpartum and under the impact of the season, summer on pasture and winter on dry diet (hay based).ResultsFat from colostrum differs depending on the postpartum day showing mean values of 11.31-7.56% (summer season) and 11.22-7.51% (winter season). These values gradually decreased starting with first day postpartum until day seven. Dry substance and protein presented a similar evolution to fat reaching the lowest values at the end of the colostral period. Lactose, ash and pH showed a gradually increase reaching the maximum on day seven postpartum. The highest titres of fatty acids from colostrum are: butyric acid (C4:0), myristic acid (C14:0), palmitic acid (C16:0), oleic acid (C18:1) and the lowest values showed up in myristoleic acid (C14:1), cis-10-pentadecanoic acid (C15:1), pentadecylic acid (C15:0) and margaric acid (C17:0) for both seasons. Higher concentrations have been recorded for the summer season in general. Cholesterol concentration decreased from 12.93 and 12.68 mg/100 mL (summer and winter season) to 9.02 and 7.88 mg/100 mL in the end of the colostral period.ConclusionsPhysicochemical compounds of buffalo colostrum were influenced by season and postpartum day of milking. Excepting lactose all other parameters gradually decreased during colostral period. Fatty acids and cholesterol showed the same evolution, presenting higher values for the summer season. Specific feeding in the summer season (on pasture) did lead in more concentrated colostrum in dry substance, fatty acids and cholesterol. |
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