A sesquiterpene
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Terrecyclic Acid

Item No. 28117

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS,4R,7R,7aR)-octahydro-8,8-dimethyl-3-methylene-2-oxo-3a,7-ethano-3aH-indene-4-carboxylic acid
CAS Number
83058-94-0
Molecular Formula
C15H20O3
Formula Weight
248.3
Purity
≥95%
Formulation (Request formulation change)
A solid
SMILES
O=C1C([C@]23[C@H](C(O)=O)CC[C@](C(C)(C)C3)([H])[C@@]2([H])C1)=C
InChi Code
InChI=1S/C15H20O3/c1-8-12(16)6-11-9-4-5-10(13(17)18)15(8,11)7-14(9,2)3/h9-11H,1,4-7H2,2-3H3,(H,17,18)/t9-,10+,11-,15-/m1/s1
InChi Key
SMAWCSOVJJHIOI-JNIYBQFBSA-N
Origin
Fungus/Aspergillus terreus
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $229

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    5 mg

    $1,018

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    Product Description

    Terrecyclic acid is a sesquiterpene originally isolated from A. terreus with antibiotic and anticancer activity.1 It is active against S. aureus, B. subtilis, and M. roseus (MICs = 25, 50, and 25 μg/ml, respectively). Terrecyclic acid induces a heat shock response, increases levels of reactive oxygen species (ROS), and inhibits NF-κB activity and cell growth in 3T3-Y9-B12 cells.2 In vivo, terrecyclic acid (0.1, 1, and 10 mg/ml) reduces the number of ascitic fluid tumor cells in a mouse model of P388 murine leukemia.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nakagawa, M., Hirota, A., Sakai, H., et al. Terrecyclic acid A, a new antibiotic from Aspergillus terreus. I. Taxonomy, production, and chemical and biological properties. J. Antibiot. (Tokyo) 35(7), 778-782 (1982).

    2. Turbyville, T.J., Wijeratne, E.M.K., Whitesell, L., et al. The anticancer activity of the fungal metabolite terrecyclic acid A is associated with modulation of multiple cellular stress response pathways. Mol. Cancer Ther. 4(10), 1569-1576 (2005).