A lignan
Related Products
Isomer(s)
70310Sesamin
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Asarinin

Item No. 27456

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,5'-[(1R,3aS,4S,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis-1,3-benzodioxole
CAS Number
133-04-0
Synonyms
  • (–)-Asarinin
  • L-Asarinin
  • Desgeranyloxyarmatumin
  • (–)-Episesamin
Molecular Formula
C20H18O6
Formula Weight
354.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/ml
λmax
237, 288 nm
SMILES
[H][C@]1([C@@H](C2=CC(OCO3)=C3C=C2)OC4)[C@]4([H])[C@H](C5=CC(OCO6)=C6C=C5)OC1
InChi Code
InChI=1S/C20H18O6/c1-3-15-17(25-9-23-15)5-11(1)19-13-7-22-20(14(13)8-21-19)12-2-4-16-18(6-12)26-10-24-16/h1-6,13-14,19-20H,7-10H2/t13-,14-,19-,20+/m1/s1
InChi Key
PEYUIKBAABKQKQ-FQZPYLGXSA-N
Origin
Plant/Magnoliae flos
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $36

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    5 mg

    $135

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    10 mg

    $236

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    25 mg

    $502

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    Product Description

    Asarinin is a lignan that has been found in A. sieboldii.1 It is an epimer of sesamin (Item No. 70310) and a noncompetitive inhibitor of Δ5-desaturase (Ki = 0.28 mM).2 It is selective for Δ5-desaturase over Δ6- and Δ9-desaturase. Asarinin is cytotoxic to A2780 and SKOV3 ovarian cancer cells (IC50s = 38.45 and 60.87 µM, respectively) but not immortalized ovarian surface epithelial cells (IC50 = >200 µM).1 It induces apoptosis and activates caspase-3, -8, and -9 in A2780 and SKOV3 cells.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jeong, M., Kim, H.M., Lee, J.S., et al. (−)-Asarinin from the roots of Asarum sieboldii induces apoptotic cell death via caspase activation in human ovarian cancer cells. Molecules 23(3), E1849 (2018).

    2. Shimizu, S., Kawashima, H., Akimoto, K., et al. Inhibition of Δ5-desaturase in polyunsaturated fatty acid biosynthesis by (−)-asarinin and (−)-epiasarinin. Phytochemistry 31(3), 757-760 (1992).