Eugenol (BioDeep_00000002269)

 

Secondary id: BioDeep_00000406524, BioDeep_00000859504

human metabolite PANOMIX_OTCML-2023 blood metabolite natural product


代谢物信息卡片


Eugenol, Pharmaceutical Secondary Standard; Certified Reference Material

化学式: C10H12O2 (164.0837)
中文名称: 烯丙基甲氧基苯酚, 异丁香酚苯乙醚, 丁子香酸, 丁子香酚, 丁香油酚, 丁香酚
谱图信息: 最多检出来源 Homo sapiens(blood) 26.55%

分子结构信息

SMILES: c1cc(c(cc1CC=C)OC)O
InChI: InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3

描述信息

Eugenol appears as clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste. (NTP, 1992)
Eugenol is a phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis. It has a role as an allergen, a human blood serum metabolite, a sensitiser, a volatile oil component, a flavouring agent, an EC 1.4.3.4 (monoamine oxidase) inhibitor, a radical scavenger, an antibacterial agent, an antineoplastic agent, an apoptosis inducer, an anaesthetic, an analgesic, a voltage-gated sodium channel blocker, a NF-kappaB inhibitor and an anti-inflammatory agent. It is a phenylpropanoid, a monomethoxybenzene, a member of phenols and an alkenylbenzene. It is functionally related to a guaiacol.
Eugenol is a naturally occurring phenolic molecule found in several plants such as cinnamon, clove, and bay leaves. It has been used as a topical antiseptic as a counter-irritant and in dental preparations with zinc oxide for root canal sealing and pain control. Although not currently available in any FDA-approved products (including OTC), eugenol has been found to have anti-inflammatory, neuroprotective, antipyretic, antioxidant, antifungal and analgesic properties. Its exact mechanism of action is unknown, however, it has been shown to interfere with action potential conduction. There are a number of unapproved OTC products available containing eugenol that advertise its use for the treatment of toothache.
Eugenol is a Standardized Chemical Allergen. The physiologic effect of eugenol is by means of Increased Histamine Release, and Cell-mediated Immunity.
Eugenol, also called clove oil, is an aromatic oil extracted from cloves that is used widely as a flavoring for foods and teas and as an herbal oil used topically to treat toothache and more rarely to be taken orally to treat gastrointestinal and respiratory complaints. Eugenol in therapeutic doses has not been implicated in causing serum enzyme elevations or clinically apparent liver injury, but ingestions of high doses, as with an overdose, can cause severe liver injury.
Eugenol is a natural product found in Dahlia sherffii, Elettaria cardamomum, and other organisms with data available.
Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. Eugenol is a member of the allylbenzene class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like odor. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia).
4-Allyl-2-methoxyphenol is a metabolite found in or produced by Saccharomyces cerevisiae.
A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS.
See also: Cinnamon (part of); Clove Oil (part of); Cinnamon Leaf Oil (part of) ... View More ...
Eugenol is an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. It is slightly soluble in water and soluble in organic solvents. It has a pleasant, spicy, clove-like aroma. Eugenol is an allyl chain-substituted guaiacol, i.e. 2-methoxy-4-(2-propenyl)phenol. It is a clear to pale yellow oily liquid extracted from certain essential oils especially from clove oil, nutmeg, cinnamon, and bay leaf. Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anaesthetic. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from petrochemicals or from by-products of paper manufacture (Wikipedia). Eugenol is used in perfumeries, flavorings, essential oils and in medicine as a local antiseptic and anesthetic. It is a key ingredient in Indonesian kretek (clove) cigarettes. It was used in the production of isoeugenol for the manufacture of vanillin, though most vanillin is now produced from phenol or from lignin. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Eugenol has a very widespread occurrence in essential oils. Major component of clove oil. Also found in citrus and thyme oils. It is found in foods such as apple, apricot, banana and cherry fruits.
Eugenol or 4-allyl-2-methoxyphenol is classified as a phenylpropanoid, formally derived from guaiacol, with an allyl chain positioned para to the hydroxy group. It is soluble in water, alcohol, chloroform, ether and oils. Eugenol is a neutral compound. It is biosynthesized from tyrosine. Eugenol is widely distributed in plants. It is a clear to pale yellow oily liquid extracted from clove oil, nutmeg, cinnamon, basil and bay leaf. It has a pleasant, spicy, clove-like odor with a spicy pungent taste. Eugenol is found in highest concentrations in cloves, allspices, and carrots and in lower concentrations in walnuts, ceylon cinnamons, and wild carrots. Eugenol has also been detected in shea tree, passion fruits, winged beans, fireweeds, and gingers, making it a potential biomarker for the consumption of these foods. Eugenol is used in perfumeries, flavorings and essential oils. It was first used for the manufacture of vanillin (https://doi.org/10.1021/ed054p776), though most vanillin is now produced from petrochemicals or from by-products of paper manufacture. Eugenol is hepatotoxic, meaning it may cause damage to the liver, if consumed in high doses. Eugenol has local antiseptic and anaesthetic properties (PMID:15089054 ; PMID:935250 ) and acts as positive allosteric modulators of the GABA-A receptor. It has high antioxidant, anti-proliferative, and anti-inflammatory activities with potential roles in alleviating and preventing cancer and inflammatory reactions (PMID:27771920 ).
A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group. It is a major component of clove essential oil, and exhibits antibacterial, analgesic and antioxidant properties. It has been widely used in dentistry to treat toothache and pulpitis.
C78272 - Agent Affecting Nervous System > C245 - Anesthetic Agent
D000890 - Anti-Infective Agents
D012997 - Solvents
[Raw Data] CB226_Eugenol_pos_10eV_CB000079.txt
[Raw Data] CB226_Eugenol_pos_20eV_CB000079.txt
[Raw Data] CB226_Eugenol_pos_40eV_CB000079.txt
[Raw Data] CB226_Eugenol_pos_50eV_CB000079.txt
[Raw Data] CB226_Eugenol_pos_30eV_CB000079.txt
Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.
Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity. Eugenol is shown to inhibit lipid peroxidation.

同义名列表

144 个代谢物同义名

Eugenol, Pharmaceutical Secondary Standard; Certified Reference Material; InChI=1/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H; Eugenol, United States Pharmacopeia (USP) Reference Standard; 2-methoxy-4-(prop-2-en-1-yl)phenol4-allyl-2-methoxyphenol; Eugenol, European Pharmacopoeia (EP) Reference Standard; EUGENOL (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]; EUGENOL (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]; Eugenol, certified reference material, TraceCERT(R); Eugenol, primary pharmaceutical reference standard; EUGENOL (CONSTITUENT OF HOLY BASIL LEAF) [DSC]; Eugenol, PESTANAL(R), analytical standard; 1-Hydroxy-2-methoxy-4-prop-2-enylbenzene; 3-(4-Hydroxy-3-methoxyphenyl)-1-propene; Eugenol, Vetec(TM) reagent grade, 98\\%; 1-Hydroxy-2-methoxy-4-propenylbenzene; Phenol, 2-methoxy-4-(2-propen-1-yl)-; 3-(3-methoxy-4-hydroxyphenyl)propene; Eugenol, tested according to Ph.Eur.; 4-Hydroxy-3-methoxy-1-allylbenzene; 1-Hydroxy-2-methoxy-4-allylbenzene; 1-Allyl-3-methoxy-4-hydroxybenzene; 1-hydroxy-4-allyl-2-methoxybenzene; 4-Allyl-1-hydroxy-2-methoxybenzene; 1-allyl-4-hydroxy-3-methoxybenzene; 2-Methoxy-1-hydroxy-4-allylbenzene; 2-methoxy-4-(prop-2-en-1-yl)phenol; Phenol, 2-methoxy-4-(2-propenyl)-; 2-Methoxy-4-(2-propen-1-yl)phenol; 2-Metoksy-4-allilofenol [Polish]; 4-Hydroxy-3-methoxyallylbenzene; 2-methoxy-4-(2-propenyl)-phenol; 2-Methoxy-4-(2’-propenyl)phenol; 4-(2-Propenyl)-2-methoxyphenol; 2-METHOXY-4-(2-PROPENYL)PHENOL; 4-Allylcatechol 2-methyl ether; 2-Methoxy-4-(2-propenyl)phenol; 2-methoxy-4-prop-2-enyl-phenol; 2-Methoxy-4-(3-propenyl)phenol; 4-Allylcatechol-2-methyl ether; Eugenol, ReagentPlus(R), 99\\%; 2-Methoxy-4-prop-2-enylphenol; Eugenol Toothache Medication; Eugenol, natural, >=98\\%, FG; AnaDent Childrens Kanka Gel; 2-Methoxy-4-[2-allyl]phenol; Phenol, 4-allyl-2-methoxy-; 2-Hydroxy-5-allylanisole; Eugenol, >=98\\%, FCC, FG; 4-allyl-2-methoxy-Phenol; Marshall Toothache Drops; EUGENOL (USP MONOGRAPH); 4-allyl 2-methoxyphenol; EUGENOL [USP MONOGRAPH]; 2-Methoxy-4-allylphenol; 4-Allyl-2-methoxyphenol; 2-Metoksy-4-allilofenol; EUGENOL (EP MONOGRAPH); EUGENOL [EP MONOGRAPH]; 4-allyl-2methoxyphenol; Eugenol, puriss., 98\\%; British Pharmacopoeia; clove oil terpeneless; eugenol for synthesis; Red Cross Toothache; clove oil fraction; flash distillation; 4-Allenylguaiacol; Caryophillic acid; Nuby Teething Gel; Caryophyllic acid; Eugenol (natural); Synthetic eugenol; WLN: 1U2R DQ CO1; Spectrum2_001264; US Pharmacopoeia; Spectrum3_000646; EUGENOL [WHO-DD]; EUGENOL (USP-RS); EUGENOL [USP-RS]; Spectrum4_001783; Spectrum5_000425; EUGENOL (MART.); UNII-3T8H1794QW; p-Allylguaiacol; 5-Allylguaiacol; phenylpropanoid; EUGENOL [MART.]; 4-Allylguaiacol; EUGENOL [VANDF]; EUGENOL [INCI]; EUGENOL (IARC); EUGENOL [FHFI]; Eugenol [USAN]; Dentek Eugenol; Tox21_111134_1; fractionation,; EUGENOL [HSDB]; redistillation; EUGENOL [IARC]; Caryophyllate; eugenic acid,; 1,3,4-Eugenol; Eugenol (USP); DivK1c_000692; EUGENOL [FCC]; Eugenol [USP]; Allylguaiacol; KBio1_000692; allylguaicol; Tox21_202040; Eugenic acid; EUGENOL (II); Tox21_300105; EUGENOL [II]; Teething Gel; EUGENOL [MI]; Tox21_111134; KBio3_001471; animal feed; IDI1_000692; CAS-97-53-0; water white; Eugenol,(S); Eugenol BP; 3T8H1794QW; p-Eugenol; AI3-00086; Eugenate; Isolate,; naturale; naturel; Engenol; alim ue; ugenol,; natural; oogenol; fami qs; Eugenol; bioxeda; EFEUF,; clove,; 3s0e; Eugenol; Eugenol



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(3)

代谢反应

157 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(4)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(151)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

838 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, CASP3, GPX1, PIK3CA, PRKAA2, PTGS1, TYR, XDH
Peripheral membrane protein 4 ACHE, CYP1B1, HSD17B6, PTGS1
Endoplasmic reticulum membrane 3 CYP1B1, HMOX1, PTGS1
Nucleus 7 ACHE, AKT1, CASP3, HMOX1, MPO, MYB, PRKAA2
cytosol 11 AKT1, CASP3, COMT, GPX1, GSR, HMOX1, LIPE, MYB, PIK3CA, PRKAA2, XDH
dendrite 2 COMT, PRKAA2
nucleoplasm 6 AKT1, CASP3, HMOX1, MPO, MYB, PRKAA2
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 5 ACHE, AKT1, COMT, LIPE, TRPV1
Cytoplasmic side 1 HMOX1
lamellipodium 2 AKT1, PIK3CA
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 TRPV1
Synapse 2 ACHE, COMT
cell cortex 1 AKT1
cell surface 1 ACHE
glutamatergic synapse 2 AKT1, CASP3
Golgi apparatus 3 ACHE, PRKAA2, PTGS1
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 3 CASP3, PRKAA2, TRPV1
postsynapse 1 AKT1
Cytoplasm, cytosol 1 LIPE
Lysosome 3 GAA, MPO, TYR
plasma membrane 6 ACHE, AKT1, COMT, GAA, PIK3CA, TRPV1
Membrane 10 ACHE, AKT1, COMT, CYP1B1, GAA, HMOX1, LIPE, MYB, PRKAA2, TRPV1
axon 2 COMT, PRKAA2
caveola 1 LIPE
extracellular exosome 5 COMT, GAA, GSR, MPO, PTGS1
Lysosome membrane 1 GAA
Lumenal side 1 HSD17B6
endoplasmic reticulum 2 HMOX1, HSD17B6
extracellular space 5 ACHE, HMOX1, IL10, MPO, XDH
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 ACHE, HMOX1, PIK3CA, TYR
intercalated disc 1 PIK3CA
mitochondrion 3 CYP1B1, GPX1, GSR
protein-containing complex 1 AKT1
intracellular membrane-bounded organelle 7 COMT, CYP1B1, GAA, HSD17B6, MPO, PTGS1, TYR
Microsome membrane 3 CYP1B1, HSD17B6, PTGS1
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 TYR
Secreted 3 ACHE, GAA, IL10
extracellular region 4 ACHE, GAA, IL10, MPO
mitochondrial outer membrane 1 HMOX1
mitochondrial matrix 2 GPX1, GSR
Extracellular side 2 ACHE, COMT
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 2 GSR, TRPV1
microtubule cytoskeleton 1 AKT1
Melanosome membrane 1 TYR
cell-cell junction 1 AKT1
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 COMT
vesicle 1 AKT1
postsynaptic membrane 1 TRPV1
spindle 1 AKT1
GABA-ergic synapse 1 TRPV1
Peroxisome 1 XDH
basement membrane 1 ACHE
sarcoplasmic reticulum 1 XDH
Mitochondrion intermembrane space 1 AKT1
mitochondrial intermembrane space 1 AKT1
secretory granule 1 MPO
nuclear speck 1 PRKAA2
Postsynaptic cell membrane 1 TRPV1
Cell projection, neuron projection 1 TRPV1
neuron projection 1 PTGS1
ciliary basal body 1 AKT1
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 PTGS1
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
tertiary granule membrane 1 GAA
Melanosome 1 TYR
cytoplasmic stress granule 1 PRKAA2
side of membrane 1 ACHE
azurophil granule 1 MPO
nuclear matrix 1 MYB
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
azurophil granule membrane 1 GAA
azurophil granule lumen 1 MPO
Single-pass type IV membrane protein 1 HMOX1
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
death-inducing signaling complex 1 CASP3
nucleotide-activated protein kinase complex 1 PRKAA2
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
autolysosome lumen 1 GAA
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
[Isoform H]: Cell membrane 1 ACHE
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Hirotaka Matsuo, Hitomi Kawakami, Naoko Anjiki, Noriaki Kawano, Hiroyuki Fuchino, Nobuo Kawahara, Kayo Yoshimatsu. Screening of growth inhibitors for epithelial-mesenchymal transition-induced cells by TGF-β from plant-based sources identified the active compound hydroxychavicol from Piper bitle. Journal of natural medicines. 2024 Jun; 78(3):774-783. doi: 10.1007/s11418-024-01785-3. [PMID: 38418720]
  • Hawraa Issa, Lionel Loubaki, Abdullah Al Amri, Kazem Zibara, Mikhlid H Almutairi, Mahmoud Rouabhia, Abdelhabib Semlali. Eugenol as a potential adjuvant therapy for gingival squamous cell carcinoma. Scientific reports. 2024 05; 14(1):10958. doi: 10.1038/s41598-024-60754-8. [PMID: 38740853]
  • Stoja Milovanovic, Darka Markovic, Ivona Jankovic-Castvan, Ivana Lukic. Cornstarch aerogels with thymol, citronellol, carvacrol, and eugenol prepared by supercritical CO2- assisted techniques for potential biomedical applications. Carbohydrate polymers. 2024 May; 331(?):121874. doi: 10.1016/j.carbpol.2024.121874. [PMID: 38388060]
  • Yae Rim Choi, Hyun-Jin Na, Jaekwang Lee, Young-Suk Kim, Min Jung Kim. Isoeugenol Inhibits Adipogenesis in 3T3-L1 Preadipocytes with Impaired Mitotic Clonal Expansion. Nutrients. 2024 Apr; 16(9):. doi: 10.3390/nu16091262. [PMID: 38732509]
  • Bhawna Kashyap, Azhar Khan, Deepak N Kapoor. Eugenol-Loaded Transethosomal Gel for Improved Skin Delivery and Treatment of Atopic Dermatitis. AAPS PharmSciTech. 2024 Apr; 25(4):72. doi: 10.1208/s12249-024-02785-y. [PMID: 38575745]
  • Chao Yang, Yongsheng Lin, Xuwen Xiang, Dandan Shao, Ziwen Qiu, Yongyu Li, Shaohua Wu. MbEOMT1 regulates methyleugenol biosynthesis in Melaleuca bracteata F. Muell. Tree physiology. 2024 Apr; 44(4):. doi: 10.1093/treephys/tpae034. [PMID: 38498320]
  • Romério Alves Silva, Benise Ferreira da Silva, Mainara Saraiva Pereira, Paulo Adenes Teixeira Coelho, Renata Albuquerque Costa, Andrey Carvalho Chaves, Isaac Goes Neto Silva, Victor Alves Carneiro. Combinatorial effects between aromatic plant compounds and chlorhexidine digluconate against canine otitis-related Staphylococcus spp. Research in veterinary science. 2024 Apr; 170(?):105182. doi: 10.1016/j.rvsc.2024.105182. [PMID: 38377791]
  • Achraf Abdou, Fatima Ezzahra Maaghloud, Abdelhakim Elmakssoudi, Aziz Aboulmouhajir, Jamal Jamal Eddine, Mohamed Dakir. Synthesis of eugenol derivative by the ring opening of epoxide eugenol and its analysis through chemical reactivity: a DFT approach. Natural product research. 2024 Apr; 38(7):1099-1107. doi: 10.1080/14786419.2022.2132242. [PMID: 36226769]
  • Xiaochong Zhu, Jieyuan Wu, Shizhong Li, La Xiang, Jian-Ming Jin, Chaoning Liang, Shuang-Yan Tang. Artificial Biosynthetic Pathway for Efficient Synthesis of Vanillin, a Feruloyl-CoA-Derived Natural Product from Eugenol. Journal of agricultural and food chemistry. 2024 Mar; 72(12):6463-6470. doi: 10.1021/acs.jafc.3c08723. [PMID: 38501643]
  • Raju Balaji, Madasamy Parani. Development of an allele-specific PCR (AS-PCR) method for identifying high-methyl eugenol-containing purple Tulsi (Ocimum tenuiflorum L.) in market samples. Molecular biology reports. 2024 Mar; 51(1):439. doi: 10.1007/s11033-024-09365-0. [PMID: 38520476]
  • Jihao Zuo, Ruopeng Lan, Ningning Lv, Yitong Lin, Li Hao, Xinhua Zhou, Hongjun Zhou. A Promising Plant-Based Eugenol-Loaded Nano Delivery System (EUG@CMC-PGMA-CS) for Enhanced Antibacterial and Insect Repellent Behavior. ACS applied bio materials. 2024 Mar; 7(3):1643-1655. doi: 10.1021/acsabm.3c01100. [PMID: 38366996]
  • Sudarshan Naidu Chilamakuri, Ankaj Kumar, A Gowri Nath, Anshu Gupta, Sudhagar Selvaraju, Sargun Basrani, Ashwini Jadhav, Arvind Gulbake. Development and In-Vitro Evaluation of Eugenol-Based Nanostructured Lipid Carriers for Effectual Topical Treatment Against C. albicans. Journal of pharmaceutical sciences. 2024 03; 113(3):772-784. doi: 10.1016/j.xphs.2023.11.031. [PMID: 38043682]
  • Seyghah S Alrashedi, Hibah A Almasmoum, Jayda G Eldiasty. The effect of dietary eugenol nano-emulsion supplementation on growth performance, serum metabolites, redox homeostasis, immunity, and pro-inflammatory responses of growing rabbits under heat stress. Open veterinary journal. 2024 Mar; 14(3):830-839. doi: 10.5455/ovj.2024.v14.i3.10. [PMID: 38682150]
  • Negin Tavvabi-Kashani, Maede Hasanpour, Vafa Baradaran Rahimi, Naser Vahdati-Mashhadian, Vahid Reza Askari. Pharmacodynamic, pharmacokinetic, toxicity, and recent advances in Eugenol's potential benefits against natural and chemical noxious agents: A mechanistic review. Toxicon : official journal of the International Society on Toxinology. 2024 Feb; 238(?):107607. doi: 10.1016/j.toxicon.2024.107607. [PMID: 38191032]
  • Linlin Fan, Wei Su, Xiaoqian Zhang, Suqun Yang, Yongsheng Zhu, Xiaoli Liu. Self-assembly of sophorolipid and eugenol into stable nanoemulsions for synergetic antibacterial properties through alerting membrane integrity. Colloids and surfaces. B, Biointerfaces. 2024 Feb; 234(?):113749. doi: 10.1016/j.colsurfb.2024.113749. [PMID: 38241893]
  • Abdullah I Kamel, Ahmed Ramadan El-Rokh, AbelAziz M Dawidar, Mamdouh Abdel-Mogib. Bioactive compounds from Retama raetam (Forssk.) Webb & Berthel. and their insecticidal activity against cotton pests Aphis gosspyii and Amrasca biguttula. Fitoterapia. 2024 Jan; 172(?):105749. doi: 10.1016/j.fitote.2023.105749. [PMID: 37972716]
  • Thomas Fezza, Todd E Shelly, Abbie Fox, Kyle Beucke, Eric Rohrig, Charlotte Aldebron, Nicholas C Manoukis. Less is more: Fewer attract-and-kill sites improve the male annihilation technique against Bactrocera dorsalis (Diptera: Tephritidae). PloS one. 2024; 19(3):e0300866. doi: 10.1371/journal.pone.0300866. [PMID: 38512951]
  • Anuwat Lakyat, Jarongsak Pumnuan, Thanaporn Doungnapa, Sudjai Phutphat, Somsak Kramchote, Kamronwit Thipmanee. Nanoemulsion-based plant essential oil formulations: in vitro evaluation of pesticidal activity against ectoparasites in poultry. Poultry science. 2024 Jan; 103(1):103245. doi: 10.1016/j.psj.2023.103245. [PMID: 38007904]
  • Chi-Chieh Hu, Chin-Yu Wu, Min-Yu Yang, Jian-Zhi Huang, Chih-Wen Wu, Chwan-Yang Hong. Catalase associated with antagonistic changes of abscisic acid and gibberellin response, biosynthesis and catabolism is involved in eugenol-inhibited seed germination in rice. Plant cell reports. 2023 Dec; 43(1):10. doi: 10.1007/s00299-023-03096-5. [PMID: 38135798]
  • Yang Wang, Xiao-Kun Bian, Li Zhang, Wen-Yan Chen, Qiu-Ju Lyu, Shu-Shan Du. The essential oil of Kochia scoparia (L.) Schrad. as a potential repellent against stored-product insects. Environmental science and pollution research international. 2023 Dec; 30(59):124416-124424. doi: 10.1007/s11356-023-31011-8. [PMID: 37996575]
  • Jinshan Dai. Antioxidant Capacity of Eugenol and Its Effect on Intestinal Flora Under in Vitro Simulated Conditions. Studies in health technology and informatics. 2023 Nov; 308(?):715-722. doi: 10.3233/shti230904. [PMID: 38007803]
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