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E1253

Sigma-Aldrich

Estriol

≥97%

Synonym(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

Empirical Formula (Hill Notation):
C18H24O3
CAS Number:
50-27-1
Molecular Weight:
288.38
Beilstein:
2508172
EC Number:
200-022-2
MDL number:
MFCD00003691
UNSPSC Code:
51111800
PubChem Substance ID:
24894396
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

Assay

≥97%

form

powder

mp

280-282 °C (lit.)

solubility

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

shipped in

ambient

storage temp.

room temp

SMILES string

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

InChI key

PROQIPRRNZUXQM-ZXXIGWHRSA-N

Gene Information

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.

Biochem/physiol Actions

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.

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Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H351,H360FD,H362

Hazard Classifications

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

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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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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