MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 591580 | Name: Eugenol
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eugenol is a phenylpropene, an allyl chain-substituted guaiacol. Eugenol is a member of the phenylpropanoids class of chemical compounds.

Chemical Structure

Eugenol
Eugenol
CAS#97-53-0

Theoretical Analysis

MedKoo Cat#: 591580

Name: Eugenol

CAS#: 97-53-0

Chemical Formula: C10H12O2

Exact Mass: 164.0837

Molecular Weight: 164.20

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
Eugenol; 4-Allyl-2-methoxyphenol; 4-Allylguaiacol; Eugenic acid; Allylguaiacol; p-Eugenol; Caryophyllic acid; NSC 209525; NSC-209525; NSC209525
IUPAC/Chemical Name
Phenol, 2-methoxy-4-(2-propen-1-yl)-
InChi Key
RRAFCDWBNXTKKO-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3,5-7,11H,1,4H2,2H3
SMILES Code
OC1=CC=C(CC=C)C=C1OC
Appearance
Liquid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Eugenol is an essential oil found in cloves with antibacterial, anthelmintic and antioxidant activity.
In vitro activity:
Eugenol caused negative inotropic and chronotropic effects in the atria. In the ex vivo arrhythmia model, eugenol decreased atrial pacing disturbance induced by ouabain. Eugenol reduced the INa in a concentration-dependent manner. Reference: Life Sci. 2021 Jul 1;282:119761. https://pubmed.ncbi.nlm.nih.gov/34217764/
In vivo activity:
Weight-drop induced TBI caused functional disabilities in the rats as indicated by impairment in locomotor activities and short term memory. The TBI also resulted in augmented neuronal cell death designated by chromatolysis. The results also showed disruption in the BBB integrity, increased edema, and lipid peroxidation in the brain of the rats exposed to trauma. Pretreatment with eugenol (100 mg/kg) ameliorated histopathological, neurochemical, and behavioral consequences of trauma. Reference: J Tradit Complement Med. 2021 Jan 8;11(4):318-327. https://pubmed.ncbi.nlm.nih.gov/34195026/
Solvent mg/mL mM
Solubility
DMSO 100.0 609.01
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 164.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Teixeira-Fonseca JL, Santos-Miranda A, da Silva JB, Marques LP, Joviano-Santos JV, Nunes PIC, Roman-Campos D, Gondim ANS. Eugenol interacts with cardiac sodium channel and reduces heart excitability and arrhythmias. Life Sci. 2021 Jul 1;282:119761. doi: 10.1016/j.lfs.2021.119761. Epub ahead of print. PMID: 34217764. 2. Takahashi K, Yoshida T, Wakamori M. Mode-selective inhibitory effects of eugenol on the mouse TRPV1 channel. Biochem Biophys Res Commun. 2021 Jun 4;556:156-162. doi: 10.1016/j.bbrc.2021.03.126. Epub 2021 Apr 8. PMID: 33839411. 3. Barot J, Saxena B. Therapeutic effects of eugenol in a rat model of traumatic brain injury: A behavioral, biochemical, and histological study. J Tradit Complement Med. 2021 Jan 8;11(4):318-327. doi: 10.1016/j.jtcme.2021.01.003. PMID: 34195026; PMCID: PMC8240337. 4. Tsaroucha A, Kaldis V, Vailas M, Schizas D, Lambropoulou M, Papalois A, Tsigalou C, Gaitanidis A, Pitiakoudis M, Simopoulos C. The positive effect of eugenol on acute pancreatic tissue injury: a rat experimental model. Pan Afr Med J. 2021 Feb 5;38:132. doi: 10.11604/pamj.2021.38.132.20202. PMID: 33912302; PMCID: PMC8052617.
In vitro protocol:
1. Teixeira-Fonseca JL, Santos-Miranda A, da Silva JB, Marques LP, Joviano-Santos JV, Nunes PIC, Roman-Campos D, Gondim ANS. Eugenol interacts with cardiac sodium channel and reduces heart excitability and arrhythmias. Life Sci. 2021 Jul 1;282:119761. doi: 10.1016/j.lfs.2021.119761. Epub ahead of print. PMID: 34217764. 2. Takahashi K, Yoshida T, Wakamori M. Mode-selective inhibitory effects of eugenol on the mouse TRPV1 channel. Biochem Biophys Res Commun. 2021 Jun 4;556:156-162. doi: 10.1016/j.bbrc.2021.03.126. Epub 2021 Apr 8. PMID: 33839411.
In vivo protocol:
1. Barot J, Saxena B. Therapeutic effects of eugenol in a rat model of traumatic brain injury: A behavioral, biochemical, and histological study. J Tradit Complement Med. 2021 Jan 8;11(4):318-327. doi: 10.1016/j.jtcme.2021.01.003. PMID: 34195026; PMCID: PMC8240337. 2. Tsaroucha A, Kaldis V, Vailas M, Schizas D, Lambropoulou M, Papalois A, Tsigalou C, Gaitanidis A, Pitiakoudis M, Simopoulos C. The positive effect of eugenol on acute pancreatic tissue injury: a rat experimental model. Pan Afr Med J. 2021 Feb 5;38:132. doi: 10.11604/pamj.2021.38.132.20202. PMID: 33912302; PMCID: PMC8052617.
1: Lv C, Wang P, Ma L, Zheng M, Liu Y, Xing F. Large-Scale Comparative Analysis of Eugenol-Induced/Repressed Genes Expression in Aspergillus flavus Using RNA-seq. Front Microbiol. 2018 May 30;9:1116. doi: 10.3389/fmicb.2018.01116. eCollection 2018. PubMed PMID: 29899734; PubMed Central PMCID: PMC5988903. 2: Binu P PhD, Priya N MPHIL, Abhilash S PhD, Vineetha RC PhD, Nair H PhD. Protective Effects of Eugenol against Hepatotoxicity Induced by Arsenic Trioxide: An Antileukemic Drug. Iran J Med Sci. 2018 May;43(3):305-312. PubMed PMID: 29892148; PubMed Central PMCID: PMC5993899. 3: Karumathil DP, Nair MS, Gaffney J, Kollanoor-Johny A, Venkitanarayanan K. Trans-Cinnamaldehyde and Eugenol Increase Acinetobacter baumannii Sensitivity to Beta-Lactam Antibiotics. Front Microbiol. 2018 May 23;9:1011. doi: 10.3389/fmicb.2018.01011. eCollection 2018. PubMed PMID: 29875743; PubMed Central PMCID: PMC5974060. 4: Murina F, Vicariotto F, Di Francesco S. Thymol, eugenol and lactobacilli in a medical device for the treatment of bacterial vaginosis and vulvovaginal candidiasis. New Microbiol. 2018 Jun 6;41(2). [Epub ahead of print] PubMed PMID: 29874389. 5: Navikaite-Snipaitiene V, Ivanauskas L, Jakstas V, Rüegg N, Rutkaite R, Wolfram E, Yildirim S. Development of antioxidant food packaging materials containing eugenol for extending display life of fresh beef. Meat Sci. 2018 May 23;145:9-15. doi: 10.1016/j.meatsci.2018.05.015. [Epub ahead of print] PubMed PMID: 29859422. 6: Abd Manan FM, Attan N, Zakaria Z, Mahat NA, Abdul Wahab R. Insight into the Rhizomucor miehei lipase supported on chitosan-chitin nanowhiskers assisted esterification of eugenol to eugenyl benzoate. J Biotechnol. 2018 May 28;280:19-30. doi: 10.1016/j.jbiotec.2018.05.015. [Epub ahead of print] PubMed PMID: 29852195. 7: de Souza Romaneli R, Boaratti AZ, Tellechea Rodrigues A, de Almeida Ueiroz DM, Khan KU, Nascimento TMT, Fernandes JBK. Efficacy of Benzocaine, Eugenol and Menthol as Anesthetics for Freshwater Angelfish (Pterophyllum scalare). J Aquat Anim Health. 2018 May 29. doi: 10.1002/aah.10030. [Epub ahead of print] PubMed PMID: 29845639. 8: Hu Q, Zhou M, Wei S. Progress on the Antimicrobial Activity Research of Clove Oil and Eugenol in the Food Antisepsis Field. J Food Sci. 2018 Jun;83(6):1476-1483. doi: 10.1111/1750-3841.14180. Epub 2018 May 26. Review. PubMed PMID: 29802735. 9: Yan H, Baudino S, Caissard JC, Florence Nicolè, Zhang H, Tang K, Li S, Lu S. Functional characterization of the eugenol synthase gene (RcEGS1) in rose. Plant Physiol Biochem. 2018 May 10;129:21-26. doi: 10.1016/j.plaphy.2018.05.015. [Epub ahead of print] PubMed PMID: 29787935. 10: Shao Y, Wu C, Wu T, Li Y, Chen S, Yuan C, Hu Y. Eugenol-chitosan nanoemulsions by ultrasound-mediated emulsification: Formulation, characterization and antimicrobial activity. Carbohydr Polym. 2018 Aug 1;193:144-152. doi: 10.1016/j.carbpol.2018.03.101. Epub 2018 Mar 30. PubMed PMID: 29773366. 11: Li Z, Hu W, Zhao Y, Ren L, Yuan X. Integrated antibacterial and antifouling surfaces via cross-linking chitosan-g-eugenol/zwitterionic copolymer on electrospun membranes. Colloids Surf B Biointerfaces. 2018 Apr 27;169:151-159. doi: 10.1016/j.colsurfb.2018.04.056. [Epub ahead of print] PubMed PMID: 29758540. 12: Pires CW, Lenzi TL, Soares FZM, Rocha RO. Zinc oxide eugenol paste jeopardises the adhesive bonding to primary dentine. Eur Arch Paediatr Dent. 2018 May 12. doi: 10.1007/s40368-018-0344-x. [Epub ahead of print] PubMed PMID: 29754275. 13: McQuate GT, Royer JE, Sylva CD. Field Trapping Bactrocera latifrons (Diptera: Tephritidae) with Select Eugenol Analogs That Have Been Found to Attract Other 'Non-Responsive' Fruit Fly Species. Insects. 2018 May 1;9(2). pii: E50. doi: 10.3390/insects9020050. PubMed PMID: 29723960. 14: Hipólito TMM, Bastos GTL, Barbosa TWL, de Souza TB, Coelho LFL, Dias ALT, Rodríguez IC, Dos Santos MH, Dias DF, Franco LL, Carvalho DT. Synthesis, activity, and docking studies of eugenol-based glucosides as new agents against Candida sp. Chem Biol Drug Des. 2018 Apr 25. doi: 10.1111/cbdd.13318. [Epub ahead of print] PubMed PMID: 29693318. 15: Wieczyńska J, Cavoski I. Antimicrobial, antioxidant and sensory features of eugenol, carvacrol and trans-anethole in active packaging for organic ready-to-eat iceberg lettuce. Food Chem. 2018 Sep 1;259:251-260. doi: 10.1016/j.foodchem.2018.03.137. Epub 2018 Mar 30. PubMed PMID: 29680052. 16: Alvira E. Theoretical Study of the β-Cyclodextrin Inclusion Complex Formation of Eugenol in Water. Molecules. 2018 Apr 17;23(4). pii: E928. doi: 10.3390/molecules23040928. PubMed PMID: 29673173. 17: Ahmad N, Ahmad R, Alam MA, Ahmad FJ. Quantification and Brain Targeting of Eugenol-Loaded Surface Modified Nanoparticles Through Intranasal Route in the Treatment of Cerebral Ischemia. Drug Res (Stuttg). 2018 Apr 18. doi: 10.1055/a-0596-7288. [Epub ahead of print] PubMed PMID: 29669380. 18: Manoukis NC, Cha DH, Collignon RM, Shelly TE. Terminalia Larval Host Fruit Reduces the Response of Bactrocera dorsalis (Diptera: Tephritidae) Adults to the Male Lure Methyl Eugenol. J Econ Entomol. 2018 Apr 12. doi: 10.1093/jee/toy095. [Epub ahead of print] PubMed PMID: 29668952. 19: Haq IU, Cáceres C, Meza JS, Hendrichs J, Vreysen MJB. Different methods of methyl eugenol application enhance the mating success of male Oriental fruit fly (Dipera: Tephritidae). Sci Rep. 2018 Apr 16;8(1):6033. doi: 10.1038/s41598-018-24518-5. PubMed PMID: 29662085; PubMed Central PMCID: PMC5902445. 20: Yagura S, Onimaru H, Kanzaki K, Izumizaki M. Inhibitory effects of eugenol on putative nociceptive response in spinal cord preparation isolated from neonatal rats. Exp Brain Res. 2018 Jun;236(6):1767-1774. doi: 10.1007/s00221-018-5254-y. Epub 2018 Apr 13. PubMed PMID: 29654351.