Skip to Content
Merck
CN
All Photos(1)

Documents

SML1609

Sigma-Aldrich

Ferutinin

≥98% (HPLC)

Sign Into View Organizational & Contract Pricing
All Photos(1)
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
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.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service