An ERα agonist
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Ferutinin

Item No. 16554

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-benzoic acid, (3R,3aS,4S,8aR)-1,2,3,3a,4,5,8,8a-octahydro-3-hydroxy-6,8a-dimethyl-3-(1-methylethyl)-4-azulenyl ester
CAS Number
41743-44-6
Molecular Formula
C22H30O4
Formula Weight
358.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
260 nm
SMILES
OC1=CC=C(C(O[C@H]2CC(C)=CC[C@]3(C)[C@]2([H])[C@@](C(C)C)(O)CC3)=O)C=C1
InChi Code
InChI=1S/C22H30O4/c1-14(2)22(25)12-11-21(4)10-9-15(3)13-18(19(21)22)26-20(24)16-5-7-17(23)8-6-16/h5-9,14,18-19,23,25H,10-13H2,1-4H3/t18-,19+,21-,22+/m0/s1
InChi Key
CYSHNJQMYORNJI-YUVXSKOASA-N
Origin
Semi-synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Ferutinin is a plant-derived ester of a sesquiterpenic alcohol that acts as an agonist for estrogen receptor (ER) α (IC50 = 33.1 nM) and an agonist/antagonist for ERβ (IC50 = 180.5 nM).1 It also demonstrates ionophoretic properties, increasing calcium permeability of lipid bilayer membranes, mitochondria, thymocytes, sarcoplasmic reticulum, and liposomes at a concentration range of 1-50 µM.2,3,4 Ferutinin is cytotoxic to MCF-7 breast and TCC bladder cancer cells as well as human foreskin HFF3 fibroblasts (IC50s = 29, 24, and 36 µg/ml in vitro after 72 hours of exposure).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ikeda, K., Arao, Y., Otsuka, H., et al. Terpenoids found in the Umbelliferae family act as agonists/antagonists for ERα and ERβ: Differential transcription activity between ferutinine-liganded ERα and ERβ. Biochem. Biophys. Res. Commun. 291(2), 354-360 (2002).

    2. Abramov, A.Y., Zamaraeva, M.V., Hagelgans, A.I., et al. Influence of plant terpenoids on the permeability of mitochondria and lipid bilayers. Biochim. Biophys. Acta 1512(1), 98-110 (2001).

    3. Matin, M.M., Nakhaeizadeh, H., Bahrami, A.R., et al. Ferutinin, an apoptosis inducing terpenoid from Ferula ovina. Asian Pac. J. Cancer Prev. 15(5), 2123-2128 (2014).

    4. Zamaraeva, M.V., Charishnikova, O., Saidkhodjaev, A., et al. Calcium mobilization by the plant estrogen ferutinin does not induce blood platelet aggregation. Pharmacol. Rep. 62(6), 1117-1126 (2010).