Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:21 UTC |
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Update date | 2020-09-17 15:33:18 UTC |
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Primary ID | FDB004676 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Heptadecanoic acid |
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Description | Heptadecanoic acid, also known as margaric acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Heptadecanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" lengths long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid is usually found in trace amounts and constitutes 0.61% of milk fat and 0.83% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products (PMID: 9701185). It is a common constituent of lipids, such as those present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid has pheromonic and allomonic properties for insects and reptiles. The subcaudal gland secretions of the European badger (Meles meles) and the occipital gland secretions of male bactrian camels (Camelus bactrianus) contain many pheromonic chemicals, including heptadecanoic acid, that aid in finding and selection of mates (PMID: 24414593). Heptadecanoic acid is an attractant of the khapra beetle (Trogoderma granarium) and the yellow fever mosquito (Aedes aegypti) but as a repellent of the common house mosquito (Culex pipiens; doi: 10.5962/bhl.title.49749). Heptadecanoic acid is also found in the precloacal gland secretions of many reptiles belonging to the order squamata, including the common leopard gecko (Eublepharis macularius; PMID 24264893) and the European viper (Vipera berus), where it is used for the identification of sexual partners (doi:10.1007/bf00579807). |
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CAS Number | 506-12-7 |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C17H34O2 |
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IUPAC name | heptadecanoic acid |
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InChI Identifier | InChI=1S/C17H34O2/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) |
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InChI Key | KEMQGTRYUADPNZ-UHFFFAOYSA-N |
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Isomeric SMILES | CCCCCCCCCCCCCCCCC(O)=O |
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Average Molecular Weight | 270.4507 |
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Monoisotopic Molecular Weight | 270.255880332 |
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Classification |
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Description | Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Long-chain fatty acids |
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Alternative Parents | |
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Substituents | - Long-chain fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Foods | Dairy products |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Cryst. (petrol) | CCD |
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Mass Composition | C 75.50%; H 12.67%; O 11.83% | CCD |
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Melting Point | Mp 62 - 63° | CCD |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-05fu-9210000000-099bddb00b5e5f57a591 | 2014-09-20 | View Spectrum | GC-MS | Heptadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-017i-0900000000-ebd7708ca40db1f69377 | Spectrum | GC-MS | Heptadecanoic acid, 1 TMS, GC-MS Spectrum | splash10-017i-1900000000-140a09beb5b6859644fd | Spectrum | GC-MS | Heptadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-017i-0900000000-ebd7708ca40db1f69377 | Spectrum | GC-MS | Heptadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-017i-1900000000-140a09beb5b6859644fd | Spectrum | GC-MS | Heptadecanoic acid, non-derivatized, GC-MS Spectrum | splash10-016r-0900000000-a9975b7f916df9242d31 | Spectrum | Predicted GC-MS | Heptadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9620000000-2e104e4843f27f81734a | Spectrum | Predicted GC-MS | Heptadecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00bi-9350000000-8e55b03dd2c18c1e3ca7 | Spectrum | Predicted GC-MS | Heptadecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-0a4i-0019000000-83d961b9674b7b1b2a65 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-0a4i-0019000000-83d961b9674b7b1b2a65 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-014i-0090000000-1e57778151b8b2a05362 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0090000000-1e57778151b8b2a05362 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014i-0090000000-1e57778151b8b2a05362 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-014i-0090000000-233b71c471008bbed61b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-014i-0090000000-94bee87e459e47f84a4d | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-014i-0090000000-1e57778151b8b2a05362 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-014i-0090000000-433ed2666c0e94078147 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-014i-0900000000-1e14b3fcd14dfdf48cbd | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0uxr-0090000000-de66caaa914ba0366a3d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-233b71c471008bbed61b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-94bee87e459e47f84a4d | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0090000000-433ed2666c0e94078147 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-014i-0900000000-1e14b3fcd14dfdf48cbd | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-0006-0190000000-0d9a873b65555a15a62e | 2020-07-21 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0006-0390000000-c2f846ea7246884b09ed | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-014i-0090000000-7aadc5ba2a6acb7162cf | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-014i-0900000000-1e14b3fcd14dfdf48cbd | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0090000000-3452bef1d9fd1091e354 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fi0-4590000000-727243a3559dd7ed991f | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05mo-9710000000-f50bf2fb7778841f9f16 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-98c6dcf5eaea4132deb7 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0gdi-1090000000-e7ed55db02f1210fe7e1 | 2015-09-15 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9230000000-24fa7a34c1095502e707 | 2015-09-15 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 10033 |
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ChEMBL ID | CHEMBL1172910 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 10465 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 32365 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB02259 |
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CRC / DFC (Dictionary of Food Compounds) ID | HCQ70-H:HCQ70-H |
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EAFUS ID | Not Available |
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Dr. Duke ID | DATURIC-ACID|MARGARIC-ACID|HEPTADECANOIC-ACID |
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BIGG ID | 215873 |
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KNApSAcK ID | C00007426 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Heptadecanoic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE |
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Enzymes | Name | Gene Name | UniProt ID |
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Liver carboxylesterase 1 | CES1 | P23141 | Pancreatic triacylglycerol lipase | PNLIP | P16233 | Hepatic triacylglycerol lipase | LIPC | P11150 | Inactive pancreatic lipase-related protein 1 | PNLIPRP1 | P54315 | Patatin-like phospholipase domain-containing protein 3 | PNPLA3 | Q9NST1 | Gastric triacylglycerol lipase | LIPF | P07098 | Endothelial lipase | LIPG | Q9Y5X9 | Pancreatic lipase-related protein 2 | PNLIPRP2 | P54317 | Lipoprotein lipase | LPL | P06858 | Patatin-like phospholipase domain-containing protein 4 | PNPLA4 | P41247 | Patatin-like phospholipase domain-containing protein 2 | PNPLA2 | Q96AD5 | Pancreatic lipase-related protein 3 | PNLIPRP3 | Q17RR3 | Cholinesterase | BCHE | P06276 | Carboxylesterase 5A | CES5A | Q6NT32 | 60 kDa lysophospholipase | ASPG | Q86U10 | Fatty acid synthase | FASN | P49327 | Galactoside-binding soluble lectin 13 | LGALS13 | Q9UHV8 | Eosinophil lysophospholipase | CLC | Q05315 | Cocaine esterase | CES2 | O00748 | Acylphosphatase-2 | ACYP2 | P14621 | Acylphosphatase-1 | ACYP1 | P07311 | Aspartoacylase | ASPA | P45381 | Aspartoacylase-2 | ACY3 | Q96HD9 | Acid ceramidase | ASAH1 | Q13510 | Homeodomain-interacting protein kinase 1 | HIPK1 | Q86Z02 | Peroxisome proliferator-activated receptor gamma | PPARG | P37231 | Long-chain fatty acid transport protein 6 | SLC27A6 | Q9Y2P4 | Long-chain fatty acid transport protein 3 | SLC27A3 | Q5K4L6 | Long-chain fatty acid transport protein 4 | SLC27A4 | Q6P1M0 | Putative neutral ceramidase C | ASAH2C | P0C7U2 | Alkaline ceramidase 2 | ACER2 | Q5QJU3 | Neutral ceramidase | ASAH2 | Q9NR71 | Alkaline ceramidase 1 | ACER1 | Q8TDN7 | Neuropathy target esterase | PNPLA6 | Q8IY17 | Carboxylesterase 3 | CES3 | Q6UWW8 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008). — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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