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E9750

Sigma-Aldrich

Estrone

≥99% (HPLC), powder, estrogen receptor agonist

Synonym(s):

1,3,5(10)-Estratrien-3-ol-17-one, 3-Hydroxy-1,3,5(10)-estratrien-17-one, Folliculin

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About This Item

Empirical Formula (Hill Notation):
C18H22O2
CAS Number:
53-16-7
Molecular Weight:
270.37
Beilstein/REAXYS Number:
1915077
EC Number:
200-164-5
MDL number:
MFCD00003620
UNSPSC Code:
51111800
PubChem Substance ID:
24278427
NACRES:
NA.77

product name

Estrone, ≥99%

biological source

synthetic (organic)

sterility

non-sterile

assay

≥99%

form

powder

mp

258-260 °C (lit.)

solubility

dioxane: 50 mg/mL, clear, colorless to very faintly yellow

shipped in

ambient

storage temp.

room temp

SMILES string

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

InChI

1S/C18H22O2/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,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

InChI key

DNXHEGUUPJUMQT-CBZIJGRNSA-N

Gene Information

human ... ESR1(2099) , ESR2(2100) , ESRRA(2101) , ESRRB(2103) , HSD17B1(3292) , SERPINA6(866)
mouse ... Esr1(13982)
rat ... Esr1(24890)

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General description

Estrone is a weak form of estrogen and exists as estrone sulphate. Estrone is a luteolytic estrogen produced by the corpus luteum. In the follicle, estrone is synthesized from androstenedione by the action of cytochrome P450 aromatase.

Application

Estrone has been used:
  • as medium supplement for hormone based degranulation studies of natural killer cells
  • as an endocrine disrupting compound for screening bacterial biosensor in toxic water.
  • as medium component for monitoring fatty acid synthase (FASN) activity in breast adenocarcinoma cell lines

Biochem/physiol Actions

Estrone is an agonist for the estrogen receptor. The estradiol to estrone interconversion is favourable in menopause. Oral hormone replacement therapy (HRT) of estradiol-17β increases circulating levels of estrone.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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Danger

Hazard Classifications

Carc. 2 - Lact. - Repr. 1A

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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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Hormone replacement with estradiol: conventional oral doses result in excessive exposure to estrone
Friel PN, et al.
Alternative Medicine Review, 10(1), 36-42 (2005)
Estrone-a partial estradiol antagonist in the normal breast
Lundstrom E, et al.
Gynecological Endocrinology, 31(9), 747-749 (2015)
Pharmacology of estrogens and progestogens: influence of different routes of administration
Kuhl H
Climacteric : The Journal of the International Menopause Society, 8(1), 3-63 (2005)
Breast cancer metabolic cross-talk: Fibroblasts are hubs and breast cancer cells are gatherers of lipids
Lopes-Coelho F, et al.
Molecular and cellular endocrinology, 462(9), 93-106 (2018)
Sex Differences in Spontaneous Degranulation Activity of Intrahepatic Natural Killer Cells during Chronic Hepatitis B: Association with Estradiol Levels
Macek J, et al.
Mediators of Inflammation, 2017(9), 747-749 (2017)
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