Homogentisic Acid lactone
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29935Karrikinolide
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Homogentisic Acid lactone

Item No. 41254

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-2(3H)-benzofuranone
CAS Number
2688-48-4
Synonyms
  • Homogentisic Acid γ-lactone
  • NSC 61996
Molecular Formula
C8H6O3
Formula Weight
150.1
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
O=C1OC2=CC=C(C=C2C1)O
InChi Code
InChI=1S/C8H6O3/c9-6-1-2-7-5(3-6)4-8(10)11-7/h1-3,9H,4H2
InChi Key
POUITAHNNRJWMA-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 mg

    $65

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    1 g

    $104

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    Cayman Chemical
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    Product Description

    Homogentisic acid lactone is a fungal metabolite that has been found in the fungus WF5, has fungicidal activity, and is the lactonized form of homogentisic acid (Item No. 20045), an intermediate in aromatic amino acid metabolism.1 It is active against the plant pathogenic fungus F. graminearum. Homogentisic acid lactone has been used as a substrate in the determination of serum paraoxonase/arylesterase 1 (PON1) activity and the chemiluminescent detection of HRP release from liposomes.2,3 It is an intermediate in the synthesis of LD-2, a near-infrared probe for the imaging of lipid droplets in live cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mousa, W.K., Schwan, A.L., and Raizada, M.N. Characterization of antifungal natural products isolated from endophytic fungi of finger millet (Eleusine coracana). Molecules 21(9), 1171 (2016).

    2. Bełtowski, J., Wójcicka, G., and Jamroz, A. Leptin decreases plasma paraoxonase 1 (PON1) activity and induces oxidative stress: The possible novel mechanism for proatherogenic effect of chronic hyperleptinemia. Atherosclerosis 170(1), 21-29 (2003).

    3. Kamidate, T., Kikuchi, N., Ishida, A., et al. Determination of peroxidase encapsulated in liposomes using homogentisic acid γ-lactone chemiluminescence. Anal. Sci. 21(6), 701-704 (2005).

    4. Wu, X., Wang, X., Li, Y., et al. A near-infrared probe for specific imaging of lipid droplets in living cells. Anal. Chem. 94(11), 4881-4888 (2022).