Estriol
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MedKoo CAT#: 315241

CAS#: 50-27-1 (free base)

Description: Estriol (also oestriol) is one of the three main estrogens produced by the human body. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School. Estriol can be a weak or strong estrogen depending on if it is given acutely or chronically when given to immature animals, but is an antagonist when given in combination with estradiol. Estriol may play a role in the development of breast cancer, but based on in vitro research does appear to act as an antagonist to the G-protein coupled estrogen receptor. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. (Source: http://en.wikipedia.org/wiki/Estriol).


Chemical Structure

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Estriol
CAS# 50-27-1 (free base)

Theoretical Analysis

MedKoo Cat#: 315241
Name: Estriol
CAS#: 50-27-1 (free base)
Chemical Formula: C18H24O3
Exact Mass: 288.17
Molecular Weight: 288.380
Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Price and Availability

Size Price Availability Quantity
1g USD 250 2 weeks
2g USD 450 2 weeks
5g USD 950 2 weeks
10g USD 1650 2 weeks
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Related CAS #: 514-68-1 (succinate); 50-27-1 (free base)  

Synonym: oestriol.

IUPAC/Chemical Name: (8R,9S,13S,14S,16R,17R)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,16,17-triol

InChi Key: PROQIPRRNZUXQM-ZXXIGWHRSA-N

InChi Code: 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

SMILES Code: OC1=CC=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)[C@H](O)C[C@@]4([H])[C@]3([H])CCC2=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Safety Data Sheet (SDS):
Biological target: Estriol is an antagonist of the G-protein coupled estrogen receptor in estrogen receptor-negative breast cancer cells.
In vitro activity: Cell number of HCC1806 cells increased at 10-8 M 17β-estradiol to 127 ± 8% of control. In cells pretreated with 10-4 M estriol cell number significantly decreased to 54 ± 7% of control (p < 0.05) despite stimulation with 10-8M 17β-estradiol (Figure 3A). In cell line HCC70 10-8 M 17β-estradiol increased cell number to 116% of control, co-treatment with 10-4 M estriol significantly decreased cell number to 64% of control (p < 0.01) (Figure 3B). Estriol clearly prevented the stimulation of proliferation by 17β-estradiol in both TNBC cell lines. Antiproliferative effects of estriol paralleled the amount of GPR30 expressed in the various cell lines (Figure 1). Reference: BMC Cancer. 2014; 14: 935. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4364648/
In vivo activity: Furthermore, clinical IAV-associated disease—defined by alterations in breathing, posture, and activity—which was evident at 8 and 11 dpi, was significantly reduced in E3 (estriol)-treated compared with placebo-treated females (Fig. 1c). Because the therapeutic benefit of E3 in ameliorating disease in the EAE mouse model has also been demonstrated in males, this study evaluated the efficacy of E3 treatment of IAV-infected male mice. Similar to the phenotype observed for females, E3 conferred significant protection against clinical disease and body weight loss in males (Fig. 1e and 1f), suggesting that E3 mediates effects independent of biological sex. Reference: Endocrinology. 2018 Sep; 159(9): 3306–3320. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6109301/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 59.0 204.59
DMF 30.0 104.03
DMF:PBS (pH 7.2) (1:1) 0.5 1.73
Ethanol 7.5 26.01

Preparing Stock Solutions

The following data is based on the product molecular weight 288.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Girgert R, Emons G, Gründker C. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11;14:935. doi: 10.1186/1471-2407-14-935. PMID: 25496649; PMCID: PMC4364648. 2. Diller M, Schüler S, Buchholz S, Lattrich C, Treeck O, Ortmann O. Effects of estriol on growth, gene expression and estrogen response element activation in human breast cancer cell lines. Maturitas. 2014 Apr;77(4):336-43. doi: 10.1016/j.maturitas.2014.01.004. Epub 2014 Jan 23. PMID: 24529907. 3. Vermillion MS, Ursin RL, Attreed SE, Klein SL. Estriol Reduces Pulmonary Immune Cell Recruitment and Inflammation to Protect Female Mice From Severe Influenza. Endocrinology. 2018 Sep 1;159(9):3306-3320. doi: 10.1210/en.2018-00486. PMID: 30032246; PMCID: PMC6109301. 4. Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PMID: 25516546; PMCID: PMC4346740.
In vitro protocol: 1. Girgert R, Emons G, Gründker C. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11;14:935. doi: 10.1186/1471-2407-14-935. PMID: 25496649; PMCID: PMC4364648. 2. Diller M, Schüler S, Buchholz S, Lattrich C, Treeck O, Ortmann O. Effects of estriol on growth, gene expression and estrogen response element activation in human breast cancer cell lines. Maturitas. 2014 Apr;77(4):336-43. doi: 10.1016/j.maturitas.2014.01.004. Epub 2014 Jan 23. PMID: 24529907.
In vivo protocol: 1. Vermillion MS, Ursin RL, Attreed SE, Klein SL. Estriol Reduces Pulmonary Immune Cell Recruitment and Inflammation to Protect Female Mice From Severe Influenza. Endocrinology. 2018 Sep 1;159(9):3306-3320. doi: 10.1210/en.2018-00486. PMID: 30032246; PMCID: PMC6109301. 2. Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PMID: 25516546; PMCID: PMC4346740.

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1: Donders G, Bellen G, Neven P, Grob P, Prasauskas V, Buchholz S, Ortmann O. Effect of ultra-low-dose estriol and lactobacilli vaginal tablets (Gynoflor®) on inflammatory and infectious markers of the vaginal ecosystem in postmenopausal women with breast cancer on aromatase inhibitors. Eur J Clin Microbiol Infect Dis. 2015 Jul 30. [Epub ahead of print] PubMed PMID: 26223323.

2: Caruso S, Cianci S, Amore FF, Ventura B, Bambili E, Spadola S, Cianci A. Quality of life and sexual function of naturally postmenopausal women on an ultralow-concentration estriol vaginal gel. Menopause. 2015 Jun 15. [Epub ahead of print] PubMed PMID: 26079974.

3: Castellani D, Saldutto P, Galica V, Pace G, Biferi D, Paradiso Galatioto G, Vicentini C. Low-Dose Intravaginal Estriol and Pelvic Floor Rehabilitation in Post-Menopausal Stress Urinary Incontinence. Urol Int. 2015 May 30. [Epub ahead of print] PubMed PMID: 26043913.

4: Soghra K, Zohreh S, Kobra AK, Reza MM. Single measurement of salivary estriol as a predictor of preterm birth. Pak J Biol Sci. 2014 May;17(5):730-4. PubMed PMID: 26031009.

5: Tomi M, Eguchi H, Ozaki M, Tawara T, Nishimura S, Higuchi K, Maruyama T, Nishimura T, Nakashima E. Role of OAT4 in Uptake of Estriol Precursor 16α-Hydroxydehydroepiandrosterone Sulfate Into Human Placental Syncytiotrophoblasts From Fetus. Endocrinology. 2015 Jul;156(7):2704-12. doi: 10.1210/en.2015-1130. Epub 2015 Apr 28. PubMed PMID: 25919187.

6: Durković J, Milenković T, Krone N, Parajes S, Mandić B. Low estriol levels in the maternal marker screen as a predictor of X-linked adrenal hypoplasia congenita: case report. Srp Arh Celok Lek. 2014 Nov-Dec;142(11-12):728-31. PubMed PMID: 25731006.

7: Liu ZH, Lu GN, Yin H, Dang Z. Do we underestimate the concentration of estriol in raw municipal wastewater? Environ Sci Pollut Res Int. 2015 Mar;22(6):4753-8. doi: 10.1007/s11356-014-3981-6. Epub 2014 Dec 24. PubMed PMID: 25537286.

8: Shirshev SV, Maslennikova IL, Nekrasova IV. [Effect of Escherichia coli secreted metabolites on functional activity of human neutrophils against the background of estriol effect]. Zh Mikrobiol Epidemiol Immunobiol. 2014 Sep-Oct;(5):65-70. Russian. PubMed PMID: 25536774.

9: Yamabe N, Kang KS, Lee W, Kim SN, Zhu BT. Estriol blunts postprandial blood glucose rise in male rats through regulating intestinal glucose transporters. Am J Physiol Endocrinol Metab. 2015 Mar 1;308(5):E370-9. doi: 10.1152/ajpendo.00209.2013. Epub 2014 Dec 16. PubMed PMID: 25516546; PubMed Central PMCID: PMC4346740.

10: Girgert R, Emons G, Gründker C. Inhibition of GPR30 by estriol prevents growth stimulation of triple-negative breast cancer cells by 17β-estradiol. BMC Cancer. 2014 Dec 11;14:935. doi: 10.1186/1471-2407-14-935. PubMed PMID: 25496649; PubMed Central PMCID: PMC4364648.