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E8126

Sigma-Aldrich

Equilin

Synonym(s):

1,3,5(10),7-Estratetraen-3-ol-17-one, 3-Hydroxy-1,3,5(10),7-estratetraen-17-one, 7-Dehydroestrone

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About This Item

Empirical Formula (Hill Notation):
C18H20O2
CAS Number:
474-86-2
Molecular Weight:
268.35
Beilstein:
2624302
EC Number:
207-488-6
MDL number:
MFCD00046223
UNSPSC Code:
12352200
PubChem Substance ID:
24894666
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

Assay

≥98% (HPLC)

form

powder

technique(s)

inhibition assay: suitable

mp

238-240 °C (lit.)

solubility

chloroform: methanol (1:1): 40 mg/mL, clear, colorless to faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3C(=CCc4cc(O)ccc34)[C@@H]1CCC2=O

InChI

1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1

InChI key

WKRLQDKEXYKHJB-HFTRVMKXSA-N

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Biochem/physiol Actions

Equilin is the Mare estrogen and is majorly used in multi-estrogen drugs for hormone replacement therapy. It is synthesized in the microsomes of mare placenta. It mediates estrogen receptor β (ERβ) expression resulting in the activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) which favors monocytes adhesion in atherosclerosis. In vitro equilin inhibits 17β-hydroxysteroid dehydrogenase type 1 (17β-HSD1) that catalyzes the conversion of estrone to 17β-estradiol.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351,H361fd,H362

Hazard Classifications

Carc. 2 - Lact. - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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Equilin and equilenin biosynthesis. Stereochemistry of aromatization of 3-hydroxy-3, 5, 7-androstatrien-17-one by horse placenta
Mitsuteru N and Yoshio O
Journal of Steroid Biochemistry, 26(1), 137-143 (1987)
Structure of the ternary complex of human 17beta-hydroxysteroid dehydrogenase type 1 with 3-hydroxyestra-1, 3, 5, 7-tetraen-17-one (equilin) and NADP+
Sawicki MW, et al.
Proceedings of the National Academy of Sciences of the USA, 96(3), 840-845 (1999)
Equilin
Handbook of Hormones, 582-582 (2016)
Ekaterina V Rokhina et al.
The Science of the total environment, 417-418, 280-290 (2012-01-17)
Estrone (E1), 17β-estradiol (E2), estriol (E3), equilin (EQ) and 17α-estradiol (17α) estrogen hormones are released by humans and animals and have been detected in the environment and municipal wastewater treatment plants. The structural and electronic properties of natural hormone molecules
Naomi Suzuki et al.
Biochemistry, 43(35), 11312-11320 (2004-09-16)
Estrogen replacement therapy (ERT), composed of equilenin, is associated with increased risk of breast, ovarian, and endometrial cancers. Several diastereoisomers of unique dC and dA DNA adducts were derived from 4-hydroxyequilenin (4-OHEN), a metabolite of equilenin, and have been detected
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