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SML1609

Sigma-Aldrich

Ferutinin

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C22H30O4
Número de CAS:
41743-44-6
Peso molecular:
358.47
UNSPSC Code:
51111800
PubChem Substance ID:
329825495
NACRES:
NA.77

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

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.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

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M V Zamaraeva et al.
Cell calcium, 22(4), 235-241 (1998-03-03)
The influence of the natural terpenoid ferutinin (4-oxy-6-(4-oxybenzoyloxy) dauc-8,9-en), isolated from the plant Ferula tenuisecta, on ion permeability of biological and artificial membranes was investigated. It was shown that ferutinin, in the concentration range 1-50 microM, increases the permeability of
Rémi Safi et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 105, 267-273 (2018-06-04)
Estrogen is considered a risk factor for breast cancer since it promotes breast-cell proliferation. The jaesckeanadiol-3-p-hydroxyphenylpropanoate, a hemi-synthetic analogue of the natural phytoestrogen ferutinin (jaesckeanadiol-p-hydroxybenzoate), is designed to be devoid of estrogenic activity. This analogue induces a cytotoxic effect 30
Daniela N Rolph et al.
Biochimica et biophysica acta. Molecular basis of disease, 1866(4), 165314-165314 (2018-11-10)
Osteoporosis is a silent systemic disease that causes bone deterioration, and affects over 10 million people in the US alone. This study was undertaken to develop a potential stem cell therapy for osteoporosis. We have isolated and expanded human dental

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