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E1253

Sigma-Aldrich

Estriol

≥97%

Synonyme(s) :

1,3,5(10)-Estratriene-3,16α,17β-triol, 16α-Hydroxyestradiol, 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene

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About This Item

Formule empirique (notation de Hill):
C18H24O3
Numéro CAS:
50-27-1
Poids moléculaire :
288.38
Numéro Beilstein :
2508172
Numéro CE :
200-022-2
Numéro MDL:
MFCD00003691
Code UNSPSC :
51111800
ID de substance PubChem :
24894396
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

200

Stérilité

non-sterile

Pureté

≥97%

Forme

powder

Pf

280-282 °C (lit.)

Solubilité

pyridine: 50 mg/mL, clear, colorless to faintly brownish-yellow

Conditions d'expédition

ambient

Température de stockage

room temp

Chaîne SMILES 

C[C@]12CC[C@H]3[C@@H](CCc4cc(O)ccc34)[C@@H]1C[C@@H](O)[C@@H]2O

InChI

1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1

Clé InChI

PROQIPRRNZUXQM-ZXXIGWHRSA-N

Informations sur le gène

human ... SERPINA6(866)
mouse ... Esr1(13982)
rat ... Ar(24208)

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Application

Estriol has been used as a sex hormone to determine its binding constants to insulin (INS), the insulin receptor (IR), and INS-like peptides derived from the IR.

Actions biochimiques/physiologiques

Estriol is a metabolite of 17β-estradiol with much lower biological activity. It is the primary estrogen found in the urine. Large quantities of estriol and estrone are produced by the placenta during pregnancy. These are also the primary estrogens produced by adipose tissue in men and post-menopausal women. Estriol may exhibit immunomodulatory benefits against various diseases such as autoimmune, inflammatory, and neurodegenerative conditions.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H351,H360FD,H362

Classification des risques

Carc. 2 - Lact. - Repr. 1A

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

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

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Estriol British Pharmacopoeia (BP) Reference Standard

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β-Estradiol meets USP testing specifications

Sigma-Aldrich

E1024

β-Estradiol

17α-Hydroxypregnenolone

Sigma-Aldrich

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17α-Hydroxypregnenolone

Equilin

Sigma-Aldrich

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Equilin

Emad S Ali et al.
Menopause (New York, N.Y.), 24(9), 1081-1085 (2017-04-05)
Estriol is the main estrogen in pregnancy, but has received less attention outside gestation. It is well known that pregnancy has an immunosuppressive effect on many autoimmune diseases such as multiple sclerosis, psoriasis, thyroiditis, uveitis, and rheumatoid arthritis. Emerging evidence
Honggang Wang et al.
Pharmaceutical research, 25(2), 444-452 (2007-09-08)
We investigated whether the pregnancy-related hormones, estriol (E3), testosterone, human placental lactogen (hPL), human prolactin (hPRL), and human chorionic gonadotropin (hCG) affect BCRP expression in human placental BeWo cells. The effects of these hormones on BCRP protein and mRNA expression
Robert Root-Bernstein et al.
Frontiers in endocrinology, 5, 118-118 (2014-08-08)
Insulin (INS) resistance associated with hyperestrogenemias occurs in gestational diabetes mellitus, polycystic ovary syndrome, ovarian hyperstimulation syndrome, estrogen therapies, metabolic syndrome, and obesity. The mechanism by which INS and estrogen interact is unknown. We hypothesize that estrogen binds directly to
Nina Sneitz et al.
Drug metabolism and disposition: the biological fate of chemicals, 41(3), 582-591 (2013-01-05)
The glucuronidation of estriol, 16-epiestriol, and 17-epiestriol by the human UDP-glucuronosyltransferases (UGTs) of subfamilies 1A, 2A, and 2B was examined. UGT1A10 is highly active in the conjugation of the 3-OH in all these estriols, whereas UGT2B7 is the most active
E Diczfalusy
Journal of steroid biochemistry, 20(4B), 945-953 (1984-04-01)
The early history of estriol is reviewed with special emphasis on its isolation, identification, quantitation in tissues and body fluids and its unique biogenesis in the human feto-placental unit. The relationship to epimeric estriols and acidic estrogens and the pharmacokinetic
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