A sesquiterpene
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Linderane

Item No. 27479

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1aS,4E,10S,10aS)-3,6,10,10a-tetrahydro-5,9-dimethyl-2H-10,1a-(epoxymethano)oxireno[4,5]cyclodeca[1,2-b]furan-12-one
CAS Number
13476-25-0
Molecular Formula
C15H16O4
Formula Weight
260.3
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:10): 0.09 mg/mlDMSO: 5 mg/mlEthanol: 0.2 mg/ml
λmax
213 nm
SMILES
CC1=COC2=C1[C@@](OC3=O)([H])[C@@H](O4)C34CC/C=C(C)\C2
InChi Code
InChI=1S/C15H16O4/c1-8-4-3-5-15-13(19-15)12(18-14(15)16)11-9(2)7-17-10(11)6-8/h4,7,12-13H,3,5-6H2,1-2H3/b8-4-/t12-,13+,15?/m0/s1
InChi Key
KBMSVODXFLAQNJ-JELGAPFCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Product Description

    Linderane is a sesquiterpene that has been found in L. aggregata.1,2 It inhibits the cytochrome P450 (CYP) isoform CYP2C9 (Ki = 1.26 μM) in an irreversible and NADPH-dependent manner.1 Linderane decreases phosphoenolpyruvate carboxykinase (Pck1) and glucose-6-phosphatase (G6pc) gene expression, cAMP concentration, and CREB phosphorylation, increases phosphodiesterase 3 (PDE3) activity, and inhibits gluconeogenesis in rat primary hepatocytes.2 In vivo, linderane (50 mg/kg twice per day) decreases serum and hepatic triglyceride levels, as well as random-fed and fasting blood glucose levels in ob/ob mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, H., Wang, K., Mao, X., et al. Mechanism-based inactivation of CYP2C9 by linderane. Xenobiotica 45(12), 1037-1046 (2015).

    2. Xie, W., Ye, Y., Feng, Y., et al. Linderane suppresses hepatic gluconeogenesis by inhibiting the cAMP/PKA/CREB pathway through indirect activation of PDE 3 via ERK/STAT3. Front. Pharmacol. 9:476, (2018).