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MedKoo Cat#: 540124 | Name: Esculetin
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Description:

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

Esculetin is a β-catenin inhibitor found in chicory and other plant sources. It displays a wide variety of activities, including inhibiting MPTP-induced neurotoxicity and neuronal apoptosis, decreasing body weight, triglyceride levels, total cholesterol and glucose levels in high-fat diet-fed animals, and suppressing proliferation of colon cancer cells.

Chemical Structure

Esculetin
Esculetin
CAS#305-01-1

Theoretical Analysis

MedKoo Cat#: 540124

Name: Esculetin

CAS#: 305-01-1

Chemical Formula: C9H6O4

Exact Mass: 178.0266

Molecular Weight: 178.14

Elemental Analysis: C, 60.68; H, 3.40; O, 35.92

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 weeks
5g USD 450.00 2 Weeks
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Related CAS #
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Synonym
Esculetin; Asculetine; 6,7-Dihydroxycoumarin; Cichorigenin; NSC 26428; NSC-26428; NSC26428
IUPAC/Chemical Name
6,7-dihydroxy-2H-chromen-2-one
InChi Key
ILEDWLMCKZNDJK-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
SMILES Code
O=C1C=CC2=CC(O)=C(O)C=C2O1
Appearance
Solid powder
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:
Esculetin inhibits platelet-derived growth factor (PDGF)-induced airway smooth muscle cells (ASMCs) phenotype switching through inhibition of PI3K/Akt pathway.
In vitro activity:
The DCF stained cells were analyzed by flow cytometer. During incubation period a significant ROS generation is noticed in cells placed with arsenic alone. Whereas cells treated with esculetin at 25 and 50 μg/mL concentrations exhibited dose-dependent inhibitory effects with IC50 value of 125 M. Reference: BMC Pharmacol Toxicol. 2021; 22: 43. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8281642/
In vivo activity:
For this purpose, AlCl3 was administrated to Wistar Albino rats at a dose of 34 mg/kg and ESC (esculetin) was administrated at a dose of 50 mg/kg for 70 days. It was determined that AlCl3 treatment reduced sperm motility and concentration, increased dead/live rate and abnormal sperm rate. It decreased serum testosterone level, and co-treatment of ESC significantly regulated these values. In the AlCl3 -treated group, MDA level increased and GSH level, GPx and CAT activities decreased compared with those of the control group. However, co-treatment of ESC showed an amelioratory effect on the values except for CAT activity. It was also determined that AlCl3 -induced tissue injury was significantly prevented by ESC co-treatment. Reference: Andrologia. 2021 Mar;53(2):e13930. https://pubmed.ncbi.nlm.nih.gov/33368464/
Solvent mg/mL mM
Solubility
DMSO 63.3 355.51
DMF 50.0 280.68
DMF:PBS (pH 7.2) (1:4) 0.2 1.12
Ethanol 2.0 11.23
Water 19.7 110.64
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 178.14 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. Pullaiah CP, Nelson VK, Rayapu S, G V NK, Kedam T. Exploring cardioprotective potential of esculetin against isoproterenol induced myocardial toxicity in rats: in vivo and in vitro evidence. BMC Pharmacol Toxicol. 2021 Jul 15;22(1):43. doi: 10.1186/s40360-021-00510-0. PMID: 34266475; PMCID: PMC8281642. 2. Cheng YJ, Tian XL, Zeng YZ, Lan N, Guo LF, Liu KF, Fang HL, Fan HY, Peng ZL. Esculetin protects against early sepsis via attenuating inflammation by inhibiting NF-κB and STAT1/STAT3 signaling. Chin J Nat Med. 2021 Jun;19(6):432-441. doi: 10.1016/S1875-5364(21)60042-0. PMID: 34092294. 3. Türk E, Ozan Tekeli I, Özkan H, Uyar A, Cellat M, Kuzu M, Yavas I, Alizadeh Yegani A, Yaman T, Güvenç M. The protective effect of esculetin against aluminium chloride-induced reproductive toxicity in rats. Andrologia. 2021 Mar;53(2):e13930. doi: 10.1111/and.13930. Epub 2020 Dec 24. PMID: 33368464. 4. Zhang Y, An Y, He X, Zhang D, He W. Esculetin protects human corneal epithelial cells from oxidative stress through Nrf-2 signaling pathway. Exp Eye Res. 2021 Jan;202:108360. doi: 10.1016/j.exer.2020.108360. Epub 2020 Nov 19. PMID: 33220236.
In vitro protocol:
1. Pullaiah CP, Nelson VK, Rayapu S, G V NK, Kedam T. Exploring cardioprotective potential of esculetin against isoproterenol induced myocardial toxicity in rats: in vivo and in vitro evidence. BMC Pharmacol Toxicol. 2021 Jul 15;22(1):43. doi: 10.1186/s40360-021-00510-0. PMID: 34266475; PMCID: PMC8281642. 2. Cheng YJ, Tian XL, Zeng YZ, Lan N, Guo LF, Liu KF, Fang HL, Fan HY, Peng ZL. Esculetin protects against early sepsis via attenuating inflammation by inhibiting NF-κB and STAT1/STAT3 signaling. Chin J Nat Med. 2021 Jun;19(6):432-441. doi: 10.1016/S1875-5364(21)60042-0. PMID: 34092294.
In vivo protocol:
1. Türk E, Ozan Tekeli I, Özkan H, Uyar A, Cellat M, Kuzu M, Yavas I, Alizadeh Yegani A, Yaman T, Güvenç M. The protective effect of esculetin against aluminium chloride-induced reproductive toxicity in rats. Andrologia. 2021 Mar;53(2):e13930. doi: 10.1111/and.13930. Epub 2020 Dec 24. PMID: 33368464. 2. Zhang Y, An Y, He X, Zhang D, He W. Esculetin protects human corneal epithelial cells from oxidative stress through Nrf-2 signaling pathway. Exp Eye Res. 2021 Jan;202:108360. doi: 10.1016/j.exer.2020.108360. Epub 2020 Nov 19. PMID: 33220236.
1: Pan H, Wang BH, Lv W, Jiang Y, He L. Esculetin induces apoptosis in human gastric cancer cells through a cyclophilin D-mediated mitochondrial permeability transition pore associated with ROS. Chem Biol Interact. 2015 Dec 5;242:51-60. doi: 10.1016/j.cbi.2015.09.015. Epub 2015 Sep 24. PubMed PMID: 26388407. 2: Kim AD, Han X, Piao MJ, Hewage SR, Hyun CL, Cho SJ, Hyun JW. Esculetin induces death of human colon cancer cells via the reactive oxygen species-mediated mitochondrial apoptosis pathway. Environ Toxicol Pharmacol. 2015 Mar;39(2):982-9. doi: 10.1016/j.etap.2015.03.003. Epub 2015 Mar 10. PubMed PMID: 25818986. 3: Rzodkiewicz P, Gasinska E, Maslinski S, Bujalska-Zadrozny M. Antinociceptive properties of esculetin in non-inflammatory and inflammatory models of pain in rats. Clin Exp Pharmacol Physiol. 2015 Feb;42(2):213-9. doi: 10.1111/1440-1681.12346. PubMed PMID: 25425056. 4: Wang J, Lu ML, Dai HL, Zhang SP, Wang HX, Wei N. Esculetin, a coumarin derivative, exerts in vitro and in vivo antiproliferative activity against hepatocellular carcinoma by initiating a mitochondrial-dependent apoptosis pathway. Braz J Med Biol Res. 2015 Mar;48(3):245-53. doi: 10.1590/1414-431X20144074. Epub 2014 Dec 12. PubMed PMID: 25517918; PubMed Central PMCID: PMC4381945. 5: Baek JM, Park SH, Cheon YH, Ahn SJ, Lee MS, Oh J, Kim JY. Esculetin attenuates receptor activator of nuclear factor kappa-B ligand-mediated osteoclast differentiation through c-Fos/nuclear factor of activated T-cells c1 signaling pathway. Biochem Biophys Res Commun. 2015 May 29;461(2):334-41. doi: 10.1016/j.bbrc.2015.04.034. Epub 2015 Apr 14. PubMed PMID: 25887803. 6: Yum S, Jeong S, Lee S, Kim W, Nam J, Jung Y. HIF-prolyl hydroxylase is a potential molecular target for esculetin-mediated anti-colitic effects. Fitoterapia. 2015 Jun;103:55-62. doi: 10.1016/j.fitote.2015.03.013. Epub 2015 Mar 20. PubMed PMID: 25797536. 7: Jeon YJ, Jang JY, Shim JH, Myung PK, Chae JI. Esculetin, a Coumarin Derivative, Exhibits Anti-proliferative and Pro-apoptotic Activity in G361 Human Malignant Melanoma. J Cancer Prev. 2015 Jun;20(2):106-12. doi: 10.15430/JCP.2015.20.2.106. PubMed PMID: 26151043; PubMed Central PMCID: PMC4492354. 8: Kadakol A, Malek V, Goru SK, Pandey A, Bagal S, Gaikwad AB. Esculetin attenuates alterations in Ang II and acetylcholine mediated vascular reactivity associated with hyperinsulinemia and hyperglycemia. Biochem Biophys Res Commun. 2015 May 29;461(2):342-7. doi: 10.1016/j.bbrc.2015.04.036. Epub 2015 Apr 15. PubMed PMID: 25887801. 9: Kim AD, Madduma Hewage SR, Piao MJ, Kang KA, Cho SJ, Hyun JW. Esculetin induces apoptosis in human colon cancer cells by inducing endoplasmic reticulum stress. Cell Biochem Funct. 2015 Oct;33(7):487-94. doi: 10.1002/cbf.3146. Epub 2015 Oct 5. PubMed PMID: 26439795. 10: Cho JH, Shin JC, Cho JJ, Choi YH, Shim JH, Chae JI. Esculetin (6,7-dihydroxycoumarin): a potential cancer chemopreventive agent through suppression of Sp1 in oral squamous cancer cells. Int J Oncol. 2015 Jan;46(1):265-71. doi: 10.3892/ijo.2014.2700. Epub 2014 Oct 7. PubMed PMID: 25310400. 11: Kimura Y, Sumiyoshi M. Antitumor and antimetastatic actions of dihydroxycoumarins (esculetin or fraxetin) through the inhibition of M2 macrophage differentiation in tumor-associated macrophages and/or G1 arrest in tumor cells. Eur J Pharmacol. 2015 Jan 5;746:115-25. doi: 10.1016/j.ejphar.2014.10.048. Epub 2014 Nov 6. PubMed PMID: 25445053. 12: Yamaoka H, Nishizawa S, Matsui M, Gonda K, Hirabayashi S, Hoshi K, Yamaoka K. The in vivo effect of esculetin ointment and esculetin-mixed Zyderm for Zyderm. Plast Reconstr Surg. 2014 Jul;134(1):50e-58e. doi: 10.1097/PRS.0000000000000304. PubMed PMID: 25028856. 13: Choi RY, Ham JR, Lee MK. Esculetin prevents non-alcoholic fatty liver in diabetic mice fed high-fat diet. Chem Biol Interact. 2016 Dec 25;260:13-21. doi: 10.1016/j.cbi.2016.10.013. Epub 2016 Oct 18. PubMed PMID: 27769711. 14: Hong SH, Jeong HK, Han MH, Park C, Choi YH. Esculetin suppresses lipopolysaccharide-induced inflammatory mediators and cytokines by inhibiting nuclear factor-κB translocation in RAW 264.7 macrophages. Mol Med Rep. 2014 Dec;10(6):3241-6. doi: 10.3892/mmr.2014.2613. Epub 2014 Oct 8. PubMed PMID: 25310143. 15: Rubio V, Calviño E, García-Pérez A, Herráez A, Diez JC. Human acute promyelocytic leukemia NB4 cells are sensitive to esculetin through induction of an apoptotic mechanism. Chem Biol Interact. 2014 Sep 5;220:129-39. doi: 10.1016/j.cbi.2014.06.021. Epub 2014 Jul 1. PubMed PMID: 24995577. 16: Zhu L, Nang C, Luo F, Pan H, Zhang K, Liu J, Zhou R, Gao J, Chang X, He H, Qiu Y, Wang J, Long H, Liu Y, Yan T. Esculetin attenuates lipopolysaccharide (LPS)-induced neuroinflammatory processes and depressive-like behavior in mice. Physiol Behav. 2016 Sep 1;163:184-92. doi: 10.1016/j.physbeh.2016.04.051. Epub 2016 Apr 29. PubMed PMID: 27133730. 17: Chang HT, Chou CT, Lin YS, Shieh P, Kuo DH, Jan CR, Liang WZ. Esculetin, a natural coumarin compound, evokes Ca(2+) movement and activation of Ca(2+)-associated mitochondrial apoptotic pathways that involved cell cycle arrest in ZR-75-1 human breast cancer cells. Tumour Biol. 2016 Apr;37(4):4665-78. doi: 10.1007/s13277-015-4286-1. Epub 2015 Oct 28. PubMed PMID: 26508031. 18: Jeon YJ, Cho JH, Lee SY, Choi YH, Park H, Jung S, Shim JH, Chae JI. Esculetin Induces Apoptosis Through EGFR/PI3K/Akt Signaling Pathway and Nucleophosmin Relocalization. J Cell Biochem. 2016 May;117(5):1210-21. doi: 10.1002/jcb.25404. Epub 2015 Oct 18. PubMed PMID: 26447856. 19: Arora R, Sawney S, Saini V, Steffi C, Tiwari M, Saluja D. Esculetin induces antiproliferative and apoptotic response in pancreatic cancer cells by directly binding to KEAP1. Mol Cancer. 2016 Oct 18;15(1):64. PubMed PMID: 27756327; PubMed Central PMCID: PMC5069780. 20: Kadakol A, Pandey A, Goru SK, Malek V, Gaikwad AB. Insulin sensitizing and cardioprotective effects of Esculetin and Telmisartan combination by attenuating Ang II mediated vascular reactivity and cardiac fibrosis. Eur J Pharmacol. 2015 Oct 15;765:591-7. doi: 10.1016/j.ejphar.2015.09.035. Epub 2015 Sep 25. PubMed PMID: 26409041.