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MedKoo Cat#: 145649 | Name: Isoegomaketone

Description:

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

Isoegomaketone (IK) is a constituent of essential oil found in P. frutescens, known for its diverse biological properties, including anti-inflammatory and antitumor effects. Isoegomaketone can mitigate the inflammatory response and oxidative stress associated with sepsis-induced ALI, showing it as a promising therapeutic agent for the treatment of sepsis-associated ALI.

Chemical Structure

Isoegomaketone
Isoegomaketone
CAS#34348-59-9

Theoretical Analysis

MedKoo Cat#: 145649

Name: Isoegomaketone

CAS#: 34348-59-9

Chemical Formula: C10H12O2

Exact Mass: 164.0800

Molecular Weight: 164.20

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

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Isoegomaketone;
IUPAC/Chemical Name
(E)-1-(furan-3-yl)-4-methylpent-2-en-1-one
InChi Key
XEYCZVQIOJGCNL-ONEGZZNKSA-N
InChi Code
1S/C10H12O2/c1-8(2)3-4-10(11)9-5-6-12-7-9/h3-8H,1-2H3/b4-3+
SMILES Code
CC(C)\C=C\C(=O)C1=COC=C1
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

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
1: Wang R, Zhang Q, Feng C, Zhang J, Qin Y, Meng L. Advances in the Pharmacological Activities and Effects of Perilla Ketone and Isoegomaketone. Evid Based Complement Alternat Med. 2022 Oct 28;2022:8809792. doi: 10.1155/2022/8809792. PMID: 36337585; PMCID: PMC9635969. 2: Rao Y, Lin H, Rao H, Rao Y, Tang X, Zuo H, Wang Y. Isoegomaketone alleviates inflammatory response and oxidative stress in sepsis lung injury. Allergol Immunopathol (Madr). 2024 Mar 1;52(2):16-22. doi: 10.15586/aei.v52i2.1030. PMID: 38459886. 3: Kim HW, Lee JW, Yu AR, Yoon HS, Kang M, Lee BS, Park HW, Lee SK, Whang J, Kim JS. Isoegomaketone exhibits potential as a new Mycobacterium abscessus inhibitor. Front Microbiol. 2024 Feb 23;15:1344914. doi: 10.3389/fmicb.2024.1344914. PMID: 38585695; PMCID: PMC10996855. 4: Kim YR, Nam B, Han AR, Kim JB, Jin CH. Isoegomaketone from Perilla frutescens (L.) Britt Stimulates MAPK/ERK Pathway in Human Keratinocyte to Promote Skin Wound Healing. Evid Based Complement Alternat Med. 2021 Feb 10;2021:6642606. doi: 10.1155/2021/6642606. PMID: 33628306; PMCID: PMC7889401. 5: Kim HM, Nam B, Paudel SB, Nam JW, Han AR, Jeong HG, Jin CH. 9‑Hydroxy‑isoegomaketone inhibits LPS‑induced NO and inflammatory cytokine production in RAW264.7 cells. Mol Med Rep. 2021 Mar;23(3):181. doi: 10.3892/mmr.2020.11820. Epub 2021 Jan 5. PMID: 33398364; PMCID: PMC7809899. 6: Jin CH, So Y, Nam B, Han SN, Kim JB. Isoegomaketone Alleviates the Development of Collagen Antibody-Induced Arthritis in Male Balb/c Mice. Molecules. 2017 Jul 19;22(7):1209. doi: 10.3390/molecules22071209. PMID: 28753954; PMCID: PMC6152219. 7: Jin CH, So YK, Han SN, Kim JB. Isoegomaketone Upregulates Heme Oxygenase-1 in RAW264.7 Cells via ROS/p38 MAPK/Nrf2 Pathway. Biomol Ther (Seoul). 2016 Sep 1;24(5):510-6. doi: 10.4062/biomolther.2015.194. PMID: 27582555; PMCID: PMC5012876. 8: Cho BO, Jin CH, Park YD, Ryu HW, Byun MW, Seo KI, Jeong IY. Isoegomaketone induces apoptosis through caspase-dependent and caspase-independent pathways in human DLD1 cells. Biosci Biotechnol Biochem. 2011;75(7):1306-11. doi: 10.1271/bbb.110088. Epub 2011 Jul 7. PMID: 21737934. 9: Zhang J, Wang R, Qin Y, Feng C. Defining the Potential Targets for Biological Activity of Isoegomaketone Based on Network Pharmacology and Molecular Docking Methods. Life (Basel). 2022 Dec 15;12(12):2115. doi: 10.3390/life12122115. PMID: 36556480; PMCID: PMC9788221. 10: Kwon SJ, Lee JH, Moon KD, Jeong IY, Yee ST, Lee MK, Seo KI. Isoegomaketone induces apoptosis in SK-MEL-2 human melanoma cells through mitochondrial apoptotic pathway via activating the PI3K/Akt pathway. Int J Oncol. 2014 Nov;45(5):1969-76. doi: 10.3892/ijo.2014.2598. Epub 2014 Aug 14. PMID: 25119993. 11: Jin CH, Lee HJ, Park YD, Choi DS, Kim DS, Kang SY, Seo KI, Jeong IY. Isoegomaketone inhibits lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages through the heme oxygenase-1 induction and inhibition of the interferon-beta-STAT-1 pathway. J Agric Food Chem. 2010 Jan 27;58(2):860-7. doi: 10.1021/jf9033333. PMID: 20030328. 12: Park YD, Jin CH, Choi DS, Byun MW, Jeong IY. Biological evaluation of isoegomaketone isolated from Perilla frutescens and its synthetic derivatives as anti-inflammatory agents. Arch Pharm Res. 2011 Aug;34(8):1277-82. doi: 10.1007/s12272-011-0806-8. Epub 2011 Sep 11. PMID: 21910048. 13: Lee JH, Cho HD, Jeong IY, Lee MK, Seo KI. Sensitization of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-resistant primary prostate cancer cells by isoegomaketone from Perilla frutescens. J Nat Prod. 2014 Nov 26;77(11):2438-43. doi: 10.1021/np500452e. Epub 2014 Oct 16. PMID: 25320841. 14: Kwon SJ, Lee JH, Moon KD, Jeong IY, Ahn DU, Lee MK, Seo KI. Induction of apoptosis by isoegomaketone from Perilla frutescens L. in B16 melanoma cells is mediated through ROS generation and mitochondrial-dependent, -independent pathway. Food Chem Toxicol. 2014 Mar;65:97-104. doi: 10.1016/j.fct.2013.12.031. Epub 2013 Dec 29. PMID: 24380754. 15: Ahmed HM. Ethnomedicinal, Phytochemical and Pharmacological Investigations of Perilla frutescens (L.) Britt. Molecules. 2018 Dec 28;24(1):102. doi: 10.3390/molecules24010102. PMID: 30597896; PMCID: PMC6337106. 16: ITO H. [STUDIES ON THE FOLIUM PERILLAE. II. ON ISOEGOMAKETONE]. Yakugaku Zasshi. 1964 Nov;84:1123-5. Japanese. doi: 10.1248/yakushi1947.84.11_1123. PMID: 14265138. 17: Nam B, Paudel SB, Kim JB, Jin CH, Lee D, Nam JW, Han AR. Preparative Separation of Three Monoterpenes from Perilla frutescens var. crispa Using Centrifugal Partition Chromatography. Int J Anal Chem. 2019 Jan 9;2019:8751345. doi: 10.1155/2019/8751345. PMID: 30728839; PMCID: PMC6343183. 18: Jin CH, Park HC, So Y, Nam B, Han SN, Kim JB. Comparison of the Anti- Inflammatory Activities of Supercritical Carbon Dioxide versus Ethanol Extracts from Leaves of Perilla frutescens Britt. Radiation Mutant. Molecules. 2017 Feb 17;22(2):311. doi: 10.3390/molecules22020311. PMID: 28218690; PMCID: PMC6155756. 19: Wang Y, Huang X, Han J, Zheng W, Ma W. Extract of Perilla frutescens inhibits tumor proliferation of HCC via PI3K/AKT signal pathway. Afr J Tradit Complement Altern Med. 2012 Dec 31;10(2):251-7. PMID: 24146448; PMCID: PMC3746572. 20: Bassoli A, Borgonovo G, Morini G, De Petrocellis L, Schiano Moriello A, Di Marzo V. Analogues of perillaketone as highly potent agonists of TRPA1 channel. Food Chem. 2013 Dec 1;141(3):2044-51. doi: 10.1016/j.foodchem.2013.05.063. Epub 2013 May 24. PMID: 23870926.

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HMS607P03

HMS607P03