Sulcatone (BioDeep_00000004252)

 

Secondary id: BioDeep_00000268013, BioDeep_00000861482

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


6-Methylheptan-5-ene-2-one

化学式: C8H14O (126.10445940000001)
中文名称: 6-甲基-5-庚烯-2-酮, 甲基庚烯酮
谱图信息: 最多检出来源 Viridiplantae(plant) 0.15%

分子结构信息

SMILES: CC(=CCCC(=O)C)C
InChI: InChI=1S/C8H14O/c1-7(2)5-4-6-8(3)9/h5H,4,6H2,1-3H3

描述信息

Sulcatone, also known as methylheptenone or fema 2707, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Sulcatone is a very hydrophobic methylketone, practically insoluble in water, and relatively neutral. It exists as a clear, colorless liquid. Sulcatone can be found in all eukaryotes, ranging from yeast to plants to humans. Sulcatone has a musty, apple green-bean, and pear-like taste. and a citrus-like lemongrass odor. It is a volatile oil component of citronella oil, lemon-grass oil and palmarosa oil. Sulcatone is naturally found in bay leaf, blackberry fruit, sour cherries, cloves, ginger and lavender. In insects and animals, it has a role as an alarm or attractant pheromone. In fact, sulcatone is one of a number of mosquito attractants, especially for those species such as Aedes aegypti with the odor receptor gene Or4 (PMID:25391959 ). Sulcatone is secreted by humans in their sweat and is a compound frequently found in human body odors (but in few other mammals). Sulcoatone is used as a pheromone by ferrets, european badgers, red foxes, treefrogs, bedbugs, wasps and butterflies. Sulcatone is one of several ketones found in Cannabis sativa (PMID:6991645 ).
Sulcatone, also known as 6-methylhept-5-en-2-one, is a member of the class of compounds known as ketones. Ketones are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, sulcatone is considered to be an oxygenated hydrocarbon lipid molecule. Sulcatone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Sulcatone is an apple, bitter, and citrus tasting compound and can be found in a number of food items such as oil palm, winter savory, european plum, and swamp cabbage, which makes sulcatone a potential biomarker for the consumption of these food products. Sulcatone can be found primarily in feces and saliva. Sulcatone exists in all eukaryotes, ranging from yeast to humans.
Sulcatone is an endogenous metabolite.
Sulcatone is an endogenous metabolite.

同义名列表

19 个代谢物同义名

6-Methylheptan-5-ene-2-one; 6-Methyl-hept-5-en-2-one; 6-Methyl hept-5-en-2-one; 2-Methyl-6-oxo-2-heptene; 6-Methyl-5-heptene-2-one; 2-oxo-6-Methylhept-5-ene; 6-Methylhept-5-ene-2-one; 2-Methyl-2-hepten-6-one; 6-METHYL-5-HEPTEN-2-ONE; 6-Methylhept-5-en-2-one; 2-Methylhept-2-en-6-one; 2-Methyl-6-heptenone; filbert heptenone B; Methylheptenone; Prenylacetone; Sulcatone; FEMA 2707; Sulcatone; 6-Methyl-5-hepten-2-one



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(2)

代谢反应

31 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(4)

WikiPathways(0)

Plant Reactome(3)

INOH(0)

PlantCyc(24)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

84 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Dalila Touhami, Adedayo O Mofikoya, Robbie D Girling, Ben Langford, Pawel K Misztal, Christian Pfrang. Atmospheric Degradation of Ecologically Important Biogenic Volatiles: Investigating the Ozonolysis of (E)-β-Ocimene, Isomers of α and β-Farnesene, α-Terpinene and 6-Methyl-5-Hepten-2-One, and Their Gas-Phase Products. Journal of chemical ecology. 2024 Jan; ?(?):. doi: 10.1007/s10886-023-01467-6. [PMID: 38195852]
  • Annika Hinze, Julien Pelletier, Majid Ghaninia, Eric Marois, Sharon Rose Hill, Rickard Ignell. Knockout of OR39 reveals redundancy in the olfactory pathway regulating the acquisition of host seeking in Anopheles coluzzii. Proceedings. Biological sciences. 2023 Nov; 290(2011):20232092. doi: 10.1098/rspb.2023.2092. [PMID: 38018099]
  • Jossiê Zamperetti Donadel, Fabio Rodrigo Thewes, Luana Ferreira Dos Santos, Erani Eliseu Schultz, Magno Roberto Pasquetti Berghetti, Vagner Ludwig, Juliana Mesadri, Bruna Klein, Flavio Roberto Thewes, Suele Fernanda Prediger Schmidt, Vanderlei Both, Auri Brackmann, Daniel Alexandre Neuwald, Roger Wagner. Superficial scald development in 'Granny Smith' and 'Nicoter' apples: The role of key volatile compounds when fruit are stored under dynamic controlled atmosphere. Food research international (Ottawa, Ont.). 2023 Nov; 173(Pt 2):113396. doi: 10.1016/j.foodres.2023.113396. [PMID: 37803734]
  • Matilda Lindmark, Suresh Ganji, Erika A Wallin, Fredrik Schlyter, C Rikard Unelius. Semiochemicals produced by fungal bark beetle symbiont Endoconidiophora rufipennis and the discovery of an anti-attractant for Ips typographus. PloS one. 2023; 18(4):e0283906. doi: 10.1371/journal.pone.0283906. [PMID: 37023040]
  • Haoran Liu, Fanliang Meng, Huiying Miao, Shanshan Chen, Tingting Yin, Songshen Hu, Zhiyong Shao, Yuanyuan Liu, Liuxiao Gao, Changqing Zhu, Bo Zhang, Qiaomei Wang. Effects of postharvest methyl jasmonate treatment on main health-promoting components and volatile organic compounds in cherry tomato fruits. Food chemistry. 2018 Oct; 263(?):194-200. doi: 10.1016/j.foodchem.2018.04.124. [PMID: 29784307]
  • Denise Tieman, Guangtao Zhu, Marcio F R Resende, Tao Lin, Cuong Nguyen, Dawn Bies, Jose Luis Rambla, Kristty Stephanie Ortiz Beltran, Mark Taylor, Bo Zhang, Hiroki Ikeda, Zhongyuan Liu, Josef Fisher, Itay Zemach, Antonio Monforte, Dani Zamir, Antonio Granell, Matias Kirst, Sanwen Huang, Harry Klee. A chemical genetic roadmap to improved tomato flavor. Science (New York, N.Y.). 2017 01; 355(6323):391-394. doi: 10.1126/science.aal1556. [PMID: 28126817]
  • Carolyn S McBride, Felix Baier, Aman B Omondi, Sarabeth A Spitzer, Joel Lutomiah, Rosemary Sang, Rickard Ignell, Leslie B Vosshall. Evolution of mosquito preference for humans linked to an odorant receptor. Nature. 2014 Nov; 515(7526):222-7. doi: 10.1038/nature13964. [PMID: 25391959]
  • Birte L Nielsen, Nathalie Jerôme, Audrey Saint-Albin, Olivier Rampin, Yves Maurin. Behavioural response of sexually naïve and experienced male rats to the smell of 6-methyl-5-hepten-2-one and female rat faeces. Physiology & behavior. 2013 Aug; 120(?):150-5. doi: 10.1016/j.physbeh.2013.07.012. [PMID: 23911690]
  • Eunae Kim, Il-Kwon Park. Fumigant antifungal activity of Myrtaceae essential oils and constituents from Leptospermum petersonii against three Aspergillus species. Molecules (Basel, Switzerland). 2012 Sep; 17(9):10459-69. doi: 10.3390/molecules170910459. [PMID: 22945026]
  • Sol A Green, Xiuyin Chen, Niels J Nieuwenhuizen, Adam J Matich, Mindy Y Wang, Barry J Bunn, Yar-Khing Yauk, Ross G Atkinson. Identification, functional characterization, and regulation of the enzyme responsible for floral (E)-nerolidol biosynthesis in kiwifruit (Actinidia chinensis). Journal of experimental botany. 2012 Mar; 63(5):1951-67. doi: 10.1093/jxb/err393. [PMID: 22162874]
  • Martin Pareja, Erika Qvarfordt, Ben Webster, Patrick Mayon, John Pickett, Michael Birkett, Robert Glinwood. Herbivory by a Phloem-feeding insect inhibits floral volatile production. PloS one. 2012; 7(2):e31971. doi: 10.1371/journal.pone.0031971. [PMID: 22384116]
  • Morten Hyldgaard, Tina Mygind, Rikke Louise Meyer. Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components. Frontiers in microbiology. 2012; 3(?):12. doi: 10.3389/fmicb.2012.00012. [PMID: 22291693]
  • Rahele Ghanbari, Farooq Anwar, Khalid M Alkharfy, Anwarul-Hassan Gilani, Nazamid Saari. Valuable nutrients and functional bioactives in different parts of olive (Olea europaea L.)-a review. International journal of molecular sciences. 2012; 13(3):3291-3340. doi: 10.3390/ijms13033291. [PMID: 22489153]
  • Khaled Hamden, Henda Keskes, Sahla Belhaj, Kais Mnafgui, Abdelfattah Feki, Noureddine Allouche. Inhibitory potential of omega-3 fatty and fenugreek essential oil on key enzymes of carbohydrate-digestion and hypertension in diabetes rats. Lipids in health and disease. 2011 Dec; 10(?):226. doi: 10.1186/1476-511x-10-226. [PMID: 22142357]
  • N L Rodríguez-Ávila, J A Narváez-Zapata, J E Ramírez-Benítez, M L Aguilar-Espinosa, R Rivera-Madrid. Identification and expression pattern of a new carotenoid cleavage dioxygenase gene member from Bixa orellana. Journal of experimental botany. 2011 Nov; 62(15):5385-95. doi: 10.1093/jxb/err201. [PMID: 21813796]
  • Marta Ferreira Maia, Sarah J Moore. Plant-based insect repellents: a review of their efficacy, development and testing. Malaria journal. 2011 Mar; 10 Suppl 1(?):S11. doi: 10.1186/1475-2875-10-s1-s11. [PMID: 21411012]
  • Federica Brandi, Einat Bar, Fabienne Mourgues, Györgyi Horváth, Erika Turcsi, Giovanni Giuliano, Alessandro Liverani, Stefano Tartarini, Efraim Lewinsohn, Carlo Rosati. Study of 'Redhaven' peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism. BMC plant biology. 2011 Jan; 11(?):24. doi: 10.1186/1471-2229-11-24. [PMID: 21269483]
  • Poluru G Padmaja, Christine M Woodcock, Toby J A Bruce. Electrophysiological and behavioral responses of sorghum shoot fly, Atherigona soccata, to sorghum volatiles. Journal of chemical ecology. 2010 Dec; 36(12):1346-53. doi: 10.1007/s10886-010-9882-3. [PMID: 21082333]
  • Thangavel Rajagopal, Govindaraju Archunan, Pitchairaj Geraldine, Chellam Balasundaram. Assessment of dominance hierarchy through urine scent marking and its chemical constituents in male blackbuck Antelope cervicapra, a critically endangered species. Behavioural processes. 2010 Sep; 85(1):58-67. doi: 10.1016/j.beproc.2010.06.007. [PMID: 20547215]
  • Yichi Xu, Sheryl Barringer. Comparison of tomatillo and tomato volatile compounds in the headspace by selected ion flow tube mass spectrometry (SIFT-MS). Journal of food science. 2010 Apr; 75(3):C268-73. doi: 10.1111/j.1750-3841.2010.01537.x. [PMID: 20492278]
  • Alessandra Bertoli, Szilvia Sárosi, Jeno Bernáth, Luisa Pistelli. Characterization of some Italian ornamental thyme by their aroma. Natural product communications. 2010 Feb; 5(2):291-6. doi: ". [PMID: 20334146]
  • Ester Innocent, Cosam C Joseph, Nicholas K Gikonyo, Mayunga H H Nkunya, Ahmed Hassanali. Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s. Journal of insect science (Online). 2010; 10(?):57. doi: 10.1673/031.010.5701. [PMID: 20569134]
  • Ben Webster, Salvador Gezan, Toby Bruce, Jim Hardie, John Pickett. Between plant and diurnal variation in quantities and ratios of volatile compounds emitted by Vicia faba plants. Phytochemistry. 2010 Jan; 71(1):81-9. doi: 10.1016/j.phytochem.2009.09.029. [PMID: 19863976]
  • Tjeerd A L Snoeren, Remco M P Van Poecke, Marcel Dicke. Multidisciplinary approach to unravelling the relative contribution of different oxylipins in indirect defense of Arabidopsis thaliana. Journal of chemical ecology. 2009 Sep; 35(9):1021-31. doi: 10.1007/s10886-009-9696-3. [PMID: 19798534]
  • Diego Orzaez, Aurora Medina, Sara Torre, Josefina Patricia Fernández-Moreno, José Luis Rambla, Asun Fernández-Del-Carmen, Eugenio Butelli, Cathie Martin, Antonio Granell. A visual reporter system for virus-induced gene silencing in tomato fruit based on anthocyanin accumulation. Plant physiology. 2009 Jul; 150(3):1122-34. doi: 10.1104/pp.109.139006. [PMID: 19429602]
  • Edna Pesis, Ana M Ibáñez, My Lin Phu, Elizabeth J Mitcham, Susan E Ebeler, Abhaya M Dandekar. Superficial scald and bitter pit development in cold-stored transgenic apples suppressed for ethylene biosynthesis. Journal of agricultural and food chemistry. 2009 Apr; 57(7):2786-92. doi: 10.1021/jf802564z. [PMID: 19253953]
  • Fong-Chin Huang, Györgyi Horváth, Péter Molnár, Erika Turcsi, József Deli, Jens Schrader, Gerhard Sandmann, Holger Schmidt, Wilfried Schwab. Substrate promiscuity of RdCCD1, a carotenoid cleavage oxygenase from Rosa damascena. Phytochemistry. 2009 Mar; 70(4):457-64. doi: 10.1016/j.phytochem.2009.01.020. [PMID: 19264332]
  • Sandrine Mathieu, Valeriano Dal Cin, Zhangjun Fei, Hua Li, Peter Bliss, Mark G Taylor, Harry J Klee, Denise M Tieman. Flavour compounds in tomato fruits: identification of loci and potential pathways affecting volatile composition. Journal of experimental botany. 2009; 60(1):325-37. doi: 10.1093/jxb/ern294. [PMID: 19088332]
  • Niels J Nieuwenhuizen, Mindy Y Wang, Adam J Matich, Sol A Green, Xiuyin Chen, Yar-Khing Yauk, Lesley L Beuning, Dinesh A Nagegowda, Natalia Dudareva, Ross G Atkinson. Two terpene synthases are responsible for the major sesquiterpenes emitted from the flowers of kiwifruit (Actinidia deliciosa). Journal of experimental botany. 2009; 60(11):3203-19. doi: 10.1093/jxb/erp162. [PMID: 19516075]
  • Ben Webster, Toby Bruce, Samuel Dufour, Claudia Birkemeyer, Michael Birkett, Jim Hardie, John Pickett. Identification of volatile compounds used in host location by the black bean aphid, Aphis fabae. Journal of chemical ecology. 2008 Sep; 34(9):1153-61. doi: 10.1007/s10886-008-9510-7. [PMID: 18584254]
  • Hongyan Gao, Hongliang Zhu, Yi Shao, Anjun Chen, Chengwen Lu, Benzhong Zhu, Yunbo Luo. Lycopene accumulation affects the biosynthesis of some carotenoid-related volatiles independent of ethylene in tomato. Journal of integrative plant biology. 2008 Aug; 50(8):991-6. doi: 10.1111/j.1744-7909.2008.00685.x. [PMID: 18713349]
  • Ross N Crowhurst, Andrew P Gleave, Elspeth A MacRae, Charles Ampomah-Dwamena, Ross G Atkinson, Lesley L Beuning, Sean M Bulley, David Chagne, Ken B Marsh, Adam J Matich, Mirco Montefiori, Richard D Newcomb, Robert J Schaffer, Björn Usadel, Andrew C Allan, Helen L Boldingh, Judith H Bowen, Marcus W Davy, Rheinhart Eckloff, A Ross Ferguson, Lena G Fraser, Emma Gera, Roger P Hellens, Bart J Janssen, Karin Klages, Kim R Lo, Robin M MacDiarmid, Bhawana Nain, Mark A McNeilage, Maysoon Rassam, Annette C Richardson, Erik Ha Rikkerink, Gavin S Ross, Roswitha Schröder, Kimberley C Snowden, Edwige J F Souleyre, Matt D Templeton, Eric F Walton, Daisy Wang, Mindy Y Wang, Yanming Y Wang, Marion Wood, Rongmei Wu, Yar-Khing Yauk, William A Laing. Analysis of expressed sequence tags from Actinidia: applications of a cross species EST database for gene discovery in the areas of flavor, health, color and ripening. BMC genomics. 2008 Jul; 9(?):351. doi: 10.1186/1471-2164-9-351. [PMID: 18655731]
  • Catherine E Garner, Stephen Smith, Ben de Lacy Costello, Paul White, Robert Spencer, Chris S J Probert, Norman M Ratcliffe. Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2007 Jun; 21(8):1675-88. doi: 10.1096/fj.06-6927com. [PMID: 17314143]
  • Martín Pareja, Maria C B Moraes, Suzanne J Clark, Michael A Birkett, Wilf Powell. Response of the aphid parasitoid Aphidius funebris to volatiles from undamaged and aphid-infested Centaurea nigra. Journal of chemical ecology. 2007 Apr; 33(4):695-710. doi: 10.1007/s10886-007-9260-y. [PMID: 17334919]
  • John C Beaulieu, Jeanne M Lea. Characterization and semiquantitative analysis of volatiles in seedless watermelon varieties using solid-phase microextraction. Journal of agricultural and food chemistry. 2006 Oct; 54(20):7789-93. doi: 10.1021/jf060663l. [PMID: 17002453]
  • Dieudonné Emmanuel Pegnyemb, Josephine Ngo Mbing, Alex de Théodore Atchadé, Raphael Ghogomu Tih, Beiban Lucas Sondengam, Alain Blond, Bernard Bodo. Antimicrobial biflavonoids from the aerial parts of Ouratea sulcata. Phytochemistry. 2005 Aug; 66(16):1922-6. doi: 10.1016/j.phytochem.2005.06.017. [PMID: 16083925]
  • M A Birkett, N Agelopoulos, K-M V Jensen, J B Jespersen, J A Pickett, H J Prijs, G Thomas, J J Trapman, L J Wadhams, C M Woodcock. The role of volatile semiochemicals in mediating host location and selection by nuisance and disease-transmitting cattle flies. Medical and veterinary entomology. 2004 Dec; 18(4):313-22. doi: 10.1111/j.0269-283x.2004.00528.x. [PMID: 15641996]
  • Frank Kjeldsen, Lars P Christensen, Merete Edelenbos. Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage. Journal of agricultural and food chemistry. 2003 Aug; 51(18):5400-7. doi: 10.1021/jf030212q. [PMID: 12926889]
  • María J Jordán, Carlos A Margaría, Philip E Shaw, Kevin L Goodner. Volatile components and aroma active compounds in aqueous essence and fresh pink guava fruit puree (Psidium guajava L.) by GC-MS and multidimensional GC/GC-O. Journal of agricultural and food chemistry. 2003 Feb; 51(5):1421-6. doi: 10.1021/jf020765l. [PMID: 12590492]
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