A furanocoumarin with diverse biological activities
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Heraclenin

Item No. 39146

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-[[(2R)-3,3-dimethyl-2-oxiranyl]methoxy]-7H-furo[3,2-g][1]benzopyran-7-one
CAS Number
2880-49-1
Synonyms
  • (+)-Heraclenin
  • Prangenin
Molecular Formula
C16H14O5
Formula Weight
286.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: SolubleDMSO: Soluble
SMILES
O=C1OC2=C(C=C3C=COC3=C2OC[C@@H]4C(C)(C)O4)C=C1
InChi Code
InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3/t11-/m1/s1
InChi Key
CTJZWFCPUDPLME-LLVKDONJSA-N
Origin
Plant/Angelicae pubescentis radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Cayman Chemical
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    Product Description

    Heraclenin is a furanocoumarin epoxide that has been found in A. marmelos and has diverse biological activities.1,2,3 It is active against P. falciparum (IC50s = 2.85 and 6 µg/ml for chloroquine-sensitive and -resistant strains, respectively).1 It is also active against the bacteria B. subtilis, B. sphaericus, S. aureus, E. coli, and C. violaceum, as well as the fungi A. niger, A. flavus, C. albicans, and S. cerevisiae in disc assays when used at a concentration of 100 µg/disc. Heraclenin (5, 10, and 20 µM) enhances osteoblastic differentiation and mineralization of primary mouse mesenchymal stem cells (mMSCs).2 In vivo, heraclenin (0.1-1 mg/kg) reduces ear edema in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gowri, P.M., Haribabu, K., Kishore, H., et al. Microbial transformation of (+)-heraclenin by Aspergillus niger and evaluation of its antiplasmodial and antimicrobial activities. Curr. Sci. 100(11), 1706-1711 (2011).

    2. Shanmugam, H., Dharun, V.N., Biswal, B.K., et al. Osteogenic stimulatory effect of heraclenin purified from bael in mouse mesenchymal stem cells in vitro. Chem. Biol. Interact. 310, 108750 (2019).

    3. García-Argáez, A.N., Ramírez Apan, T.O., Parra Delgado, H., et al. Anti-inflammatory activity of coumarins from Decatropis bicolor on TPA ear mice model. Planta Med. 66(3), 279-281 (2000).