Chemistry:Decenoic acid

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Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C–(CH2)k–CH=CH–(CH2)7-k–H, where k is between 0 and 7 inclusive. There are fifteen of these compounds, that can be identified by the position k+2 of the double bond and (for k ≤ 6) the configuration (cis or trans) of the single bonds adjacent to it.

Decenoic acids are technically mono-unsaturated fatty acids (with code C10:1), although they are relatively rare in nature.

Examples

Free acids and esters

Some isomers (and esters thereof) that have received attention are

  • cis-2-decenoic acid or (2Z)-dec-2-enoic acid. (CAS 15790-91-7, Nikkaji J1.577.978K) Produced by Pseudomonas aeruginosa, inhibits biofilm formation.[1]
  • trans-2-decenoic acid or (2E)-dec-2-enoic acid. Flavoring agent (CAS 334-49-6, Nikkaji J98.042K, FEMA 3913, JECFA 1372, FDA 332T8TH7B1);[2] Density: 0.92-0.93 25 °C. Refractive Index: ~1.46 at 20.00 °C. MP: 12 °C BP: 161-162 °C. at 15.00 torr, 278-279 °C. at 1 atm. Odor described as "fresh, fruity (peach), slightly oily and waxy".[3] Stimulates nerve cell regeneration[4] and biofilm disintegration.[5] Excreted by the caries bacterium Streptococcus mutans and inhibits growth of the fungus Candida albicans.[6]
    • ethyl trans-2-decenoate (CAS 7367-88-6, Pubchem 5463904, 6047581, Nikkaji J212.367C, J1.075.382A, FDA B2K05S6L5Q, JECFA 1814, FEMA 3641) Flavoring agent. BP: ~134 °C. at 20.00 torr, 140 °C. at 30.00 torr. Odor described as "green, fruity (apple, pear), waxy."[7] "peely citrus".[8]
  • cis-3-decenoic acid or (3Z)-dec-3-enoic acid. (CAS 2430-93-5, Nikkaji J3.028G) The female sex pheromone of the furniture carpet beetle Anthrenus flavipes.[9] Odor deascribed as "fatty".[10]
  • trans-3-decenoic acid (CAS 53678-20-9, Beilstein 1722688, Pubchem 5282725, Nikkaji J98.043I) Occurs in some natural extracts.[11]
  • cis-4-decenoic acid or (4Z)-dec-4-enoic acid. (CAS 505-90-8, Pubchem 5312351, Nikkaji J79.643C, FDA 6PR4L1KTAZ) A metabolite found in human plasma in certain pathologies.[12] Odor described as "fatty, green".[13]
    • ethyl cis-4-decenoate (CAS 7367-84-2, Pubchem 5463488, Nikkaji J212.366E) Flavoring agent. Density: 0.883 at 20 °C. Refractive Index: 1.438 at 20 °C. BP: 128 °C. at 30 torr, 236-237 °C. at 1 atm.[14]
  • trans-4-decenoic acid or (4E)-dec-4-enoic acid. (CAS 57602-94-5, Pubchem 5282726, Nikkaji J98.044G, FDA S0TXC5QGPU) Result of reacting 1‐octene and manganese(III) acetate.[15]
    • ethyl trans-4-decenoate (CAS 76649-16-6, Pubchem 5362583, Nikkaji J208.443K, FDA 3I89X5937N, JECFA 341, FEMA 3642) Density: ~0.876 at 25.00 °C. Refractive Index: ~1.437 at 20.00 °C. BP: 72.00 °C. at 0.10 torr. Odor described as "green, fruity (pineapple, apple), waxy, cognac".[7][16]
  • cis-5-decenoic acid (CAS 84168-28-5, Pubchem 15101542, Nikkaji J2.261.052J, FDA 5R82Y8PAHS) Odor described as "fatty, green".[17]
  • trans-5-decenoic acid (CAS 16424-55-8, Nikkaji J2.261.051A, Pubchem 5362593, FDA P9YWE0K08Y) Odor described as "milky, fatty".[18]
  • caproleic acid, 9-decenoic acid, or dec-9-enoic acid. (CAS 14436-32-9, PUBchem 61743, FEMA 3660, Nikkaji J81.770H, FDA U2E27P3TGK) Small amounts in goat and cow milk,[19][20][21] and oils of Sapium sebiferum[22] and Litsea cubeba.[23] Traces also in beer, wine, clams, Parmesan cheese and snails.[24] Broad-spectrum antimicrobial.[25] Flavoring agent (FEMA 3660, JECFA 328).[26] Density: ~0.9 at 20.00 °C. BP: ~270 °C at 1 atm, 130-135 °C at 1-3 torr, 95 °C at 0.1 torr. Refractive index nD20: 1.4488.[24][19] Irritating to skin.[24] Used as flavouring agent. Odor described as milky,waxy,green,fatty,soapy,creamy,cheesy".[7]
    • ethyl caproleate, 9-decenoic acid ethyl ester (CAS 67233-91-4, Pubchem 522255, Nikkaji J976.137C, FDA OI02K838CN) used as flavoring agent. Odor described as "fruity". Density: ~0.878 at 25.00 °C. Refractive Index: ~1.44 at 20.00 °C. BP: 249-250 °C. at 1 atm.[27]

Unspecified isomers and mixtures

The following unspecified isomers or mixtures have also been mentioned:

  • From 3-decenoic acid:
    • butyl 2-decenoate, isomer unspecified (CAS 7492-45-7, Pubchem 5463906, Nikkaji J421.861B, FDA 38KP1S005I, JECFA 1348, FEMA 2194), is a flavoring agent with odor described as "fruity (peach, apricot), green, fatty, coconut, walnut". Density: 0.87-0.88 at 25.00 °C. Refractive Index: ~1.45 at 20.00 °C. BP: 290-291 °C. at 1 atm. Flavouring agent.[28]
    • methyl 2-decenoate, isomer unspecified (CAS 2482-39-5, Pubchem 5368064, Nikkaji J110.937E, FDA 7YEW204WFW), is used as flavouring ingredient, with odor described as "mushroom".[29]
  • 4-decenoic acid, unspecified isomer (CAS 26303-90-2, Nikkaji J39.562E, FDA S0TXC5QGPU, JECFA 1287, FEMA 3914), is said to occur in hops and beer. It is a flavoring agent, with odor described as "fruity". Density: ~0.92 at 20.00 °C. Refractive Index: ~1.15 at 20.00 °C. BP: 97.00 to 98.00 °C. at 0.30 torr.[30] It is listed as "no concern" food additive (FEMA 3914, JECFA 1287) by the FAO/WHO JECFA.[31]
  • A mixture of 5-decenoic and 6-decenoic acids (JECFA 327, FDA 8H370297TA), with the trade name "milk lactone", is allowed in the US as Generally Recognized as Safe (GRAS) flavorings, such as in imitation dairy products with common name "milk lactone" for their milk-like aroma.[32][33]

Derivatives

Derivatives of these acids include:

  • 4-Hydroxy-4-methyl-cis-7-decenoic acid. Its gamma lactone is a flavoring agent (FEMA 3937, JECFA 1159).[34]
  • 5-hydroxy-7-decenoic acid. Its lactone was identified as a significant component of the aroma of black tea, reminiscent of flowers and dried fruit,[35] and is a flavoring agent (FEMA 3745, JECFA 247).[36]
  • 9-hydroxy-trans-2-decenoic acid. Another queen bee pheromone.[37]
  • 9-oxo-cis-2-decenoic acid. Is converted to the trans isomer by light and may function as inhibitor of bee colony settlement.[38]
  • 9-oxo-trans-2-decenoic acid.A pheromone produced by queen bees.[37][39]
  • 10-hydroxy-trans-2-decenoic acid, "queen bee acid" (CAS 14113-05-4, Pubchem 5312738, Nikkaji J838.856C, FDA 76B519G7TJ). The main fatty acid in bee's royal jelly.[40][41] Characteristic odor.[42]
  • 10-oxo-7-hydroxy-trans-8-decenoic acid. Formed by plants in response to mechanical trauma.[43]
  • 10-oxo-trans-8-decenoic acid. A metabolite of the mushrooms Agaricus bisporus[44] and Pleurotus pulmonarius.[45] Possibly a fungal growth hormone.[46]

See also

References

  1. ↑ Davies, DG; Marques, CN (2009). "A fatty acid messenger is responsible for inducing dispersion in microbial biofilms". Journal of Bacteriology 191 (5): 1393–403. doi:10.1128/JB.01214-08. PMID 19074399. 
  2. ↑ FAO/WHO JECFA (2004): "(E)-2-Decenoic acid". Compound 1372 data sheet. Note: says cis but should be trans. Accessed on 2020-08-21.
  3. ↑ Good Scents Company (2020): "(E)-2-decenoic acid". Accessed on 2020-08-21.
  4. ↑ A. Hirakawa, K.Shimizu, H. Fukumitsu, H. Soumiya, M. Iinuma, and S. Furukawa (2010): "2-Decenoic acid ethyl ester, a derivative of unsaturated medium-chain fatty acids, facilitates functional recovery of locomotor activity after spinal cord injury". Neuroscience, volume 171, issue 4, pages 1377-1385. doi:10.1016/j.neuroscience.2010.10.004
  5. ↑ Pei-Jie Cai, Xiang Xiao, Yan-Rong He, Wen-Wei Li, Lei Yu, and Han-Qing Yua (2013): "Disintegration of aerobic granules induced by trans-2-decenoic acid", Bioresource Technology, volume 128, pages 823-826. doi:10.1016/j.biortech.2012.10.071
  6. ↑ Ramiro Vílchez, André Lemme, Britta Ballhausen, Verena Thiel, Stefan Schulz, Rolf Jansen, Helena Sztajer, and Irene Wagner‐Döbler (2010): "Streptococcus mutans inhibits Candida albicans hyphal formation by the fatty acid signaling molecule trans‐2‐decenoic acid". ChemBioChem, volume 11, issue 11, pages 1552-1562. doi:10.1002/cbic.201000086
  7. ↑ 7.0 7.1 7.2 Mosciano, Gerard P&F 18, No. 5, 39, (1993)
  8. ↑ Good Scents Company (2020): "ethyl (E)-2-decenoate". Accessed on 2020-08-21.
  9. ↑ Michael Ma, Hans E. Hummel, and Wendell E. Burkholder (1980): "Estimation of single furniture carpet beetle (Anthrenus flavipes LeConte) sex pheromone release by dose-response curve and chromatographic analysis of pentafluorobenzyl derivative of (Z)-3-decenoic acid". Journal of Chemical Ecology, volume 6, pages 597–607. doi:10.1007/BF00987672
  10. ↑ Good Scents Company (2020): "(Z)-3-decenoic acid". Accessed on 2020-08-21.
  11. ↑ Good Scents Company (2020): "(E)-3-decenoic acid". Accessed on 2020-08-21.
  12. ↑ M. Duran, L. Bruinvis, D. Ketting, J. B. de Klerk, and S. K. Wadman (1988): "Cis-4-decenoic acid in plasma: a characteristic metabolite in medium-chain acyl-CoA dehydrogenase deficiency". Clinical Chemistry, volume 34, issue 3, pages 548–551. doi:10.1093/clinchem/34.3.548
  13. ↑ Good Scents Company (2020): "(Z)-4-decenoic acid". Accessed on 2020-08-21.
  14. ↑ Good Scents Company (2020): "ethyl (Z)-4-decenoate". Accessed on 2020-08-21.
  15. ↑ W. J. de Klein (1975): "Copper(II)‐catalyzed formation of decenoic acids from manganese(III) acetate and 1‐octene in acetic anhydride/acetic acid mixtures". Recueil des Travaux Chimiques des Pays-Bas, volume 94, issue 7, pages 151-153. doi:10.1002/recl.19750940703
  16. ↑ Good Scents Company (2020): "ethyl (E)-4-decenoate". Accessed on 2020-08-21.
  17. ↑ Good Scents Company (2020): "(Z)-5-decenoic acid". Accessed on 2020-08-21.
  18. ↑ Good Scents Company (2020): "(E)-5-decenoic acid". Accessed on 2020-08-21.
  19. ↑ 19.0 19.1 P. G. Keeney and S. Patton (1955): "Elimination of 9-decenoic acid as a precursor of δ-decalaetone in milk fat". Journal of Dairy Science, volume 38, page 1390. doi:10.3168/jds.S0022-0302(55)95122-5
  20. ↑ Antonella Caterina Boccia, Erica Cusano, Paola Scano, and Roberto Consonni (2020): "NMR lipid profile of milk from Alpine goats with supplemented hempseed and linseed diets". Molecules, volume 25, issue 7, article 1491. doi:10.3390/molecules25071491
  21. ↑ Laziz Bouzidi, Shaojun Li, Steve Di Biase, Syed Q. Rizvi, and Suresh S. Narine (2013): "Lubricating and waxy esters. 4. Synthesis, crystallization behavior, melt behavior, and flow behavior of linear monoesters incorporating 9-decenol and 9-decenoic acid". Industrial Engineering and Chemical Research, volume 52, issue 7, pages 2740–2749 doi:10.1021/ie302995z
  22. ↑ Bo Zhou, Wenjie Fei, Shiquan Yang, Feng Yang, Gaoyi Qu, Weiwei Tang, Jianping Ou, Dan Peng (2020): "Alteration of the fatty acid composition of Brassica napus L. via overexpression of phospholipid: Diacylglycerol acyltransferase 1 from Sapium sebiferum (L.) Roxb.". Plant Science, volume 298, article 110562. doi:10.1016/j.plantsci.2020.110562
  23. ↑ Xiaoci Zhuang, Zhen Zhang, Yong Wang, and Ying Li (2018): "The effect of alternative solvents to n-hexane on the green extraction of Litsea cubeba kernel oils as new oil sources". Industrial Crops and Products, volume 126, pPages 340-346. doi:10.1016/j.indcrop.2018.10.004
  24. ↑ 24.0 24.1 24.2 Good Scents Company (2020): "9-decenoic acid". Accessed on 2020-08-21.
  25. ↑ Andrew P. Desbois (2012): "Potential applications of antimicrobial fatty acids in medicine, agriculture and other industries". Recent Patents on Anti-Infective Drug Discovery, volume 7, issue 2, pages 111-122 doi:10.2174/157489112801619728
  26. ↑ FAO/WHO JECFA (1998): "9-Decenoic acid". Compound 328 data sheet. Accessed on 2020-08-21.
  27. ↑ Good Scents Company (2020): "ethyl 9-decenoate". Accessed on 2020-08-21.
  28. ↑ Good Scents Company (2020): "butyl 2-decenoate". Accessed on 2020-08-21.
  29. ↑ Good Scents Company (2020): "methyl 2-decenoate". Accessed on 2020-08-21.
  30. ↑ Good Scents Company (2020): "4-decenoic acid". Accessed on 2020-08-21.
  31. ↑ FAO/WHO JECFA (2003): "4-Decenoic acid". Compound 1287 data sheet. Unspecified isomer. Accessed on 2020-08-21.
  32. ↑ Flavor and Extract Manufacturers Association (1985): "Recent Progress in the Consideration of Flavoring Ingredients Under the Food Additives Amendment: 14. GRAS Substances". Food Technology, November 1985, pages 108-117.
  33. ↑ Good Scents Company (2020): "5(6)-decenoic acid". Accessed on 2020-08-21.
  34. ↑ FAO/WHO JECFA (2003): "4-Hydroxy-4-methyl-7-cis-decenoic acid gamma lactone" Unspecified isomer. Compound 1159 data sheet. Accessed on 2020-08-21.
  35. ↑ Paul Cazenave and Ian Horman (1974): "Sur la composition de l'arôme de thé noir V". Helvetica Chimica Acta, volume 57, issue 1, pages 209-211. doi:10.1002/hlca.19740570126
  36. ↑ FAO/WHO JECFA (1997): "5-Hydroxy-7-decenoic acid delta-lactone". Unspecified isomer. Compound 247 data sheet. Accessed on 2020-08-21.
  37. ↑ 37.0 37.1 Kevin W. Wanner, Andrew S. Nichols, Kimberly K. O. Walden, Axel Brockmann, Charles W. Luetje, and Hugh M. Robertson (2007): "A honey bee odorant receptor for the queen substance 9-oxo-2-decenoic acid". Proceedings of the National Academy of Sciences (PNAS), volume 104, issue 36, pages 14383-14388. doi:10.1073/pnas.0705459104
  38. ↑ R. E. Doolittle, M. S. Blum, and R. Boch (1970): "cis-9-Oxo-2-decenoic acid: Synthesis and evaluation as a honey bee pheromone and masking agent". Annals of the Entomological Society of America, volume 63, issue 4, pages 1180–1185. doi:10.1093/aesa/63.4.1180
  39. ↑ D. T. Cromer and A. C. Larson (1972): "The crystal structure of queen substance, 9-keto-trans-2-decenoic acid, the sex pheromone of the honeybee". Acta Crystalligraphica Series B, volume B28, pages 2128-2132. doi:10.1107/S0567740872005655
  40. ↑ Murray S. Blum, Arthur F.Novak, and Stephen Taber III (1959): "10-Hydroxy-Δ2-Decenoic Acid, an Antibiotic Found in Royal Jelly". Science, volume 130, issue 3373, pages 452-453. doi:10.1126/science.130.3373.452
  41. ↑ Keita Takahashi, Tsuyoshi Sugiyama, Shunji Tokoro, Paola Neri, and Hiroshi Mori (2012): "Inhibition of interferon-γ-induced nitric oxide production by 10-hydroxy-trans-2-decenoic acid through inhibition of interferon regulatory factor-8 induction". Cellular Immunology, volume 273, issue 1, pages 73-78. doi:10.1016/j.cellimm.2011.11.004
  42. ↑ Good Scents Company (2020): "(E)-10-hydroxy-2-decenoic acid". Accessed on 2020-08-21.
  43. ↑ Anna Nakashima, Stephan H. von Reuss, Hiroyuki Tasaka, Misaki Nomura, Satoshi Mochizuki, Yoko Iijima, Koh Aoki, Daisuke Shibata, Wilhelm Boland, Junji Takabayashi and Kenji Matsui (2013): "Traumatin- and dinortraumatin-containing galactolipids in Arabidopsis: Their formation in tissue-disrupted leaves as counterparts of green leaf volatiles". Journal of Biological Chemistry, volume 200, pages 26078-26088. doi:10.1074/jbc.M113.487959
  44. ↑ Margot Wurzenberger and Werner Grosch (1984): "Origin of the oxygen in the products of the enzymatic cleavage reaction of linoleic acid to 1-octen-3-ol and 10-oxo-trans-8-decenoic acid in mushrooms (Psalliota bispora)". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, volume 794, issue 1, pages 18-24. doi:10.1016/0005-2760(84)90292-3
  45. ↑ Smadar Assaf, Yizhak Hadar, and Carlos G. Dosoretz (1995): "Biosynthesis of 13-hydroperoxylinoleate, 10-oxo-8-decenoic acid and 1-octen-3-ol from linoleic acid by a mycelial-pellet homogenate of Pleurotus pulmonarius". Journal of Agricultural and Food Chemistry, volume 43, issue 8, pages 2173–2178. doi:10.1021/jf00056a040
  46. ↑ Robert B. Beelman, Gregory R. Ziegler, and Jeng-Leun Mau (1992): "Use of 10-oxo-trans-8-decenoic acid in mushroom cultivation". US Patent 5681738. Filed on 1992-03-19, granted on 1997-10-28, assigned to Penn State Research Foundation; expired on 2014-10-28.



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