Heptanal (BioDeep_00000004183)

 

Secondary id: BioDeep_00000629894

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


Oenanthic aldehyde

化学式: C7H14O (114.1045)
中文名称: 正庚醛, 庚醛
谱图信息: 最多检出来源 Homo sapiens(feces) 66.53%

分子结构信息

SMILES: CCCCCCC=O
InChI: InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3

描述信息

Heptanal, also known as enanthal or N-heptaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, heptanal is considered to be a fatty aldehyde lipid molecule. It is a colourless liquid with a strong fruity odor, which is used as precursor to components in perfumes and lubricants. Heptanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heptanal exists in all eukaryotes, ranging from yeast to humans. Heptanal is an aldehydic, citrus, and fat tasting compound. heptanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and sweet oranges and in a lower concentration in lemons, wild carrots, and carrots. heptanal has also been detected, but not quantified, in several different foods, such as horned melons, common beets, dills, red bell peppers, and malus (crab apple). This could make heptanal a potential biomarker for the consumption of these foods. The formation of heptanal in the fractional distillation of castor oil was already described in 1878. The large-scale production is based on the pyrolytic cleavage of ricinoleic acid ester (Arkema method) and on the hydroformylation of 1-hexene with rhodium 2-ethylhexanoate as a catalyst upon addition of some 2-ethylhexanoic acid (Oxea method):Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus). Heptanal is a potentially toxic compound. Heptanal has been found to be associated with several diseases such as ulcerative colitis, crohns disease, uremia, and nonalcoholic fatty liver disease; also heptanal has been linked to the inborn metabolic disorders including celiac disease. The compound has a flash point of 39.5 °C. The explosion range is between 1.1\\% by volume as the lower explosion limit (LEL) and 5.2\\% by volume as the upper explosion limit. Heptanal or heptanaldehyde is an alkyl aldehyde. Full hydrogenation provides the branched primary alcohol 2-pentylnonan-1-ol, also accessible from the Guerbet reaction from heptanol. A by-product of the given reaction is the unpleasant rancid smelling (Z)-2-pentyl-2-nonenal. Heptanal forms flammable vapor-air mixtures. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor, which is miscible with alcohols and practically insoluble in water. Heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90\\%) to alpha-pentylcinnamaldehyde (also called jasmine aldehyde because of the typical jasmine odor), which is mostly used in many fragrances as a cis/trans isomer mixture.
Found in essential oils of ylang-ylang, clary sage, California orange, bitter orange and others. Flavouring agent

同义名列表

26 个代谢物同义名

Oenanthic aldehyde; Enanthic aldehyde; N-Heptylaldehyde; Heptyl aldehyde; Oenanthaldehyde; N-Heptaldehyde; Enanthaldehyde; Heptanaldehyde; 1-Heptaldehyde; Heptylaldehyde; Aldehyde C-7; Heptaldehyde; Heptan-1-al; Aldehyde C7; N-C6H13CHO; Oenanthole; N-Heptanal; 1-Heptanal; Enanthole; FEMA 2540; Oenanthal; Oenanthol; Heptanal; Enanthal; Heptanal; Heptanal



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

176 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ALDH3A2, ALDH9A1, AOX1, MYLK, PYGB, SPOP, SSX2IP, XDH
Peripheral membrane protein 1 ACHE
Endoplasmic reticulum membrane 1 ALDH3A2
Nucleus 3 ACHE, SPOP, SSX2IP
cytosol 8 ACOX1, ALDH3A2, ALDH9A1, AOX1, LIPE, MB, MYLK, XDH
nucleoplasm 2 ANO2, SPOP
Cell membrane 5 ACHE, ANO2, LIPE, OR3A1, P2RX3
Cytoplasmic side 1 ALDH3A2
Cleavage furrow 1 MYLK
lamellipodium 1 MYLK
Multi-pass membrane protein 3 ANO2, OR3A1, P2RX3
Synapse 2 ACHE, MYLK
cell surface 2 ACHE, TNFRSF10B
glutamatergic synapse 1 ANO2
Golgi apparatus 2 ACHE, ATRN
neuromuscular junction 1 ACHE
postsynapse 1 P2RX3
presynaptic membrane 1 ANO2
Cytoplasm, cytosol 2 ALDH9A1, LIPE
plasma membrane 8 ACHE, ANO2, ATRN, MYLK, OR3A1, P2RX3, TNFRSF10B, TPSG1
Membrane 10 ACHE, ACOX1, ALDH3A2, ANO2, LIPE, OR3A1, P2RX3, PYGB, TNFRSF10B, TPSG1
axon 1 P2RX3
caveola 1 LIPE
extracellular exosome 6 ALDH2, ALDH9A1, AOX1, ATRN, MB, PYGB
extracellular space 4 ACHE, ATRN, TPSG1, XDH
perinuclear region of cytoplasm 1 ACHE
Schaffer collateral - CA1 synapse 1 P2RX3
adherens junction 1 SSX2IP
mitochondrion 2 ALDH2, ALDH9A1
protein-containing complex 1 SSX2IP
intracellular membrane-bounded organelle 1 ALDH3A2
Microsome membrane 1 ALDH3A2
Single-pass type I membrane protein 1 ATRN
Secreted 2 ACHE, CGB5
extracellular region 3 ACHE, CGB5, PYGB
Single-pass membrane protein 2 ALDH3A2, TPSG1
hippocampal mossy fiber to CA3 synapse 1 P2RX3
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 1 ALDH2
mitochondrial matrix 1 ALDH2
Extracellular side 1 ACHE
centriolar satellite 1 SSX2IP
actin cytoskeleton 1 MYLK
sarcoplasm 1 MB
Cell projection, lamellipodium 1 MYLK
Cell junction, adherens junction 1 SSX2IP
Peroxisome 3 ACOX1, ALDH3A2, XDH
basement membrane 1 ACHE
sarcoplasmic reticulum 1 XDH
peroxisomal matrix 1 ACOX1
peroxisomal membrane 2 ACOX1, ALDH3A2
nuclear speck 1 SPOP
receptor complex 1 P2RX3
neuron projection 1 ANO2
ciliary basal body 1 SSX2IP
cell leading edge 1 SSX2IP
Cytoplasm, cytoskeleton, cilium basal body 1 SSX2IP
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriolar satellite 1 SSX2IP
non-motile cilium 1 ANO2
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
Cul3-RING ubiquitin ligase complex 1 SPOP
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
chloride channel complex 1 ANO2
Nucleus speckle 1 SPOP
side of membrane 1 ACHE
stress fiber 1 MYLK
azurophil granule lumen 1 PYGB
Cytoplasm, cytoskeleton, stress fiber 1 MYLK
synaptic cleft 1 ACHE
[Isoform 1]: Cell membrane 1 ATRN
Cytoplasm, sarcoplasm 1 MB
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Qiwei Wang, Jialing Xie, Lilei Wang, Yongwen Jiang, Yuliang Deng, Jiayi Zhu, Haibo Yuan, Yanqin Yang. Comprehensive investigation on the dynamic changes of volatile metabolites in fresh scent green tea during processing by GC-E-Nose, GC-MS, and GC × GC-TOFMS. Food research international (Ottawa, Ont.). 2024 Jul; 187(?):114330. doi: 10.1016/j.foodres.2024.114330. [PMID: 38763633]
  • Yipeng Liu, Sai Zhang, Song Cao, Emmanuelle Jacquin-Joly, Qiong Zhou, Yang Liu, Guirong Wang. An odorant receptor mediates the avoidance of Plutella xylostella against parasitoid. BMC biology. 2024 Mar; 22(1):61. doi: 10.1186/s12915-024-01862-9. [PMID: 38475722]
  • F Farahbakhsh, A Massah, H Hamzehzarghani, M Yassaie, Z Amjadi, H El-Zaeddi, A A Carbonell-Barrachina. Comparative profiling of volatile organic compounds associated to temperature sensitive resistance to wheat streak mosaic virus (WSMV) in resistant and susceptible wheat cultivars at normal and elevated temperatures. Journal of plant physiology. 2023 Feb; 281(?):153903. doi: 10.1016/j.jplph.2022.153903. [PMID: 36608365]
  • Sheng-Fa Li, Shuai-Bing Zhang, Yang-Yong Lv, Huan-Chen Zhai, Yuan-Sen Hu, Jing-Ping Cai. Transcriptome analysis reveals the underlying mechanism of heptanal against Aspergillus flavus spore germination. Applied microbiology and biotechnology. 2022 Feb; 106(3):1241-1255. doi: 10.1007/s00253-022-11783-8. [PMID: 35075519]
  • Anthony Zhu, Xuan Luo. Detection of Covid-19 through a Heptanal Biomarker Using Transition Metal Doped Graphene. The journal of physical chemistry. B. 2022 01; 126(1):151-160. doi: 10.1021/acs.jpcb.1c09580. [PMID: 34982559]
  • W S Harwood, B G Carter, D C Cadwallader, M A Drake. The role of heat treatment in light oxidation of fluid milk. Journal of dairy science. 2020 Dec; 103(12):11244-11256. doi: 10.3168/jds.2020-18933. [PMID: 33010920]
  • Mahmoud Tabibpour, Yadollah Yamini, Seyyed Hamid Ahmadi, Ali Esrafili, Kourosh Tabar Heydar, Seyed Ali Javad Mousavi, Mahroo Baharfar. Microextraction on a screw for determination of trace amounts of hexanal and heptanal as lung cancer biomarkers. Journal of pharmaceutical and biomedical analysis. 2020 Nov; 191(?):113528. doi: 10.1016/j.jpba.2020.113528. [PMID: 32916561]
  • Riska Rian Fauziah, Shinjiro Ogita, Tomoyuki Yoshino, Yukihiro Yamamoto. Effect of Molecular Form of Conjugated Linoleic Acid on Oxidative Stability : Comparison of Triacylglycerol and Phosphatidylcholine Form. Journal of oleo science. 2020 Aug; 69(8):801-807. doi: 10.5650/jos.ess20028. [PMID: 32641609]
  • Antoine Hoffmann, Thomas Bourgeois, Alicia Munoz, Sylvia Anton, Jeremy Gevar, Matthieu Dacher, Michel Renou. A plant volatile alters the perception of sex pheromone blend ratios in a moth. Journal of comparative physiology. A, Neuroethology, sensory, neural, and behavioral physiology. 2020 07; 206(4):553-570. doi: 10.1007/s00359-020-01420-y. [PMID: 32335729]
  • Francesca Bennato, Denise Innosa, Andrea Ianni, Camillo Martino, Lisa Grotta, Giuseppe Martino. Volatile Profile in Yogurt Obtained from Saanen Goats Fed with Olive Leaves. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102311. [PMID: 32423117]
  • Hao Xu, Guoxin Zhou, Stefan Dötterl, Irmgard Schäffler, Thomas Degen, Li Chen, Ted C J Turlings. Distinct Roles of Cuticular Aldehydes as Pheromonal Cues in Two Cotesia Parasitoids. Journal of chemical ecology. 2020 Feb; 46(2):128-137. doi: 10.1007/s10886-019-01142-9. [PMID: 31907752]
  • Leyla Alizadeh, Khadije Abdolmaleki, Kooshan Nayebzadeh, Reyhane Shahin. Effects of tocopherol, rosemary essential oil and Ferulago angulata extract on oxidative stability of mayonnaise during its shelf life: A comparative study. Food chemistry. 2019 Jul; 285(?):46-52. doi: 10.1016/j.foodchem.2019.01.028. [PMID: 30797371]
  • Juliah W Jacob, David P Tchouassi, Zipporah O Lagat, Evan M Mathenge, Collins K Mweresa, Baldwyn Torto. Independent and interactive effect of plant- and mammalian- based odors on the response of the malaria vector, Anopheles gambiae. Acta tropica. 2018 Sep; 185(?):98-106. doi: 10.1016/j.actatropica.2018.04.027. [PMID: 29709631]
  • Marta Cialiè Rosso, Erica Liberto, Nicola Spigolon, Mauro Fontana, Marco Somenzi, Carlo Bicchi, Chiara Cordero. Evolution of potent odorants within the volatile metabolome of high-quality hazelnuts (Corylus avellana L.): evaluation by comprehensive two-dimensional gas chromatography coupled with mass spectrometry. Analytical and bioanalytical chemistry. 2018 Jun; 410(15):3491-3506. doi: 10.1007/s00216-017-0832-6. [PMID: 29313080]
  • Bebiana C Sousa, Andrew R Pitt, Corinne M Spickett. Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds. Free radical biology & medicine. 2017 10; 111(?):294-308. doi: 10.1016/j.freeradbiomed.2017.02.003. [PMID: 28192230]
  • Anderson Luiz Oenning, Lucas Morés, Adriana Neves Dias, Eduardo Carasek. A new configuration for bar adsorptive microextraction (BAμE) for the quantification of biomarkers (hexanal and heptanal) in human urine by HPLC providing an alternative for early lung cancer diagnosis. Analytica chimica acta. 2017 May; 965(?):54-62. doi: 10.1016/j.aca.2017.02.034. [PMID: 28366212]
  • Di Chen, Jun Ding, Ming-Ke Wu, Tian-Yi Zhang, Chu-Bo Qi, Yu-Qi Feng. A liquid chromatography-mass spectrometry method based on post column derivatization for automated analysis of urinary hexanal and heptanal. Journal of chromatography. A. 2017 Apr; 1493(?):57-63. doi: 10.1016/j.chroma.2017.02.071. [PMID: 28292517]
  • Xiaowei Xin, Qingshen Liu, Yingying Zhang, Demin Gao. Chemical composition and antibacterial activity of the essential oil from Pyrrosia tonkinensis (Giesenhagen) Ching. Natural product research. 2016; 30(7):853-6. doi: 10.1080/14786419.2015.1062759. [PMID: 26214127]
  • Jiu-Feng Liu, Bi-Feng Yuan, Yu-Qi Feng. Determination of hexanal and heptanal in human urine using magnetic solid phase extraction coupled with in-situ derivatization by high performance liquid chromatography. Talanta. 2015 May; 136(?):54-9. doi: 10.1016/j.talanta.2015.01.003. [PMID: 25702985]
  • Ryota Motooka, Atsushi Usami, Hiroshi Nakahashi, Satoshi Koutari, Satoshi Nakaya, Ryoyu Shimizu, Kaoru Tsuji, Shinsuke Marumoto, Mitsuo Miyazawa. Characteristic odor components of essential oils from Eurya japonica. Journal of oleo science. 2015; 64(5):577-84. doi: 10.5650/jos.ess14225. [PMID: 25843279]
  • Raymond T Marsili, Charles R Laskonis. Odorant synergy effects as the cause of fishy malodors in algal marine oils. Journal of agricultural and food chemistry. 2014 Oct; 62(40):9676-82. doi: 10.1021/jf502252q. [PMID: 25232667]
  • Antoine Chaffiol, Fabienne Dupuy, Romina B Barrozo, Jan Kropf, Michel Renou, Jean-Pierre Rospars, Sylvia Anton. Pheromone modulates plant odor responses in the antennal lobe of a moth. Chemical senses. 2014 Jun; 39(5):451-63. doi: 10.1093/chemse/bju017. [PMID: 24798893]
  • Jong Hyun Lim, Juhun Park, Eun Hae Oh, Hwi Jin Ko, Seunghun Hong, Tai Hyun Park. Nanovesicle-based bioelectronic nose for the diagnosis of lung cancer from human blood. Advanced healthcare materials. 2014 Mar; 3(3):360-6. doi: 10.1002/adhm.201300174. [PMID: 23868879]
  • Fang Chen, Chunqiu Wang, Meijiang Zhang, Xiaoli Zhang, Yan Liu, Jiannong Ye, Qingcui Chu. Sensitive determination of endogenous hexanal and heptanal in urine by hollow-fiber liquid-phase microextraction prior to capillary electrophoresis with amperometric detection. Talanta. 2014 Feb; 119(?):83-9. doi: 10.1016/j.talanta.2013.10.052. [PMID: 24401388]
  • A J Fox, T J Smith, P D Gerard, M A Drake. The influence of bleaching agent and temperature on bleaching efficacy and volatile components of fluid whey and whey retentate. Journal of food science. 2013 Oct; 78(10):C1535-C1542. doi: 10.1111/1750-3841.12251. [PMID: 24102418]
  • Ingrid Kohl, Jonathan Beauchamp, Ferguel Cakar-Beck, Jens Herbig, J Dunkl, Olaf Tietje, Martin Tiefenthaler, Claudia Boesmueller, Armin Wisthaler, Martin Breitenlechner, Stephan Langebner, August Zabernigg, Florian Reinstaller, Klaus Winkler, Rene Gutmann, Armin Hansel. First observation of a potential non-invasive breath gas biomarker for kidney function. Journal of breath research. 2013 Mar; 7(1):017110. doi: 10.1088/1752-7155/7/1/017110. [PMID: 23446042]
  • Nicholas P L Tuckey, Jacqueline R Day, Matthew R Miller. Determination of volatile compounds in New Zealand Greenshell™ mussels (Perna canaliculus) during chilled storage using solid phase microextraction gas chromatography-mass spectrometry. Food chemistry. 2013 Jan; 136(1):218-23. doi: 10.1016/j.foodchem.2012.07.118. [PMID: 23017416]
  • Y F Ma, C Xiao. Push-pull effects of three plant secondary metabolites on oviposition of the potato tuber moth, Phthorimaea operculella. Journal of insect science (Online). 2013; 13(?):128. doi: 10.1673/031.013.12801. [PMID: 24786822]
  • In Hee Cho, Hyun Jeong Lee, Young-Suk Kim. Differences in the volatile compositions of ginseng species (Panax sp.). Journal of agricultural and food chemistry. 2012 Aug; 60(31):7616-22. doi: 10.1021/jf301835v. [PMID: 22804575]
  • Hiroshi M Ueno, Makoto Shiota, Noriko Ueda, Tomoyuki Isogai, Toshiya Kobayashi. Iron-lactoferrin complex reduces iron-catalyzed off-flavor formation in powdered milk with added fish oil. Journal of food science. 2012 Aug; 77(8):C853-8. doi: 10.1111/j.1750-3841.2012.02809.x. [PMID: 22860577]
  • S Jervis, R Campbell, K L Wojciechowski, E A Foegeding, M A Drake, D M Barbano. Effect of bleaching whey on sensory and functional properties of 80\% whey protein concentrate. Journal of dairy science. 2012 Jun; 95(6):2848-62. doi: 10.3168/jds.2011-4967. [PMID: 22612922]
  • Antoine Chaffiol, Jan Kropf, Romina B Barrozo, Christophe Gadenne, Jean-Pierre Rospars, Sylvia Anton. Plant odour stimuli reshape pheromonal representation in neurons of the antennal lobe macroglomerular complex of a male moth. The Journal of experimental biology. 2012 May; 215(Pt 10):1670-80. doi: 10.1242/jeb.066662. [PMID: 22539734]
  • Hisashi Omura, Nanako Yanai, Keiichi Honda. Sexual dimorphism in scent substances and cuticular lipids of adult Papilio protenor butterflies. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2012 May; 67(5-6):331-41. doi: 10.1515/znc-2012-5-614. [PMID: 22888540]
  • Hui Xu, Shuyu Wang. A novel sorptive extraction method based on polydimethylsiloxane frit for determination of lung cancer biomarkers in human serum. Analytica chimica acta. 2012 Apr; 724(?):61-6. doi: 10.1016/j.aca.2012.02.046. [PMID: 22483210]
  • Hui Xu, Zhihua Yan, Dandan Song. Development of a novel monolith frit-based solid-phase microextraction method for determination of hexanal and heptanal in human serum samples. Journal of separation science. 2012 Mar; 35(5-6):713-20. doi: 10.1002/jssc.201100908. [PMID: 22271665]
  • Pierluigi Caboni, Nikoletta G Ntalli, Nadhem Aissani, Ivana Cavoski, Alberto Angioni. Nematicidal activity of (E,E)-2,4-decadienal and (E)-2-decenal from Ailanthus altissima against Meloidogyne javanica. Journal of agricultural and food chemistry. 2012 Feb; 60(4):1146-51. doi: 10.1021/jf2044586. [PMID: 22224661]
  • Nina Deisig, Jan Kropf, Simon Vitecek, Delphine Pevergne, Angela Rouyar, Jean-Christophe Sandoz, Philippe Lucas, Christophe Gadenne, Sylvia Anton, Romina Barrozo. Differential interactions of sex pheromone and plant odour in the olfactory pathway of a male moth. PloS one. 2012; 7(3):e33159. doi: 10.1371/journal.pone.0033159. [PMID: 22427979]
  • Mengyao Liu, Hui Zhu, Jinquan Li, Cristiana C Garcia, Wenchao Feng, Liliya N Kirpotina, Jonathan Hilmer, Luciana P Tavares, Arthur W Layton, Mark T Quinn, Brian Bothner, Mauro M Teixeira, Benfang Lei. Group A Streptococcus secreted esterase hydrolyzes platelet-activating factor to impede neutrophil recruitment and facilitate innate immune evasion. PLoS pathogens. 2012; 8(4):e1002624. doi: 10.1371/journal.ppat.1002624. [PMID: 22496650]
  • Ingrid Elisia, David D Kitts. Quantification of hexanal as an index of lipid oxidation in human milk and association with antioxidant components. Journal of clinical biochemistry and nutrition. 2011 Nov; 49(3):147-52. doi: 10.3164/jcbn.10-142. [PMID: 22128211]
  • Diego L García-González, Jorge Vivancos, Ramón Aparicio. Mapping brain activity induced by olfaction of virgin olive oil aroma. Journal of agricultural and food chemistry. 2011 Sep; 59(18):10200-10. doi: 10.1021/jf202106b. [PMID: 21838262]
  • Rossella Guadagni, Nadia Miraglia, Angela Simonelli, Angela Silvestre, Monica Lamberti, Daniela Feola, Antonio Acampora, Nicola Sannolo. Solid-phase microextraction-gas chromatography-mass spectrometry method validation for the determination of endogenous substances: urinary hexanal and heptanal as lung tumor biomarkers. Analytica chimica acta. 2011 Sep; 701(1):29-36. doi: 10.1016/j.aca.2011.05.035. [PMID: 21763805]
  • Yongxia Xu, Qingchan Chen, Shengjiao Lei, Peng Wu, Gang Fan, Xiaoyun Xu, Siyi Pan. Effects of lard on the formation of volatiles from the Maillard reaction of cysteine with xylose. Journal of the science of food and agriculture. 2011 Sep; 91(12):2241-6. doi: 10.1002/jsfa.4445. [PMID: 21618545]
  • Kevin Huvaere, Jacob Holm Nielsen, Mette Bakman, Marianne Hammershøj, Leif H Skibsted, John Sørensen, Lene Vognsen, Trine Kastrup Dalsgaard. Antioxidant properties of green tea extract protect reduced fat soft cheese against oxidation induced by light exposure. Journal of agricultural and food chemistry. 2011 Aug; 59(16):8718-23. doi: 10.1021/jf201139e. [PMID: 21721579]
  • M Whitson, R E Miracle, E Bastian, M A Drake. Effect of liquid retentate storage on flavor of spray-dried whey protein concentrate and isolate. Journal of dairy science. 2011 Aug; 94(8):3747-60. doi: 10.3168/jds.2010-4045. [PMID: 21787911]
  • John J Beck, Noreen E Mahoney, Daniel Cook, Wai S Gee. Volatile analysis of ground almonds contaminated with naturally occurring fungi. Journal of agricultural and food chemistry. 2011 Jun; 59(11):6180-7. doi: 10.1021/jf200739a. [PMID: 21528918]
  • Tatjana Abaffy, Anthony R Defazio. The location of olfactory receptors within olfactory epithelium is independent of odorant volatility and solubility. BMC research notes. 2011 May; 4(?):137. doi: 10.1186/1756-0500-4-137. [PMID: 21548958]
  • Romina B Barrozo, David Jarriault, Nina Deisig, Cesar Gemeno, Christelle Monsempes, Philippe Lucas, Christophe Gadenne, Sylvia Anton. Mating-induced differential coding of plant odour and sex pheromone in a male moth. The European journal of neuroscience. 2011 May; 33(10):1841-50. doi: 10.1111/j.1460-9568.2011.07678.x. [PMID: 21488987]
  • Hui Xu, Shuyu Wang, Ganbing Zhang, Shiqiang Huang, Dandan Song, Yanping Zhou, Guangdou Long. A novel solid-phase microextraction method based on polymer monolith frit combining with high-performance liquid chromatography for determination of aldehydes in biological samples. Analytica chimica acta. 2011 Mar; 690(1):86-93. doi: 10.1016/j.aca.2011.02.006. [PMID: 21414440]
  • K C Nam, K S Seo, C Jo, D U Ahn. Electrostatic spraying of antioxidants on the oxidative quality of ground beef. Journal of animal science. 2011 Mar; 89(3):826-32. doi: 10.2527/jas.2010-3326. [PMID: 21097682]
  • M Øverland, G I Borge, G Vogt, H F Schøyen, A Skrede. Oxidative stability and sensory quality of meat from broiler chickens fed a bacterial meal produced on natural gas. Poultry science. 2011 Jan; 90(1):201-10. doi: 10.3382/ps.2010-00784. [PMID: 21177461]
  • Simon Wan Chan, Peter C Dedon. The biological and metabolic fates of endogenous DNA damage products. Journal of nucleic acids. 2010 Dec; 2010(?):929047. doi: 10.4061/2010/929047. [PMID: 21209721]
  • Romina B Barrozo, Christophe Gadenne, Sylvia Anton. Switching attraction to inhibition: mating-induced reversed role of sex pheromone in an insect. The Journal of experimental biology. 2010 Sep; 213(Pt 17):2933-9. doi: 10.1242/jeb.043430. [PMID: 20709921]
  • I W Liaw, H Eshpari, P S Tong, M A Drake. The impact of antioxidant addition on flavor of cheddar and mozzarella whey and cheddar whey protein concentrate. Journal of food science. 2010 Aug; 75(6):C559-69. doi: 10.1111/j.1750-3841.2010.01695.x. [PMID: 20722911]
  • Baojun Shi, Wei Liu, Shao-Peng Wei, Wen-Jun Wu. Chemical composition, antibacterial and antioxidant activity of the essential oil of Bupleurum longiradiatum. Natural product communications. 2010 Jul; 5(7):1139-42. doi: ". [PMID: 20734959]
  • Mark Eggink, Maikel Wijtmans, Ansgar Kretschmer, Jeroen Kool, Henk Lingeman, Iwan J P de Esch, Wilfried M A Niessen, Hubertus Irth. Targeted LC-MS derivatization for aldehydes and carboxylic acids with a new derivatization agent 4-APEBA. Analytical and bioanalytical chemistry. 2010 May; 397(2):665-75. doi: 10.1007/s00216-010-3575-1. [PMID: 20238107]
  • A E Croissant, E J Kang, R E Campbell, E Bastian, M A Drake. The effect of bleaching agent on the flavor of liquid whey and whey protein concentrate. Journal of dairy science. 2009 Dec; 92(12):5917-27. doi: 10.3168/jds.2009-2535. [PMID: 19923595]
  • Carmen Formisano, Felice Senatore, Giovanna Della Porta, Mariarosa Scognamiglio, Maurizio Bruno, Antonella Maggio, Sergio Rosselli, Pietro Zito, Maurizio Sajeva. Headspace volatile composition of the flowers of Caralluma europaea N.E.Br. (Apocynaceae). Molecules (Basel, Switzerland). 2009 Nov; 14(11):4597-613. doi: 10.3390/molecules14114597. [PMID: 19924088]
  • 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]
  • M A Lloyd, M A Drake, P D Gerard. Flavor variability and flavor stability of U.S.-produced whole milk powder. Journal of food science. 2009 Sep; 74(7):S334-43. doi: 10.1111/j.1750-3841.2009.01299.x. [PMID: 19895500]
  • F Sympoura, A Cornu, P Tournayre, T Massouras, J L Berdagué, B Martin. Odor compounds in cheese made from the milk of cows supplemented with extruded linseed and alpha-tocopherol. Journal of dairy science. 2009 Jul; 92(7):3040-8. doi: 10.3168/jds.2008-1802. [PMID: 19528581]
  • Petra Beatriz Navas. [Chemical composition of the virgin oil obtained by mechanical pressing form several grape seed varieties (Vitis vinifera L.) with emphasis on minor constituents]. Archivos latinoamericanos de nutricion. 2009 Jun; 59(2):214-9. doi: ". [PMID: 19719020]
  • Cung Thi To Quynh, Yoko Iijima, Yasujiro Morimitsu, Kikue Kubota. Aliphatic aldehyde reductase activity related to the formation of volatile alcohols in Vietnamese coriander leaves. Bioscience, biotechnology, and biochemistry. 2009 Mar; 73(3):641-7. doi: 10.1271/bbb.80709. [PMID: 19270388]
  • Matthew E Szapacs, Hye-Young H Kim, Ned A Porter, Daniel C Liebler. Identification of proteins adducted by lipid peroxidation products in plasma and modifications of apolipoprotein A1 with a novel biotinylated phospholipid probe. Journal of proteome research. 2008 Oct; 7(10):4237-46. doi: 10.1021/pr8001222. [PMID: 18778096]
  • Mónica Fernández-Aparicio, Anna Andolfi, Alessio Cimmino, Diego Rubiales, Antonio Evidente. Stimulation of seed germination of Orobanche species by ophiobolin A and fusicoccin derivatives. Journal of agricultural and food chemistry. 2008 Sep; 56(18):8343-7. doi: 10.1021/jf801727y. [PMID: 18763781]
  • Majid Ghaninia, Mattias Larsson, Bill S Hansson, Rickard Ignell. Natural odor ligands for olfactory receptor neurons of the female mosquito Aedes aegypti: use of gas chromatography-linked single sensillum recordings. The Journal of experimental biology. 2008 Sep; 211(Pt 18):3020-7. doi: 10.1242/jeb.016360. [PMID: 18775939]
  • Junheon Kim, Sun-Mi Seo, Sang-Gil Lee, Sang-Chul Shin, Il-Kwon Park. Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), Oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus). Journal of agricultural and food chemistry. 2008 Aug; 56(16):7316-20. doi: 10.1021/jf800780f. [PMID: 18605734]
  • B S Patton, E Huff-Lonergan, M S Honeyman, J D Crouse, B J Kerr, S M Lonergan. Effects of deep-bedded finishing system on market pig performance, composition and pork quality. Animal : an international journal of animal bioscience. 2008 Mar; 2(3):459-70. doi: 10.1017/s1751731107001292. [PMID: 22445049]
  • Hui-Juan Zhang, Jing-Fang Huang, Bo Lin, Yu-Qi Feng. Polymer monolith microextraction with in situ derivatization and its application to high-performance liquid chromatography determination of hexanal and heptanal in plasma. Journal of chromatography. A. 2007 Aug; 1160(1-2):114-9. doi: 10.1016/j.chroma.2007.04.015. [PMID: 17466319]
  • Selvaraj Poonguzhali, Munusamy Madhaiyan, Tongmin Sa. Quorum-sensing signals produced by plant-growth promoting Burkholderia strains under in vitro and in planta conditions. Research in microbiology. 2007 Apr; 158(3):287-94. doi: 10.1016/j.resmic.2006.11.013. [PMID: 17350232]
  • H Orhan, H Gurer-Orhan, E Vriese, N P E Vermeulen, J H N Meerman. Application of lipid peroxidation and protein oxidation biomarkers for oxidative damage in mammalian cells. A comparison with two fluorescent probes. Toxicology in vitro : an international journal published in association with BIBRA. 2006 Sep; 20(6):1005-13. doi: 10.1016/j.tiv.2005.12.012. [PMID: 16488111]
  • M S Havemose, M R Weisbjerg, W L P Bredie, H D Poulsen, J H Nielsen. Oxidative stability of milk influenced by fatty acids, antioxidants, and copper derived from feed. Journal of dairy science. 2006 Jun; 89(6):1970-80. doi: 10.3168/jds.s0022-0302(06)72264-0. [PMID: 16702260]
  • Matthias Laska, Dipa Joshi, Gordon M Shepherd. Olfactory sensitivity for aliphatic aldehydes in CD-1 mice. Behavioural brain research. 2006 Feb; 167(2):349-54. doi: 10.1016/j.bbr.2005.09.022. [PMID: 16253352]
  • Andreas Jürgens, Stefan Dötterl, Ulrich Meve. The chemical nature of fetid floral odours in stapeliads (Apocynaceae-Asclepiadoideae-Ceropegieae). The New phytologist. 2006; 172(3):452-68. doi: 10.1111/j.1469-8137.2006.01845.x. [PMID: 17083676]
  • E J Lee, D U Ahn. Quality characteristics of irradiated turkey breast rolls formulated with plum extract. Meat science. 2005 Oct; 71(2):300-5. doi: 10.1016/j.meatsci.2005.03.017. [PMID: 22064229]
  • Taufika Islam Williams, Mark A Lovell, Bert C Lynn. Analysis of derivatized biogenic aldehydes by LC tandem mass spectrometry. Analytical chemistry. 2005 May; 77(10):3383-9. doi: 10.1021/ac048265+. [PMID: 15889933]
  • A M Descalzo, E M Insani, A Biolatto, A M Sancho, P T García, N A Pensel, J A Josifovich. Influence of pasture or grain-based diets supplemented with vitamin E on antioxidant/oxidative balance of Argentine beef. Meat science. 2005 May; 70(1):35-44. doi: 10.1016/j.meatsci.2004.11.018. [PMID: 22063278]
  • Maria Laura Immordino, Paola Brusa, Flavio Rocco, Silvia Arpicco, Maurizio Ceruti, Luigi Cattel. Preparation, characterization, cytotoxicity and pharmacokinetics of liposomes containing lipophilic gemcitabine prodrugs. Journal of controlled release : official journal of the Controlled Release Society. 2004 Dec; 100(3):331-46. doi: 10.1016/j.jconrel.2004.09.001. [PMID: 15567500]
  • Hilmi Orhan, Berry van Holland, Betty Krab, Janine Moeken, Nico P E Vermeulen, Peter Hollander, John H N Meerman. Evaluation of a multi-parameter biomarker set for oxidative damage in man: increased urinary excretion of lipid, protein and DNA oxidation products after one hour of exercise. Free radical research. 2004 Dec; 38(12):1269-79. doi: 10.1080/10715760400013763. [PMID: 15763951]
  • M Corradi, P Pignatti, P Manini, R Andreoli, M Goldoni, M Poppa, G Moscato, B Balbi, A Mutti. Comparison between exhaled and sputum oxidative stress biomarkers in chronic airway inflammation. The European respiratory journal. 2004 Dec; 24(6):1011-7. doi: 10.1183/09031936.04.00002404. [PMID: 15572547]
  • Min Lu, Lena Staszewski, Fernando Echeverri, Hong Xu, Bryan D Moyer. Endoplasmic reticulum degradation impedes olfactory G-protein coupled receptor functional expression. BMC cell biology. 2004 Sep; 5(?):34. doi: 10.1186/1471-2121-5-34. [PMID: 15369603]
  • Michele Morsch, Leury G J Girardi, Valdir Cechinel-Filho, Christiane Meyre-Silva, Clóvis Antonio Rodrigues. Separation of flavonoids from Aleurites moluccana leaves using chitosan modified with heptaldehyde. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2004 Sep; 59(9-10):649-52. doi: 10.1515/znc-2004-9-1007. [PMID: 15540596]
  • Massimo Corradi, Israel Rubinstein, Roberta Andreoli, Paola Manini, Andrea Caglieri, Diana Poli, Rossella Alinovi, Antonio Mutti. Aldehydes in exhaled breath condensate of patients with chronic obstructive pulmonary disease. American journal of respiratory and critical care medicine. 2003 May; 167(10):1380-6. doi: 10.1164/rccm.200210-1253oc. [PMID: 12522029]
  • B Chantegrel, C Deshayes, A Doutheau, J P Steghens. Synthesis of 9,9,9-trideutero-1,4-dihydroxynonane mercapturic acid (d3-DHN-MA), a useful internal standard for DHN-MA urinalysis. Lipids. 2002 Oct; 37(10):1013-8. doi: 10.1007/s11745-006-0994-z. [PMID: 12530562]
  • Saskia M van Ruth, Carmel King, Persephoni Giannouli. Influence of lipid fraction, emulsifier fraction, and mean particle diameter of oil-in-water emulsions on the release of 20 aroma compounds. Journal of agricultural and food chemistry. 2002 Apr; 50(8):2365-71. doi: 10.1021/jf011072s. [PMID: 11929298]
  • S Mashiba, Y Wada, M Takeya, A Sugiyama, T Hamakubo, A Nakamura, N Noguchi, E Niki, A Izumi, M Kobayashi, K Uchida, T Kodama. In vivo complex formation of oxidized alpha(1)-antitrypsin and LDL. Arteriosclerosis, thrombosis, and vascular biology. 2001 Nov; 21(11):1801-8. doi: 10.1161/hq1101.098232. [PMID: 11701469]
  • X Zhu, K Wang, J Zhu, M Koga. Analysis of cooking oil fumes by ultraviolet spectrometry and gas chromatography-mass spectrometry. Journal of agricultural and food chemistry. 2001 Oct; 49(10):4790-4. doi: 10.1021/jf001084y. [PMID: 11600023]
  • C Wang, J Xing, C K Chin, C T Ho, C E Martin. Modification of fatty acids changes the flavor volatiles in tomato leaves. Phytochemistry. 2001 Sep; 58(2):227-32. doi: 10.1016/s0031-9422(01)00233-3. [PMID: 11551543]
  • T L Zielinski, S A Smith, J J Pestka, J I Gray, D M Smith. Elisa to quantify hexanal-protein adducts in a meat model system. Journal of agricultural and food chemistry. 2001 Jun; 49(6):3017-23. doi: 10.1021/jf001151o. [PMID: 11410003]
  • S Srivastava, S J Watowich, J M Petrash, S K Srivastava, A Bhatnagar. Structural and kinetic determinants of aldehyde reduction by aldose reductase. Biochemistry. 1999 Jan; 38(1):42-54. doi: 10.1021/bi981794l. [PMID: 9890881]
  • T Ogihara, K Hirano, T Morinobu, H S Kim, M Hiroi, H Ogihara, H Tamai. Raised concentrations of aldehyde lipid peroxidation products in premature infants with chronic lung disease. Archives of disease in childhood. Fetal and neonatal edition. 1999 Jan; 80(1):F21-5. doi: 10.1136/fn.80.1.f21. [PMID: 10325806]
  • M Yazdanpanah, X Luo, R Lau, M Greenberg, L J Fisher, D C Lehotay. Cytotoxic aldehydes as possible markers for childhood cancer. Free radical biology & medicine. 1997; 23(6):870-8. doi: 10.1016/s0891-5849(97)00070-1. [PMID: 9378366]