SML1609

Ferutinin

≥98% (HPLC)

• Synonym(s): 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, 4-Oxy-6-(4-oxybenzoyloxy)dauc-8,9-en, Ferutinine, Tefestrol
• Empirical Formula (Hill Notation): C₂₂H₃₀O₄
• CAS Number: 41743-44-6
• Molecular Weight: 358.47
• PubChem Substance ID: 329825495
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• storage condition: protect from light
• color: white to beige
• storage temp.: 2-8°C
• SMILES string: CC1=CC[C@](CC[C@@]2(O)C(C)C)(C)[C@@]2([H])[C@@H](OC(C3=CC=C(O)C=C3)=O)C1
• 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

Description

General description

Ferutinin, a daucane phytoestrogen, is found in the Ferula genus. It is a natural terpenoid and a calcium ionophore.

Biochem/physiol Actions

Ferutinin can suppress tumor development without causing systemic toxicity in various tumor cells and animal cancer models. It possesses estrogenic properties and a protective role against uterine carcinoma. Ferutinin exhibits anti-cancer action in estrogen-dependent breast cancer cells.

Ferutinin is a strong agonist for estrogen receptor (ER)α and agonist/antagonist for Erβ with IC50 values of 33.1 nM for ERα and 180.5 nM for Erβ. It has been shown to have both ionophoretic and apoptotic properties. It increases calcium permeability in the lipid bilayer and has been shown to improve bone regeneration in a rat study. It caused significant regression in tumor size in a mouse colon cancer model.

Safety Information

• Hazard Statements: H413
• Precautionary Statements: P273 - P501
• Hazard Classifications: Aquatic Chronic 4
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable