A labdane diterpenoid lactone with diverse biological activities
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Marrubiin

Item No. 33876

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2aS,5aS,6R,7R,8aR,8bR)-6-[2-(3-furanyl)ethyl]decahydro-6-hydroxy-2a,5a,7-trimethyl-2H-naphtho[1,8-bc]furan-2-one
CAS Number
465-92-9
Synonyms
  • NSC 36693
  • (+)-Marrubiin
Molecular Formula
C20H28O4
Formula Weight
332.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: solubleEthanol: soluble
λmax
213 nm
SMILES
C[C@@]12[C@@]3([H])[C@](C[C@H]([C@]2(O)CCC4=COC=C4)C)([H])OC([C@]3(CCC1)C)=O
InChi Code
InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1
InChi Key
HQLLRHCTVDVUJB-OBHOOXMTSA-N
Origin
Plant/Marrubium vulgare
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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    Product Description

    Marrubiin is a labdane diterpenoid lactone originally isolated from M. vulgare that has diverse biological activities.1,2,3 It inhibits potassium chloride-induced contractions of rat aortic rings (IC50 = 24 µM).1 Marrubiin (100 mg/kg) inhibits ovalbumin-induced allergic ear edema in mice.2 It inhibits acetic acid-induced writhing and capsaicin-induced paw licking in mice with ID50 values of 2.2 and 28.8 µmol/kg, respectively.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. El Bardai, S., Morel, N., Wibo, M., et al. The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Med. 69(1), 75-77 (2003).

    2. Stulzer, H.K., Tagliari, M.P., Zampirolo, J.A., et al. Antioedematogenic effect of marrubiin obtained from Marrubium vulgare. J. Ethnopharmacol. 108(3), 379-384 (2006).

    3. De Jesus, R.A., Cechinel-Filho, V., Oliveira, A.E., et al. Analysis of the antinociceptive properties of marrubiin isolated from Marrubium vulgare. Phytomedicine 7(2), 111-115 (2000).