A coumarin with diverse actions
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Esculetin

Item No. 19286

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,7-dihydroxy-2H-1-benzopyran-2-one
CAS Number
305-01-1
Synonyms
  • Aesculetin
  • Cichorigenin
  • 6,7-Dihydroxycoumarin
  • NSC 26427
Molecular Formula
C9H6O4
Formula Weight
178.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mLDMF:PBS (pH 7.2) (1:4): 0.2 mg/mLDMSO: 30 mg/mLEthanol: 2 mg/mL
λmax
229, 258, 300, 351 nm
SMILES
OC1=C(O)C=C(C=CC(O2)=O)C2=C1
InChi Code
InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChi Key
ILEDWLMCKZNDJK-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $153

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    10 g

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    25 g

    $587

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    Product Description

    Esculetin is a coumarin that has been found in Euphorbia and has diverse biological activities.1,2,3,4,5 It inhibits 5-lipoxygenase (5-LO) and 12-LO (IC50s = 4 and 2.5 µM, respectively), as well as the histone demethylase jumonji AT-rich interactive domain 1B (JARID1B; IC50 = 4.6 µM).1,2 Esculetin is active against B. cereus, S. lutea, S. aureus, S. lactis, A. faecalis, and E. coli.3 It reduces production of hydrogen peroxide induced by the leucin-rich repeat kinase 2 (LRRK2) mutant LRRK2G2019S, which is linked to neurotoxicity and Parkinson’s disease, in Drosophila brain lysates and decreases cell death in LRRK2G2019S-expressing primary human cortical neurons.4 Esculetin (1.68 µmol/ear) reduces croton oil-induced ear edema in mice.5 It also inhibits acetylcholine-induced writhing in mice (ED50 = 69 mg/kg).

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Neichi, T., Koshihara, Y., and Murota, S.I. Inhibitory effect of esculetin on 5-lipoxygenase and leukotriene biosynthesis. Biochim. Biophys. Acta 753, 130-132 (1983).

    2. Sayegh, J., Cao, J., Zou, M.R., et al. Identification of small molecule inhibitors of Jumonji AT-rich interactive domain 1B (JARID1B) histone demethylase by a sensitive high throughput screen. The Journal of Biological Chemisty 288(13), 9408-9417 (2013).

    3. Jurd, L., Corse, J., King, A.D., Jr., et al. Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy-, 6-hydroxy- and 8-hydroxycoumarins. Phytochem. 10(12), 2971-2974 (1971).

    4. Angeles, D.C., Ho, P., Dymock, B.W., et al. Antioxidants inhibit neuronal toxicity in Parkinson’s disease-linked LRRK2. Ann. Clin. Transl. Neurol. 3(4), 288-294 (2016).

    5. Tubaro, A., Del Negro, P., Ragazzi, E., et al. Anti-inflammatory and peripheral analgesic activity of esculetin in vivo. Pharmacol. Res. Commun. 20(5), 83-85 (1988).