Isoeugenol (BioDeep_00000268418)

Main id: BioDeep_00000008108

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Phenol, 2-methoxy-4-(1-propenyl)-, (E)- (9CI)

化学式: C10H12O2 (164.0837)
中文名称: 丙烯基愈创木酚, 异丁香酚(正+反), 异丁香酚, (E)-2-甲氧基-4-(1-丙烯基苯酚)
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C=C/c1ccc(O)c(OC)c1
InChI: InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3

描述信息

A phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group.
It is used in flavourings. Occurs in ylang-ylang and other essential oils. Isoeugenol is found in many foods, some of which are celeriac, spearmint, kale, and pepper (c. baccatum).
Isoeugenol is an essential oil constituent of nutmeg, clove, and cinnamon. Isoeugenol inhibits growth of Escherichia coli and Listeria innocua with MICs of 0.6 mg/mL and 1 mg/mL, respectively[1].
Isoeugenol is an essential oil constituent of nutmeg, clove, and cinnamon. Isoeugenol inhibits growth of Escherichia coli and Listeria innocua with MICs of 0.6 mg/mL and 1 mg/mL, respectively[1].

同义名列表

61 个代谢物同义名

Isoeugenol; trans-Isoeugenol; Phenol, 2-methoxy-4-(1-propenyl)-, (E)- (9CI); 3-06-00-04993 (Beilstein Handbook Reference); 3-Methoxy-4-hydroxy-1-propen-1-ylbenzene; 1-Hydroxy-2-methoxy-4-propen-1-ylbenzene; 4-Hydroxy-3-methoxy-1-propen-1-ylbenzene; 1-(3-Methoxy-4-hydroxyphenyl)-1-propane; Phenol, 2-methoxy-4-(1-propenyl)-, (E)-; 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol; Phenol,2-methoxy-4-(1E)-1-propen-1-yl-; 1-Hydroxy-2-methoxy-4-propenylbenzene; 4-Hydroxy-3-methoxy-1-propenylbenzene; Phenol, 2-methoxy-4-propenyl-, (E)-; (E)-2-Methoxy-4-(prop-1-enyl)phenol; 4-Hydroxy-3-methoxypropenylbenzene; Phenol, 2-methoxy-4-(1-propenyl)-; trans-2-Methoxy-4-propenylphenol; 2-methoxy-4-prop-1-enyl-phenol; 2-METHOXY-4-(1-PROPENYL)PHENOL; Phenol, 2-methoxy-4-propenyl-; 2-methoxy-4-prop-1-enylphenol; 4-PROPENYLGUAIACOL (TRANS); 2-methoxy-4-propenylphenol; trans-p-Propenylquaiacol; Isoeugenol trans-form; WLN: 2U1R DQ CO1 -E; 4-Propenylguaiacol; EINECS 227-678-2; EINECS 202-590-7; WLN: 2U1R DQ CO1; W246808_ALDRICH; NCGC00091470-02; NCGC00091470-01; Isoeugenol (I); (E)-Isoeugenol; I17206_ALDRICH; FEMA No. 2468; 34038_RIEDEL; ZINC00391122; 58850_FLUKA; BRN 1909602; CHEBI:18224; BRN 2046156; NCI-C60979; NSC 209522; 5932-68-3; CCRIS 744; AI3-15356; ST5407449; NSC209522; NSC 6769; 97-54-1; NSC6769; C10469; 2-methoxy-4-(prop-1-en-1-yl)phenol; e-isoeugenol; iso-Eugenol; Isoeugenol; Propenylguaiacol; Isoeugenol



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(2)

BioCyc(1)

PlantCyc(1)

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)

124 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 AKT1, BCL2, CAT, CYP1A1, MAPK14, NFKB1, NFKBIA, PTGS2
Peripheral membrane protein 4 ACHE, CYP1A1, CYP1B1, PTGS2
Endoplasmic reticulum membrane 4 BCL2, CYP1A1, CYP1B1, PTGS2
Nucleus 8 ACHE, AKT1, BCL2, JUND, MAPK14, MYB, NFKB1, NFKBIA
cytosol 9 AKT1, BCL2, CAT, GSR, MAPK14, MYB, NFKB1, NFKBIA, NGF
dendrite 1 NGF
nucleoplasm 7 AKT1, ATP2B1, JUND, MAPK14, MYB, NFKB1, NFKBIA
RNA polymerase II transcription regulator complex 2 JUND, MYB
Cell membrane 4 ACHE, AKT1, ATP2B1, CD86
lamellipodium 1 AKT1
Multi-pass membrane protein 1 ATP2B1
Synapse 2 ACHE, ATP2B1
cell cortex 1 AKT1
cell surface 2 ACHE, CD86
glutamatergic synapse 3 AKT1, ATP2B1, MAPK14
Golgi apparatus 2 ACHE, ATRN
mitochondrial inner membrane 1 CYP1A1
neuromuscular junction 1 ACHE
postsynapse 1 AKT1
presynaptic membrane 1 ATP2B1
synaptic vesicle 1 NGF
plasma membrane 6 ACHE, AKT1, ATP2B1, ATRN, CD86, NFKBIA
synaptic vesicle membrane 1 ATP2B1
Membrane 8 ACHE, AKT1, ATP2B1, BCL2, CAT, CD86, CYP1B1, MYB
axon 1 NGF
basolateral plasma membrane 1 ATP2B1
caveola 1 PTGS2
extracellular exosome 5 ATP2B1, ATRN, CAT, CD86, GSR
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 6 ACHE, ATRN, CXCL8, IL2, IL4, NGF
perinuclear region of cytoplasm 1 ACHE
mitochondrion 7 BCL2, CAT, CYP1A1, CYP1B1, GSR, MAPK14, NFKB1
protein-containing complex 4 AKT1, BCL2, CAT, PTGS2
intracellular membrane-bounded organelle 4 ATP2B1, CAT, CYP1A1, CYP1B1
Microsome membrane 3 CYP1A1, CYP1B1, PTGS2
Single-pass type I membrane protein 2 ATRN, CD86
Secreted 5 ACHE, CXCL8, IL2, IL4, NGF
extracellular region 8 ACHE, CAT, CXCL8, IL2, IL4, MAPK14, NFKB1, NGF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 2 CAT, GSR
Extracellular side 1 ACHE
transcription regulator complex 2 JUND, NFKB1
centriolar satellite 1 CD86
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 CD86, GSR
microtubule cytoskeleton 1 AKT1
cell-cell junction 1 AKT1
vesicle 1 AKT1
Mitochondrion inner membrane 1 CYP1A1
pore complex 1 BCL2
focal adhesion 1 CAT
spindle 1 AKT1
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
lateral plasma membrane 1 ATP2B1
nuclear speck 1 MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
ciliary basal body 1 AKT1
chromatin 2 JUND, NFKB1
cell projection 1 ATP2B1
spindle pole 1 MAPK14
Basolateral cell membrane 1 ATP2B1
Lipid-anchor, GPI-anchor 1 ACHE
[Isoform 3]: Secreted 1 ATRN
endosome lumen 1 NGF
Presynaptic cell membrane 1 ATP2B1
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 3 CAT, MAPK14, NFKB1
Golgi lumen 1 NGF
endoplasmic reticulum lumen 1 PTGS2
nuclear matrix 1 MYB
transcription repressor complex 1 JUND
specific granule lumen 1 NFKB1
immunological synapse 1 ATP2B1
synaptic cleft 1 ACHE
[Isoform 1]: Cell membrane 1 ATRN
transcription factor AP-1 complex 1 JUND
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 2 NFKB1, NFKBIA
NF-kappaB p50/p65 complex 1 NFKB1
[Isoform H]: Cell membrane 1 ACHE


文献列表

  • Lakshmi Goswami, Lovely Gupta, Sayantan Paul, Pooja Vijayaraghavan, Asish Kumar Bhattacharya. Design and Synthesis of 1,3-Diynes as Potent Antifungal Agents Against Aspergillus fumigatus. ChemMedChem. 2023 Feb; ?(?):e202300013. doi: 10.1002/cmdc.202300013. [PMID: 36852543]
  • Takao Koeduka, Bunta Watanabe, Konomi Shirahama, Masaru Nakayasu, Shiro Suzuki, Takumi Furuta, Hideyuki Suzuki, Kenji Matsui, Tomoyuki Kosaka, Shin-Ichi Ozaki. Biosynthesis of dillapiole/apiole in dill (Anethum graveolens): characterization of regioselective phenylpropene O-methyltransferase. The Plant journal : for cell and molecular biology. 2023 02; 113(3):562-575. doi: 10.1111/tpj.16068. [PMID: 36534115]
  • Xiaoling Zhang, Susan P Felter, Anne Marie Api, Kaushal Joshi, Dan Selechnik. A Cautionary tale for using read-across for cancer hazard classification: Case study of isoeugenol and methyl eugenol. Regulatory toxicology and pharmacology : RTP. 2022 Dec; 136(?):105280. doi: 10.1016/j.yrtph.2022.105280. [PMID: 36367523]
  • Lakshmi Goswami, Lovely Gupta, Sayantan Paul, Maansi Vermani, Pooja Vijayaraghavan, Asish K Bhattacharya. Design and synthesis of eugenol/isoeugenol glycoconjugates and other analogues as antifungal agents against Aspergillus fumigatus. RSC medicinal chemistry. 2022 Aug; 13(8):955-962. doi: 10.1039/d2md00138a. [PMID: 36092146]
  • Yi Zhou, Zhanqiang Li, Dejun Zhang, Benyin Zhang. Screening of bioactive ingredients of Tsantan Sumtang in ameliorating H9c2 cells injury. Journal of ethnopharmacology. 2022 Mar; 285(?):114854. doi: 10.1016/j.jep.2021.114854. [PMID: 34808301]
  • Hajime Ono. Functional characterization of an olfactory receptor in the Oriental fruit fly, Bactrocera dorsalis, that responds to eugenol and isoeugenol. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology. 2022 Feb; 258(?):110696. doi: 10.1016/j.cbpb.2021.110696. [PMID: 34800681]
  • Waleed Bakry Suleiman. In vitro estimation of superfluid critical extracts of some plants for their antimicrobial potential, phytochemistry, and GC-MS analyses. Annals of clinical microbiology and antimicrobials. 2020 Jul; 19(1):29. doi: 10.1186/s12941-020-00371-1. [PMID: 32680515]
  • Anton C de Groot. Fragrances: Contact Allergy and Other Adverse Effects. Dermatitis : contact, atopic, occupational, drug. 2020 Jan; 31(1):13-35. doi: 10.1097/der.0000000000000463. [PMID: 31433384]
  • Lijun Zhou, Zhilin Zhang, Mi Wei, Yongjian Xie, Shan He, Hongan Shi, Zhufeng Lin. Evaluation of the antifungal activity of individual and combined monoterpenes against Rhizopus stolonifer and Absidia coerulea. Environmental science and pollution research international. 2019 Mar; 26(8):7804-7809. doi: 10.1007/s11356-019-04278-z. [PMID: 30675711]
  • Sarmistha Saha, Ramtej J Verma. Molecular interactions of active constituents of essential oils in zwitterionic lipid bilayers. Chemistry and physics of lipids. 2018 07; 213(?):76-87. doi: 10.1016/j.chemphyslip.2018.03.008. [PMID: 29596800]
  • Toshiki Furuya, Mari Kuroiwa, Kuniki Kino. Biotechnological production of vanillin using immobilized enzymes. Journal of biotechnology. 2017 Feb; 243(?):25-28. doi: 10.1016/j.jbiotec.2016.12.021. [PMID: 28042012]
  • Christina Krogsgård Nielsen, Jørgen Kjems, Tina Mygind, Torben Snabe, Karin Schwarz, Yvonne Serfert, Rikke Louise Meyer. Antimicrobial effect of emulsion-encapsulated isoeugenol against biofilms of food pathogens and spoilage bacteria. International journal of food microbiology. 2017 Feb; 242(?):7-12. doi: 10.1016/j.ijfoodmicro.2016.11.002. [PMID: 27851985]
  • Aaron D Gross, Kevin B Temeyer, Tim A Day, Adalberto A Pérez de León, Michael J Kimber, Joel R Coats. Interaction of plant essential oil terpenoids with the southern cattle tick tyramine receptor: A potential biopesticide target. Chemico-biological interactions. 2017 Feb; 263(?):1-6. doi: 10.1016/j.cbi.2016.12.009. [PMID: 27986436]
  • Larissa Rangel Peixoto, Pedro Luiz Rosalen, Gabriela Lacet Silva Ferreira, Irlan Almeida Freires, Fabíola Galbiatti de Carvalho, Lúcio Roberto Castellano, Ricardo Dias de Castro. Antifungal activity, mode of action and anti-biofilm effects of Laurus nobilis Linnaeus essential oil against Candida spp. Archives of oral biology. 2017 Jan; 73(?):179-185. doi: 10.1016/j.archoralbio.2016.10.013. [PMID: 27771586]
  • Waheba Elsayed, Lamia El-Shafie, Mohamed K Hassan, Mohamed A Farag, Sherif F El-Khamisy. Isoeugenol is a selective potentiator of camptothecin cytotoxicity in vertebrate cells lacking TDP1. Scientific reports. 2016 05; 6(?):26626. doi: 10.1038/srep26626. [PMID: 27220325]
  • Nur Fariza M Shaipulah, Joëlle K Muhlemann, Benjamin D Woodworth, Alex Van Moerkercke, Julian C Verdonk, Aldana A Ramirez, Michel A Haring, Natalia Dudareva, Robert C Schuurink. CCoAOMT Down-Regulation Activates Anthocyanin Biosynthesis in Petunia. Plant physiology. 2016 Feb; 170(2):717-31. doi: 10.1104/pp.15.01646. [PMID: 26620524]
  • Nami Kim, Jung Ok Lee, Hye Jeong Lee, Yong Woo Lee, Hyung Ip Kim, Su Jin Kim, Sun Hwa Park, Chul Su Lee, Sun Woo Ryoo, Geum-Sook Hwang, Hyeon Soo Kim. AMPK, a metabolic sensor, is involved in isoeugenol-induced glucose uptake in muscle cells. The Journal of endocrinology. 2016 Feb; 228(2):105-14. doi: 10.1530/joe-15-0302. [PMID: 26585419]
  • Alok K Gupta, Ines Schauvinhold, Eran Pichersky, Florian P Schiestl. Eugenol synthase genes in floral scent variation in Gymnadenia species. Functional & integrative genomics. 2014 Dec; 14(4):779-88. doi: 10.1007/s10142-014-0397-9. [PMID: 25239559]
  • I Lynch Ianniello, M Battán Horenstein, M C Lábaque, A Luna, R H Marin, R M Gleiser. Fly emergence from manure of Japanese quail fed thymol- or isoeugenol-supplemented diets. Poultry science. 2014 Oct; 93(10):2449-56. doi: 10.3382/ps.2014-03951. [PMID: 25104767]
  • M N Gallucci, M E Carezzano, M M Oliva, M S Demo, R P Pizzolitto, M P Zunino, J A Zygadlo, J S Dambolena. In vitro activity of natural phenolic compounds against fluconazole-resistant Candida species: a quantitative structure-activity relationship analysis. Journal of applied microbiology. 2014 Apr; 116(4):795-804. doi: 10.1111/jam.12432. [PMID: 24387763]
  • T Koeduka, K Sugimoto, B Watanabe, N Someya, D Kawanishi, T Gotoh, R Ozawa, J Takabayashi, K Matsui, J Hiratake. Bioactivity of natural O-prenylated phenylpropenes from Illicium anisatum leaves and their derivatives against spider mites and fungal pathogens. Plant biology (Stuttgart, Germany). 2014 Mar; 16(2):451-6. doi: 10.1111/plb.12054. [PMID: 23889818]
  • Indu Kumari Renu, Inamul Haque, Manish Kumar, Raju Poddar, Rajib Bandopadhyay, Amit Rai, Kunal Mukhopadhyay. Characterization and functional analysis of eugenol O-methyltransferase gene reveal metabolite shifts, chemotype specific differential expression and developmental regulation in Ocimum tenuiflorum L. Molecular biology reports. 2014 Mar; 41(3):1857-70. doi: 10.1007/s11033-014-3035-7. [PMID: 24420851]
  • Sung-Jin Kim, Daniel G Vassão, Syed G A Moinuddin, Diana L Bedgar, Laurence B Davin, Norman G Lewis. Allyl/propenyl phenol synthases from the creosote bush and engineering production of specialty/commodity chemicals, eugenol/isoeugenol, in Escherichia coli. Archives of biochemistry and biophysics. 2014 Jan; 541(?):37-46. doi: 10.1016/j.abb.2013.10.019. [PMID: 24189289]
  • Katja Nehrenheim, Imke Meyer, Heidi Brenden, Gabriele Vielhaber, Jean Krutmann, Susanne Grether-Beck. Dihydrodehydrodiisoeugenol enhances adipocyte differentiation and decreases lipolysis in murine and human cells. Experimental dermatology. 2013 Oct; 22(10):638-43. doi: 10.1111/exd.12218. [PMID: 24079732]
  • Martin Zabka, Roman Pavela. Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. Chemosphere. 2013 Oct; 93(6):1051-6. doi: 10.1016/j.chemosphere.2013.05.076. [PMID: 23800587]
  • Eric Andres, Vanessa M Sá-Rocha, Carla Barrichello, Tina Haupt, Graham Ellis, Andreas Natsch. The sensitivity of the KeratinoSens™ assay to evaluate plant extracts: a pilot study. Toxicology in vitro : an international journal published in association with BIBRA. 2013 Jun; 27(4):1220-5. doi: 10.1016/j.tiv.2013.02.008. [PMID: 23428960]
  • Sathya N Prasad, Muralidhara. Evidence of acrylamide induced oxidative stress and neurotoxicity in Drosophila melanogaster - its amelioration with spice active enrichment: relevance to neuropathy. Neurotoxicology. 2012 Oct; 33(5):1254-64. doi: 10.1016/j.neuro.2012.07.006. [PMID: 22841601]
  • Esra Fındık, Mustafa Ceylan, Mahfuz Elmastaş. Isoeugenol-based novel potent antioxidants: synthesis and reactivity. European journal of medicinal chemistry. 2011 Sep; 46(9):4618-24. doi: 10.1016/j.ejmech.2011.07.041. [PMID: 21843909]
  • Thomas A Colquhoun, Joo Young Kim, Ashlyn E Wedde, Laura A Levin, Kyle C Schmitt, Robert C Schuurink, David G Clark. PhMYB4 fine-tunes the floral volatile signature of Petunia x hybrida through PhC4H. Journal of experimental botany. 2011 Jan; 62(3):1133-43. doi: 10.1093/jxb/erq342. [PMID: 21068208]
  • . Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). National Toxicology Program technical report series. 2010 Sep; ?(551):1-178. doi: . [PMID: 21372857]
  • Nicholas P L Tuckey, Malcolm E Forster, Steven P Gieseg. Effects of rested harvesting on muscle metabolite concentrations and K-values in Chinook salmon (Oncorhynchus tshawytscha) fillets during storage at 15 degrees C. Journal of food science. 2010 Jun; 75(5):C459-64. doi: 10.1111/j.1750-3841.2010.01648.x. [PMID: 20629868]
  • Ben Spitzer-Rimon, Elena Marhevka, Oren Barkai, Ira Marton, Orit Edelbaum, Tania Masci, Naveen-Kumar Prathapani, Elena Shklarman, Marianna Ovadis, Alexander Vainstein. EOBII, a gene encoding a flower-specific regulator of phenylpropanoid volatiles' biosynthesis in petunia. The Plant cell. 2010 Jun; 22(6):1961-76. doi: 10.1105/tpc.109.067280. [PMID: 20543029]
  • Ji-Young Ryu, Jiyoung Seo, Tatsuya Unno, Joong-Hoon Ahn, Tao Yan, Michael J Sadowsky, Hor-Gil Hur. Isoeugenol monooxygenase and its putative regulatory gene are located in the eugenol metabolic gene cluster in Pseudomonas nitroreducens Jin1. Archives of microbiology. 2010 Mar; 192(3):201-9. doi: 10.1007/s00203-010-0547-y. [PMID: 20091296]
  • D G Cook, A J Holland, A R Jerrett, M E Forster. Effect of harvest treatment on biochemical properties of farmed Chinook salmon (Oncorhynchus tshawytscha) tissue during frozen and thawed storage. Journal of food science. 2009 Sep; 74(7):C543-8. doi: 10.1111/j.1750-3841.2009.01264.x. [PMID: 19895458]
  • Takao Koeduka, Irina Orlova, Thomas J Baiga, Joseph P Noel, Natalia Dudareva, Eran Pichersky. The lack of floral synthesis and emission of isoeugenol in Petunia axillaris subsp. parodii is due to a mutation in the isoeugenol synthase gene. The Plant journal : for cell and molecular biology. 2009 Jun; 58(6):961-9. doi: 10.1111/j.1365-313x.2009.03834.x. [PMID: 19222805]
  • Nicholas P L Tuckey, Malcolm E Forster, Steven P Gieseg. Lipid oxidation is inhibited by isoeugenol exposure in chinook Salmon (Oncorhynchus Tshawytscha) fillets during storage at 15 degrees C. Journal of food science. 2009 May; 74(4):C333-8. doi: 10.1111/j.1750-3841.2009.01135.x. [PMID: 19490320]
  • Sen-Sung Cheng, Ju-Yun Liu, Ed-Haun Chang, Shang-Tzen Chang. Antifungal activity of cinnamaldehyde and eugenol congeners against wood-rot fungi. Bioresource technology. 2008 Jul; 99(11):5145-9. doi: 10.1016/j.biortech.2007.09.013. [PMID: 17945485]
  • Takao Koeduka, Gordon V Louie, Irina Orlova, Christine M Kish, Mwafaq Ibdah, Curtis G Wilkerson, Marianne E Bowman, Thomas J Baiga, Joseph P Noel, Natalia Dudareva, Eran Pichersky. The multiple phenylpropene synthases in both Clarkia breweri and Petunia hybrida represent two distinct protein lineages. The Plant journal : for cell and molecular biology. 2008 May; 54(3):362-74. doi: 10.1111/j.1365-313x.2008.03412.x. [PMID: 18208524]
  • Pål A Olsvik, Kai K Lie, Ernst M Hevrøy. Do anesthetics and sampling strategies affect transcription analysis of fish tissues?. BMC molecular biology. 2007 Jun; 8(?):48. doi: 10.1186/1471-2199-8-48. [PMID: 17559653]
  • W Uter, J Geier, A Schnuch, P J Frosch. Patch test results with patients' own perfumes, deodorants and shaving lotions: results of the IVDK 1998-2002. Journal of the European Academy of Dermatology and Venereology : JEADV. 2007 Mar; 21(3):374-9. doi: 10.1111/j.1468-3083.2006.01973.x. [PMID: 17309462]
  • Masatoshi Kondo, Naomi Oyama-Okubo, Masanori Sagae, Toshio Ando, Eduardo Marchesi, Masayoshi Nakayama. Metabolic regulation of floral scent in Petunia axillaris lines: biosynthetic relationship between dihydroconiferyl acetate and iso-eugenol. Bioscience, biotechnology, and biochemistry. 2007 Feb; 71(2):458-63. doi: 10.1271/bbb.60507. [PMID: 17284848]
  • Richard Dexter, Anthony Qualley, Christine M Kish, Choong Je Ma, Takao Koeduka, Dinesh A Nagegowda, Natalia Dudareva, Eran Pichersky, David Clark. Characterization of a petunia acetyltransferase involved in the biosynthesis of the floral volatile isoeugenol. The Plant journal : for cell and molecular biology. 2007 Jan; 49(2):265-75. doi: 10.1111/j.1365-313x.2006.02954.x. [PMID: 17241449]
  • Takao Koeduka, Eyal Fridman, David R Gang, Daniel G Vassão, Brenda L Jackson, Christine M Kish, Irina Orlova, Snejina M Spassova, Norman G Lewis, Joseph P Noel, Thomas J Baiga, Natalia Dudareva, Eran Pichersky. Eugenol and isoeugenol, characteristic aromatic constituents of spices, are biosynthesized via reduction of a coniferyl alcohol ester. Proceedings of the National Academy of Sciences of the United States of America. 2006 Jun; 103(26):10128-33. doi: 10.1073/pnas.0603732103. [PMID: 16782809]
  • Yong-Hong Li, Zhi-Hao Sun, Li-Qing Zhao, Yan Xu. Bioconversion of isoeugenol into vanillin by crude enzyme extracted from soybean. Applied biochemistry and biotechnology. 2005 Apr; 125(1):1-10. doi: 10.1385/abab:125:1:001. [PMID: 15834158]
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