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Key Documents

E4389

Sigma-Aldrich

β-Estradiol-Water Soluble

BioReagent, suitable for cell culture

Synonym(s):

Cyclodextrin-encapsulated 17β-estradiol

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About This Item

MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

sterility

non-sterile

product line

BioReagent

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

H2O: 25 mg/mL, clear to slightly hazy

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1CC[C@@H]2O.C[C@@H]5[C@@H](O)[C@@H]6O[C@H](CO)[C@H]5O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]9O[C@H](CO)[C@@H](O[C@H]%10O[C@H](CO)[C@@H](O[C@H]%11O[C@H](CO)[C@@H](O[C@H]%12O[C@H](CO)[C@@H](O6)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8OCCCO)[C@H](O)[C@H]7O

InChI

1S/C46H78O35.C18H24O2/c1-12-20(55)40-68-13(5-48)32(12)75-41-26(61)25(60)37(18(10-53)69-41)81-46-39(67-4-2-3-47)31(66)38(19(11-54)74-46)80-45-30(65)24(59)36(17(9-52)73-45)79-44-29(64)23(58)35(16(8-51)72-44)78-43-28(63)22(57)34(15(7-50)71-43)77-42-27(62)21(56)33(76-40)14(6-49)70-42;1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h12-66H,2-11H2,1H3;3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t12-,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23-,24-,25-,26-,27-,28-,29-,30-,31+,32+,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,43-,44-,45-,46-;14-,15-,16+,17+,18+/m11/s1

InChI key

XMURHKLFGRLVRW-JKDYGSMVSA-N

General description

β-estradiol is a natural human estrogen. It is vital for the growth of breast and reproductive epithelia, maturation of long bones and development of secondary sexual characteristics. Estradiol is produced by immature germ cells, spermatozoa, Leydig cells and Sertoli cells. β-estradiol acts as a menopausal hormones. It is involved in replacement therapy for female hypogonadism or primary ovarian failure. Reduced levels of β-estradiol are linked to heart disease and osteoporosis. Estradiol plays a critical role in proliferation, modulation of ion transport and control of apoptosis in Sertoli cells. It maintains sperm concentration, motility and morphology.

Application

β-estradiol has been used:
  • to culture differentiated adipocytes
  • for estradiol treatment in rats
  • for oocyte maturation in vitro
β-Estradiol is used to study cell differentiation and transformations (tumorigenicity). This product is not recommended for use in binding assays.

Packaging

Package size based on estradiol

Other Notes

Contains 40-55 mg estradiol per gram of solid; balance 2-hydroxypropyl-β-cyclodextrin.

related product

Pictograms

Health hazardEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 1 - Carc. 2 - Lact. - Repr. 1A

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3


Certificates of Analysis (COA)

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Estradiol activates PI3K/Akt/GSK3 pathway under chronic neurodegenerative conditions triggered by perinatal asphyxia
Saraceno GE, et al.
Frontiers in Pharmacology, 9, 335-335 (2018)
Impact of l-carnitine on lipid content and post thaw survivability of buffalo embryos produced in vitro
Verma M, et al.
Cryobiology, 82(, 99-105 (2018)
Maria M Escribese et al.
Blood, 112(12), 4574-4584 (2008-09-20)
Dendritic cells (DCs) play a central role in initiating and polarizing the immune response. Therefore, DC maturation represents a key control point in the shift from innate to adaptive immunity. It is suspected that during pregnancy, hormones are critical factors
Mathanraj Packiam et al.
Infection and immunity, 78(1), 433-440 (2009-11-11)
Acute gonorrhea in women is characterized by a mucopurulent exudate that contains polymorphonuclear leukocytes (PMNs) with intracellular gonococci. Asymptomatic infections are also common. Information on the innate response to Neisseria gonorrhoeae in women is limited to studies with cultured cells
Keith T Akama et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 23(6), 2333-2339 (2003-03-27)
Estrogens induce synaptogenesis in the CA1 region of the dorsal hippocampus during the estrous cycle of the female rat. Functional consequences of such estrogen-mediated synaptogenesis include cyclic changes in neurotransmission and memory. At the molecular level, estrogen stimulates the rapid

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