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Decenoic acid

April 12, 2024

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–(CH
2)
k–CH=CH–(CH
2)
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 edit

Free acids and esters edit

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 edit

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 edit

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 edit

References edit

  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. PMC 2648214. 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. ^ a b c 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. ^ a b 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. ^ a b c 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. ^ a b 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.

April 12, 2024
decenoic, acid, mono, carboxylic, acid, with, unbranched, chain, carbons, connected, eight, single, bonds, double, bond, that, chemical, compound, with, formula, where, between, inclusive, there, fifteen, these, compounds, that, identified, position, double, b. 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 Contents 1 Examples 1 1 Free acids and esters 1 2 Unspecified isomers and mixtures 1 3 Derivatives 2 See also 3 ReferencesExamples editFree acids and esters edit 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 edit 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 edit 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 editDecanoic acid capric acid HO O C CH2 9 H Decadienoic acidReferences edit 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 PMC 2648214 PMID 19074399 FAO WHO JECFA 2004 E 2 Decenoic acid Compound 1372 data sheet Note says cis but should be trans Accessed on 2020 08 21 Good Scents Company 2020 E 2 decenoic acid Accessed on 2020 08 21 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 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 Ramiro Vilchez Andre Lemme Britta Ballhausen Verena Thiel Stefan Schulz Rolf Jansen Helena Sztajer and Irene Wagner Dobler 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 a b c Mosciano Gerard P amp F 18 No 5 39 1993 Good Scents Company 2020 ethyl E 2 decenoate Accessed on 2020 08 21 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 Good Scents Company 2020 Z 3 decenoic acid Accessed on 2020 08 21 Good Scents Company 2020 E 3 decenoic acid Accessed on 2020 08 21 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 Good Scents Company 2020 Z 4 decenoic acid Accessed on 2020 08 21 Good Scents Company 2020 ethyl Z 4 decenoate Accessed on 2020 08 21 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 Good Scents Company 2020 ethyl E 4 decenoate Accessed on 2020 08 21 Good Scents Company 2020 Z 5 decenoic acid Accessed on 2020 08 21 Good Scents Company 2020 E 5 decenoic acid Accessed on 2020 08 21 a b P G Keeney and S Patton 1955 Elimination of 9 decenoic acid as a precursor of d decalaetone in milk fat Journal of Dairy Science volume 38 page 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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 a b c Good Scents Company 2020 9 decenoic acid Accessed on 2020 08 21 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 FAO WHO JECFA 1998 9 Decenoic acid Compound 328 data sheet Accessed on 2020 08 21 Good Scents Company 2020 ethyl 9 decenoate Accessed on 2020 08 21 Good Scents Company 2020 butyl 2 decenoate Accessed on 2020 08 21 Good Scents Company 2020 methyl 2 decenoate Accessed on 2020 08 21 Good Scents Company 2020 4 decenoic acid Accessed on 2020 08 21 FAO WHO JECFA 2003 4 Decenoic acid Compound 1287 data sheet Unspecified isomer Accessed on 2020 08 21 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 Good Scents Company 2020 5 6 decenoic acid Accessed on 2020 08 21 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 Paul Cazenave and Ian Horman 1974 Sur la composition de l arome de the noir V Helvetica Chimica Acta volume 57 issue 1 pages 209 211 doi 10 1002 hlca 19740570126 FAO WHO JECFA 1997 5 Hydroxy 7 decenoic acid delta lactone Unspecified isomer Compound 247 data sheet Accessed on 2020 08 21 a b 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 R E Doolittle M S Blum and R Boch 1970 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Accessed on 2020 08 21 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 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 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 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 Retrieved from https en wikipedia org w index php title Decenoic acid amp oldid 1154246566, wikipedia, wiki, book, books, library,

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