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Merck

E8126

Equilin

synthetic (organic), ≥98% (HPLC), 17β-HSD1 inhibitor, powder

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
NACRES:
NA.77
PubChem Substance ID:
24894666
UNSPSC Code:
12352200
EC Number:
207-488-6
MDL number:
MFCD00046223
Beilstein/REAXYS Number:
2624302

Product Name

Equilin,

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

SMILES string

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

InChI key

WKRLQDKEXYKHJB-HFTRVMKXSA-N

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

Quality Level

100

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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

signalword

Warning

Hazard Classifications

Carc. 2 - Lact. - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6427
MKCV6134
MKCV5803
MKCV4767
MKCV4692

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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
Sari Alho-Richmond et al.
Molecular and cellular endocrinology, 248(1-2), 208-213 (2006-01-18)
Estrogens, especially estradiol, have been shown to stimulate the proliferation of hormone-dependent types of breast cancer cells. 17Beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) enzyme catalyses the synthesis of the active female estrogen, estradiol and is thus an attractive target for structure-based
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