Isoeugenol (BioDeep_00000008108)

 

Secondary id: BioDeep_00000177216, BioDeep_00000268418

human metabolite PANOMIX_OTCML-2023 natural product Volatile Flavor Compounds


代谢物信息卡片


Isoeugenol, predominantly trans, analytical standard

化学式: C10H12O2 (164.0837252)
中文名称: (E)-2-甲氧基-4-(1-丙烯基苯酚), 异丁香酚(正+反), 异丁香酚, 4-丙烯基-2-甲氧基苯酚, 丙烯基愈创木酚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.05%

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/b4-3+

描述信息

Isoeugenol is a pale yellow oily liquid with a spice-clove odor. Freezes at 14 °F. Density 1.08 g / cm3. Occurs in ylang-ylang oil and other essential oils.
Isoeugenol is a phenylpropanoid that is an isomer of eugenol in which the allyl substituent is replaced by a prop-1-enyl group. It has a role as an allergen and a sensitiser. It is a phenylpropanoid and an alkenylbenzene. It is functionally related to a guaiacol.
Isoeugenol is a commonly used fragrance added to many commercially available products, and occurs naturally in the essential oils of plants such as ylang-ylang. It is also a significant dermatologic sensitizer and allergen, and as a result has been restricted to 200 p.p.m. since 1998 according to guidelines issued by the fragrance industry. Allergic reactivity to Isoeugenol may be identified with a patch test.
Isoeugenol is a natural product found in Chaerophyllum macrospermum, Origanum sipyleum, and other organisms with data available.
Isoeugenol is is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil and cinnamon. It is very slightly soluble in water and soluble in organic solvents. It has a spicy odor and taste of clove. Isoeugenol is prepared from eugenol by heating. Eugenol is used in perfumeries, flavorings, essential oils and in medicine (local antiseptic and analgesic). It is used in the production of isoeugenol for the manufacture of vanillin. Eugenol derivatives or methoxyphenol derivatives in wider classification are used in perfumery and flavoring. They are used in formulating insect attractants and UV absorbers, analgesics, biocides and antiseptics. They are also used in manufacturing stabilizers and antioxidants for plastics and rubbers. Isoeugenol is used in manufacturing perfumeries, flavorings, essential oils (odor description: Clove, spicy, sweet, woody) and in medicine (local antiseptic and analgesic) as well as vanillin. (A7915).
E-4-Propenyl-2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae.
Isoeugenol is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as ‚ÄúFragrance‚Äù rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID:10554062 ). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID:6991645 ).
(e)-isoeugenol, also known as 2-methoxy-4-propenylphenol or propenylgualacol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety (e)-isoeugenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (e)-isoeugenol is a sweet, carnation, and clove tasting compound and can be found in a number of food items such as corn salad, coconut, flaxseed, and winter squash, which makes (e)-isoeugenol a potential biomarker for the consumption of these food products (e)-isoeugenol can be found primarily in saliva (e)-isoeugenol exists in all eukaryotes, ranging from yeast to humans (e)-isoeugenol is a non-carcinogenic (not listed by IARC) potentially toxic compound.
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

103 个代谢物同义名

Isoeugenol, predominantly trans, analytical standard; 2-methoxy-4-(1-propenyl)phenol (ACD/Name 4.0); 3-06-00-04993 (Beilstein Handbook Reference); 4-06-00-06324 (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-propenylphenol (isoeugenol); 2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol; 1-(3-Methoxy-4-hydroxyphenyl)-1-propene; (E)-2-Methoxy-4-(prop-1-en-1-yl)phenol; Phenol,2-methoxy-4-(1E)-1-propen-1-yl-; 4-Hydroxy-3-methoxy-beta-methylstyrene; 1-Hydroxy-2-methoxy-4-propenylbenzene; 4-Hydroxy-3-methoxy-1-propenylbenzene; 3-Methoxy-4-hydroxy-1-propenylbenzene; (E)-2-Methoxy-4-(1-propen-1-yl)phenol; (E)-2-methoxy-4- (1-propenyl)-Phenol; trans-2-methoxy-4-(1-propenyl)phenol; 2-Methoxy-4-(1E)-1-propen-1-ylphenol; Phenol, 2-methoxy-4-(1-propen-1-yl)-; Phenol, 2-methoxy-4-(1E)-1-propenyl-; 4-Hydroxy-3-methoxy-β-methylstyrene; Phenol, 2-methoxy-4-propenyl-, (E)-; 2-methoxy-4-[(E)-prop-1-enyl]phenol; (E)-2-methoxy-4-(1-propenyl)-Phenol; 2-Methoxy-4-[(1E)-1-propenyl]phenol; (E)-2-Methoxy-4-(prop-1-enyl)phenol; 4-Hydroxy-3-methoxypropenylbenzene; 2-methoxy-4-(prop-1-en-1-yl)phenol; 3-Methoxy-4-hydroxypropenylbenzene; (E)-2-METHOXY-4-(1-PROPENYL)PHENOL; 2-Methoxy-4-[(E)-1-propenyl]phenol; Phenol, 2-methoxy-4-(1-propenyl)-; 2-Methoxy-4-(1-propen-1-yl)phenol; trans-2-Methoxy-4-propenylphenol; Isoeugenol, analytical standard; (E)-2-methoxy-4-propenyl-Phenol; 2-Methoxy-4(E)-1-propenylphenol; Isoeugenol, predominantly trans; 2-methoxy-4-(1-propenyl)-Phenol; 2-Methoxy-4-[1-propenyl]phenol; Isoeugenol,predominantly trans; 2-METHOXY-4-(1-PROPENYL)PHENOL; Isoeugenol, natural, 99\\%, FG; Phenol, 2-methoxy-4-propenyl-; 2-methoxy-4-propenyl-Phenol; ISOEUGENOL TRANS-FORM [MI]; 2-methoxy-4-propenylphenol; trans-p-Propenylquaiacol; trans-p-Propenylguaiacol; trans-4-Propenylguaiacol; trans-4-Propenylgualacol; isoeugenol extra nat us; 4-(1-Propenyl) Guaiacol; isoeugenol, sodium salt; Isoeugenol, cis + trans; (E)-4-PROPENYLGUAIACOL; Isoeugenol and isomers; isoeugenol, (Z)-isomer; isoeugenol, (E)-isomer; Isoeugenol trans-form; WLN: 2U1R DQ CO1 -E; ISOEUGENOL, TRANS-; 4-Propenylguaiacol; iso eugenol 88\\%+; WLN: 2U1R DQ CO1; trans-Isoeugenol; ISOEUGENOL, (E)-; Propenylguaiacol; Propenylgualacol; UNII-28FSR1NAY4; UNII-5M0MWY797U; isoeugenol tech; Isoeugenol (I); isoeugenol fcc; (E)-Isoeugenol; Isoeugenol,c&t; ISOEUGENOL, E-; Tox21_111138_1; iso-Eugenol 2; e-isoeugenol; Tox21_202433; Phenol, (E)-; Tox21_300303; Isoeugenol Z; Isoeugenol E; Tox21_111138; Iso eugenol; Iso-eugenol; CAS-97-54-1; IE TRANS 92; 28FSR1NAY4; Isoeugenol; 5M0MWY797U; isougenol; AI3-15356; CHISOEUG; Isoeugenol; Propenylguaiacol; Isoeugenol



数据库引用编号

30 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

152 个相关的代谢反应过程信息。

Reactome(2)

  • Olfactory Signaling Pathway: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13
  • Sensory Perception: GTP + odorant:Olfactory Receptor:GNAL:GDP:GNB1:GNG13 ⟶ GDP + odorant:Olfactory Receptor:GNAL:GTP:GNB1:GNG13

BioCyc(3)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(147)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

131 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

  • 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]
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  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
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  • 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]
  • 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]
  • 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]
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  • 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]
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  • 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]
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  • 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]
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